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.




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.



Paid auditions are just that, opportunities to work with someone before you tie the knot and become employee and employer.

And there are three reasons why you should them.

The first is that no matter how confident you are in your ability to hire, no matter the process you use, the only way to understand technical competence and ‘fit’ is to work with that person. By extension, if you don’t use a paid audition, you significantly increase the risk to your company. Hiring the wrong person can bring your company to the brink of collapse. Most founders have a story like this to recount. I know I do.

The second reason is that the risk in hiring isn’t just on the company side. It’s also on the candidate side. There is a growing acceptance that the pitch (from an employer) rarely correlates with the reality once on the inside.

Candidates know this.

They’re more reluctant than ever, at least for startups, to leave a safe job behind in exchange for this risk of a new venture working out. It makes sense that there be an opportunity to ‘try before you buy’. In the case of a paid audition, the candidates get paid to try before they buy.

The third reason is the benefit of ‘fresh eyes’. The regular introduction of people into your business sheds new light on issues and almost always exposes new ways to increase momentum.

If you subscribe to one or all of these benefits, the next step is to get practical by asking yourself one question…

Can they be my ally?

This is the question you as the hiring manager should be asking yourself. You’re looking for an ally and not for someone to join ‘your family’.

Think about this carefully.

Entrepreneurs often use the term ‘nurture’ when describing the business, relationships and culture they’ve created from nothing. Nurturing also happens in families to help children grow and flourish but it’s dangerous for a founder to think about hiring in the same terms. Families are complicated and don’t rely on product and financial performance to be sustainable.

On the other hand, allies share a common, performance-based belief system where allies stand to benefit individually when they collectively achieve success. LinkedIn co-founder Reid Hoffman goes into great detail on this in The Alliance (highly recommended).

To that end, hiring managers need to ask themselves will this person:

  1. Bring their full expertise to help achieve the milestones essential to my company's success?
  2. Act like an owner?
  3. Be strong, kind and humble in the good times and when the going gets tough?

I use these questions as the basis for starting and ultimately concluding the success of a paid audition.

Can I do my life’s best work here?

This is the question a potential hire should be asking themselves as they consider and enter a paid audition. As a sign of respect and in an effort to further develop our relationship, I prompt candidates to continually ask themselves this question as they consider and undertake the paid audition.

Ultimately, if they are excited to learn, achieve, solve the challenge at hand and get well compensated for their investment in time, they will do their life’s best work.

Remember, they are assessing you as much as you are assessing them!

For the most part, paid auditions fail for 6 reasons:

  1. The purpose of the business is unclear
  2. Milestones aren’t crystal clear
  3. Candidates feel like an outsider
  4. Duration is too short (or too long)
  5. Assessment happens at the end
  6. Agreement was made to work for free

They also lead to competitive advantage

However you arrive at the decision to enter into a paid audition, turn the following steps into a habit that differentiates your business.

Introduce the mission

This step is often overlooked. Hiring managers or the founder assume the world has completely understood the vision and purpose of the business through their marketing efforts.

Assume this is never true (because it rarely is!).

Go into all the detail necessary to help the candidate feel inspired by the mission you will achieve. You might confidentially share sales collateral and pitch decks with them to land this message. It will make all the difference.

Create crystal clear milestones

Each task that a candidate will undertake must be clear, specific, time-bound, measurable and most important, practical. With the ‘Can they be my ally?’ question in mind, I frame the auditions like this:

  • Provide sales targets and a challenge to optimise existing sales processes for sales candidates
  • Set feature enhancement tasks which rely on hypothesis-led and data-driven experiments with customers or people who use the product for product candidates
  • Design and implementation of campaigns that demonstrate a change in the company's core metrics can be the ask of marketing candidates

These are just some examples which also apply when auditioning freelancers.

Eliminate potential for candidates to feel like outsiders

The first step is to welcome candidates into your company's way of communicating. This means making yourself as available to the candidate as you would any other team member. If you use Slack or another team-based messaging service, get the candidate on there too. They should also be part of businesses standup rituals and one-on-one meet routines where their schedule allows.

Nuance alert: The nature of paid auditions is that they nearly always happen outside of normal hours. This allows the candidate to keep their day job while auditioning for you.

This means candidates won’t always be able to make standups or respond to emails or Slack messages as quickly as you or the team would like.

Be explicit on how you and your candidate will communicate with one another.

This is the lynchpin of the audition.

Over-communicate how you will communicate.

If you don’t, you and your team will become frustrated and this is the single greatest way to make your candidate feel like an outsider.

Set an audition of between 6 and 10 weeks

Most candidates will be juggling their day job and auditioning at your company and they will need time to demonstrate their expertise and fit.

I find that a paid audition duration of 6 and 10 weeks works well.

They can be shorter but the risk in this is that you don’t get past the honeymoon period. This can mean that you don’t get the opportunity to see the candidates true colours…the whole point of the paid audition!

Assess progress each week

Leaving assessment to the end of the paid audition is a recipe for disaster. The hiring manager won’t be able to recall everything that happened during the last 6 to 10 weeks. There is also a good chance that the candidate may also move off task through a lack of guidance. The bigger issue here is that the candidate will get an insight into how the business is run. If you’re not serious about performance now, will that change in the future?

Set up a weekly conversation to exchange ideas, coach your candidate and assess performance.

Pay for the candidate’s time

Time is your most valuable asset. The same is true for each candidate. Pay them an agreed hourly rate for an agreed amount of time. In the case of a sales audition, this might include a commission.

It’s a mistake to agree to audition for free. It simply doesn’t represent a fair exchange of value and this lack of incentive impacts motivation.

Closing thought

Three questions usually come up when talking about paid auditions. The first is isn’t this the same as a probation period? The answer is no. The probation period comes after the hire is made. Consider it a secondary opt-out mechanism for both the candidate and the company.

The second question is how is this different to an internship? The reality is that a paid audition and an internship are structurally very similar. As I’ve written about before, I look at internships as an opportunity to bring new but less experienced talent into a business. A paid audition is more focused on introducing experienced talent to help accelerate growth and momentum.

The final question relates to paperwork. Is there an agreement template I should use? A paid audition should use a standard contractor agreement which covers appropriate legal and confidentiality matters.

The best part of a paid audition is that it offers the chance to learn quickly.

If it doesn’t work out, the candidate gets paid, you learn and you mitigate the risk of hiring the wrong person.

And if it does work out, you’re off to a flying start!




These 12 lessons come from notes I’ve made each week in 2017. I find it useful to do wholesale reflection at this time every year to make sense of the year that was, gain clarity on lessons learned and create my 10 objectives for 2018. More on that later.

