I’m a big fan of team reflection. The opportunity for team members at different levels and functions to collectively share what they have seen and learned is refreshing.

It also delivers four benefits to company culture.

First, it’s a great leveller. Founders need to depart from the hand-waving sales narrative and talk straight with their teams. And team members need to organise their thoughts and communicate in ways that contribute to the discussion. In both cases, this can feel uncomfortable, but it does break down perceived hierarchies and remind the team that you’re all in it together.

Second, hearing and analysing the reflections from team members can help founders identify blind spots in how they have interacted with their teams over the last year. If the founders and management team are open to it, these blind spots present opportunities to improve planning and communications in the year to come.

Third, reflection provides perspective. On how much the team has achieved and how many fires have been fought and extinguished along the way. The force multiplier is that perspective, like humour, is free, infectious and a great circuit breaker.

Finally, team reflection can be cathartic. And this is particularly important after a big year when the team is running on fumes and doing everything possible to close our pre-holiday milestones.

Before I share the process that I find useful, I want to be clear that an annual reflection habit complements existing reflection practices. In other words, teams shouldn’t only find time to reflect once each year. It should be happening as part of regular rituals, including 1:1’s and all-hands meetings.

Annual reflection timing 

I start this process in early December, and it usually happens in two steps. The first step is a prelude to a team conversation. It involves, often in a weekly standup, providing the team with a structure for how the reflection should work. I also describe what I will be looking for in judging whether the reflection has been successful or not. I ask the team to think about my criteria for success and encourage them to form their own too. This step helps them internalise what success might look like and also helps them prepare for the conversation.

I have two success criteria for the annual reflection.

Hearing thoughtful reflections from each team member is the first. This demonstrates that they have taken the time to identify critical events. They may have been surprised, confused, frightened or elated by those events. But if they have identified them, there is a good chance they have learned from each situation, and that is critical.

Second, I see that by sharing their insights, each team member feels a sense of satisfaction and to some extent, relief. I think this catharsis and perspective provides the team with a kind of permission to enjoy their upcoming holiday.

It’s important to realise that this exercise is not an after-action review (AAR). The role of an AAR’s is to take immediate action after project or mission execution to capitalise on what went well and what can be improved. The annual reflection is a less formal and less structured event and designed to help the team reflect on a broader timeframe.

Preparation is simple

Ask your team to review their diaries and look for two standout meetings, events or milestones for each month of the calendar year. It should take 15-20 minutes. As part of this review, ask them to note down why the meeting, event or milestone was important to them.

When it comes to the annual reflection conversation, divide the year into quarters. Then ask each team member to raise one meeting, event or milestone from each quarter.

In addition to presenting my reflections, I actively listen out for observations that surprise me. I consider these my blindspots.

If I can ask a clarifying question to dive deeper into the topic without disrupting the flow of the session I do, otherwise, I followup separately.

In any case, my experience is that these sessions yield a rich cross-section of events and lessons.

One last thing…

As I’ve written about before, routines and rituals are the keys to establishing and maintaining a companies drumbeat. This reflection process is an essential ritual because it provides a platform for conversation and lesson-sharing as a means to create perspective after a busy year.

New comers benefit from annual reflection as much as team members who have worked the entire year. It’s also an essential exercise for solo entrepreneurs who should be doing an annual reflection with mentors and advisors.

This is an exercise I wished I had known about a decade ago and I hope it helps you too.



Each time my wife or I travel for work, there is an impact on our daughters. They miss us, and of course, we miss them. And like most working parents, we try to explain why we work, what we do at work and how we are trying to make an impact by investing time away from them.

These explanations can help, but I’m never sure if they make a difference.

If you are a regular consumer of my content, you will know my ‘family first’ philosophy. I walk the talk on this by planning my travel and meeting schedule to minimise my time away from family. That's a good start, but I’ve been thinking more about how I can reduce the impact while I’m away.

I have employed two tactics that you might find useful if you’re a parent that travels for work.

A story to explain love

I tell my wife and kids that I love them as often as possible. As our girls are now in the habit of writing and telling stories, I followed suit.

Here is a story I wrote on the outbound flight of my current visit to Singapore.

Each time the door closes

Each time the door closes, I miss you.

When I close your bedroom door at night.

When I say goodbye at the school gate.

When they close the aircraft door. 

These are hard moments because I love and value every minute with you. And like your Mumma, always want more. 

I saw your brave eyes this morning when you realised that I had to leave for the airport. And I feel your sadness when I travel away from you, but I want you to know that I go because it helps us give you what you need. 

Like our safe and loving home and each opportunity that helps you grow and learn.

When I travel, I want you to know that I never stop thinking about you. 

I am always wondering what you’re thinking about, smiling about and worrying about. 

That is my job, my privilege, and I truly love it. 

You are my most precious and incredible achievement. 

And I know your Mumma feels exactly the same way. 

Each time the door closes, I miss you. And I think about how I can be a better dad. I can’t wait to see you in my dreams and don’t worry; I’ll be home soon. 

Sweet dreams my loves.

Daddy xx

My wife tells me the message landed. There were tears, but I’m holding onto the fact that they were happy tears.

Storytime. Playschool style. 

Storytime is a big deal in our house. And as much as we try to make time zones work when travelling, we sometimes struggle to FaceTime before the girls turn in.

The second tactic involves packing some of their favourite bedtime stories. I record myself reading the stories and ship the video to my wife so it can be played at the right time.

Much like how the hosts of playschool read stories, just far poorer production quality!

In doing this, I’m trading off pre-bed screen time (which I’m not a fan of) with trying to be closer to the girls while away. It’s not perfect, but it’s an attempt to reinforce their importance in our lives.

One last thing...

I’m by no means a perfect parent, but I do believe that we, as parents, are in the memory creation game. These two tactics are attempts we are making to help cushion the effects or work travel.

These tactics might not work, but I hope they help.



Being new is daunting. Particularly when joining a new school. One virtue that my daughters’ school injects into new students and their parents is that they are only new on the first day. From day two, they are members of a community designed to foster learning and progress.

This philosophy has remarkable results which engage the entire culture of the school.

For students, it accelerates how they accept their new environment and helps them start learning and participating the moment they walk in the door. Teachers plan their first day and over-index on assisting students in feeling welcome. And older students, who have benefited from the same tradition, participate with enthusiasm as if the better the reception they received.

Not surprisingly, schools that pay little attention to welcoming newcomers have different effects on students. The bottom line is that students take longer to open up and participate. And this can have significant downstream consequences.

The same is true for companies.

I’ve written about how founders can help new team members demonstrate their worth. But I’d like to share some thoughts on how to create the best first day for new team members. One that has significant positive flow-on effects for the team, new team members, and how the company approaches hiring.

Founders control the first-day experience

I think about the first-day experience in the same way Brian Chesky feels about the guest experience at Airbnb. Each level of the experience has a star rating, but it doesn’t end at a five or even six-star experience. It ends at whatever ‘awesome’ is for the experience you are trying to create.

The ‘no-star’ first experience is no one is there to meet the new team member.

The ‘one-star’ experience involves someone being there, but they don’t know the new team member, who comes in and sits in the corner until their hiring manager arrives.

‘Two-star’ experiences look like a hiring manager being there to greet the new starter who is then shown to a desk and asked to complete mandatory online training before being asked to sit in endless meetings to ‘learn the business’.

Imagine a ‘five-star’ experience. The new team member arrives and is welcomed by a few of their colleagues, gets swag and is granted access to essential systems within an hour of arriving.

Most people would think that’s pretty good but imagine a ’12-star’ experience.

The entire company throws a party to welcome the new starter. Jerry Seinfeld is on stage doing comedy celebrating the new arrival. There is swag that includes a new, top of the line laptop and phone that are gifts for personal use and Morgan Freeman has recorded a personal welcome film directed by Michael Bay. And as if that wasn’t enough, the new starter gets the desk of their choice and gets a bonus four weeks vacation.

The point is that founders control the first-day experience and by extension, the first impression of the companies culture.

This first impression must be remarkable.

Because this is how new starters will talk about and characterise the company that week and well into the future to friends, family and other potential hires. It’s also how they will act for the next new team member.

If the experience is poor, that will be the message and the behaviour when a new hire arrives.

A first day that starts with the unexpected

Creating the best first day doesn’t mean showering a new starter with expensive swag. The ambition is to ensure that they only feel new on day one and from day two, they feel part of a learning and progress-oriented community.

I learned while building AirShr that a remarkable first day starts with the unexpected. Let me explain.

Nova Entertainment, a national Australian radio broadcaster, agreed with AirShr to pilot our technology. This pilot took place at their Brisbane station, Nova106.9, One morning, as I entered the Nova offices, as I had done dozens of times previously, I entered the lift and started the ride to the studio floor. I was on the phone and the only person in the elevator. When the lift doors opened party crackers and music erupted. A red carpet was laid out in front of me, and the entire Nova staff started to cheer and dance. They formed an arch to walk through that extended more than forty meters.

“I’ll have to call you back”, and I hung up. The unexpected greeting was a complete surprise. And not for me!

They thought that I was a new starter, scheduled to arrive at 9 am. The Nova team reset and moments later, started again for the actual new team member.

Observing this for a second time, I could see the smile and disbelief on the new arrivals face. But the first-day experience didn’t stop there. After being shown to her desk and getting access to email and other systems, the team invited her out for lunch before she could head home. Her first day was a half-day.

This experience is a remarkable ritual at Nova that engages every member of the organisation.

How we do it

As I designed the onboarding process at Drop, I asked colleagues about their approaches. Some great suggestions included cultural rituals, swag and unique experiences. One company does a little social stalking to learn more about what their new team members love. They then include an experience that relates to that passion as part of their onboarding which is deeply thoughtful, and remarkable.

I’m aiming for an 8-star first-day experience at Drop which balances remarkability with the practicalities of a venture at our stage of growth

New Team Member Onboarding Process 

The first day for a new team member is a momentous occasion and a critical first impression. It is our first true demonstration of culture, and this day must be consistent and memorable for everyone who joins Drop, and unlike any other first day that they have experienced in their career.

Our aim is for people to finish their first day feeling like they are no longer new. This is the beginning of a process to help them learn what we know and for us to understand their ambition in the context of Drop’s vision. 

Here is how we approach each first day for new team members.

Each new team member is assigned a ‘buddy’. They are responsible for welcoming them to Drop. This includes:

    • Sending the new team member a welcome email on Friday before they start (there’s a template below)  
    • Welcoming the new team member at the office on their first day and then introducing them on Slack when they first log in 
    • Being the go-to person to ask questions about the ins and outs about Drop and ‘how we work around here’ 

They start on Tuesdays. This allows them a long weekend and helps us move through our weekly kickoff meetings, for which new team members won’t have context

We spend the first two hours of their day at a coffee shop learning about why they joined Drop and our reasons for joining and ambitions for the company

When they arrive back in the office, they receive online access. In addition to receiving wi-fi access, their email address has been set up, and when they sign in, they will see emails inviting them to join Slack, Trello as well as invitations to key team meetings. If they haven’t already updated their LinkedIn profile with their shiny new role, they can do that too.

Their swag is also on their desk! This includes a Drop KeepCup, notebook, a $50 Hey You voucher (to keep them in coffee) and a copy of Deep Medicine to see what’s coming and Bad Blood to understand modern history.

Then, lunch! The buddy, available team members and the new team member head out for lunch after which the team member gets the afternoon off. This is a chance for them to reflect on what they have seen and heard during the day, relax and then come fully charged to start on Wednesday!

And so the journey begins!

One last thing…

The onboarding process will no doubt evolve as the company and team grow. The key takeaway, however, is that the founders control this experience. It has cultural ripple effects that compound with time.

I didn’t use to value the importance of creating the best first day for new team members. But I do now because you learn what matters over time.

I’d love to know how you welcome new team members. Leave a comment below or shoot me an email!



Parents are essential to my company. When we started to create the culture frameworks for Drop, I gave a lot of thought to how to help parents fit.

Drop, like many companies, is in a perpetual hiring cycle. We look for the brightest minds in science, engineering and marketing to join our mission. While 'bright' implies several qualities like a high rate of learning, it doesn't necessarily mean young. Bright minds are also experienced hands, and in most specialities, including science and engineering, experience comes with time. And a major life change that comes with time can be becoming a parent.

Here is how I think about the value proposition for parents in a startup. I'd also love to hear your thoughts too. Leave a comment below or email me here.

What you're about to read can also apply to more mature companies. But startups are uniquely unpredictable and an environment where patience and urgency need to be carefully regulated to ensure survival to achieve product/market fit.

My thesis is that working parents understand the value of time because they have two full-time jobs. One a parent and one as a professional. By creating an environment that simultaneously rewards each role, they will thrive, become more productive and feel more fulfilled at work and home.

Three principles help this thesis come to life.

Family comes first, period. This first principle means that when an issue arises, the team member can focus all effort on supporting their family member in need. This principle also means that the team finds a way to maintain momentum in their colleague's physical or emotional absence.

Second, experience and expertise shouldn't be traded off against being a great parent. As parents, we are in the memory creation game for our children. They are the mission, and this can co-exist with the purpose of our venture(s).

Third, most pressures felt by people, as a parent or not, arise from an issue at home or with family.

Parents of today and tomorrow

Parenting is tough and beautiful in equal measure. Parents with children living at home face different challenges to those with children living their own life. And it's difficult for people without children to understand these challenges and the wonder that comes with being a parent.

Conversations at work between team members that introduce their family members and situations go a long way to establishing context. It's an essential first step, but I think the real opportunity with implementing a parent value proposition involves creating ongoing compassion for the parenting balancing act. That means founders need to own and reward the behaviours that make this proposition part of company culture or 'how things are done around here'.

I also want to be clear that developing a parent value proposition does not mean that founders are hiring people to join 'their family'. A parent value proposition should acknowledge that performance is essential and expected from every team member. In the same way that ongoing compassion for parenting is critical, this performance expectation helps to manage potential tensions between those team members with and without children.

Core ingredients 

Beyond a paid audition, the core ingredients of a parent value proposition should be the same as other team members. They should include specific details about the role, remuneration (cash, options and equity), leave and desired objectives from their tour of duty with the company.

This last point is possibly the single most significant people and culture revelation in today's networked age. Reid Hoffman presented this in The Alliance, a book he co-authored which also introduces the idea of employees and employers entering into 'tour of duty' agreements as a means to reframe the working relationship.

The underlying philosophy of The Alliance is compelling and grounded in the idea of turning employees and employers into allies where they can develop a relationship based on adding value to each other.

In addition to helping leaders move away from archaic methods used to engage with employees, it sets the groundwork for developing incremental trust between employees and employers no matter what level they enter or grow within the company.

Parent-specific ingredients

Here are the five parent-specific elements I think are essential to startup employee value propositions for parents:

  1. Office time - This includes nominating the earliest and latest meeting times that can work for parents involved in school runs. This means having a conversation to determine when meetings should start and not nominating an arbitrary time like 8:30 am because that's when the people think work should start. This ingredient also extends to how often team members should be encouraged to work from home. We know how productive meeting-free time can be.
  2. Memory time - I mentioned before that parents are in the memory creation game. Occasions like concerts and sports days, most of which don't require a full day off, are marked as time off. Parents should be available to help create those memories.
  3. Professional development - Parenting is a constant outflow of energy. Relevant and exciting professional development goes a long way to increasing company capability and meeting your commitment as an ally, as well as helping to re-fill the energy tank.
  4. Time optimisation tools - Introduce a list of tools that can complement parents' existing practices or expose new ways to optimise time. Any tool that helps to manage administration and logistics is usually well-received.
  5. Team communication - Giving a new team member access to Slack and showing them how to 'chat' falls a long way short of effective team communication. This ingredient focused on teaching people how to use specific and sometimes unfamiliar tools, so they enable productivity and don't create another level of complexity and frustration. It also extends to time-based practices, for example scheduling emails to send at 8 am the following morning for any emails ready to be sent after 9 pm. This gesture goes a long way to removing any undercurrent of 'performance agenda.'

Other interesting tactics to include:

  • Circulating holiday activities to help alleviate the pressure that comes with juggling holiday childcare
  • Sharing a list of date-night events to inspire busy couples to find time to nurture their relationships
  • Asking about the family during 1: 1's to enable a better understanding of life outside of work. This context can be beneficial as issues arise and to help leaders understand that parents face different challenges.