The other 40 observations are interesting but these 12 have shaped my thinking on family, inkl, mentoring, my social performance in supporting veterans and women founders and being an entrepreneur with more windups than exits.

1: Thinking publicly is no longer optional

As I wrote last week, to think publicly means you place your ideas into the hands of others. The underlying motive is to learn as quickly as possible and then move an idea forward or to kill it and move one.

I do this by writing this blog each week. The precision of thought that writing provides me is immense.

And writing is just one example. Many of my colleagues and mentees have found the courage in 2017 to share big issues with their team in order to increase solution surface area. And the results have surprised them (in a good way).

Find a method that works for you. The crowd’s wisdom has never been more abundant and you have nothing to lose.

2: Investor expectations on traction are very different to two years ago

The funding cycle for consumer technology ventures is maturing. Capital is available but it’s increasingly expensive in the face of soft traction. Two years ago $30K in monthly recurring revenue (MRR) would start a conversation with Series A investors, today $100K MRR is where the conversation begins.

Seed investors also require a lot more than a 10-slide vapourware pitch deck to get excited. And those investors who once specialised in Series A investments, for the most part, have moved further upstream and now invest in Series B and C.

The reality for entrepreneurs is that the rate at which a business can capture monetizable value for its customers is the main game.

3: Scenario planning is your best friend (in all circumstances)

It’s dangerous to assume people think about scenarios the same way. No matter the situation, be it a major decision or tactical campaign, there is always a best-case, worst-case and a few mid-case scenarios that could reasonably eventuate.

Spend time working through and agreeing the three actions that apply to each scenario with your team. It will reveal blind spots, establish a consistent level of awareness across the team and minimise stress caused by knee-jerk reactions to scenarios you could have foreseen.

4: Cherish life. It ends unexpectedly.

When you think about someone close to you, someone who brings value to your life, express your gratitude in that moment. Don’t wait. You might not get another opportunity.

5: Being ‘venture-backed’ isn’t a business model

On four separate occasions this year I was stunned to learn that a product that I expected to be paid (and I was ready to pay for) was free because the company was ‘venture-backed’. In each case, this message came from a front-line salesperson (?).

This turn of phrase means that a company has raised money from investors and is focused on growing the number of people who use their service and considers generating revenue a secondary priority. This can make sense when building a marketplace business model where you monetise people’s engagement (like Facebook does with advertisers).

If this isn’t the case, one of two bigger problems is lurking below the surface.

The first problem may be that the company doesn’t know how or lacks the confidence to price its product. The second problem is that the company may have become reliant on raising capital from investors in order to survive. Either way, neither one is conducive to survival so why buy from them?

6: Understanding incentives is 80% of forging great partnerships

In other words, if you don’t have an intimate understanding of what’s in it for the other party you’re trying to forge a partnership with, there will be no partnership. You might establish a transactional relationship but the value to be limited to that relationship and it probably won’t grow.

The key is to find ways to make your partners shine.

7: Growth changes everything but it’s rarely linear

The reason that growth isn’t (often) linear is that it requires a venture to undertake continuous experimentation. Each experiment is designed to edge a product closer to its ‘fit’ with a target market. More experiments fail than succeed until one day the unrelenting focus on optimising a collection of processes or features hits the mark and a ten-year-in-the-making-overnight-success is born.

Growth changes everything but thinking it will just happen with the current version of a product is a mistake.

8: “In the spirit of radical candour….” was the most productive sentence-starter of the year

Radical Candour was published by Kim Scott earlier this year and it was a game changer. It means to challenge directly while showing you care personally. It’s a simple construct and one I’ve used it at least twice a week this year. I also introduced it to our team at inkl.

Radical Candour has helped me deliver and receive difficult feedback in 2017. And in 100% of cases, the outcome was better than I could have expected. If this book is new to you, get it here or listen to it here.

9: Trust is a competitive advantage

There is only one way to develop trust between a product and the person using it: Continuously deliver on the expectation you set with them.

Achieve trust and people will talk about it.

Break trust and people will talk about it.

It’s your call.

10: Beware the shadow cast by disrupters

Every leader creates a shadow within their organisation. Like children taking cues from their parents, employees take cues from their leaders, in most cases more than leaders realise.

Leaders who seek to change the status quo create a ‘disrupters shadow’. There are those leaders who espouse a do-whatever-it-takes attitude and those who consider every option but act after considering risk. The latter may still proceed with an ‘if it won’t break the organisation, then just do it’ approach but the difference is they are sufficiently self-aware to make that call.

Uber is an easy target for the do-whatever-takes camp. To be fair, they had to fracture deeply entrenched, multigenerational taxi cartels in order to change personal transport as we know it. But a lack of self-awareness has introduced dire risk into its business which could have been avoided.

If you’re looking to join a high-growth venture, look for evidence of self-aware leaders. They will flex their style according to the situation, admit mistakes and consistently practice a growth mindset.

11: The soul of a product is as important as its function

A new feature might magically unveil a previously unavailable convenience.

A personal touch that a founder makes to thank you for joining their movement might surprise you.

Or it might be an elegant effect that helps express your reaction or makes you say, “that’s cool”.

Each of these is examples of how the soul of a product captures a person’s imagination. In 2017 it was interesting but not enough to simply save people time. This trend will no doubt continue in 2018 as product managers fight for people’s attention.

12: History doesn't repeat itself but it often rhymes

This quote, often attributed to Mark Twain, says it all. Somewhere in our history, there is evidence of an idea or an outcome that can accelerate learning and decision making. There is immense value in examining history. If you genuinely believe an idea is novel, there’s a better than average chance you haven’t used Google properly.

Closing Thought

At this time last year we began winding up AirShr. As each member of that team underwent their version of reinvention, I committed to doubling down on learning and optimising for time as my two core priorities for 2017. That decision has paid off in spades and I plan to continue that pursuit in 2018.

So before I get into my 10 objectives for next year, what are your key lessons from 2017?



Entrepreneurs win for 10 reasons. Military forces win for different reasons and it might surprise you to learn that these reasons often overlap.

Last week I shared those 10 reasons with members of the Army, Navy and AirForce from three nations at the Australian Defence College.

I’ve seen these reasons play out time and time again in the ventures I’m involved in and through countless conversations with world-class founders. I hope they're useful to you too.

1. Time Is THE ONLY Currency

The single most important resource available to entrepreneurs (and intrapreneurs) isn’t domain expertise or their track record.

It’s time.

Time is every precious moment you have from the instant you decide to start working on a new business model. How you decide to use time governs how productive you will be, how quickly you can fail and above everything else, how quickly you will learn.