Making it work

Implementing a startup employee value proposition for parents is not complicated, but it does require deliberate behaviours. Both on the part of the founders and their teams. And like any system, there is potential for abuse.

One way to manage this risk is to set reasonable limits. For example, one leave day per child per term which doesn't accrue if unused. A second strategy is to insist that leave for memory time is booked at least six months in advance.

Parents who leverage 'memory time' through planning and exceed expectations on workload understand that productivity is based on outcomes and not hours worked. They rarely abuse this system.

Those who leverage memory time and consistently fall short on expected workloads may not be the right fit for the company.

One last thing…

As reported recently in the New York Times, founders of successful tech companies are mostly middle-aged. These people and their teams are in the same perpetual hiring cycle for great talent. A key differentiator can be an employee value proposition for parents.

My message to founders is to own the hiring environment and conditions for parents.

We have the tools to enable work to happen differently and respect the downtime required to have a career and be a great parent. I chose to enable those careers at Drop and hire both young and experienced talent to advance our mission.

The question is, will you?



Every product has unintended consequences. That is because people often use or adapt products in ways that are different from the designers intent.

Some unintended consequences are benign, while others are profound or difficult to imagine. I’ve been giving this topic a lot of thought recently in the context of my company Drop Bio. The trends in healthcare and biotechnology, data ownership and the roles that doctors and regulators play in keeping people safe are changing rapidly.

Like most sectors undergoing disruption, new business models are being tested to see which ones affect change and generate value. This form of experimentation is likely to result in many unintended consequences.  

As founders, we have three doors we can walk through when it comes to unintended consequences.

First, follow Facebook’s philosophy of ‘running fast and breaking things’ as a means to learn and iterate quickly. The desire to identify and act on unintended consequences is relatively low in this model.

Second, cautiously develop products knowing that unintended consequences are imminent. This situation can paralyse, or significantly slow momentum as founders seek permission or in-depth validation before moving to the next stage of product development.

Third, forecast unintended consequences to the fullest extent possible and embed this knowledge into products.

I choose door number three and here’s why and how I bring that philosophy to life.

The unexpected consequence ‘line of sight’ 

When founders start building companies, their view of unintended consequences is often limited to their understanding of competition and the feedback they receive in response to investment pitches.

In other words, the potential to understand unexpected consequences is limited to the people who will listen to a founder's pitch and what the founder can Google about their competition.

And while frequently asked questions and observations will arise as founders pitch to more people over time, we don’t ask for explicit feedback on unintended consequences. If we did, it might derail the pitch. A more likely outcome is that FAQs become perceived as objections. As a result, founders reframe the feedback (which may well be highlighting a consequence of the model) to a well-crafted response designed to overcome the objection and maintain momentum in a conversation.

Wouldn’t you want to know?

This question comes up a lot in predictive and digital healthcare. If an algorithm, doctor or product could reliably predict a genetic pre-disposition or deliver early warning of a disease, would you want to know?

There is a fear that comes with knowing the future. And a range of near-term and abstract ’what if’ scenarios can be overwhelming if they lack a framework to organise and understand each situation.

However, the bottom line is that knowledge contributes to high-quality decision making. A lack of information usually leads to poor decision making. Take an extreme situation like a cancer diagnosis. Most people who receive this news undergo shock and then develop an insatiable appetite to learn about their condition, and lifestyle and treatment options.

When it comes to building a company, founders, like team members, investors and partners, work to de-risk, stabilise and grow a business model. Much of this journey is unpredictable, and no one wants or needs any more surprises. But there is a way to forecast unintended consequences. To be forearmed and on the front foot.

Forecasting unintended consequences

This process involves three ingredients.

First, a list of consistent feedback a founder receives when pitching. The statements of most interest, in the context of unexpected consequences, are the ones that focus on the implications of the product and less on the product itself. For example, feedback on how a social media platform might change consumer attention is more critical than the app's onboarding flow. These statements may be interesting during the pitch but can be downplayed or dismissed because of the need to convince an investor to engage. I log these statements in my notes app soon after meetings with potential investors, hires and partners. It’s part of my after-action review, so I don’t forget these statements as I move from one meeting to another.

Second, a small amount of incentive-free team time. Founders and their teams are usually smart people. They have dedicated their lives to solving the problem at hand, and there is a good chance that unintended consequences are continually processing in their minds. I think it’s essential to allow teams the time to openly discuss and express how they perceive unintended consequences from their vantage point.

‘Incentive-free’ time means permitting them to speak about those consequences in ways that don’t threaten their incentives, for example, their jobs, options or reputation.

Third, triangulating unintended consequences with six kinds of people, including:

  1. Ally - a colleague, co-founder, investor or advisor
  2. Friend - a non-work related relationship who knows you well
  3. Devil’s advocate - someone who brings constructive yet argumentative logic to most conversations
  4. Uninitiated - a potential customer or user of your product who has not heard the pitch before
  5. Widely informed - a journalist that focuses on world affairs
  6. Narrow specialist - a person who has intimate knowledge of the status quo

With each of these people, generally in separate meetings, I pitch the idea, business model or issue and ask them one question, What could be the unintended consequences, both good and bad?

Answers from this one question can reinforce what’s already known or surface new thinking. However, the point is that diverse perspectives help to triangulate unintended consequences objectively.

Preparing to learn

Identifying unintended consequences is the first step in this process. The next step in a Google Sheet with your team is to: 

  • Rank each unintended consequence in order of perceived importance to the business
  • List three scenarios for how each consequence could play out in the next two years
  • Draft a statement about how our company would respond to each scenario

We then schedule a time to revisit this assessment every quarter. This move ensures the team is ready to learn and maintain a unique self-awareness continually.

One last thing…

I have been using this framework for some time, and others use similar models (like on the Should This Exist Podcast). There is also a good chance that your team and investors are already thinking about these consequences. So it makes sense to capitalise on the collective wisdom of your team, those you’ve pitched to and the six types of people I described above.

I find this process very useful, and while you might not have resolutions to every unintended consequence, forewarned is forearmed. And that’s a great help when you’re trying to create a new order.



Managing the need to provide is a constant stress for people with obligations. It is especially acute for parents who are founders given the risks of building a company and extends to founders with teams and those who would like to provide for their parents and siblings.

The need to provide is always in my mind. I became more aware of it when I married my wife, and it escalated when we welcomed our eldest daughter into the world. For me, the need to provide is a desire to be an equal contributor to the team that is my wife and me. I also used to find that my confidence and relative self-worth oscillated depending on my capacity to provide, which was tied where I was in the company-building rollercoaster. It could be high one day and gone the next. 

But unlike other stressors in entrepreneurship which are difficult to predict, like customer growth or hiring fit, I think managing the need to provide is much more controllable. 

It takes practice and relies on self-awareness. The switch that flicked in my mind years ago was to control the narrative in my mind instead of the need to provide controlling how I made decisions. 

It’s easy to say with hindsight, but it was a revelation at the time.

Keeping the need to provide in check

The tactic I use to think about managing the need to provide involves regularly asking myself five questions. To keep myself honest, I have a quarterly calendar appointment called ‘Need To Provide’, which prompts me to ask these questions.

These five questions are not difficult to answer, and at the most basic level, they are designed to help founders achieve perspective.

If managing the need to provide enters your mind regularly, ask these questions of yourself as often as you need to.

This tactic has helped me, my team members and those I mentor, some of whom are parents while others are single or in relationships with no children.

Q1 How much do I need? 

Not to be confused with what a person wants, this question focuses on a financial budget to make ends meet and to live a relatively comfortable but not extravagant life.

I also use this question when hiring at Drop. As is the case with most early-stage ventures, paying the market rate is usually not an option. Paying some cash and topping up with equity and options is doable, but it requires the potential hire to know how much they need.

I’m often surprised by the number of people applying for startup roles who don’t have an annual salary in mind that is their ‘I need this to survive’ number. Everyone aspiring to work in a startup should know their number.

Outside of this hiring scenario, founders need to be realistic about what they need to provide.

Entrepreneurship is not about entitlement or market rates based on previous salaries. It’s about solving problems that will affect the lives of many and surviving in the market long enough to crack the product/market fit code.

If a venture’s rate of learning is consistently high, the timing is right, and luck plays its part, founders, team members and investors will capture value. In some cases, they will never need to think about how much they need again. Consider that the exception to the rule until it happens to you.

Q2 How do I contribute?

This question isn’t just about how much you contribute financially. It’s about how you contribute.

Audit your non-financial contribution and become the laundry guy, cook, morning routine ninja or witching hour warrior. Changing up how domestic activities or time invested in the family can have significant positive consequences.

Q3 How long is my runway?

Run the numbers and always be clear about the length of your venture or project’s runway. That means knowing weekly (cash) burn rates and how growth and hiring will influence how long you can be in the market.

Tactically, this will also help in decision making and how you prioritise tasks. Most importantly, it reduces the chance of founders breaking the golden rule in entrepreneurship, no surprises.

Full post on that here.

Q4 How do I communicate?

There are two parts to this question. The first relates to people outside your venture. Does your partner, family or close friends know your venture’s mission and progress to date? Most founders under-communicate their day job to those closest to them for fear of sounding repetitious or of them not understanding how real the struggle is to build a business. As I’ve written about before, these people can be your closest allies.

The second part relates to the extent to which communication has improved with your team, partners and investors. I heard a great adage the other day; if you hear nothing after an update to your organisation, partners or investors, something is wrong.

The punchline: Always be trying to improve communication, in all aspects of life.

Q5 What was my last lesson?

This question helps to remind you about the speed at which you are travelling. Lessons can get lost in the daily cut and thrust of building a company. Taking time to realise just how much has been learned and how cumulative lessons are building towards a greater capacity to provide is essential.

One last thing...

The answers to some of these questions may bring founders closer to the realisation that their business model is or will fail. Or, it may help calm the angst that comes with managing the need to provide. In both cases, this model helps give perspective to what can be a tricky topic.

Try asking these five questions once a quarter and let me know how you get on. Managing the need to provide is much less of an issue for me than it used to be, and I hope that in a short time, you will be able to say the same.



Do you know what your teams tells are? If the term 'tell' is unfamiliar, it comes from the card game, poker. 

Poker, like leadership, is entirely based on human interaction. And it's the clues or tells in a person's demeanour that provides indications of the strength or weakness of the cards they have in their hand. 

Identifying your team's tells is critical to gauging internal momentum. I also think it's the first step in understanding how to circuit-break stress and learn more about why they decided to work for you in the first place. 

I apply the same philosophy to understanding my team's tells as I do when building products.  In product development, my objective is to move people closer to happiness or move them away from fear. In my mind, the same rule applies to the momentum of a team building a startup.

Where cash is tight, fires are burning and you're in the cut and thrust of uncertainty, the rate at which a team can learn and effectively communicate will determine success. 

If a team or a team member is moving away from happiness or closer to fear, momentum will slow and tells will start to emerge. And in my experience, tells are unconscious, reliable and for the most part, hide in plain sight.

He (or she) always does that

I was talking to my friend and colleague Megan Flamer about this recently. Megan is a serial entrepreneur and mindfulness expert, and we talked about what to look for in a person's tell. 

Unlike poker where tells are often subtle, tells in life and at work can range from subtle to verbose and outrageous. 

The trick is to look for behaviours that occur outside the norm. 

An example of a subtle tell might be a team member going to get coffee three times in one day when they are generally content with one coffee per day. 

A less subtle tell might be a team member ranting about a situation that they find unacceptable when they are ordinarily level-headed.

'He (or she) always does that', can be a normal reaction to either tell. I take that statement to mean people are observing a behaviour but stopping short of understanding why it manifest in the first place. 

And herein lies the cue to learn more. 

Learning about a tell

There are several ways to try and understand why a person's tell has come to the surface. 

I'm no psychologist, but I have developed a curiosity for learning about my team's tells and those of my partners, investors and mentees. 

There are some circumstances where you can ask, why? Even though it's not a closed question, it does have the potential to be perceived as confrontational. 

There are three words that I have come to rely on to learn more about a tell. Ironically, they have also been used on me when my tells have come to the surface. 

Those three words are 'talk to me.'

This statement, possibly made famous by Maverick when talking to Goose in Top Gun, is a neutral offer to start a conversation. 

It comes with no expectation but a desire to help. 

My team and people close to me know that I often make this statement when I observe their tell. A conversation may start with 'talk to me' as my opening statement, or it might begin with, 'I could see you were a little upset this morning, talk to me'.

The main benefit of these words is that if the person isn't ready to talk, they know that you care enough to ask. 

Your working relationship is an alliance

Understanding the tells of a team member is essential to a healthy relationship. It's also a two-way street. Leaders have tells. Team members have tells. And team members should develop the confidence to say 'talk to me' to their managers. 

That's because, and as I've written about before, a working relationship is an alliance. People no longer spend the majority of their career at that same company or the same industry. When someone interviews to join my team, I make it clear that their time at the company will be a tour of duty. As part of the hiring process, we make sure that their objectives (and their next job) are well known. By understanding their incentives and by them knowing yours, you can work to help achieve each other's goals. 

I raise this here because understanding incentives in the context of an alliance can also help to identify, understand and work through each other's tells. 

One last thing...

There are two choices when you see a team member do something a little out of the ordinary. Do nothing and shrug it off as a behaviour that manifests in times of stress. Or identify and understand the tell. 

I recommend the latter. 

Because it's human and it helps to galvanise relationships, build trust and accelerate momentum.

These qualities are as essential in a startup as they are in life. 

Try saying 'talk to me' and see what happens. 



‘Incentives are a superpower’ is a phrase made famous by Charlie Munger, an investor and partner of Warren Buffett at Berkshire Hathaway.

Incentives drive just about every human behaviour. And for the most part, the stronger the incentive, the more immediate the change in behaviour. 

Smokers who survive heart attacks are more likely to give up smoking than those who are at risk of a heart attack. And in the same way a salesperson is more likely to say what a customer needs to hear to secure their commission, a person who wants to achieve a lifelong ambition to be a doctor will study their heart out to achieve the required standard.

As a founder in a startup or a high growth company, incentives play a central role in performance and milestone achievement.

I look for incentives that drive my team, partners, potential hires, customers, investors and people in our communities. 

My radar is also always on to identify triggers that may change those incentives. 

Because incentives are a leading indicator of behaviour. 

Leadership is a contact sport

Two friends of mine, Ben Pronk and Tim Curtis, often refer to the idea that leadership is a contact sport. It means that you need to repeatedly engage, one on one, with the people you lead or the communities you seek to influence. 

This contact is the only way founders can understand incentives. Or detect when they start to shift.

Otherwise, there is a high chance the assumptions you make as to why a new hire joins, a team member quits or an investor decides to withdraw at the eleventh hour will be wrong. 

I’ve found that a mix of trust (i.e. being consistent over time) and respectfully-asked, direct questions are crucial to understanding incentives. 

While I’m no psychologist, I have found that people often act based on two types of incentives. I’ll call one ‘human' and the other ‘functional’. 

The human incentive is underpinned by curiosity and to some extent, altruism. The functional incentive tends to be more about how money can be made, and how influence can be developed. 

Human and functional incentives coexist. Think of them as a pie chart, their sum is 100%. They change based on circumstance, life stage and a myriad of other factors. 

The point is that two factors drive incentives. Those factors change with time. And the only way a founder can understand or influence the resulting behaviour is to lead, knowing that leadership is a contact sport.

Uncovering incentives

I have a set of questions that I use to uncover incentives. Much like validated questionnaires that use just a few questions to help establish risk factors for health, these questions help me develop an understanding of a person's incentives.

The questions below are not an exhaustive list, more my starting point.

  • When interviewing candidates: What is the next job you hope to secure after your time at Drop comes to an end?
  • When meeting with a customer: How can we help take you closer to happiness (and further away from fear)?
  • When meeting investors: What do you need to believe to invest in our team?
  • When brokering a distribution partnership: What is the fastest way to create value for your customer?
  • When building a community: What is important to you about our vision?

Each of these questions is designed to start a conversation and I try asking them in the first meeting. 

I also tend to revisit these questions from time to time in the relationship as a means to gauging if incentives are shifting. 

One last thing...

Understanding incentives is critical because they help to predict behaviour. In addition to asking the questions above, I also find myself asking why? as the follow-up question. A lot.

These questions have helped increase the quality of my decision making, saved me a ton of time and short-circuited what could have been (very) poor hiring decisions. 

My last question is for you. What techniques do you use to uncover incentives? 



The number one thing I look for when hiring is ‘makers angst’.

More than just startup experience, makers angst is the lived experience of trying to build a product or company. It’s the combined highs and lows, stress, reflection, learning, and adapting on the fly that can only come from experience. And I consider it one of the lead indicators of whether someone will be successful in a paid audition and then as a full-time team member. 

I look for makers angst because the number one misconception about startups is that they are training grounds. For those recently graduated from school or university or transitioning from a different career. 

Startups are not training grounds

They are intense, cash poor, high-risk and fluid environments. 

In other words, the time and space to coach, train and formally develop people simply doesn’t exist in the same way it might in more mature organisations. 

It’s a harsh message, but it’s true.

And a fair rebuttal would be that you often hear me evangelise that a high rate of learning is a secret weapon for founders and their ventures. 

That rate, however, depends on two factors. First, a base level of competence in a functional area, like product management, marketing, sales or science or engineering. Second, a demonstrated ability to create momentum from a standing start. And more importantly, within a month of joining a new venture. 

Of course, the irony for most founders is that finding people who they can afford who fit this bill is difficult. And while founders are constantly battling trade-offs, the one factor that should be traded off the least is the quality of talent joining your team. 

Hiring mistakes that we all make remind us of this. They might cost money or cause a short term hit to the venture’s reputation. But the most significant negative impact, which is also the most difficult to recover from, is the stalling of precious momentum that comes from hiring the wrong people. 

Lived experience 

The first interaction I have with a potential new hire is often in response to a job ad, a referral from a trusted source, a tweet or a LinkedIn message. Before I respond, I scan their LinkedIn profile looking for signs of makers angst. I’m looking to see if they have founded a venture, been an intrapreneur, or been one of the first five or ten hires at a startup? 

If they have, and there is some detail about that chapter online, they can be assured that the first part of our conversation will focus on that period, what they learned and how it shaped them as a person. 

The same is true if they haven’t listed details online, but the referring party has mentioned that part of their history as the reason for the referral. 

My theory is that people with this type of experience, having experienced makers angst, are more likely to bring perspective and a different approach to problem-solving in chaotic environments that those who are new to startups. When this theory plays out to be true, these people also tend to consistently live up to the value of ‘acting like an owner’. Because they have felt what it’s like to be the owner before, and this is incredibly valuable. 

But what about my opportunity cost?

The opportunity cost of me joining your venture is very high. I could be earning a lot more elsewhere. 

I have heard this argument made many times. It’s usually posed by people without startup experience who are trying to convince the founder of their worth and instil a sense of FOMO (fear of missing out). 

This kind of argument is a red flag for two reasons. First, the person making the argument hasn’t realised how value is generated in a startup. Sacrifices are made every day by the team in the spirit of achieving a startup’s vision. If one person is focused on their opportunity cost, then there is a good chance they will undervalue the contributions of other team members if they are hired. 

Second, and I think this is more important, opportunity cost goes both ways. The opportunity cost of a startup employing someone means they can’t deploy that capital to other things. And while that might sound obvious, founders have a habit of achieving a lot with a little. I could pay $50K per annum for someone with limited experience. 

They might be able to achieve some parts of some tasks and learn a massive amount along the way. Or I could hire freelancers to help me execute more efficiently. I know it’s not that binary because the 50K hire could end up developing into a valuable team member. 

But the point is that founders have the choice.

When faced with hiring decisions, it is essential to consider the opportunity cost and how else that capital can be deployed. I often think about the opportunity cost in terms of software engineering time. In other words, how many hours of a software engineer’s time could be used to build a product if I didn’t spend money on the alternative?

My friend Gautam Mishra taught me this, and I use it a lot. 

Makers angst starts with making

This post and philosophy are not about a hiring policy that screens out people without startup experience. My message is that to be effective in a startup, you need to have felt the discomfort and exhilaration that comes with making a product or service. Education and non-startup work experience in and of itself will not make you productive. 

You need to have tried to make something. So do that. 

Use the many free resources online, like my blog and podcast, to create a side hustle. 

Learn to validate an idea in 30 days. 

Be able to talk to this direct experience. 

It will prove you can get (back) on the tools, learn and be humbled by the experience. More importantly, and for those who come from senior roles in government or corporate organisations, it will help prove to the founders that you can bring real value to their business.

Like many founders, I am wary of senior managers who want to make the transition to startup for the first time. They may bring a host of relationships that they think they can be leveraged, which can be helpful. But since moving off their early career tools and transitioning into management, these candidates often develop and over-value their capability to manage priorities and navigate politics. While managing time and priorities is essential in a startup, managing politics is not.

One last thing…

If you want to join a startup, prove that you have attempted to make a product or service. Be ready to tell that story, especially if it failed. This experience will help you see around corners in chaotic startup environments and start adding real value quickly. 

And if you are a founder or employee of a failed startup, understand that your experience is immensely valuable. You hold the cards when it comes to makers angst. Put them to good use as a mentor of mine says, ‘confound the critics and build a great company’.



Lessons are the byproduct of failure. How quickly people arrive at lessons usually separates those who wallow in defeat from those who extract knowledge and keep moving. 

I make the same number of mistakes as most founders each day and failure can hurt. Sometimes it’s important to feel sorry for yourself to process and make sense of mistakes or failure. However, the name of the game, especially in the face of chaotic uncertainty, is to increase your rate of learning. 

Until recently, I hadn’t articulated the basic math I do in my mind each time I fail. And on reflection, I’ve been running this algorithm in the back of my mind for years. I hope you find it useful too.

Clocking failure

I respect founders who have developed a habit for ‘clocking failure’. In other words, they have found a way to pause and reflect when failure strikes. It’s much harder said than done. The high volume of decision-making and firefighting that founders do each day can easily result in a mindset of ‘moving to the next thing’ without diagnosing why failures happen.

As much as I tried to create the conditions to stop and reflect, it didn’t work. That was me in my two ventures. That changed when I started thinking about how much a lesson had cost and began comparing the cost of different lessons. 

While it seems obvious in hindsight, I was mapping each unexpected (or unwanted) result against a four-step chain of events. 

Context > Decision > Failure > Lesson

Lessons that come from failure start with (often misunderstood) context that leads to a decision or decisions. But here’s the thing. Learning a lesson might only result in the acknowledgement of the context or decision. It might not actually change behaviour. And when you’re a founder, and you and your team just don’t seem to be changing behaviour quickly enough, even though a lesson has been acknowledged, you might want to think about adding one additional step.

Context > Decision > Failure > Lesson > Cost

Financial cost often helps focus founders. And placing a monetary value on lessons delivers two critical benefits, one of which can have a significant impact on scaling a ‘high rate of learning’ culture. 

Calculating lesson cost

Take the total cost of an activity and divide it by the number of lessons learned. The result of this math is the cost per lesson.

Thinking about a $100 marketing campaign. If I invested a total of $100 buying a product I want to sell, designing social media ads and paying for advertising only to have sold nothing but I have 10 lessons that come from that experience, then I have achieved $10 cost per lesson or a $10 lesson cost.

$10 per lesson is cheap! 

If I wanted to make this $100 marketing campaign scenario more realistic, I would also add a cost for the person’s time who was running this campaign. 

In any case, the lesson cost is a relatively quick-to-calculate guide that can help you and your team understand the value of time invested. One of the benefits of measuring cost per lesson (and not only a marketing-specific metric like the cost of acquisition) is that lesson costs can be compared side by side between different projects and campaigns. 

The second benefit that I hinted at before that relates to scaling a ‘high rate of learning’ culture relates to the denominator of the lesson cost calculation. 

The higher the number of lessons, the lower the cost per lesson. 

When you start introducing this metric into your psyche, you will find yourself and your team becoming more deliberate about identifying lessons because you will want the lesson cost to be as low as possible. 

One last thing

This method of calculating lesson cost works for when things don’t go to plan as well as when they do. And the math to achieve lesson cost is straightforward so it can be done quickly and intuitively. 

But the main point I would like to leave you with is that calculating lesson cost has forced me to stop and look for lessons in failure (and success). 

When done consistently, lesson cost becomes a source of pride and an acceptable range of lesson cost emerges to become a part of everyday thinking and conversation. 

And for founders who are trying to accelerate their teams’ rate of learning to combat ever shortening runways, that is a good thing. 



As an optimist, I believe people want to contribute to a purpose greater than themselves. The most direct path to achieving this aspiration is to join a movement, a startup, an established company or a branch of government.

While hiring practices between organisations will vary, candidates that make it through can expect one certainty; a unique culture. And more often than not it will be a culture they didn’t expect.

By joining the military, you will be greeted by the idea of the daily renewable contract. By joining Apple, being the best in the world at the role for which you were hired is the main game.

There is an example for every organisation.

More established organisations have resources and infrastructure to afford new hires a grace period while they learn the ropes. This is a luxury most startups try to extend to new hires but often fall short due to the perennial fight against the ever-shortening runway. And it’s not just the cash burn that comes with adding new hires that worries founders. It’s whether new hires can increase the ventures’ overall momentum.

The reality is that founders need new hires to demonstrate their worth as quickly as possible or move them on. It’s particularly stressful for founders when the company has less than 20 employees because every dollar and day count. And the cost of a hiring mistake not only slows momentum, but it can also bring it to a complete stall.

Where the new hire experience falls short

Every culture has a standard. An amalgam of overt and hidden behaviours and expectations that reveals itself with time. If the founders have done an excellent job, a ventures values will set the scaffolding for that standard.

Unfortunately, this is rarely the case. Instead, I suspect most new hire experiences follow a pattern not dissimilar to:

  1. Being welcomed and introduced to their team at the beginning of a working week
  2. Gaining access to hardware and services
  3. Spending time with their manager to discuss their role (which may or may not have been oversold)
  4. Completing mandatory online compliance training
  5. Attending meetings to ‘learn how the business operates’ (and the personalities and politics at play)

Putting aside the fun and brilliantly executed first-day welcome rituals for which some companies are renowned (none better than Nova 106.9FM), these five steps are a practical approach to on-boarding. But it’s functional (and beige). It also leaves new hires to work out ‘how work is done’ in their new workplace.

Where time is of the essence, and as a founder you’ve made the call to bring a new person onto the team, I think there is a way to new hires more productive.

This idea has come from mulling this question.

How can I help new team members demonstrate their worth?

My hypothesis is that new hires are left to demonstrate their worth using only a portion of a venture’s cultural information.

Let me explain.

Whether you conduct paid auditions (the playbook I use is here) or hire directly from a resume and interview process, there is a good chance you hire new people and expect them to deliver exceptional results in the shortest possible time. Even if the five-step on-boarding process (above) is only broadly consistent with what happens at your venture, you are relying on that new team member to interpret A LOT about how work gets done.

Dig a little further, and you’ll soon see that this means you are relying on them to decipher personalities, develop context, understand competing priorities and determine their version of the companies values. Sound troubling? You bet it is.

I often think about LinkedIn CEO Jeff Weiner’s rocket ship analogy, ‘a small mistake can leave you very far off track in the long run’. Leaving a new hire to do this level of interpretation is a small mistake that can be corrected before significant medium and long-term issues arise.

I also believe that when new team members are allowed to demonstrate their skills and earn respect and recognition of their peers (i.e. prove their worth), they not only drive the venture forward, they deepen the quality of our culture.

Here is how I coach new hires to help them demonstrate their worth from day one.

1. Walk through the values. Together.

Most company values have been crafted after much thought and reflection. New hires have few ways to access that context, even when each value is clear and relatively easy to understand. By way of example, here are the values of my venture, Drop Bio (People first, science second. Every idea matters. Champion the mission. Make every day count. Thoughtfully disagree). Most of these make sense at first glance, but they have specific context given our work.

Team members should understand each value. And it’s not enough for the CEO to be the only one describing these values to new hires. I’m a fan of having two team members meet with a new hire for coffee to explain each company value. The intent of this ritual in a growing company is to provide each new hire with a clear explanation and a diverse set of examples to illustrate each value. This sets the new hire up with a clear basis to contribute and make decisions. This is an essential and often over-looked step in on boarding new hires..

2. Ask thoughtful questions and make calculated comments

We have all been in meetings where unfounded observations have taken conversations off-track and resulted in people unnecessarily investigating an anomaly. Notwithstanding the waste of time, this can have limited repercussions for a senior manager. However, the reputation damage to a new hire can be significant.

I coach new hires to prepare thoughtfully for each meeting in three ways.

First, come armed with at least three thoughtful questions. The meeting topic and attendees will be known ahead of time, so look into the subject matter and interrogate the minutes of the previous meeting, if available. A good question can change the game.

Second, offer comments and observations that are grounded in evidence. And be able to share the evidence as requested.

Third, and instead of blurting out a comment grounded in personal bias, offer a statement that inspires debate by saying ‘my hypothesis is that [complete propose thought]’

3. Bring a bit of life to work

We all have lives outside work. I encourage new hires to share a little about their family, professional journey and interests as a way to develop bonds with their teammates. It also provides a basis from which humour can develop, and we all know the power that humour plays in circuit-breaking difficult situations.

One last thing…

I am all for giving new hires the latitude they need to demonstrate their worth. And while I am also performance focused, I’m no fan of micro-management as a means to extract performance. My point is that all new hires should be given the information they need to demonstrate their worth and confidently establish their place in a team. This is particularly important when a company has different disciplines, each of which has inherently strong and sometimes competing cultures.

Instead of letting new hires assimilate through corridor conversations and interpreting cultural cues, give them the information they need to do their life best work. I suspect it will help accelerate momentum. And that will help you, as a founder, sleep a little easier.

ooda loop


The OODA loop is the observe–orient–decide–act cycle developed by military strategist and United States Air Force Colonel John Boyd. It is a framework designed for pilots involved in air combat operations which has moved into mainstream business and entrepreneurship.

There are two subtleties in an OODA loop.

The first is that the O’s in the OODA loop deliberately force you to stop and understand a situation in more detail than you otherwise would before making a decision. Even in chaotic environments.

The second subtlety is that while OODA loops can be applied to resolve acute issues (like those in a fighter jet cockpit), they can also be applied to reflect on challenges and opportunities that do not require split-second responses like the strategic decisions founders need to make.

I have become better at using OODA loops as a daily habit to accelerate learning. They feature most days as we build Drop and I also use them each week when I reflect using my blog.

Given the conversations I’ve had this past month about finding time to reflect, I’m reposting my thoughts on why writing each week matters. I hope it helps you too.

Why writing each week makes all the difference

There was never a time early in life when I enjoyed writing. As I learned to write at school, it always seemed more a skill to acquire and less a craft to enjoy and master.

Of course, I wrote assignments at school, at college and graduate school and then internal reports at banks and pitch documents for ventures. I struggled with writing and the irony is that I don’t recall a time when I was inspired to become a great writer or even just a better writer.

In hindsight, the reason I wasn’t enjoying writing, and by extension not practising to improve, was because I wasn’t doing it for me.

I was writing for someone who would award me a grade, pay me a bonus or invest in a venture.

That changed in 2008 when at 30 I discovered blogging and wrote my first post.

Writing became a weekly habit in 2014 when I started my second venture with a vision and very little domain expertise (former soldier, medical science undergrad, MBA launching an audio recognition business).

I took inspiration from Fred Wilson, who often refers to how blogging helps him reflect and sharpen his thinking, and I haven’t looked back.

I write each week with two people in mind.

Me and one other person.

I don’t know that other person.

They change each week according to the replies I get from the newsletter I send each Sunday.

Whoever they are, they receive help and that makes my day.

Those who say ‘I don’t know where you find the time’ are missing the point.

Because it’s not about finding extra time.

Writing is part of my routine and I’ve found that writing each week frees up time.

Instead of constantly processing half-formed thoughts, I produce an artefact that I know is valuable and one I’m proud of.

And although I write for two people, I write for four reasons.

I write to clarify my thoughts, it separates me from my psychology and the precision of thought that writing provides me is immense.

I write to help others learn from my experience in building companies because I believe in paying it forward and delivering 51% to anyone who wants it.

I write to leave a calling card.

But the most selfish of the reasons is about control.

Amid the turbulence of growing a business, I can predictably control the crafting and delivery of what I write. It might sound strange, but it’s energising to be able to control one thing amongst the chaos.

Just start.

It’s not rocket science but there are three reasons why you won’t.

It may be that you doubt yourself. You might fear how people will respond to your thoughts. Or you might be convinced that there isn’t a story to tell.

You’re wrong.