I was asked about how to manage time if you’re working on a side project while working a day job. The reality is that nearly every new venture starts this way. If you want to know if there is a there, there (i.e. if people want to buy what you’re selling), you’ve got between 9pm and 2am each day to work it out. It’s that simple.

And if you’re wondering how to stop pontificating and starting doing, here’s how to validate an idea in 30 days.

2. Urgent Focus

Urgency characterises Steve Jobs and other immortal entrepreneurs - Malcolm Gladwell

'Urgent focus' is the potent byproduct of knowing time is running out and an insatiable appetite to learn in order to move toward.

When you break this behaviour down, urgency drives entrepreneurs to keep looking everywhere to get answers. We look for where the components of our future business models have been tried before and we use every manner of sticky tape to bring them together to prove a concept.

Focus comes from knowing the question we want to be answered and acknowledging the path to the answer will be anything but linear. In other words, it will take time to answer and that’s OK but it doesn’t mean generating activity (picture of a lot of people just doing stuff) in the hope the answer will reveal itself. It means conducting experiments to validate (or invalidate) hypotheses in order to learn as quickly as possible.

And herein lies the litmus test between entrepreneurs and those playing entrepreneur.

The latter is busy doing stuff, unclear on their central thesis and being easily distracted by new opportunities that vaguely fit with a vision they have trouble articulating.

By contrast, entrepreneurs create momentum by continually testing to validate and learn against their central thesis. And it’s this approach that delivers a massive competitive advantage to founders: the ability to determine the difference between an opportunity and a time suck.

3. Think Publicly

If you think you know what people need before you ask them there’s a great chance you’re wrong.

Sharing ideas with others is not only essential to understand the demand for products and services, but also to unveil adjacent opportunities and applications.

And before you think people will be critical of your idea or that it will be stolen, think again.

Whenever I’ve provided the right context for a new idea and given permission to receive point blank and unbiased feedback, I’ve always received it.

When it comes to an idea being stolen, people don’t realise that it takes tons and tons of heart to bring a new business model to life. You have to love it. You can tell when entrepreneurs love what they’re building. It’s a mistake to think that two people will have identical motives and identical drive to see the job through. And even if there is more than one person with a similar idea, that’s fine. It’s called competition. So compete!

If you’re wondering how to think publicly, start with a group of ‘friendlies’. These are people you know and trust, and who have permission to give you feedback and suggest new ways to think about the idea. For me, I either start with my mentors or my mentees, a collective of emerging founders in my private Slack channel who provide rich and rapid perspectives on ideas.

Tip: Develop a group of five friendlies who act as your early sounding board. Given them permission to help you, thank them and develop a habit of thinking publicly.

4. No Original Idea

Someone somewhere has thought of your idea and/or tried to bring it to market.

This is my underlying hypothesis for all ideas and I’m waiting for it to be invalidated.

An outcome which I’ve heard many times before, which is a by-product of identifying wrong competition, ignoring obvious competition or missing previous pioneers is this: “No one is doing what we’re doing.” 

If this is your perspective, remember this from Guy Kawasaki:

This is a bummer of a lie because there are only two logical conclusions. First, no one else is doing this because there is no market for it. Second, the entrepreneur is so clueless that he can’t even use Google to figure out he has competition. Suffice it to say that the lack of a market and cluelessness is not conducive to securing an investment. As a rule of thumb, if you have a good idea, five companies are going the same thing. If you have a great idea, fifteen companies are doing the same thing.

Tip: When you have a new idea, spend $50 doing this.

5. Network Is Essential

Networks are to entrepreneurs what force multipliers are to the military. In other words, the strength of the network often correlates with how quickly an entrepreneur can learn and move forward.

And networks aren’t just ‘business contacts’. They include mentors, friends, family, other entrepreneurs, business partners and investors, to name a few.

Entrepreneurs are weapons at networking and the best ones abide by the 51% rule as they create, grow and nurture relationships in their network. If you think sending thousands of random LinkedIn invitations is the way to go, you’ve missed the point.

6. Bet On Strengths

It’s no secret that people love doing what they’re good at. And while it might not always be practical to do what you love, there is a strong chance you’ll achieve more doing things that leverage strengths when compared to tasks that don’t.

If you overlay this idea with the value of time, it makes sense to double down on strengths and find ways (e.g. freelance talent) to manage weaknesses.

7. Infinite Learners

Entrepreneurs are infinite learners. We consume incredible volumes of blogs, books, podcasts and courses because we are genuinely interested in learning. Our brains are hardwired for curiosity. An interesting byproduct of this obsession for founders is that this knowledge becomes inevitably useful as you continue to fight fires at every turn. Reid Hoffman does an excellent job of explaining the infinite leaner psychology in this episode of his Masters of Scale podcast.

8. One > Zero

Many people have ideas. Very few do anything with them and that’s because convincing someone to buy something you’re selling is tough and getting tougher as people’s attention spans continue to shrink.

Traction starts with getting one person to act and then 10 people to act, then 100 and then 1,000 and then 10,000 and so on. It doesn’t start with 1% of a population doing something (like so many first-time founders misjudge when trying to quantify their target market).

When building a business it’s easy to forget how much fun it is to create a custom experience for the first people who engage with what you’re making. Enjoy and learn from it because there will come a time when this luxury won’t exist.

9. Set The Failure Standard

The byproduct of failure is a lesson. Lessons drive momentum. Momentum creates change.

It is as simple as this and it’s up to leaders to set the tolerance for failure. In doing so, they have two binary choices.

  1. Condemn failure, in the slightest way, and you can kiss goodbye to any implicit desire to improve and evolve.
  2. Establish behaviours that always surface and understand lesson(s) that prevent failures from being repeated.

Option two always wins.

10. Know There Is ALWAYS A Way

There is always a way. Period.

People who disagree do so for two reasons.

The first is they are tired.

The second is they are caught up in their own thinking. They usually aren’t thinking publicly. If you’re wondering what I mean, think about the last time you shared a problem with someone else and they gave you a really simple answer and for whatever reason, a weight lifted from your shoulders. Got it?

There is always a way. Entrepreneurs usually find it.



I have discovered a way to keep up with the world and it’s thanks to a guy called Tom Wharton.

The world was a busy place in 2017. The good, bad and ugly seemed to be on fast forward and I expect 2018 to be no different.

A different type of FOMO

There were many times this year when I wanted the information merry-go-round to stop. I deleted Facebook from my phone in an attempt to slow the pace of information being served at me. It helped but within a week an unexpected type of FOMO (fear of missing out) started to take hold.

I wasn’t worried about missing the endless updates from Facebook friends. And I certainly wasn’t missing the advertising.

The FOMO was connected to wisdom. I was starving for it and reading the news helped but it wasn’t enough.

As I’ve written about before, the best products and services in the world help people in one of two ways. They either move people away from fear or closer to happiness.