The world is drowning in information and starving for wisdom. From the mistakes you’ve made and how they are propelling you forward.

And all you need to do is help one person.

Here’s how I got started.

I took Andrew Chen’s advice.

While I’ve been writing on Medium since 2014, I also took Andrew’s advice to write with decades in mind.

That’s why what I write usually ends up on my blog first.

I also took Gary Vaynerchuk’s advice.

Document. Don’t create.

And I took Jon Westenberg’s advice.

Plan what you’re going to write on paper first. Target 400 words to start. Deliver useful lessons. Spend equal time writing and editing. Publish at the same time each day, week or month and be religious about it. It’s how communities are born.

As I wrote about recently, it’s no longer optional to think publicly. I do this by writing my blog each week.

Find a method that works for you.

If that method is writing, just start writing.

Here’s what I would say to my 30-year-old self about writing: Start on Medium. It’s the one corner of the internet where ideas are cherished and where many writers in the world first felt the exhilaration of pressing Publish.



Today is International Women’s Day. The truth is I love this occasion for two very different reasons.

I identify as a feminist in the same way I do a father, husband and business leader. 

I take great pride in doing my part to increase opportunities for women and girls. That includes combating outdated stereotypes, the consequences of which women and girls have been subjected for the longest time. 

In fact, standing shoulder to shoulder alongside women like my wife, Jo Burston, Rhonda Brighton-Hall and Julie Bishop (to name a few) and taking daily strides to create an equal footing for women and girls is invigorating. 

Because we are on a mission. Together. 

IWD reminds us of our collective contribution and our conviction towards one day declaring that this day we celebrate is redundant.

IWD also provides a platform to remind people of a choice that is well within their control. 

The choice

When people are reminded of IWD through social media or workplace celebration, they either embrace it or (metaphorically) roll their eyes. 

The metaphorical eye rolling is easy to spot, and I’ve learned a lot from people who do. While our calendars are littered with an increasing number of occasions to celebrate, people in this eye-rolling bucket, for the most part, don’t feel that way because they are sexist. Their reaction is a consequence of not knowing how to engage. 

One explanation that stayed with me compared the inequality of women and girls to climate change. The crux of the argument was that both are big issues. They both live in our consciousness, but it’s difficult to know how to start playing a meaningful role due to the sheer size of the problem. 

You might consider this legitimate or an excuse. 

I subscribe to the idea that a person can act if they invest in understanding the challenge. The higher the understanding, the larger the set of opportunities from which one can act. 

The same choice is made by people wanting to change their life, their context or the world.

Learn or remain anchored in your perceived reality. 

It’s a simple choice. 

Choose learning

Whenever I chose to learn, I am opting into a self-reinforcing cycle. The cycle starts with absorbing multiple perspectives that inform. This is followed by a healthy albeit growing insecurity that I might be missing something. 

I am very aware of the role of that insecurity.

I build companies designed to change the world. On this journey, it becomes apparent that your rate of learning is the secret weapon. And as this increases so does the risk of ‘missing something’. 

In every business I have started insanely capable, curious and good-humoured women and men have not only accelerated the company's rate of learning, but they also narrowed the risk of missing something. 

Together. Women and men. At the top of their game.

Quotas don’t work, inspired leaders do 

Let’s get practical. Take a moment to think about your target customers. 

Where do women play a role in the purchase decision? They may not be the decision maker, but there is a high likelihood that they influence the purchase. 

Now, look at your team. 

Are there enough women to balance out the male ego and bias laced within your product?

Assuming the answer is NO, and you want to use IWD as the catalyst to make a change, start by thinking about how you hire.

I understand that hiring is one part of the talent equation and that people might jump to the notion of creating a quota system. 

For the record, I don’t believe in quotas for hiring women at any level of an organisation. I strive to be a leader who develops teams which are remembered for their high-quality decision making, high rate of learning and ability to not miss things. 

This mix of results can only come from hiring the most capable women and men you can afford. You might be nodding as you read this at the same time you realise you don’t know where to begin. 

Tried and tested 

Try Textio. This online platform, which you can start using for free, analyses the gender bias and comprehensiveness of your current position descriptions. 

Once you overcome the (unexpected) gender bias implicit in your position descriptions, Textio guides you step by step on how to balance or speak more directly to prospective women candidates.

Kieran Snyder and the team at Textio have done a fantastic job with the product and in doing so lowered the barrier to hiring more gender-balanced teams. The only things missing is a small company pricing tier. But I’m sure they’re thinking about it.

One last thing…

On this, IWD 2019, and every day after think about gender balance as a capability that accelerates learning and decreases the chance of missing what’s essential. This is as important to building companies as it is to all parts of civil society. 

As a husband, father of girls and business leader, I am optimistic about the future. 

And to every person who champions women and girls, thank you. 

The mission continues.



Ask another founder to join the interview. That's the punchline because when you start hiring in a startup, there are two factors you can count on. It will be done in a bubble, and there will be a time constraint.

These two factors have a strange way of reinforcing each other. As a consequence, additional and unnecessary pressure is put on the founders making the hiring decision.

I think there’s a way to short circuit this issue. And I’ve been working with some founder friends to test the hypothesis that experienced founders can help hiring founders to identify and prevent a bad hiring decision by being part of the hiring process.

Practically this means joining late-stage interviews to ask one or two different questions and add a different perspective on the candidate. More on that later.

Compounding factors

Hiring plans are considered best practice in startups. In fact, they are a requirement for most seasoned early stage investors. Unfortunately, most hiring processes start after founders realise they need a skillset.

A short time later the role description is drafted by the founder(s). And if the role is new to the business, there is a good chance the role description is copied and evolved from one they found online.

Job board listings return a mixed bag of candidates, but like most things in a startup, the founder believes they are running out of time, so they create a shortlist and soon after the interview process starts.

This is relatively typical in startup hiring.

And even if the founder involves other team members in the interviews, the process remains nonetheless insular. The factor that compounds this issue is the desire for the decision to be made quickly and efficiently.

Talent makes or breaks companies.

This ‘heads down and get it done’ approach has catastrophic potential. One bad hire can bring a company to its knees. I’ve been there, and it’s an episode I wouldn’t wish on any entrepreneur.

Increasing your interview luck surface area

When a candidate looks great on paper, it’s difficult not to think (or hope) that they might be the one. But this bias can result in founders looking for what they want to see when it comes to the interview process.

Speaking from experience, I used to overlook or trade-off qualities that were previously non-negotiable in favour of making a quick hire and hoping they would work out.

Increasing your interview luck surface area means finding ways to ensure you arrive a high-quality YES or NO.

First-time founders or those with small teams may not have the depth of experience needed to help identify and hire quality candidates. Similarly, they might not have board members that they can introduce into the hiring process to get a second opinion.

I have an experienced team and a board who I can ask to join the hiring process yet I still apply the following advice: Ask another founder to enter the interview process.

This means asking a friend who is also a founder to join late stage interviews with you. Ask them to act as a colleague. Give them a title if need be for the purposes of the call with a prospective hire.

They inevitably ask different questions, pick up on different cues and have a different set of biases. These are good things. But possibly the most important benefit is that as a friend who wants to see you succeed and as a founder who has been there before, they are very likely to speak truth to power.

They will tell you point blank if they see a red flag in the candidate. They will also call you out if they see you turning a blind eye or trading off value or quality that they know will cause grief.

And this can only increase the likelihood or you arriving a high-quality YES or NO.

The quid pro quo

Ask a founder friend to sign up to doing three late-stage interviews with you. And offer to do the same in return.

It is a simple trade and each amount of time provided should be valued. That means that the founder friend is only called into late-stage interviews, not the first one.

It also means scheduling the meetings, so it’s convenient for the founder friend to attend. Having them dial in is ideal. It’s an interesting test to see how well they handle a mix of in person and online conversations.

One last thing…

No one has a perfect hiring record, and the cost of getting hiring wrong can be immense. Increase your interview luck surface area by introducing a founder friend into the late stage interview mix. They don’t necessarily need to be a seasoned entrepreneur, but they do need to be outside of your business.

Using this process has already saved me from making one hiring mistake, and I hope it helps you too.

And if you don’t have any founder friends, get networking. A strong community of founders is worth its weight in gold.



Acting like an owner or some version of this ambition is a value that many founders try to instil in their teams.

And like most values, there is an assumption that team members (including co-founders) will automatically understand and embrace the ideal. While this rarely happens, I think there are three reasons why founders continue to commit to this assumption.

First, founders have been living their company values in their minds for a time. It is often months, if not years, from the time that founders start working on a business model to when they onboard their co-founders and first team members. During that time the values they want to have in their business are being subliminally formed and locked into place. The issue is that they are only intimately understood by the founder.

Second, founders believe (and hope) that they have hired outstanding people. As a result, there is an expectation that they will be quick studies about product, marketing and distribution, to name a few. While this might be the case, even the smartest people in the room will find it tough to understand the intricate details of each company value fully.

Third, the values are written on the wall (literally), on business cards and on email auto-signatures. Founders believe it will sink in eventually. Don’t laugh. Unfortunately, this is a thing.

It’s for these reasons that all team members should be invited to conversations to interpret and understand company values. And if there is one lesson from this post, making time for this conversation is non-negotiable. I write this knowing that I once thought ‘who has the time for this’.

Acting like an owner

I’m going to using 'acting like an owner' as a case in point. While it is a behaviour applicable to any team member in a new or growing venture, it is also, in my opinion, the one value that can deliver a force multiplier effect to founders and shareholders.

Acting like an owner means making decisions similar to those that a founder would make if they were in the room.

And ‘similar’ is the operative word.

Team members will never have the context, experience or the exacting clarity of vision held by the founder. Because they are not the founder. They are, however, people who have bought into the vision and have convinced the founder and their team that they are worthy of ally status.

When I explain the value of acting like an owner, I use a ‘de-risk, leverage and stabilise’ framework.

These three words are the themes that often underpin the work being done in pre-scale ventures. In other words, from the time a business model is conceived to the moment the team feels they are achieving product/market fit, startup teams should be focused on three types of work.

The subtlety that I also explain is that this framework is always front of mind for me. And it guides much of my decision-making.

This not only strengthens the relationship between my team and me, it also helps them understand how they can make decisions when leaders aren’t in the room.


De-risking involves eliminating uncertainty. This relates to how products are built and distributed, how supply chains (will) function, how the business will be financed, how the product’s core message(s) will be received and how regulation plays a role in getting to market.

The idea is that the more you can be sure that an input to the business is well-known and will remain predictable for a given period, the more ‘de-risked’ that input is.

Given the number of moving parts in a venture, I ask team-members to achieve relative certainty. This encourages the team, and particularly new hires, to strive for high-quality confidence without seeking perfection which can lead to an over-engineered outcome.   

De-risking is often best put into action when prioritising tasks that exist on a spectrum between ‘interesting to know’ and ‘essential to grow’. Work that creates predictability and value for your customers de-risks a business model. Work that answers questions that are interesting to know is a hobby.


Leverage is the use of something to create the maximum advantage. Depending on the context of your venture, leverage could be a track record of customer growth or novel data from scientific studies, to name a few.

For those looking at a venture from the outside, they are looking for results that speak for themselves for two reasons. First, partners and customers will want to be confident that engaging with you is based on more than just intent. Second, hand waving and selling your religion will only go so far.

In fact, I think it’s never been easier to determine if a venture has any real substance behind it or not.

When it comes to acting like an owner, doing work to create leverage is essential. And because most team members in startups have a degree of creative licence in their roles, the question you want them to ask themselves (and their teammates) is, ‘will what we’re doing contribute to creating leverage with [insert customers, partners, investors or regulators]?’


It’s not enough to de-risk and create leverage. Because as soon as you do, a new expectation about growth will emerge.

At the very beginning of the journey, when you don’t have a product, isn’t the time focus on stabilisation. However, as soon as you have a minimum viable experience that people start to love, your team needs to start thinking about how they will stabilise the product and business model.

Let’s unpack this a little further.

You sell software as a service to other businesses.

A customer is inspired by your pitch and buys.

You know you’re not ready, but you find a way to deliver.

You were always pushed for time, but now instead of you hustling to close sales, you have a customer recommending your product.

The inevitable dilemma founders now face is to either stabilise their product so that a few customers derive even more value (and as a consequence sing your praises more widely) or use the leverage with the first customers and invest in selling the product that is held together with duct tape.

Some will argue that a tradeoff doesn’t exist and to do both.

But like most things in a startup, decisions like this are rarely that binary.

The fact is that a stable product enables scale.

And the question each team member should be continuously asking is, ‘if our customers or users doubled tomorrow, could our product handle that load?’

This question often changes how teams think about their company and how they build scalability into their products.

One last thing…

The safest assumption founders can make about how their team will embrace values is that they won’t. At least not in the way that the founder hopes.

Invest time in debating scenarios for each value so you can learn how different team members think about each value. This applies to co-founders and your board just as much as it does to junior hires.

I always start with is ‘acting like an owner’ because of its force multiplier effect. It also creates a framework within which team members can act and reflect.

Focusing on de-risking, leverage and stability also helps to focus the team’s intent and curiosity.

Chaotic environments demand high-quality decision making to stay in motion on the mission. I’ve found this framework useful to scale decision making across businesses, and I hope it helps you too.



I have written before about how comments can be misinterpreted by team members. A well-intentioned comment can be latched onto and deviate team members and specialists supporting a business to tasks well off the critical path. With that in mind, I think comments in meetings generally fall into three categories; benign, valuable and distracting.

Benign comments are pleasantries, agreements and throw away lines. They help people feel comfortable and turn meetings into conversations.

Valuable comments are insights and observations that help teams run an opportunity or issue to ground. These types of comments often set teams off on critical thinking tangents that helps galvanise a point of view and create a path forward. I accept meetings expecting (and perhaps hoping) that they will be a collection of benign and valuable comments. And for the most part, this is what they are.

But every so often a comment is made that begins with ‘it would be interesting to understand if [insert topic]’.

While there are others, I think this comment has the highest potential to distract teams.

A comment is like a grenade

When mishandled, they can cause immense damage. Think about the last time you heard, thought or said ‘it would be interesting if...’

People make this comment for one of two reasons.

First, they have heard a person with experience and stature say it. It sounded timely and intelligent, and other people in the conversation agreed. This agreement is a reward for this comment. And because you reinforce what you reward, others will use the same comment to want to be like that person. Or demonstrate a behaviour that shows they are on track to be like that person.

Second, they are genuinely interested.

While the intent in both cases is admirable, this comment needs to be deployed very carefully.

Junior team members can interpret this ‘interest’ as an instruction or vague cue to investigate and report back on whatever the topic was, no matter how unrelated the topic is to their mission.

Consultants not embedded with teams can follow a similar path.

They are often information sponges, and because they are not in every meeting and miss the water cooler conversation around the office, they can misinterpret the ‘interesting’ topic as an important input to their role. Before long they can build a larger narrative around the topic of ‘interest’, just to later discover that what they heard was something of personal interest and little more.

In both cases, vast amounts of time can be wasted with team members being pulled off-mission.

Interesting is forever interesting

I want to be clear and say that I am not suggesting that conversation about interesting topics within or across teams should stop. Interesting ideas are the cornerstone of entrepreneurship.

The thing to keep in mind is that it is all too easy to postulate about how one interesting idea can intersect or build on another interesting idea. If people did this all day long no progress would ever be made!

Inspire debate

There is an antidote to avoiding time being invested (and wasted) on topics that arise from ‘it would be interesting if…’ comments. It involves inspires a debate.

In other words, instead of saying ‘it would be interesting to understand if..’, say ‘I think we need to think about [insert topic] and I would like the team’s thoughts on this’.

This surfaces the topic in a way that inspires debate. This more assertive approach is relatively straightforward for more experienced leaders to implement, but it can be a daunting prospect for team members. Nonetheless, I think it’s important for all team members to be coached and encouraged to inspire debate on topics that they believe could be interesting.

And multiple benefits arise from the debate at a team level.

First, team members have to think through and formulate an argument for the topic of interest.

Second, the topic of interest is brought to a forum where more minds can pour onto the idea which is never a bad thing.

Third, the area of interest can be progressed with the explicit support of the team, or it will be killed quickly, and the team can move on.

In any case, time is saved. And that’s always a good thing.



Do you think about business development as the acts to develop a business or just strategic sales?

This question has been at the heart of a dozen conversations I’ve had with my mentees in the last month.