It's called a wrap

Tom helps move me (and people in 199 countries) move away from FOMO by writing a weekly wrap on world affairs.

It explains complex issues.

It elevates issues that I didn’t even know were issues!

Most importantly, it increases my knowledge surface area because it helps me better understand the world. Not so I can be the smartest guy in the room. So I can make better decisions to help raise my daughters, be a better husband and be more useful to those I care about.

Tom is inkl’s staff writer. In 2017 we have become colleagues and friends. And when I think about the things I am grateful for this year, making his acquaintance is certainly at the top of the list.

Here are three of his wraps which changed the game for me in 2017:

The first one…

…the second one

And the third one

Tom’s weekly wrap comes free with inkl. This is how I plan to keep up with the world again in 2018 and I hope it helps you too.

losing your way



Feeling lost as a founder happens to us all at some point.

You might be being told 'No' more than you expect after pitching new customers or investors.

You might be seeing changes in your industry and feel that pivot options are in short supply based on what you’ve built.

You might be trying to balance being a parent and/or partner with building a company and you’re fatigued and running low on answers.

It happens.

It’s part of being an entrepreneur. And no one said it would be easy.

Getting back on track relies on one simple truth

Getting back on track when you lose your way relies on understanding that people’s capacity to process information decreases as fatigue and pressure increase.

And it’s a cumulative effect.

The longer the pressure or fatigue, the lower the processing power until, eventually, it renders a person more or less paralysed. At this point it doesn’t matter how capable you think you are at problem-solving (or strategy or marketing or coding or growth hacking or leadership...), your mind becomes an echo-chamber of the same thoughts.

If this sounds familiar, you’ve probably also felt anxious, can’t sleep well, drink more caffeine, don’t feel fully present for your family or team but still think that working harder is the solution.

It doesn’t take much to see when a founder is on track to get to this place. They usually look exhausted (and they’re trying to hide it, which is impossible by the way) and they use a statement like this:

‘I’m the founder, I’ll work it out’

Yes, you are and no, you won’t.

This is a ‘brave face’ statement. It’s made by people full of pride, hoping that the answer will just present itself as long as they just keep working hard.

I’ve made this statement countless times before realising that sometimes the reality is you will lose your way. The good news is that there is a way to negotiate these times. And perhaps not surprisingly, it takes practice to move through these times because as an entrepreneur it doesn’t just happen once.

Losing your way is the result of losing perspective. Recapture it.

The steps that follow have become somewhat of a prescription over the years for me and those I mentor.

Step 1: Revisit your original inspiration

Starting a venture, for most founders, is usually a well-considered decision (and usually a step that comes after a fair bit of side-hustling and experimentation). That single decision to start is usually born from a repeated experience combined with a nagging desire to create a new order.

Whatever that experience was, the one that started you on today’s journey, find evidence of it. The first text you sent to your friend telling them you’re going to start a business, the street corner where you saw the need hiding in plain sight, or the disappointment you had when a product let you down and you thought you could do it better.

Whatever it was, find it.

It will show you how far you’ve come.

Step 2: Call your mentor

If you don’t have a mentor, get one.

If you have one, call them and ask for help by explaining how you’re feeling and how you’re framing the issues that are making you feel the way are feeling.

Be vulnerable. Tell it how it is. Mentors are a founder’s safe place because nine times out of ten, we’ve been there too! Let them hear what you’re thinking.

As difficult as it might be, pay very close attention to what they have to say. More often than not, they will be helping you break down the issues that feel insurmountable. The value they will present you is perspective.

Step 3: Sleep + Exercise. Repeat.

Get home, switch off your phone, put it anywhere that isn’t your bedroom and sleep. Wake up the next morning and exercise. Then turn your phone on.

Beyond the immediate benefits to your brain’s chemistry, you’ll become reacquainted with the world. And perspective.

Step 4: Complete a business model canvas

This one-pager (and I prefer the free one from helps ask the fundamental macro questions that are essential to any venture. The speed at which founders run and adjust often means that they will lose sight of who their target customer is, how they want to make money (compared to how to actually make money) and a suite of other fundamentals.

Get reacquainted with the business model you’re building. Not only will this show you how far you’ve come, it may also show you what changes need to be made for you to regain an even footing. Every time I’ve done this, it’s provided much-needed perspective.

Step 5: Pay it forward by helping others

‘When we help others, the focus of our mind assumes a broader horizon within which we are able to see our own petty problems in a more realistic proportion. What previously appeared to be daunting and unbearable, which is what often makes our problems so overwhelming, tends to lose its intensity.’ - Dalia Lama

On last thing...

The root causes of most things that result in a founder losing their way can be identified and managed when they have perspective.

This is a hypothesis that I’ve seen proven time and time again. This doesn’t mean that difficult decisions are made easier. It means that those decisions can be taken objectively.

Tactical, day-to-day issues will always conspire against perspective. That's why it's our job as entrepreneurs to recapture perspective as often as possible.

If you learned something new, let me know by leaving a comment below, thanks!



I leave this here as a reminder to me and to you that building a business is hard. It is the most succinct summary of thoughts and emotions that entrepreneurs can feel on any given day and it was written by Ben Horowitz, an entrepreneur turned investor, who wrote The Hard Things About Hard Things.

Ben makes it his business to mentor founders and share knowledge while investing in the world's emerging technologies.

The Struggle

The Struggle is when you wonder why you started the company in the first place.

The Struggle is when people ask you why you don’t quit and you don’t know the answer.

The Struggle is when your employees think you are lying and you think they may be right.

The Struggle is when food loses its taste.

The Struggle is when you don’t believe you should be CEO of your company. The Struggle is when you know that you are in over your head and you know that you cannot be replaced. The Struggle is when everybody thinks you are an idiot, but nobody will fire you. The Struggle is where self-doubt becomes self-hatred.

The Struggle is when you are having a conversation with someone and you can’t hear a word that they are saying because all you can hear is The Struggle.

The Struggle is when you want the pain to stop. The Struggle is unhappiness.

The Struggle is when you go on vacation to feel better and you feel worse.

The Struggle is when you are surrounded by people and you are all alone. The Struggle has no mercy.

The Struggle is the land of broken promises and crushed dreams. The Struggle is a cold sweat. The Struggle is where your guts boil so much that you feel like you are going to spit blood.

The Struggle is not failure, but it causes failure. Especially if you are weak. Always if you are weak.

Most people are not strong enough.

Every great entrepreneur from Steve Jobs to Mark Zuckerberg went through The Struggle and struggle they did, so you are not alone. But that does not mean that you will make it. You may not make it. That is why it is The Struggle.

The Struggle is where greatness comes from.