The agenda for these conversations started out focusing on how to close strategic partnerships or secure investment. Each founder considered closing deals or financing rounds as discrete episodes. And those who had experience closing deals with customers and investors reflected on each event with relief that it was over.

There’s no doubt that protracted negotiations with customers and investors can be tiring and frustrating. I’ve been there many times before. But what occurred to me during these meetups was the homogeneity of the mindset that these founders apply to getting deals done.

And the best analogy I can think of to describe this is a car starting and stopping in traffic vs driving on a freeway.

Start-stop driving requires much higher energy consumption versus more economical freeway driving.

These founders are starting and stopping in traffic.

Each time they need investment or focus on closing a new partnership they start (hopefully close) and stop (move onto the next thing).

This might sound like an efficient way to compartmentalise important tasks, particularly given how much a founder has to focus on each day.

It’s not. It’s a false economy.

How To Think About Business Development

Here is how I think about business development. The mindset I apply to develop a business is more ‘freeway driving’ and less start-stop in traffic and it involves two interconnected philosophies.

First, business development is the act of continuously being in motion on raising capital, developing partnerships, hiring and nurturing influencers.

This means always having your radar on to identify and engage with people who are potential investors, customers, team members and evangelists. And by definition, this also means disconnecting from the belief that funding rounds, sales and recruitment are episodic.

The second philosophy is that business development is about keeping the venture alive long enough to achieve product/market fit. Or in other words, surviving false starts, failed experiments, poor decisions and allowing luck to play its part.

The second philosophy (staying alive) is the motivation for the first philosophy (always be closing).

Investors help inject capital into businesses. Strategic partners help expand reach. Hires help create revenue-generating products. Evangelists help generate influence. And the net result of these combined philosophies is that it makes it easier to keep cash in the bank.

Why Developing Businesses This Way Matters

In no one’s universe is it true that an entrepreneur wakes up one morning with a desire to raise capital and then days later the financing round closes. This is also true of hiring. As much as we would like this to happen, you never find the ideal candidate days after posting a job ad.

It takes time to develop relationships and demonstrate momentum.

This is the experience of every entrepreneur, no matter how urgent we are.

The reason it’s so important to approach business development using the freeway driving approach is that you will come into the lives of prospective investors, customers, team members and advocates at different times.

In some (rare) cases the timing will be right for you to strike a deal, start building a relationship and generate value. For the most part though, timing usually only favours one of the parties. We have all been in the situation where you are ready to sign a new partnership but your prospective partner isn’t ready to engage.

By always being ready to engage, you increase the chances of understanding when prospective investors, customers, team members and advocates are ready to start working together. I think the reality for entrepreneurs that approach business development as just sales or as a stop-start, episodic set of events is that they miss these all-important timing cues.

And timing is everything.      

How To Do Business Development

It’s simple. Block out 50 minutes each business day to nail two tasks.

First, invest in searching LinkedIn, Crunchbase and AngeList (and other industry-specific publications) to identify prospective hires, investors, partners and influencers that can help develop your business. List them down or begin engaging with them as soon as possible.

Second, follow up with people you have met who fit this mould. So many opportunities are missed due to a lack of follow-up!

Make this 50 minutes a daily, uninterruptible ritual.

Take a minute to block out this time in your diary.

Soon it will become a game-changing habit like it is for me.

One last thing …

Understanding what business development actually means in the context of startup and shifting the mindset from a stop-start, episodic approach to completing discrete tasks to having your radar continuously open to opportunities accelerates the momentum of ventures.

If a lightbulb has just gone off your mind, block out time in your diary and start a business development habit. If your experience is anything like mine, you won’t regret it.



Thank you for joining me and for your attention this year. For reading, listening, sharing and sending me emails to dig deeper on areas that interest you. It seriously makes my day.

The writing and podcasting are my side-hustles. They help clarify my thoughts and as I’m told, help others as they develop their company-building craft.

As this year draws to a close, I have encouraged my mentees to take some time to reflect on what they have achieved this year.

I can trace many of 2018’s achievements (and the softening of events that would have been far more painful) to how ruthlessly I have valued time this year.

That theme will continue into next year and speaking of 2019, I am really excited about two projects that will come out of stealth mode.

The first is my new venture called DROP. From a finger-prick drop of blood taken at home, we will determine the genetic risk profile for chronic inflammation and other common diseases. We also determine the concentration of specific inflammatory markers over time to provide a detailed understanding of how genetics and lifestyle are manifested for each person.

If you’re wondering why this is important, chronic inflammation is the lead indicator of cancer, diabetes and most other chronic diseases. DROP provides this early warning to consumers and this has profound implications for personalised health around the world.

You can learn more and sign up for launch notifications at

The second project to launch is BeInMotion, a company dedicated to delivering unexpected encouragement.

Imagine sending a small gift or a card with words of encouragement to a friend, colleague, family member, or acquaintance.

They receive a physical package or envelop, open it and find an unexpected and highly personalised message of congratulations or encouragement, only they don’t know who it’s from.

When the recipient visits our website and enters a code that is enclosed in their package or envelop, the sender is revealed and then they are encouraged to repeat the experience for another person.

Resilience has two ingredients, hardship and encouragement. I’m launching BeInMotion because our world needs more resilience and because the encouragement component is often more difficult to find.

You can learn more about the underlying philosophy of BeInMotion here or follow us on Instagram for pre-launch updates.

Much of this year has been spent investing in capabilities to ensure I can focus on DROP while enabling other teams to breathe life into BeInMotion and I’m excited to share both with you in 2019.

In the meantime, from my family to yours, have a safe, happy and restful holiday season!

advisory board PHILHSC


Advisory boards are recruited to help leaders make high-quality decisions and expand influence. They are useful mechanisms in resource-constrained environments and hence popular at startups and not-for-profits.

I serve on numerous advisory boards. And while these roles are different to company directorships where I manage fiduciary responsibilities with my board member colleagues, I enjoy both styles of engagement.

I formed my first advisory board nearly 15 years ago. The key reflection from that first one, those I have formed since and through serving on advisory boards today is that the formation step is only a small part of the journey. The underlying routines and rituals that generate value from the advisory board is the main game.

Founders contemplating the establishment of an advisory board will nod in conceptual agreement. It’s these same founders who 12 months later lament how disappointed they are with the group they brought together.

Predicting advisory board demise

The recruitment and formation of members to their advisory board might have felt like the assembly of a grand coalition of the willing. A formidable team destined to achieve greatness. But something went wrong along the way. Greatnesses is still a long way off. Advisory board members seem disinterested or hard to reach and the founder feels like a significant piece of their armour is missing.

This is not a new issue.

In fact, the pattern of decay is predictable and it begins after the formation honeymoon is over and the advisory boards slip into becoming an ‘advised boards’. This is a state where founders start infrequently sharing large volumes of information as progress updates with the expectation that advisory board members will fully digest, internalise and self-organise into action.

I have shared the following thoughts with my mentees and portfolio companies to avoid this fate. Business schools teach this as ‘Forming, Storming, Norming, and Performing’ but, like most concepts, it oversimplifies the solution due to its lack of context. Here is one lens of the startup context and I hope you find it useful.

In 12 months the advisory board will be remembered for…

As I’ve written about before, imaging how the advisory board will be remembered is the all-important first step. Most founders start by trying to answer questions about the capabilities, personalities or experience that they think they need on an advisory board today. In my experience, this leads to answers that are more focused on near-term issues.

For example, founders might be obsessing about hiring a Chief Technology Officer or key engineering talent if that is an acute pain point today. This insecurity leads them to think they need ‘technology’ people on their advisory board. While that might be true, technology is a broad church and the tactical issue to be solved isn’t a technology issue. It’s a hiring issue. Rushing to find a ‘technology’ advisory board member to help solve a hiring problem isn’t likely to create the value needed when it comes to deep knowledge and relationships that the founders may need on specific technologies.

While this example might suggest a focus on advisory boards for software companies, it also extends to solo founders and entrepreneurs building professional services companies where the challenge is how to scale you.

To that end, I correlate how advisory boards will be remembered with the most vulnerable parts of the business model. For young companies, technology is often a vulnerable part but usually nowhere near as vulnerable as how the product is packaged and distributed. And just to be clear, I’m not talking about physical packaging, I’m talking about how a product is created and sold directly to consumers or businesses or as an ingredient of a larger product.   

To start answering the question about how their advisory board will be remembered, I recommend that founders think about their key growth metric, the 12-month forecast for that metric and then specify as precisely as possible the five bullet-points of what needs to be built to achieve the forecast.

This is useful for two reasons. First, it clarifies the types of help that are needed and second, each bullet point provides a clue for the type of person needed on an advisory board.

Understand and play to incentives

As Berkshire Hathaway Vice Chairman Charlie Munger is famous for saying, ‘incentives are superpowers’.

He’s right.

When founders leverage their networks to create advisory boards, they do it for the right reasons. They need expertise and support to solve problems and there are people out there that want to help. But for all the thought that goes into the controllable aspects of an advisory board, e.g. structure, function and meeting schedules) very little time is often devoted to understanding the uncontrollable aspects, chief of which is why a candidate would join.

As remuneration is typically low or non-existent, candidates usually join advisory boards for one of two reasons. First, they have bought into the mission and are convinced their skills can be put to good use (missionary). Second, they can advance towards their personal ambitions which might include expanding their network to elevating their personal brand (mercenary).

Both of these motives are perfectly acceptable.

Due to the power imbalance that founders think exists between themselves and potential advisory board members, they often place emphasis on the missionary motive. The irony is that they downplay the mercenary motive while knowing the other party will probably only engage if there is something in it for them.

PRO TIP: Be authentic and forthright. If an advisory board candidate says they ‘just want to help’, treat this as a half red flag. The value must flow both ways. Remove the half red flag if they acknowledge value will come in time or if they suggest a value exchange you are comfortable with. But move to full red flag if they insist that they just want to help and deprioritise them as a candidate.

This might sound like a strange thing to do. They want to help. The founder needs help.

The objective is to find people who can play the long game. In my experience, ‘just wanting to help’ is nice but usually reflects a short-term intent. And when a founder comes to rely on that person over the medium term and their desire to engage wanes because the value is only flowing in one direction, it can lead to a breakdown in the relationship.

How incentives can translate to value

Founders can create financial and non-financial value for advisory board members. And these should be determined by the founder prior to engaging with prospective candidates.

In terms of financial value, founders can consider offering options as part of an employee share plan. This requires the advisory board member to have a formal agreement with the venture and that can be a good thing for two reasons. First, it helps the advisory board member becomes clear on how they need to contribute to meet milestones in order for their options to convert into shares. Second, it aligns them to the same strategic objectives as other team members.

Non-financial value is just as important. It can meet more immediate needs, especially when offering financial value is not an immediately available option. Non-financial value for advisory board members can include:

  • Listing them on the venture's website
  • Authorising them to highlight their involvement on their LinkedIn profile
  • Asking them to attend and speak at events as the venture’s representative
  • Including them on early conversations about new strategies or product developments

PRO TIP: Incentives change with time. Advisory board members, like other team members, will be exposed to new opportunities, need to refocus their efforts or will want to increase their contribution at different points in time. Some of these changes will be easily identifiable whereas others will be more opaque. In any case, each of these scenarios brings with them a change in incentives. To ensure founders aren’t spending too much time trying to understand these changes, I recommend each advisory board member agreement have a 12-month duration. This can be reviewed annually and extended if both parties are excited to continue engaging.

Identifying candidates

I use the bullet point summary, incentives and a simple framework to identify (and deprioritise) advisory board candidates which I consider non-negotiable:

  1. Expertise - They have lived experience, are at the top of their game, are radically candid and come with humour and compassion. These are a unique set of qualities which in my experience can be found in other entrepreneurs and founders-turned-investors.
  2. Available - They are available when you need them, not when they have time. Practically, this means they respond to you within 24 hours of you reaching out to them. This also means they are ready and have a track record of proactively looking for ways to help.
  3. Ready to play the long game - They instinctively know that value will ‘come out in the wash’. This means they are ready to put their reputation and relationships to work and less worried about immediate remuneration

I don’t compromise on these characteristics because life is too short to be surrounded by mediocrity.

A little formality is a good thing

I think it’s important to formalise relationships with advisory board members. It can be a two-page document that talks about the role, the 12 month tenure and expectations about conduct and confidentiality.

While more formal documentation will be entered into where options are made available, this two-pager should be a plain language document that is signed by both parties. This is simply good governance.

Working together

Gone are the days when an advisory board meets twice a year to discuss a high-level agenda.

While this biases the founder, advisory boards needs to be available and highly responsive to support the venture. Today’s advisory boards operate in Slack (and other team messaging services) where they can be called on for micro-advice and be kept up to speed on company conversations. Of course, you can use email, phone and video calls to similar effect but the point is that speed and availability are key to a high-performance advisory board.

I think it’s also useful to bring the advisory board together once a quarter as a team to have a broader conversation. This is where they can contribute their perspective on relevant industry trends and engage in debate with their colleagues.

PRO TIP: One quality of high performing advisory boards is when members start engaging on other business outside of the venture. It reflects cohesion which usually ends up benefitting the venture in unexpected ways.

When you are asked to join an advisory board

It is always humbling to be asked to join an advisory board. And while each request should be judged on its merits, I find that founders often make the request because they need help focusing on what’s important and being held to account. Consequently, I have learned to ask if a founder needs help with focus and accountability each time I am asked to join an advisory board.

I highly recommend you do the same. It often accelerates relationship development and exposes new ways to add value.

One last thing…

Advisory boards are small teams of three to five outstanding people who can help founders achieve the unachievable.

If you are a founder, invest time in setting up and operating an advisory board that can be nothing but high performing. Be clear on how this group will be remembered in 12 month’s time. Align incentives, create value and get to work.

If you are a prospective advisory board member, join for the right reasons and start generating value as quickly as possible.

At the end of the day, advisory boards can be highly valuable or just another ‘thing’ for founders to manage. Like most things in life, you get out what you put in and advisory boards are no different.



Wellness is a loaded term. It means too many things to too many people. And when it comes to scaling a business and teams, wellness isn’t on the critical path which is ironic given how important team performance is to a venture's success.

Some founders consider wellness a personal responsibility of each team member (that was me).

Others solve for wellness by introducing yoga, healthy snacks and flexible work arrangements (to name a few) for their teams to access.

These two approaches (and every option in between) are opt-in and neither one mandates co-founder participation.

And herein lies the issue.

Team members are cue sponges. They notice when co-founders or any person perceived to be a leader starts acting in ways to improve or degrade their wellbeing, regardless of whether the leader is acting consciously or subconsciously. It’s an unavoidable fact that they respond and modify their behaviours based on what their leaders say and do.

For the record, I think wellness should get more airtime than it does today. I think it’s an undervalued asset for teams starting or scaling ventures. And while wellness isn’t likely to stand shoulder to shoulder with product, technology or marketing on the critical path, it is simple to scale.

The key to this simplicity is the example co-founders set and talk about with their teams.

It’s all good. Until it’s not.

If I’m honest I only started embracing wellness as an ideal when I started thinking about it in terms of how I perform in the service of my wife, daughters, friends and teammates.

I reframed wellness from being an esoteric, nice-to-have cliche and began thinking about it as a core capability I needed to be successful.

Sound strange?

Ask or observe most entrepreneurs and you’ll find that they possess a kind of invincibility psyche. This manifests in a number of ways but it boils down to their mindset being something like this: ‘If I’m always on and upbeat, I will overcome all odds and others will believe we are worth backing’.

These same founders scoff at the idea of work/life balance and dismiss the ‘marathon, not a sprint’ analogy. To them, their venture, identity and livelihood are so inextricably linked that they see no other option but to never stop. This can end badly.

Team members see this behaviour and try to match it in order to fit in. Or they burn out trying to. And while it’s true that entrepreneurship isn’t for everyone, no investor wants to see a company fold because its founders implode.

Founders who are scaling their business constantly navigate a slew of known and expected obstacles. Ironically, scaling wellness involves implementing 10 simple tactics.

I encourage founders to do all 10 and then share them with their team in a kind of checklist format. Set the example and then ask the team to follow suit. It will change the game for you, your team and your business.   

10 ways founders can scale wellness

Here are the 10 ways I think about scaling wellness and how I bring them to life.

It’s also important to tell your team that you do these things so they can take your cue and also feel permission to do the same.

That’s the secret to scaling wellness.