That's right, Hairy Maclary from Donaldson’s Dairy.

Most parents, grandparents, aunts and uncles know of Hairy Maclary. For the uninitiated, Hairy is a fictitious dog who lives at a dairy and embarks on adventures with his friends. Each story is playfully illustrated, written in rhythmic verse and begs the reader to deliver each page with theatrical enthusiasm.

I owe a great deal to New Zealand author Dame Lynley Dodd, the creator of this great character.

An embarrassing realisation

My introduction to Hairy Maclary took place when our eldest daughter was a small number of months old. Until that point, I had been winging it. As clumsily as one could, I had been making my way through our story time routine using stilted and stutter-filled language. It didn’t seem to matter until one day our daughter looked up at me when I tripped over a simple phrase, again and again. The look on her face said, ‘what’s wrong?’

Filled with shame, I had no response.

Through no fault of her own, this grew worse when my wife was in the room. More often than not I would defer to her incredible narration skills, born of being a voracious reader throughout her life, to deliver a far more elegant experience to our little angel. I would stay and watch in wonder as the littlest member of our family absorbed every syllable and developed her unique sense of language.

On reflection, I can trace this internal torment to my childhood. I was an awkward first child growing up in Australia’s capital in the late 1970’s. I have vivid memories of wanting to fit in and be part of the cool kids gang but when the opportunity presented to say something, to communicate my worth, I stuttered.

It became a vicious cycle and the ridicule that followed for many years afterward placed a toll on my self-confidence. For some reason, however, I knew there was a way through it, I just didn’t realise, aged five, that my course of action would have sustained unintended consequences.

I had to practice speaking out loud. What would new friends ask me? How were other children in the playground responding to one another? Which answers made sense, which didn't? Which sounded good, which didn't?

Walking around school speaking out loud to myself wasn’t about to win me new friends so I hatched a plan to reduce the likelihood of appearing to be a complete lunatic. If I wasn’t remaining silent, I would still speak but as a kind of ventriloquist. I could still hear myself speak but others wouldn’t see me speaking.

This happened many times each day, at school, at home, anywhere. The habit was fuelled by the positive feedback that my thoughts became clearer. The very significant downside was that I started to mumble. Badly. And this made me withdraw further.

At all costs, I would avoid public speaking and presentations through school, the army, my undergraduate degree, as a national athlete and the early parts of my career, particularly as the founder of my first company.

This couldn’t continue but I was clueless on how to change.

My first visit to Donaldson’s Dairy

The day I first read Hairy Maclary to our daughter and felt that shame coincided with the year I was finishing my MBA. I was well aware, through my experience in the army and triathlon, of the impact that training has on preparation, and by extension, success.

Later that evening, I took the three Hairy Maclary books we had in the house, went to laundry beneath our home and read each story out aloud over and over for hours and hours. I practiced theatrical delivery in different forms, each time imaging I was sitting in front of my daughter. I did this for months.

I noticed gradual improvements until one day, as if by adding some compound to catalyse a chemical reaction, the confidence I had been pursuing for 30 years appeared!!

Not only could I entertain my little angel at story time (with or without my wife in the room), public speaking and presentations became occasions I genuinely got excited about and looked forward to.

Dame Lynley Dodd and Hairy Maclary (and Hercules Morse as big as a horse, Bottomley Potts all covered in spots, Muffin McLay like a bundle of hay, Bitzer Maloney all skinny and boney and Schnitzel Von Krumm with a very low tum) helped me realise that change was desperately needed. I will be forever grateful.

We all have vulnerabilities

This was one of mine. And if my experience is any measure, it only takes a small, conscious step and practice to change a behaviour. For me, it started with Hairy Maclary.

How will it start with you?



Disruption comes with two inconvenient truths.

The first is that it's happening every day, in every industry, in every sector. And while you think disruption is a cliche, the reality is that if an industry hasn’t already been displaced or isn’t grappling with how to respond to new threats, it’s very likely that it lacks the self-awareness to appreciate that its future exists on borrowed time.

In the last month, I have twice presented a perspective on how disruption plays out. On both occasions, the audiences were companies who are responding to disruption. They were looking for advice on how to innovate. Instead, they were greeted with the second inconvenient truth; that failure drives innovation.

The irony, beyond showing how disruption plays out to organisations being disrupted, is that there IS time to fail and by extension, time to innovate.

And here’s the grossly obvious, frog-in-boiling-water punchline: The longer an organisation postpones decisions to refactor its core businesses, the shorter the available time it has to experiment and learn (through failure) and ultimately benefit from reinvention.

Disruption doesn't happen overnight, but it will happen.

It takes time for disruption to play out. It can decades but more recently, decades have become years. And there are usually two reasons why it takes this long.

The first is that new threats in the form of start-ups, led by enlightened industry veterans or naive entrepreneurs, need time in the market to refine their proposition so that they can deal sufficient damage to incumbent business models.

The second reason hails from the romance tied to how money has been made in the past. The human addiction to familiarity and relative stability for the ‘tried and tested’ more often than not drives decisions that favour the status quo and more importantly the misdiagnosis of threats.

This combination of sustained ambition from entrepreneurs, fuelled by vision and the size of the prize (which isn’t always financial) and slow speed of appropriate response from incumbents sets the stage for inevitable disruption. And by the time spectators feel confident to call out that a company or industry is facing disruption, the horse has already bolted.

The fascinating idea here is that incumbents were once start-ups.

There are 5 steps to industry disruption

There is an alarming precision with which these steps play out. Transportation, retail and media are the popular case study but take a moment to consider just how practical these steps are and the fact that the closer you get to the fifth step, the smaller the available time to experiment, fail and reinvent.

Step 1: Competitive response

On realising a threat has emerged, incumbents create a short term competitive response, usually price driven, to flex their market muscle. This is designed to discourage start-ups or new entrants for proceeding but this is like bringing a knife to gun fight. It never works. Not only does it provide new players with competitive intelligence on how incumbents react, it’s usually the only response they have which isn’t sustainable.

Step 2: Underestimate the full scope of disruption

“It’s just an app.” How many times do you think these words were spoken by management teams at Budget, Avis and other car rental companies when they first learned of Lyft and Uber? That romance for how money is made is also responsible for narrowing how people analyse trends, meet needs and do business. After all, their rewards are tied to delivering in the short term.

This is disastrous because it means the full breadth and depth of the pending disruption is either ignored or completely misunderstood.

Step 3: Invest in the wrong innovation

Setting up a corporate venture fund to invest in startups is in vogue. However, the hard truth about these funds is that they invest in interesting startups that aren’t likely to resolve the core issues of the parent company. In other words, these investments don’t create capabilities that the parent company can use to out-manoeuvre threats.