1. Lock in time for the annual vacation

Do this on 1 January each year. This delivers two benefits. First, it creates an event that you and/or your family can look forward to. One that is jam-packed with relaxation.

Second, you and your team can manage the workload up to and around that period so you can recharge while on vacation.

2. Lock in a closing time for each day and each week

My day ends at 9:30 pm. Period. It starts at 4 am. I’m better in the morning than at night time and I play to that strength. I hold the line on those times so I can be present for my family, my team and those I enjoy supporting.

My week ends on Friday night and spins up again on Sunday night.

3. Codify your rules and your exceptions

This builds on the second principle. There are always exceptions to the rule but most founders don’t lock down which is which and as a consequence they become interchangeable. Being clear on both. By way of example, I have my rule for daily and weekly closing times. There are times when exceptions play out like having to pull the odd all-nighter. That’s OK but it’s not the rule, it’s the exception.

4. Get an alarm clock

This is code for park your phone at your bedroom door. Many of us use our phone as an alarm clock. The problem with that isn’t the function of the alarm clock, it’s the fact that once you switch off the alarm on your phone, the next immediate step is to check email, Facebook, Instagram or Twitter. All of a sudden, the rest is gone and you’re into a hectic start of the day.

Give yourself a chance to wake up. Like a human.

5. Move once a day

If you struggle to make time to exercise, take people you need to meet with on a walk and meet while you’re walking.

6. Get relief (and perspective) through a side hustle

A side hustle can be a hobby, a small business or just spending time learning something new but they all have one thing in common, they allow you time to disconnect from your venture. This is important as the by-product of briefly disconnecting from the all-consuming work of growing a business is perspective which is essential to maintain high-quality decision-making. My side hustle is writing a weekly post.

7. Get tactical on focus

This is all about being deliberate about crushing tasks. Here are the three tactics I use. First, make a list each night of the three things you need to nail the following day. These are not strategic questions you need to mull. They are tasks you need to complete to create or maintain momentum. Second, block out time each day to think and get work done. For me, that is 2pm to 4pm each work day. Third, switch off notifications that don’t matter. This includes managing notifications in Slack, email and social media. Every app we use comes with a built-in way to manage and customise notifications. Get good at this.

8. Teach once a quarter

Paying knowledge forward is energising. Offer to speak on a panel, write a blog, be a guest presenter. Put what you learn as a founder into the minds of people just starting out. It will help you realise just how far you’ve come.

9. Ask Jaime Oliver what to eat once a week

Managing weight and energy levels is at least 80% based on what goes into your mouth. If eating habits aren’t a strong suit or you’re bored of the food you do eat, cook a Jaime Oliver recipe once a week.

10. Get radically candid by asking one question

This is about self-awareness and I wrote about it recently.

One Last Thing …

Founders have nothing to lose and everything to gain by stepping up to implement these 10 steps. I have been doing these 10 things for some time and I encourage my mentees and the founders leading ventures I’m involved with to do the same.

The key to scaling wellness is leading by example and being overt about what you are doing to make wellness a priority. Set the example and then ask the team to follow suit. It will change the game for you, your team and your business. And if you don’t want to take my word for it, listen to what Reid Hoffman has to say about it.



Asking the right question at the right time is an art. As my good friend Melissa Rosenthal says, it takes practice and when you get it right, it pays off in spades.

Over the years I have learned that the 'right' questions often have three dimensions;

  • They are open (cannot be answered by a simple Yes or No);
  • They require thought and are delivered with context; and
  • They contain an element of reflection (they require the person answering to explain their logic).

I have also become reliant on asking these questions for two reasons, both of which have to do with self-awareness.

The first relates to pursuing a problem.

Like most people I have biases and like most entrepreneurs, I come with high levels of built-in conviction for the problems I want to solve.

The problem is that bias multiplied by conviction creates a potent combination that narrows the aperture to how one considers the history and future possibilities for the business model they are building.

First-time founders often suffer from this. The few that don’t have a habit of continually asking questions. They and their more seasoned colleagues know that their rate of learning is driven by thoughtful disagreement which in turn is driven by regularly asking ‘why?’ and other well-considered questions.

Building mission-driven teams is the second reason I strive to ask the 'right' questions.

I believe that a culture of radical transparency is one of the most important preconditions for creating a place that attracts the best people to do career-defining work. It also helps determine those who may not be a fit. In any case, this can only be achieved if every team member feels like they can ask well-considered questions to anyone in the organisation.

If this principle appeals to you, I recommend adding Kim Scott’s audiobook called Radical Candour to your listening lineup.

The Question I Ask Twice A Year

Here it is and I love asking it:

What could I do or stop doing that would make it easier for you to work with me?

This is the one question I ask co-founders, teammates, partners, customers and investors twice a year. The answers are always useful and if you listen, learn and evolve as a consequence, the answers change over time. And that’s what you want.

Expect people to have this ponder the answer before delivering their response.

One Last Thing …

There are two keys to receiving thoughtful answers to this question.

First, explain that you expect radical candour and no sugar coating but that if you were answering the same question, your objective would be to deliver the message in a way that shows you care personally while challenging directly.

Second, ask your team to ask you the same question.

I have benefited significantly from asking this question and I hope it helps you too.



Hiring makes and breaks startups. One mistake in the first 10 hires at a new company can spell disaster.

I've been there and so have most investors.

So when it comes time to raise seed phase capital and investors gain comfort with how the venture can capture a massive opportunity, they turn to the hiring plan. This is because, for all the knowns and unknowns that add risk to a venture, the right team can go a long way to de-risking the business.

The hiring plan for most founders starts and ends at the ‘team’ slide of their pitch deck. For early ventures, this slide includes roles that are ‘soon to be filled’.

Founders in this scenario are (desperately) hoping they can find rockstars to take up these roles. And they might be quietly confident they can make this happen. Or they hope their future investors will dip into their networks and magically pull candidates from nowhere.

If this is you, that team slide isn’t a hiring plan. It’s an ambition or in the words of a friend of mine, ‘they’re selling talent religion and I’ve never seen religion de-risk a business’.

And hence the title of this post.

Hiring superb people is hard

There are very few of us who can pluck battle-tested operators from our networks who are known quantities and ready to join the business at short notice.

You know it and investors know it.

They will assume, as you should, that hiring key roles will be difficult. Really difficult. And the longer your team operates without outstanding talent operating in key roles, the higher the drag on momentum.

I feel a sense of relief when I go through the process of writing and iterating hiring plans. They give me a basis from which to be confident that my business knows the type of people we need to solve the problem we’re pursuing. From there I can start sounding people out for their interest in roles.

And the sooner a hiring plan exists, the sooner I can put my network, and my advisers and investors, to task to identify candidates. Most importantly, hiring plans provide the basis for thoughtful disagreement about why these roles matter to our future.

After all, what I think about which key roles may matter to our success is a sample size of one. I want to know if I’m wrong from well experienced and believable people.

Hiring plan ingredients

Writing a hiring plan (or summarising it into a slide) is the simple part. It’s the four ingredients that take time to create and understand. And each one is worth their weight in gold.

Ingredient 1 - Clear Job Description

If you need a Chief Technology Officer, a Vice President of Regulatory Affairs or any other senior role, don’t sum up their job in three bullet points on the fly. If only I had a dollar for every time I’d seen that happen…!

Create a crystal clear job description that defines their functional and cultural contribution. Also, ensure it includes the financial incentives on offer and how they should expect to be known inside and outside the organisation if they are successful in the first two years and then after five years at your company. This is important because it will help candidates understand that you are in search of an ally, not just employees.   

Not having this will mean you can’t adequately talk to potential candidates about them joining your business. And if you do start talking to candidates about roles without having clarified what you want the role to achieve, there is an excellent chance the candidate will form their own perspective about the role.

Fast forward a little further.

You court them.

They join based on a loose and generic role description.

Then you, your company and the candidate lose because after six months you part ways because expectations and incentives were misaligned from the start.

Ingredient 2 - Candidate List

When I construct a candidate list I look into my network and those who I trust to make a referral. I don’t want to waste their time so in asking who they might know I ask them to provide a brief description of the potential candidate.

In other words, I ask them to think about how people describe other people, particularly in a professional context. This description usually consists of four factors in one sentence and how I/we know them. For example, Melissa June: Spent 15 years in biotech, launched [product name], went to med school at Stamford, married with kids. Met via John Mayo.

Obviously, there is a lot more detail that sits beneath this description but you get the point. It’s important to succinctly understand why a candidate may be a fit.

My candidate list is full of descriptions like this accompanied by a link to their LinkedIn profile so I can learn more about the candidate if need be.

Ingredient 3 - Candidate Incentives

There is only one way to know candidate incentives. By talking to them. And because incentives aren’t the first thing that comes up in conversations, you’ll need to have spoken to each candidate multiple times. After pitching them on the vision, meeting with them a couple more times to understand their questions and where they’re at, you’ll reach a point where it’s OK to ask what it will take to convince them to join.

Common incentives (like salary and equity) are simple to describe but almost never get to ‘why’ someone is thinking of joining.

I ask one or a combination of the following questions to get a read on a candidate's incentives:

  1. What could working with [company name] do to help your family?
  2. What’s missing from your LinkedIn profile that this role could help with?
  3. How do you hope you’ll be remembered professionally?
  4. What interest outside of work do you want to advance the most in the next five years?     

Incentives often fall into family, professional and community-related pursuits. While there are some exceptions, this knowledge can help create the conditions through which a compelling offer can be made to a candidate.

Ingredient 4 - Likelihood To Join Framework

This essential ingredient requires judgement. The ‘likelihood to join’ frameworks isn’t just about how convincing you are to get a potential candidate to say yes and join the company. It’s also about determining whether the candidate is a fit, will excel in the role on offer and is available given your timeline and their priorities.

At this point, you will have shared a lot with the candidate. They might have signed a non-disclosure agreement, heard your pitch multiple times, queried parts of your business model, done their own diligence and expressed an interest to join.

In addition to their interest, I also make a judgement on their likelihood to join based on their:

  • Performance in a paid audition
  • Incentives
  • Expectations of what the business needs to be able to offer them (eg must close a financing round of $XXM)
  • Appetite to leave what they are doing
  • Availability to start

I usually represent these items, where possible, using Harvey Balls in a hiring plan slide.

One last thing ...

Hiring plans are powerful tools for many reasons. My favourite is that it helps people close to me weigh in and help add candidates to my list because they know what I’m looking for. These same people can also improve the overall hiring plan by pointing out blind spots in the roles that the organisation thinks are important.

If you found this post useful and would like a copy of the Hiring Plan slide I use in pitch decks, let me know and I’ll send you a copy.



Startup founders are advice magnets. Friends, family, investors, self-proclaimed experts and pundits, users and customers all like to share their two cents worth.

Most founders I know do their best to balance this advice against their vision but it’s not easy.

A thread on LinkedIn brought this issue to light and people from across the advice spectrum weighted in. Those on the sidelines argued that diversity of perspective is important. Founder’s said that the quality of advice from those without ‘garage experience’ is highly variable at best and that they rely on themselves to filter out the noise.

I side with the latter argument as do many of my colleagues and mentees. Yet screening for advice amidst the noise remains a daily challenge. This is because founder’s don’t have all the answers all the time and insights can come from the strangest of sources. This paradox usually manifests through a fear of missing out (FOMO) or the ‘need to please’.

FOMO is a fine balance of curiosity and paranoia but often favours the latter.

The ‘need to please’ plays out where a perceived power imbalance exists. In the context of entrepreneurship, that perception comes from one party (investors) appearing to have more experience or capital than the other party (founders). And in order to access more experience and capital, using the thesis that more of both will accelerate growth, founders tend of over index the importance placed on advice from these people.

These two emotions are real and increase a founder’s advice surface area but that doesn’t help with screening for noise.

Avoiding advice doesn’t work

An alarm sounds in my mind when I hear founders say things like ‘we know our product best’ in the context of receiving advice.

It suggests they are overwhelmed with advice or have decided to stop listening because they think they know best.

In either case, the quality of their decision making and consequently their rate of learning is about to stall if it hasn’t already. And that’s not a good thing given a major superpower of entrepreneurs is their rate of learning.

I also know that perspective and fatigue also influence the extent to which founders are willing to receive and act on advice. The less perspective and the more tired a founder is, the lower their bandwidth is to process any kind of advice. The opposite is also true.

That said, I know that advice will always be a core ingredient to an entrepreneur’s rate of learning. And to deal with the rollercoaster which we all ride, I have come to rely on a framework to rapidly triage advice and arrive at the inputs that matter.

Triaging advice

I use three questions to triage advice. I apply them to unrequited advice as much as the counsel I seek from friends, colleagues and mentors. The objective is to screen out the noise and over time this framework has become less process and more instinct.

And while I’m a lot quicker to call B/S on poor advice and more effective at putting the high-quality advice to work, I keep an open mind to advice wild cards. These are the one in ten comments or insights that might be worth listening to. I keep an open mind because history has taught me that relying on absolute beliefs can be dangerous.

1. Have they been in the trenches?

I have a strong bias for listening to operators, those people who have built businesses, been beaten up (figuratively) and have had the grit to keep going.

Nine times out of ten these people bring rich, empathic and action-oriented insight to the table.

People who offer advice without ever having tried to build a business won’t often get past this step. If these same people come with the label of ‘business’ or ‘innovation’ coach, it’s an immediate game over.

2. Why are they offering the advice?

Magic happens when incentives are aligned. People who pass the first test will often offer genuine insight and help because they can empathise with your situation. And more often than not, they would prefer to spare someone the pain they went through.

These people may also consider the act of offering advice as a relationship development opportunity. That’s a good thing because they may come back to you for help at some point in the future.

Consider the alternative. If someone’s incentive to engage is to make money (directly or indirectly), the advice is likely to be less useful.

3. Will it increase my rate of learning?

This is the most important question of this framework.

Think about the last piece of advice you received. If you followed through with it, would it help you learn more about your customers, your users, your team and culture, your market opportunity, your profitability or your sales processes?

And if the answer is YES, how quickly could you quickly make a course correction to realise the value of what you learned?

If the answer is ‘a matter of days’ given your competing priorities, then the advice is probably worth accepting.

Two last things ...

While the right mentors will always be an essential ingredient to a founders success, the other great support structure is other founders. Create value-first relationships with founders who have been there before. I don’t mean indiscriminately friending people on Facebook or sending contextless invitations to connect on LinkedIn. I mean having the patience to invest in building deep relationships. The ones that result in support being a two-way street, whenever it’s needed.

The last point relates to thoughtful disagreement. It’s a principle I learned from Ray Dalio’s book called Principles - Life & Work. The underlying intent of his message is that being clear on your principles will help you succeed and become better at failing. His view on thoughtful disagreement focused on the idea of listening and being motivated by a genuine fear of missing important perspectives.

I use Ray’s advice to stay reminded of the value that advice can bring, be it a wildcard or guidance from people I trust or those more experienced in the craft.

At the end of the day, founders will keep being bombarded with advice. How you triage advice can make all the difference and I hope this approach helps you too.



The shock I’m talking about isn’t the trauma-inducing kind. Although it might be to some.

The shock I’m talking about is the kind that helps new hires at startups become acquainted with a venture’s cultural urgency.

Set by the founder(s), this urgency is driven by one ever-present idea: We need to survive in the market long enough to achieve product/market fit.

While this idea is often communicated in terms of runway length or the proximity the next investment round, its implications aren’t usually felt as acutely by staff as by the founders. That’s not likely to change.

However, the founders can influence urgency in a different way.

Urgency, Valuing Time & Rate of Learning

Every decision, experiment and dollar spent influences how long a venture remains in the market. For that reason, most founders think about urgency in terms of results. The number of conversions from marketing campaigns, deals closed by the sales team or product updates shipped.

And this is almost the right way to frame urgency.

However, it falls short because it doesn’t take into account two factors that are unique and different for every hire. First, how they value time and second, their rate of learning.

Not knowing about these two factors for each new hire usually means a founder’s call for urgency will be misunderstood or seem to fall on deaf ears. Even if the new hire’s desire is to respect the founders' expectation to be (more) urgent.

And this is why I think urgency is a product of how someone values time and their rate of learning.

Assuming a new hire buys into the founder's vision, they will arrive wanting to make an impact. If they think achieving their first milestone quickly equates to six months and their rate of learning is slow then it’s fair to say their impact will be (very) low.

This usually unfolds with the new hire investing four to six months in pursuing one or two key activities. These big bang efforts draw down on company capital, come with stories of how they worked at previous organisations and promise learnings upon the final milestone being achieved.