Step 4: Cut costs

There’s only so many times you can cut costs.    

Step 5: Look to consolidation to drive sustainability

The cumulative effect of the first four steps drives companies to the brink where the only real option for survival is joining forces with or being acquired by another company.

The Red Pill And The Blue Pill

With disruption taking place everywhere there are two options to consider.

The red pill: Discard disruption as a fad and take your chances with the five steps of industry disruption. That’s it. Good luck.

The blue pill: Accept disruption is normal and become a badass innovator. Here are the six behaviours that these people live by:

1. They value time

They know it’s the most important asset and they treat it as such.

2. They think in public

There is next to no value in an idea that no one knows about and people don’t (often) steal ideas so learn by getting your idea to people that can help you learn and evolve.

3. They experiment in short cycles

There’s something wrong if you’re not learning something new every week about what you’re building. The faster the learning cycle, the faster the progress.

4. They celebrate lessons (the byproduct of failure)

People fail. Products fail. Markets fail. That’s reality and how humans learn. Celebrate the lesson learned and be ok with the idea that failure and learning are inextricably linked.

5. They are aware of luck

Whether you like it or not, luck has a role to play in just about everything. Innovators and entrepreneurs know that. They don’t rely on it. They just know it exists and that helps when the unexpected, good or bad, happens.

6. They create air cover

It’s wrong to assume that leaders are the only source of air cover for divisions and teams. Colleagues and teammates are the primary sources of air cover and this comes in the form of having their backs while at the same time living up to high shared standards.


At the end of the day, there's no reason why you can't take the blue pill and it's also important to be aware that it's not just David's fighting Goliath's fighting it out. Start-ups are also disrupting start-ups. Game on!

If you learned something, let me know by leaving a comment. Thanks!

Founder / Family Fit

I recently shared my thoughts on company building on a new podcast hosted by Shu Das. I laud Shu’s initiative. It’s not easy to put yourself out there with the ambition to create value for others.

We had a great time and covered a lot of ground before he asked me about how I integrate family with entrepreneurship. Although this question was unexpected, I constantly think about this pursuit. And, as any parent will attest, there are few things in life more challenging than raising a family while working.

Here’s how I answered Shu’s question (scroll to 49:10 if it plays from the beginning).

And here’s the complete episode.

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Please consider tipping if you learned something (every cent goes to Soldier On).



My good friend Jo Burston asked me a question during a panel discussion for Inspiring Rare Birds last week. We were talking about mentoring as a competitive advantage to entrepreneurs.

“What is the best advice you’ve received from your mentors?”

I responded with two thoughts which are always in the back of my mind and were handed down to me by my mentors.

1. If they’re not laughing at you, you’re working on the wrong stuff.

The language used to describe the intent of this advice has morphed over time but the core idea is to accept that as entrepreneurs (and intrapreneurs) we see opportunity where other’s do not. Some ideas will be genuinely contrarian, while others will seem inspired or just plain strange.

This advice is a constant reminder that it’s OK to operate outside the bounds of established conventions and seek to create value in ways that create habits that change people’s lives for the better. You don’t have to look far in history to find the once fringe dwellers who at some point inspired change in the world.

2. This, Too, Shall Pass

This holds true no matter the situation. Difficult times ultimately don’t last forever and the same is true for purple patches. For me, this advice serves as a reminder to remain self-aware. Armed with the knowledge that this, too, shall pass adds context to situations that might ordinarily trigger a fight or flight response (tough times) or blind optimism (purple patches).

- - -

I expect all entrepreneurs to have mentors. Those who don't are operating at a disadvantage because whether you believe it or not, it is close to impossible to grow a company or build a movement without them.

I also really enjoyed the advice that Jo shared. Jo's mentor taught her to religiously ask each day "what were yesterday's sales and how much cash is in the bank?"

What’s the best advice you’ve received from your mentor?


Co-Founders Need To Be On Your Work Bucket List

A couple of times each month I see questions pop up in different forums about the ideal founding team size for new ventures.

The answers are typically framed from the point of view of a venture capital or angel investor who is (correctly) concerned about de-risking the business. Often times this will be described as an appropriate mix of quality technical and business development skillsets matched by the founders’ ability to balance workload and deliver on a hiring plan to match growth ambitions.

There are those that say ventures can have a single founder (that was me once) and the same people, including Fred Wilson at Union Square Ventures, note that it can be done but it’s a lonely existence. Experience tells me that the optimal number of founders in a new venture is three but it turns out that this is (at best) a second order consideration. The primary consideration is who your co-founders should be.

Your future co-founders must be on your work bucket list.

That's the bottom line.

My work bucket list is a very short list of (at the moment) eight people who I would love to work with before it’s too late. Whether through an existing relationship or via their own admission (because I only know half of my bucket list personally), each person:

  • Is insanely curious
  • Uses empathy and compassion to lead
  • Is at the top of their game
  • Has a great sense of humour
  • Loves learning

Gautam and Opher were on my work bucket list when I formed AirShr because they each have these qualities in spades.

But here’s the thing, the true awesomeness of these guys has really only been revealed when the going has gotten tough like when pressure mounts because raising capital is taking longer than expected or life is a bit overwhelming because you haven’t slept properly in two years.

This all might seem obvious but it seems to me that when founders are out seeking partners they tend to lead with a function-first approach (i.e. I need a chief technology officer or a VP business development). In doing so their first step is to look at a candidate’s ‘on-paper’ track record and give little consideration to qualities that really matter, particularly when the going gets tough.

If you haven’t done this before, perhaps give some thought to your work bucket list and why people would earn the right to be on your list.

I don’t know when and I don’t know how but I also look forward to one day working with Jeff Weiner and Emily Ma.

Now you know half of my work bucket list. Who’s on yours?



There are countless references to ‘the roller coaster’ of emotions felt by entrepreneurs (and by association their family and friends). The analogy of the rollercoaster is an attempt to describe the speed and amplitude with which situations can change and, given the situation, how much more or less likely you are to achieving you venture’s next milestone.

It’s not until committing to a venture full-time that it becomes clear that roller coaster actually means making continuous decisions in overwhelming and chaotic environments where the future is deeply uncertain.

Effective decision making relies on the capacity to process information. And everyone has a threshold up to which they can efficiently process information, even the most decisive leaders. Pilots refer to the distance between this threshold and relatively normal situations as ‘spare capacity’ (to cope with the unforeseen or unexpected). Spare capacity becomes compromised as the need to resolve multiple interlinked decisions increases. When spare capacity runs out stress and anxiety can make even the most elementary tasks impossible to conquer.

Founding or co-founding a venture inevitably means people are covering multiple roles, acting on imperfect information and driving urgently to get, keep and grow customers to demonstrate traction before running out of cash. The 100-hour weeks that this typically demands creates an ideal setting to erode spare capacity.

I could say that there are ways to avoid the roller coaster altogether or quarantine spare capacity for the times that you really need it but that would be untrue.

The reality is that the unforeseen and unexpected, both good and bad, will happen most days. It’s what you sign up for when you opt-in to building something from nothing.

Here’s what I do and encourage my mentees to do to reduce the roller coaster effect:

1. Open your calendar and count the number of days since your last small win.

One of the greatest risks to a founder is the narrowing of their contextual awareness. That is to say that focus to achieve the next big milestone can often be at the expense of celebrating progress and reflecting on learnings. Often founders are closer than they think to achieving their next milestone but when spare capacity is in short supply maintaining a balanced view on the state of the venture is difficult so take the step to count (out loud!) when your last small win took place. Prepare to be reminded that it was more recent than you thought.

2. Go one step beyond a mentor, have an entrepreneur buddy.

I have both and a couple in each camp because these two groups play different roles. An entrepreneur buddy is someone who’s been a founder before or is at a similar stage to you and whom has empathy and compassion for your circumstance(s). Call them and vent. And don’t worry, they’ll return the favour soon enough. Sometimes it takes someone who’s been there before to help navigate through complexity.

3. Exercise. 

There is an enormous body of medical and psychological research that points to the positive effects that exercise has on brain chemistry. Help your brain perform at a new level by incorporating exercise at least once every two days.

4. Take time to think about a pet project.

At the risk of drawing criticism for not insisting you direct 150% focus towards your venture, be OK with thinking about other ideas that have piqued your interest. I’m not advocating for this to be a distraction, what I’m encouraging is to grant yourself permission to periodically think about ideas that free up creative mental horsepower, the exact ingredient that is likely to help you solve issues at your venture.

So, Is it easier for serial entrepreneurs?

To some extent, yes. There is benefit in relying on experience to help regulate the emotions and fatigue brought on by the roller coaster but no first-time or serial entrepreneur is immune to its effects. I say that after having one of those weeks.



Am I ready for start-up?

People asking this question have usually been thinking about it for a while. They are looking for validation, one way or the other, that they are going to make the right decision.

People in this situation are, quite reasonably, worried about change in income and lifestyle, the opportunity cost of not progressing along their existing career trajectory and the uncertainty of the outcome. The fear of the unknown and failure mixed with the exhilaration of creating a new order makes these considerations more complicated.

The irony about the level of emotional effort invested in considering the move to start-up is that a) it’s framed incorrectly; and b) makes soon-to-be first-time founders lose sight of what they’ll actually be doing in a startup (as if it will all become clear after the decision to move to start-up has been made).

Gone are the days where a company has to be incorporated in order to see if an idea is going to work. The reason people still do this (and engage lawyers and accountants and rent office space) is because these are the things they can instigate and control. It makes them feel as though they’re making progress. This is the wrong way to frame the decision to move to a startup because zero evidence exists that the idea has potential.

The right way to frame the decision is to put a hypothesis to the test quickly and cheaply to learn as much as possible. There are many ways to do this and most begin with a business model canvas and easy to establish experiments. The bottom line: Learn in safety before introducing risk.

At this point if you’re a soon-to-be first-time founder you’re probably thinking one of two things:

“Yes, that makes sense, I plan to learn in safety before introducing risk. I’m not entirely sure how but, yes, that’s my plan”. This is the blue pill. If you’re in this camp, your odds of success just went up a few points.


“Yeah, yeah, I’ll be fine, I back myself”. This is the red pill and this is how it usually plays out:

  • You either have your idea perfectly mapped out in your mind (good luck with that) or have a long but well-formatted business plan that you’ve been angsting over for a while, it contains language that’s somewhat vague but it’s comforting knowing there’s words on the page, even if they only make sense to you; OR
  • You’re reluctant to send it to anyone because of the intellectual property it contains; OR
  • Your first moves to start your entrepreneurial journey have involved doing things you can control (like hiring an accountant to incorporate a company or engaging a lawyer to start drafting patent applications); OR
  • You’re aware that there are mountains of learnings from founders and VCs online but you’ll get to them later.

Thinking this way has significantly increased the risk of your idea failing. This was me in my first venture and this thinking very nearly bankrupted me financially and emotionally.

So how do you know when the time is right to start a new venture or jump into a start-up full-time?

The answer is when you have conviction and evidence that your idea has real potential and when you’re ready to hustle like never before.


Conviction isn’t blind faith. It’s the capacity to be stubborn on vision and flexible on details and it’s essential. Conviction only gets more powerful when mixed with a thirst for continuous learning and ability to adapt. Collectively, these behaviours are the best armour against the invariable onslaught of setbacks that face every entrepreneur, the base layer of which is conviction.

Think back to a time where you overcame the odds to succeed. At the heart of that effort was conviction.

Take the red pill and conviction will take you a long way but only so far.


Your mission is to prove that your idea has real potential to be an easily addictive convenience for people you don’t know (at all). The ‘what if’ around amassing evidence usually stops soon-to-be, first-time founders in their tracks.

What if no-one likes my idea? Yep, it’s possible but celebrate knowing that if well tested, you’ve not wasted time (your MOST valuable asset) on taking the idea forward. Move onto the next idea.

Alternatively, what if people like my idea? It’s a good problem to have, evolve the experiments to continue validating your hypothesis and start exploring how to gather resources to get version one of the product into the hands of customers.

‘Get out of the building’ is a suggestion often made to soon-to-be, first-time founders. It means to get feedback and evidence to back an idea. Nothing beats seeing how someone responds to your idea, one-on-one and face to face. Where that’s not possible I use

Take the red pill and you’ll be a rely-on-instinct, personal experience and desk research kind of person.

Getting a feeling for how the red pills play out…?


To hustle means to capitalise on opportunity. Practically it also means acting on ‘you don’t ask, you don’t get’, knowing that when you’re told no, it means no at that point in time and being aware that there is always another option, another way, to solving an issue.

As a founder hustling is part of everyday and it goes well beyond selling. You hustle in developing partnerships, raising capital, corralling resources, hiring – everything. And it goes without saying that there is an authentic and an inauthentic way to hustle. The authentic hustler listens, exercises empathy and reads the play well in most if not all situations which allows them to know when and how to push for the outcome their team and venture needs.

The inauthentic hustler, the ones often associated with used car salesmen, is the direct opposite. They fail.