In contrast to this worse case scenario, a new hire is quick to set up a framework that validates hypotheses of the ways things are done today and another set of experiments to move the dial forward in the first 30, 60 and 90 days.

Implicit with the latter hire is a test and learn approach to cast fresh eyes on how business is done today. They are also focused on creating momentum in their job area. This is also inherently more cost-effective because they can course correct as they learn.

Urgency Math

Here’s the rough method I use to assess each new hire.

Urgency = Value of Time + Rate of Learning assuming that:

  • Perfect urgency = 20 (i.e. that of the founder)
  • Value of time is a measure between 0 and 9
  • Rate of learning is a measure between 0 and 9
  • New hire will never eclipse the founder in terms of urgency
  • Measurement is taken 4 times during a 12 week paid audition

A solid new hire might score 7 on valuing time and 8 for their rate of learning based on what they say in the interview process. 7 + 8 = 15, the urgency score. They will also score similarly during each checkpoint of a paid audition.

Measuring urgency over time is important. Think of it as a lead indicator of how consistently urgent the new hire will be.

This is a framework and providing you apply it consistently, the results will be helpful. But don’t overthink it.

Be concerned if a new hire consistently scores below 10. Be impressed if they score above 14 on average on a paid audition.

The first, worse case scenario hire would score well below 10 on average across the paid audition. And they probably shouldn’t survive the paid audition.

Why shock?

Because people joining ventures, who come from a large company or government roles, have lost touch with the value of time and money. Their roles have often driven them to become a custodian of a function or department and less of a business builder.

That will sound harsh, but for the most part, it’s true.

This is not to diminish their work experience, network or skill set. They are important. But the consequence of being a custodian, managing budgets that don’t directly affect their hip pocket and investing time in large organisation politics is a divorce away from the two lifebloods of startup ventures, time and capital.

Two tests

The first test focuses on time. More specifically, it is designed to (re)acquaint a new hire with the value of time.

The question is how much momentum will the new hire create each week in the first four weeks? In other words, you want to see how much the new hire can learn as quickly as possible.

So, ask them, ‘What sort of experiments do you plan to run to create momentum in your new role in the next 30 to 90 days?’

Learning comes from experimentation. And at the heart of experimentation is methodical testing, listening and observation.

Effective new hires are quick to frame hypothesis and sense check them with existing team members. Soon afterwards they present a plan to start testing. Within days they will be launching experiments and feeding results back to you and the team.

This test is not at the expense of a new hire getting settled, asking questions or understanding their new environment. The point is solid new hires do this and start experimenting very early in their tenure. I’ll also point out that this test is for startups. Parallel processing like this soon after someone joins a large organisation is difficult.

The ‘money test’ comes second.

This test is designed to (re)acquaint the new hire with the value of a dollar.

Give the new hire $50 and tell them that’s their stationary budget for the next six months.

They can go anywhere they want. Target, Officeworks, anywhere.

They will return with less than they expected and if this surprises them, the exercise was effective. This is particularly useful with hires who have just come from a large organisation where items like stationary aren’t usually given a second thought.

You can extend the money conversation by showing them how founders think about money which I wrote about recently.

The founder/new hire two-way street

While these tests are useful, the paid audition or probation period is the one time when new hires and founders can determine ‘fit’ with little blowback if it doesn’t work out.

While founders don’t want to be overly prescriptive so as to observe curiosity and industriousness, there is a need to determine 'fit' as quickly as possible.

Similarly, new hires don’t want to assume too much about the company they’ve just joined and they need time to observe, learn and reflect.

The point here is that while founders can observe the activities and actions of new hires, it takes conversations to unpack what they are learning, even if they are displaying extreme urgency. Don’t welcome them, set them tests or objectives and then check in with them in a few weeks.

Schedule time to speak with them at least weekly. Encourage them to ask even the most obvious question and invite them to query you on the hypotheses that lead you as the founder to make the decisions that have led the business to where it is today.

It will make the inevitable exercise of sizing up one another more transparent and productive.

One last thing…

Hiring is difficult. We all get hiring decisions wrong from time to time and the financial and emotional consequences of those wrong bets can devastate a startup.

Experience tells me that urgency is a capability that startup hires need to possess to be successful. As a founder, the big idea of this post is to have a framework to assess urgency and the best way to put that framework into action is via a paid audition.



I often hear that software developers are the most difficult hire for non-technical founders.

The process and questions to determine a candidate’s fit is a mystery to most of these founders. And regardless of whether they’re looking for a Chief Technology Officer or a freelancer to help hack the first version of a product, they often feel completely out of their depth when speaking with developer candidates.

As a result, they rely on what they think they know about recruiting talent.  For the most part, this means relying on their own experience in hiring people which as it turns out is usually, at least for first-time founders, very limited. And let’s be honest, there are few people in the world who have a perfect hiring track record.

If your venture relies on software, and just about all do, the need to get hiring decisions right is important. In fact, it’s crucial because (and speaking from experience) getting it wrong can be terminal.

At a macro level software developers are (and will continue to be) in high demand. But the rate at which developers churn from one business to another is also very high as is the number of graduates from software development courses.

So if there are software developers looking for their next opportunity why are they so difficult to find?

It often comes down to how the founders approach the hiring process. The punchline is that they forget, deprioritise or don’t give any consideration to seven important ideas.

1. Thinking of developers as machines

This might sound strange but non-technical founders have a strange affinity for relating software development output i.e. code, with the idea that it is created by a machine.

This notion becomes even stranger when these same founders think that all machines are created equally. In other words, they think that developers know everything there is to know about software development.

This bias influences hiring and workplace practices and fundamentally devalues the role that developers play in digital companies.

As obvious as this sounds, developers are people. Treat them like people.

2. You never captured their imagination

Following on from the first idea, many non-technical founders never sell the vision to developers in the same way they would to investors, partners or customers. Instead, they lead with the task or capability-based job description or worse still, software ‘requirements’ documents to gauge interest.

The ‘why’ matters to every hire.

I remember making this mistake at AirShr when we engaged an offshore software development team to accelerate product development. They were polite, competent and delivered what we asked. The only issue was that I completely forget to explain why they were working with us.

Their output tripled once they learned AirShr’s why because they could relate to the use case. They also saw the global application for the technology they were building. Most importantly, they started to act like owners and make appropriate risk-weighted decisions when we couldn’t be contacted because they understood the context and mission.    

3. You think engineering is all science…and no art

This point also ties back to the first idea and the notion that code looks structured and scientific to non-developers. The reality is that while there are best practices for how to write, structure, annotate and deploy code across the many software languages, there is also a myriad of ways that code can be written, structured, annotated and deployed.

This is because at its most fundamental, writing software is all about creating and making. It is a very artistic pursuit and one that takes time.

This point is often missed by non-technical founders. As a consequence, they can become frustrated with developers reluctance to provide concrete deadlines for delivery of tasks, particularly those which require building features or whole products from scratch.

4. You think developers assimilate quicker than other people

Imagine this. It’s 12 pm and a friend walks into your office and asks for your feedback on a 10,000 word university assignment. The assignment carries a significant weighting for the final mark and they have left it to the last minute. Your review is critical and you would love to help but they need your feedback by 4 pm because it’s due for submission at 5 pm.

Could you provide detailed feedback in time? Probably not.

I use this anecdote with non-technical founders who are frustrated when it takes more than a day for a newly appointed developer to get ‘their head around’ a code base they had no hand in writing.

Whatever your estimate of time for new developers is to become familiar with your code, quadruple it.

They need time to understand what’s there.

Pro-Tip: As part of the onboarding process, ask the new developer how they would write the code if they could start from scratch. This will make for a productive start to the relationship.

5. You don’t audition each other

I’ve written about this many times. Do a paid audition.

6. You expect to be in a monogamous relationship

Never happens. Every software developer has a side project.

Providing it doesn’t adversely impact the agreed workload, be good with it. Ultimately, this is helping the developer improve their skillset.

7. You lead with the wrong incentives

Startups are resource constrained. You know it and so do developers.

The opening gambit from most non-technical founders is to offer equity to offset the discounted wage that they have no choice but to offer. That is in the best interest of the company but it’s usually a long way from satisfactory for the developers.

Apart from developers being very sensitive about not getting paid for work they have done (there are too many experiences where developers have been short-changed by founders due to various misunderstandings), founders often forget three fundamentals.

First, developers will engage if the problem is interesting enough. If there is lukewarm interest, there is no point talking incentives because you are likely to get lukewarm performance (at best!).

Second, developers, like everyone else have expenses and need to be paid. Don’t overplay the value of equity as a means to pay them less. This will be harmful to the relationship in the medium term, especially if it’s later discovered you could afford to pay more. In any case, developers understand the risk of startups and know the chance of equity appreciating is always lower than advertised.

And as the old adage goes, you get what you pay for.

One last thing …

While I have written about the mistakes I’ve made hiring freelancers online, I didn’t think there was ever a need to write this post. But conversations with non-technical founders over the last year has taught me that, due to their own experience, they think about developers in a different way.

If you can relate to this, or find yourself agreeing with any one of these seven reasons, the solution is relatively straightforward: Think about developers as people first.



The punchline: Think first about how you want to be remembered. It will help you answer what you want to do in life.

So, what do you want to do?

I struggled with this question for the longest time.

There was a storm inside me that constantly reminded me of my potential. The problem was I didn’t know how to apply it to answer this question.

Practicality told me to earn money to pay rent.

Experience told me to rust on to the best leaders to accelerate my learning.

Military service told me to never underestimate the power of high calibre teams and mateship.

My upbringing told me to respect people’s perspectives, motives and religion.

And hope told me that hard work’s payoff would reveal my ‘why’.

But hope isn’t a strategy and I was also no closer to answering what I wanted to do when asked by friends, colleagues or recruiters. And when the question came up when a military career was no longer an option and after my first venture failed, saying ‘I don’t know’ or fabricating an answer was exhausting.

I was desperate for an answer. The frustration was palpable and it kept me awake at night.

That’s no longer a problem.

Answer a better question

In 2015 LinkedIn acquired, an online guided learning platform. The acquisition was a push towards LinkedIn CEO Jeff Weiner’s strategy to increase the importance and convenience of education.

I remember reading a summary of an interview between co-founder and CEO Lynda Weinman and Jeff soon after the deal closed. Jeff asked Lynda about her future ambitions. Much to his surprise, Lynda responded that she prefers to think about how she with be remembered.

Jeff was astounded by Lynda’s answer. I was too.

Lynda started with the end in mind. Her end in mind. She could clearly describe how she wanted to contribute.

In strategy, that would be called describing a vision. Lynda didn’t talk about the intermediate steps or objectives. Instead, she outlined the principles or guideposts for how she would make career decisions.

Strategy set by organisations guides a large proportion of our working life. Unfortunately, corporate strategy often lacks clarity and meaning to inspire the people who are employed to deliver it.

This is because defining strategy starts at what’s known before attempting the very difficult task of describing the future state. Ironically, and to Lynda’s point, people charged with strategy at an organisational or profession level rarely ask how it will be remembered.

For example, if you’re a doctor the career path comes with some choices but it’s relatively linear. The same is true for bankers, electricians, teachers and other important jobs in established professions.

The thing is that if you fit into a traditional profession or organisation, answering what you’re going to do is largely already decided for you.

The bigger issue, as I’ve written about before, is that a growing number of people don’t fit into a traditional career mould. And for those who do, their institutions are facing massive disruption. This means that organisations face the real threat of becoming utilities (e.g. financial services companies) or just obsolete.

The net effect is that traditional employment pathways are breaking down. Consequently, those people who used to be guided by tradition movements within an industry or profession will start being asked ‘what do you want to do?’ more often.

In other words, they will start joining entrepreneurs, those transitioning from the military and corporate refugee who is being asked the same question.

How do you want to be remembered?

The penny immediately dropped for me when I heard Lynda’s comment. Shortly afterwards I had clarity on how to guide career decisions.

The most liberating aspect of this shift was that it didn’t rely on highly specific and exhaustive rules.

I want to be remembered for being family first, increasing collective wisdom and making the greatest net-positive impact on the world possible.

That’s my answer to ‘what would you like to do?’ and here’s how actions map to philosophy:

On being family-first

Anyone with children will tell you how priorities change when they arrive and how quickly they grow up. We’ve made a decision to choose ventures and companies to work with that enable us to minimise (or concentrate) time spent travelling for business. Sometimes that means leaving money on the table, but rarely.

On a practical level that means being able to be home for bath time (for little ones), getting them into bed and then jumping back into work afterwards.   

On increasing collective wisdom

This means putting experience-based knowledge into the hands of people who can use it to move the world forward.

This journey consists of two parts, both of which are works in progress.

The first is learning. For me, learning comes from:

  • Finding ways to collaborate as quickly as possible to understand perspectives and incentives
  • Speaking last as often as possible so as to not bias conversations
  • Fighting to thoughtfully disagree which essentially means not reacting but thinking about and formulating an argument that will (hopefully) yield a positive learning experience for those involved. It’s not always possible but you know it’s working when the people you thoughtfully disagree with come back for more.
  • Finding rooms where I am easily the least smart!

The second part is paying the knowledge forward. I do that by making the time to write each week and surfacing interesting conversations with other entrepreneurs.

On making the greatest net-positive impact

This is all about time and how you invest it to get this return. For me, that means being curious about big problems and enjoying the process of sizing the opportunity (which I love).

It also involves:

  • Exercising humility because you won’t always get it right
  • Being kind because the world is in a massive deficit and being kind creates unexpected opportunities with others
  • Being strong because building new things is bloody hard
  • Making every day count because you’re running out of time

While these ideals aren’t unique, and I’m sure many subscribe to similar notions, these three are specific enough to help me and my wife make decisions about how to invest time.

One last thing...

I reflected on this event as part of writing In Between. It was a major psychological shift and turning point for me even having already started two companies at the time.

There is an inherent simplicity in this approach, like most things with hindsight, and I do hope it’s as valuable for you as it was for me.



Below is an excerpt from my forthcoming book, In Between.

I’m bringing this forward as a result of an unexpected conversation I had with a 24-year-old first-time founder this week. While his venture failed and his circumstances are synonymous with the risk and journey of entrepreneurship, he has a bright future.

In Between lays out the approach to help entrepreneurs move between ventures. And this approach extends beyond entrepreneurs to apply to people and communities who experience profound changes in personal context, including families transitioning from the military and those departing long-term careers.

In Between didn’t start as a book. It began as an investigation into how to grieve for a failed business. I had been there twice before as an ambitious founder and in both cases, the businesses failed.

The aftermath of the first business failure was catastrophic and put me within days of personal bankruptcy. To say it was a turbulent spin-cycle of emotions is an understatement and many know this feeling.

I studied grief as a means to add a rational perspective to the emotions I was feeling. It had a limited effect because the ‘so what?’ from the literature was missing. In other words, it described how I should feel at each stage of the grieving process but provided little context-specific help.

In Between is designed to answer that ‘so what?’ of grief for entrepreneurs (and veteran families and long-term career refugees). And as many colleagues have validated in conversations on my Founder To Founder podcast, starting new chapters is an essential habit that improves with practice.

The softer landing I experienced when my second venture failed is a testament to this approach (and I wish I would have known this when it came time to leave the military).

My hope is that this book will resonate with many.

It is grounded in practical actions to navigate emotions that are taboo or misunderstood by those who haven’t lived the transition from a business, the military or a long-term career.

It will also shorten the time it takes to navigate the ‘in between’ and put you in motion to your next play.

In Between Excerpt: Chapter 6 - Sizing Up Your Next Play

Seeing yourself as part of a new opportunity is the first sign that you are in motion towards your next play.

The next step is having a framework to run a ruler over different opportunities as they appear. Remember that you are now armed with lessons and experiences that when channelled into the right opportunity will compound your rate of learning and the value you can generate.

The consequences of considering opportunities without a framework increase the risk of being oversold and investing time in organisations where you reach only a fraction of your potential.

There is a five-question framework that I use to assess opportunities. This started as a checkbox exercise. I would add these five questions in a left-hand column of a spreadsheet and then list the opportunities in a row across to the top. Each question is equally weighted and requires a simple YES or NO.

The opportunities included jobs that piqued my interest, organisations I wanted to work for (without knowing an exact role), businesses I was asked to mentor and not-for-profits I wanted to support.