Hustling is essential for one simple reason. You don’t have resources you need and hustling helps you get them. Make no mistake, having your hustle on continuously is tiring BUT here’s the thing: Being an always-on, authentic hustler helps you create your own luck because you make that last meeting that others wouldn’t, you send that well-crafted InMail to create a new LinkedIn relationship, you deliver your pitch one more time and you engage (at your most tired) with a stranger interested in your idea at a startup expo.

The bottom line is that being an authentic hustler pays.

Conviction, evidence and hustle are as essential as the need to, as Fred Wilson said recently, take risks, work hard and get lucky. At the end of the day, start with the end in mind and take the blue pill.



Before pitch decks, product prototypes, marketing plans, company registrations or investors there is an intoxicating moment when you wholeheartedly believe an idea has game-changing merit.

The inevitable need to collaborate inspires conversations with people who complement your skills and share your excitement and vision. After what seems like countless late night Skype calls and the exchanging of ideas and business models, prospective co-founders begin to emerge from your list of friends and classmates.

It’s important to be real about what’s happening here. It’s one thing to share your vision as a means to solicit feedback, it’s quite another to engage with a friend or classmate on the basis that they may, sometime in the future, become your partner. The exchanging of ideas and business models during those copious Skype calls is helping you perform due diligence on them as a prospective partner. And they are doing the same with you.

This process usually adds a new dimension of trust and respect to the relationship which will prove essential if you collectively agree to pursue the vision. Equally, this process will also help determine early on whether a partnership is not going to productive.

Are they co-founder material?

It’s relatively easy to work out of if someone is well suited to being a partner. The reality is that achievements during their work history will tell you a lot about the quality and complementarity of their skills. And the all important capacity for industriousness and humour will become self-evident from working up the business model on Skype. The other essential ingredient in a partnership is trust and respect. If through the back and forward of Skype calls and the exchange of ideas your spider senses tingle because you’re detecting a lack of trust or respect, end the prospective co-founder conversation. Instinct usually prevails and you can almost guarantee that these behaviours will amplify when the going gets tough, and it will.

Combine these factors with your pre-venture relationship and you’ll quickly arrive at a decision about entering into a partnership. Using this approach made it a no-brainer to start AirShr with Opher and Gautam because they tick every box (and then some!). Remember that finding the right partner isn’t trivial and that’s why this activity is more or less an audition. And that’s OK because you might not find the right partner(s) immediately. It requires the seriously brilliant partners to create a great company. Don’t settle, keep looking if you need to.

Three events place your new venture at risk from day one.

No matter how much you think you’re in control, start-up chaos begins the day you and your new co-founders start working to validate your business model. This chaos can affect people in different ways and when you boil down the reasons why founding teams don’t survive the early stages of company building, it’s typically because a founder:

  1. discontinues their involvement due to personal circumstances; or
  2. discontinues their involvement due to a breach of an obligation or has irreconcilable differences with the other founder(s); or
  3. has been unable to perform duties due to prolonged ill health (or death).

Assume one of these scenarios will play out.

Be ready — In plain English.

The first step that co-founders need to take before starting to validate any business model is agreeing on the expectations they have of one another in plain English both operationally and in the face of the above scenarios.

Standard long-form shareholder agreements may address these issues but if you’re validating a business model, why would you already be incorporated (and therefore have a shareholder agreement)? In other words, you haven’t determined if there is value in the business model so spending money on forming a company, at this stage, is overkill and does nothing to help achieve traction.

Instead, use this.

This is the agreement we first used at AirShr and it served us well. It’s practical and easy to understand, sufficiently comprehensive to meet all early stage circumstances and its terms are transferable to long-form shareholder agreements at the appropriate time.

Many first-time founders have benefited from using this agreement and I hope it’s useful to you too.

Thanks also to Stephane Chatonsky, my venture capital professor at business school, for helping to create this document.


Purpose unlocks potential.

The evidence is anywhere you see people with a clear sense of resolve or determination. For these people, a weight has lifted from their shoulders because instead of trying to work out how they fit in the world, they can focus on optimising and being the best at their craft.

If you’ve discovered your purpose you know the feeling. It’s incredible!

If you haven’t, discovering your purpose isn’t as elusive as you think. It comes down to two clues, both of which hide in plain sight for most of us.

Let’s rewind. For years I felt lost. And there are few things more frustrating than knowing you have much to offer the world but remaining clueless about how to put that energy to good use.

Knowing what I know now, I’ve always been an entrepreneur. I started my first venture aged 10, organising kids in the neighbourhood (and ‘borrowing’ their parent’s gardening tools) to convince neighbours to pay $20 to ‘fix’ their garden. The model was simple. We spent about an hour tidying up the garden (and working out how to use the tools we had acquired) before moving on to the next house. All the money we made was split equally among the posse of kids who worked. Of course, at such an early age financial gain wasn't sufficient to the maintain the team’s interest and the model proved unsustainable.

When I put Reid’s advice and that of my daughter’s school principal to the test, this story served as early evidence of my purpose.

Clue 1: Where Your Mind Wanders When You ‘Zone-Out’

This clue is all about the themes you think about when you have a moment to yourself. Take a moment to be mindful. Where did your mind go when you zoned-out the last five or ten times?

There is a strong chance that thematic consistency connects each of these ‘zone-out’ events. These themes are important because this is your mind taking you to a place of natural curiosity and interest. Imagine if your mind could spend a lot of time there?

This clue, via Reid, is THE essential first step.

For me, my mind naturally goes to ‘what if we could…’, and business models and extends to the fascination of how we (as founders) can bring ideas to life that create habits to change the world and the lives of many.

Side Note — If the answer to the questions above is ‘lying on a beach’, ‘visiting the snow’ or ‘taking a year off to travel’, you need a vacation so take one! Don’t mistake your zone-out thoughts for where you would rather be at that particular point in time.

Clue 2: Your Heart Song

This beautiful phase comes from my daughter’s school principal. You know your heart is singing when you’re thinking or talking about a topic that makes your eyes light up, makes you stand a little taller and takes you closer to being the best version of yourself.

When was the last time you sang your heart song?

It won’t surprise you to know that thematic consistency usually connects each of these events too. Make a note of when this happens and the topic. It happened to me just yesterday as I talked product and market entry with the amazing Rhonda Brighton-Hall and the team at MWAH.

Next, Examine The Overlap.

Take the themes arising from where your mind wonders and when your heart sings.

Purpose can be found where these themes overlap.

It might reveal the unexpected. It might be confronting. It might challenge your lifestyle or the investment you’ve made in your career and education to date. However, if you discover your purpose a weight will lift from your shoulders. And now, instead of trying to determine how you fit in the world, you can focus on optimising and being the best in a potentially different craft.

So as you reflect on the year that was and perhaps your purpose, I hope these two clues help provide you with the same potent clarity I enjoy.