As I developed a habit of using this five-question framework, I moved from spreadsheets to doing ‘the math’ in my mind each time an opportunity was presented.

This has two important benefits.

First, you become increasingly aware of the type of opportunities you want to engage in. The by-product over time is that you make quicker decisions about how to value your time and in doing so reduce the time you spend dwelling on the opportunity. Those asking you to engage also benefit by getting a quick ‘thanks, but no thanks’.

The second benefit is that you have a structured basis from which to discuss the opportunity with your partner or mentor. This increases the richness of the discussion because you’re able to dive deeper into the important factors that influence a 'Go / No-Go' decision.

Today, using this framework is more instinct than process.

Question 1: Does the subject excite my mind and capture my imagination?

Most people instinctively know when an idea or opportunity is captivating. They won’t often be able to articulate why. But the look on their face combined with ‘that’s cool!’ tells the story. This reaction comes before any calculation can be made about whether their skillset and experience mean they are a fit.

If this describes your reaction, answer YES to this question.

Question 2: Can I create fanatical lovers of a product or service if I were to start working on this opportunity?

This is as important for those starting a venture as it is for those building a product or business within a large business. In a startup, my measure for the number of fanatical lovers I need to create as quickly as possible is 1,000. I consider this a first major milestone. Fanatical lovers are highly likely to evangelise your product to others more effectively than your marketing efforts could hope to achieve. This drives virality that is essential to rapid growth.

The number might differ from business to business but if you are convinced that you can quickly create a large group of fanatical lovers for the problem you are solving, the answer to this question is YES.

Question 3: Can I bring my experience and expertise to the problem?

After achieving Defragmentation in Chapter 3, you are now armed with clear lessons and a narrative about your skills and capabilities. Apply them when answering this question.     

This question also has a subtle secondary meaning related to learning. By documenting lessons in Defragmentation, you are now familiar with your rate of learning. So the second part of this question is, ‘Will I have the chance to keep learning or accelerate my rate of learning?’

Answer YES if you can bring your experience and expertise to the table AND if there is an opportunity to increase your rate of learning.   

Question 4: Is there a model hiding in plain sight?

This question is asking if you can see how money is or could be made. 

For established organisations, the continuous challenge is to avoid over-romanticising how money is made and finding ways to disrupt their own business model before it’s too late.

For startups, the focus is growth. This involves experimenting with ways to make money that fuel and reinforce that growth.

For not-for-profits, the focus is growing a sustainable donor base.

Answer YES if you can see how money can be made or how this can be evolved.

Question 5: Is there room for serendipity to play out?

Call it chance, call it luck or call it faith. There is uncertainty in all facets of life and by default, there is room for happy coincidence or serendipity to play out. This question provides a guard rail for the four questions that preceded it. You can answer YES to the other four questions but you might ask this question and find that there is a very small margin for serendipity, what some might call a ‘Hail Mary’, i.e. a plan or project with a very little chance of success. This might be due to industry dynamics, an organisation in decline that lacks the ability to innovate or other environmental factors. 

If the response is more Hail Mary and less serendipity, answer NO.


One last thing…

There will be 20 pre-launch copies of In Between for those reading this post. Shoot me an email if you would like a copy. First in, first served!



Stress is an unavoidable part of a startup. It affects team members in different ways and it’s constant in a founders life.

There is a long list of situations, decisions and expectations that create stressful conditions. Add fatigue and a perfect storm of stress can easily besiege even the most accomplished entrepreneur.

It would be easy to lump startup stress management with the founding team but I think it is, and always will be, a team effort.

It’s one thing to set the cultural tone, it’s quite another to expect an evolving culture to have built-in ways to manage stress.

And let’s be honest, unless you’ve worked together with someone while you've had your feet held to their fire, you won’t know how others will respond to stress.

Founders are in the business of hiring the best people they can afford. This hopefully means they are hiring leaders. People who fit the mound of ‘best in class’. They know stress and bring an array of tactics to work through difficult times. Harnessing this experience is essential.

But how many founders do?

Time usually isn’t devoted to conversations about how people manage stress. And when high-pressure situations come knocking, we’ve been taught to look to the leader at the top for guidance. This can work, but it’s rarely full-proof.

Here are three ways to make managing startup stress a team effort. To solve problems more effectively, provide support to the CEO (who at the end of the day is only human) and unleash the stress management experience of leaders your company has worked so hard to hire.

1. Acknowledge the fear-tension-pain cycle

I first learned of this cycle in a prenatal class. The midwife shared details about how fear, tension and pain are not only interrelated but a virtuous cycle. This simple principle, where greater fear leads to more tension and increased pain, was coined in the mid-1900s and usually affects first-time expectant mothers.

And although stress in startups and childbirth is very different, knowledge is the circuit-breaker in both cases.

The more a mother (and partner) know about pregnancy and childbirth, the more they are able to manage their fear, tension and pain.

Startup teams see the fear-tension-pain cycle play out most days. Acknowledge it and starting conversations that show a willingness to introduce the right circuit-breaking knowledge goes a long way to removing fear and breaking the cycle.

2. Share problems across the business

I’ve written before about the attitude founders often bring to their startup.

The ‘it’s my venture and my issue so I’ll work it out’ mindset is a waste of time.

If you’re thinking this or worried about not having all the answers, you’re thinking about this the wrong way.

The answer to problem-solving in most cases is not to reduce the number of brains working on the problem.

If you look to military special forces around the world you’ll find a surprising fact that escapes most people due to their perception that the military is all about command and control.

Regardless of the size of a team, the leader always knows they are leading other leaders. For this reason, and after establishing the situation and context, they ask their team members for input before making a decision on how to proceed.

This team effort almost always yields a better solution.

And the more prepared you can make your team to engage in a ‘problem-led’ discussion, especially if you ask for their input at short notice, the better it can be for the situation.

I use an approach adapted from a process designed by my friend Adam Mather to give people the best chance of helping me solve issues.

Before bringing people into a conversation, I make sure that:

  1. Context is clear - what the situation is, how it evolved and the fact that I’m not sure how to approach it.
  2. I can articulate the problem - be specific about the nub of the issue
  3. Homework is done - come to the conversation with well-researched options in the mind but do not offer them so as to avoid biasing your team’s input. Instead, have them up your sleeve to respond to probing questions or suggestions from team members

3. Over-communicate

This doesn’t mean sending more slack messages or email. Over-communicate in this context means finding ways to better express intent.

Think about the emails you write and the slack messages you send. Although emojis might help, email and slack messages can’t express the stress, angst or happiness that sits behind what’s written. In fact, they do a good job of removing intent from communications altogether.

The best way to reinstall intent, particularly if your team is not colocated is to communicate, as often as possible, using video.

Do not underestimate the importance of seeing the face and the cues of your teammates. If you use Slack, use their video calling feature. If you don’t (and why don’t you again?) look at Zoom.

One last thing…

The most underrated circuit-breakers in managing stress are humour and optimism. They are infectious and cost nothing. Using them in combination with sharing problems across the business and over-communicating has helped reduce stress in my businesses and I hope it helps you too.



An old friend, Fulton Smith, asked me recently if there is a role for entrepreneurs in shaping the social conscious.

The answer is yes. And while I can’t speak on behalf of other entrepreneurs, I think shaping the social conscious can happen in two ways.

The first is through the products you make and how they influence people.

The second way is more personal and begins with an awareness of social performance or the way you contribute to the world as part of your work.

Influence through product

If you look closely at the anatomy of great products built by entrepreneurs they help their user achieve one of two objectives.

They move a person further from fear or they move a person closer to happiness.

It is as binary as it sounds and usually underlying the motivation to build a product that has one of these two effects on its users is the desire of the founder to create a happier life for a stranger.

And herein lies the entrepreneurs' superpower when it comes to shaping the social conscious.

Not only are they intrinsically motivated by some form of social performance, entrepreneurs expose new ways to crack problems and more importantly, provide evidence that it can be done at scale.

Influence through social performance

A little over a decade ago an anthropologist introduced me to social performance. She shared its three tenets with incredible clarity and they have stayed with me ever since.

1. Social performance is the personal pursuit to improve the happiness of one other person.

It can scale to millions of people but it starts with just one person. The point here is that happiness is the quality to improve and whilst subtle, this is important because most people associate the word ‘social’ with disadvantage.

2. The measure of social performance is subjective.

In other words, you are the one to consciously self-assess whether your efforts to improve the happiness of another person meet your own standards, not someone else’s.

3. Social performance has its own network effect.

Efforts to increase the happiness of others will be magnetic to people you do and don’t know if you make known what you do. In other words, people can’t be what they can’t see.

Today, ten years on, these tenets influence my contribution to family, how I build businesses and why I support women entrepreneurs, donate blood and work to reintegrate veterans.

Everyone will describe the important themes of their life differently. These are mine and this structure helps me to maximise my contribution, which also means I deliberately don’t invest capital or effort in other areas.

Being louder on social issues

Fulton also asked if I thought the voice of entrepreneurs should be louder on social issues?

The answer is also yes but that said I hear the voices of my colleagues on social issues loud and clear, and I have for some time.

If you’re not hearing them, I suggest you take a look at what they’re building. There’s a good chance they’re speaking through their product.

One last thing...

If the idea of social performance is appealing and you’re wondering how to make it part of life, here are the two questions I ask myself most days.

First, am I increasing the happiness of at least one person every day? The answer is yes if your actions map to moving someone closer to happiness or away from fear.

The second question is ‘am I doing enough to make a difference?’ Although a deeply subjective question, the answer is relatively straightforward. If you think you can do more, do more.

I hope that’s helpful.



This weeks topic is as pervasive as it is taboo in entrepreneurship.

It’s a blunt message that’s contrary to entrepreneurship’s often upbeat narrative, and while difficult to talk about, I'd like to know founder and investor perspectives on this topic, so please leave a comment.

Isolation, depression and being an entrepreneur

Well-known to some and an unexpected to others, isolation and depression (not just being tired but feelings of severe despondency and dejection) don’t affect every founder, but it’s more common than you might think.

These topics often come up in conversations with my founder friends and mentees because they (and their spouses who are along for the ride) are the operators, those building businesses.

Those who recoil at these seemingly extreme conditions are people on the sidelines. They are observers of a popular culture, one synonymous t-shirts, jeans, sticker-clad laptops, pitch competitions and product launches.

They rightly admire the tenacity, resilience and conviction of founders and walk away for startup events feeling inspired and craving more of the infectious vibe.

Meanwhile, the operators continue to drive hard in shadows.

While trying to be the best they can for the people they love, they are always running out of time to grow their business. They are always trying to learn in the face of compounding fatigue and they are always trying to increase the quality of their decision making.

At the same time, they are under no illusion that they are volunteers.

Founders readily admit that they didn’t expect to have to wage such a sustained campaign to stay in market long enough to achieve their vision. And the irony isn’t lost on them that everything they have built, everything you see today, is always only a small part of their ambition.

The founder’s struggle is real but it’s not new.

The entrepreneurial pop culture is only a decade old. For generations before this business women and men faced the same challenges, the same isolation and the same risk of depression.

Veneer of positivity 

Founders are optimists. We know that in just about all circumstances a positive attitude is infectious and shouldn’t be underestimated. It helps us to inspire teams, partners and customers, and see silver linings amid the startup chaos.

But positivity can go too far and here's the punchline:

The strongest signal of founder isolation is when every answer to every question asked by everyone is positive.

This veneer of positivity deflects away from talking about issues. It’s protection from answering even the most innocent of questions.

Take, for example, asking a founder ’how’s it all going?’

You might get a brief bullet-point summary of milestones. An isolated founder will almost certainly think ‘there’s no point explaining, they won’t get it’ and respond with a deflecting ‘all good!’

And the context is important.

When you ask a founder a question there is also a very good chance that they’ll be processing a ton of decisions in parallel (that’s always happening). But outside of their family, founders spend 80 to 100-hour weeks building products, selling and forging partnerships, nurturing teams and managing finance and operations, all in the face of nailing one win for every 50 setbacks.

They are all in. Family, reputation, relationships, capital. Everything. The feeling of responsibility that founders live with to deliver is enormous.

It takes a village to build a business

I’m continuously on the lookout for signs of all-positive-all-the-time answers, the isolation signal, from friends building businesses and my mentees.

I know enough to know it’s naive to think the relationship between isolation and depression is linear but I take this signal of isolation seriously because I’ve seen it as the precursor to depression too many times. I also understand that isolation is relative and dynamic. And not surprisingly, it often correlates to the entrepreneur’s rollercoaster.

That said, I hope you open your radar to this signal and act differently when it emerges with your founder friends. Here’s what I do:

Check in regularly.

Instead of asking ‘how’s everything going?’, ask them about their family or the common ground you share.

Then serve them this:

I know you have a lot on but I want to help you with one issue you’re trying to work through. So, how can I help?

And if they cannot provide an answer, follow up with a message a week later letting them know that the offer is still on the table. Then deliver on the offer.

Isolation is eliminated by meaningful help from people you trust. It’s no more complex than that.

It's also up to the founder

Most founders have mentors. We’ve made the ask to people that can help and we speak with them regularly to get help.

If you’re a mentor-less founder, that needs to change. You can't build a successful business on your own.

It starts with a simple ask to a person you know can provide value to your thinking, 'can we connect for 45 minutes each fortnight for the next three months to work through issues and opportunities for my business?'

Not everyone has the time to mentor but many do. Expect this to be a relationship based on the exchange of value. You might not know how to thank them for their time but if my experience is anything to go by (and female entrepreneurs please explore this), it all comes out in the wash.

Strengthening the core

Isolation can also be brought home. And because the nature of the relationship at home with your partner is more intimate, I think about isolation differently.

At home, isolation leads to the creation of what’s known as an entrepreneur’s widow(er).

Next stop, relationship breakdown.

I’ve written about this before and at the centre of the solution is over-communication with your partner.

As a first time founder in 2008 I struggled immensely with communicating the challenges I faced each day in building my company to my loved ones and in particular my partner.

Some challenges were petty, others were significant and at the end of each long day, exhausted and with traction and capital waning, I often didn’t have the words to describe the current state, let alone find a way through it. And at the end of the day, I didn’t want my partner to be burdened with my challenges.

I started this venture.

These were my issues to solve.

I was also convinced that she wouldn’t understand, not because she wasn’t capable or thoughtful, but because she wasn’t in the trenches. How could she possibly understand and even if she did, where would I start?

But she felt the same stress, angst and jubilation that I did. It’s easy to forget that our partners are riding the same rollercoaster as us. They carry the load when business travel calls, they provide encouragement from the sidelines, and they help pick up the pieces when luck is in short supply. And they do all of this with only a fraction of the context and information in our heads.

By the way, if you’re a founder and thinking ‘thanks, but this isn’t a thing’, you’re either single or about to become single.

Relationships fail when information sharing stalls

In most normal, low-pressure environments over-communicating is the act of repeating the same message ad nauseam.

The context for founders is usually different. They usually under-communicate with their partner. The good news is that over-communicating is straightforward but like any disciple takes practice.

And at its core over-communicating means finding common ground to create a shared understanding that will short-circuit angst while further strengthening a relationship.

Start by asking 5 questions

Here are five questions that entrepreneurs should ask their partner. This isn’t an exhaustive list and not all of them relate to building a company.

1. Can I practice pitch with you?

Founders should always be closing deals with new customers, partners, investors or hires. The safest audience is your partner so give them permission to adopt the character and pitch them.

2. Can I get your thoughts on this value proposition?

If you’re spinning your wheels on developing messaging for a new feature or product, ask your partner for their input and how they would describe it to a friend over coffee.

3. Can you play with this new version of our product?

This is an easy one and it’s all about observing and capturing how your partner engages with the product. Try also asking what it would take for your partner to share your product with everyone she knows.

4. Do you have any thoughts on how to manage [insert tricky situation]?

Entrepreneurship is like fire-fighting. There is always a spot fire to extinguish and a tricky situation to manage. Ask your partner’s opinion about how they would handle the tricky situation at hand.

5. How can I help?

This is probably THE most important question that a founder should ask their partner each week, if not each day. This question is a surefire way to reconnect and put your money where your mouth is in terms of being mindful and engaged in your relationship.

Closing thoughts

If you know someone building a business and they're being too positive, act.

If you don't have mentors and you're building a business, change that.

And if your partner is on the ride with you, ask them five questions.

Just don't ignore it. Being isolated is a sad existence which can lead to a devastating outcome.

Consider this the start of a conversation, let me know your thoughts below.