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.

I'm joining inkl!

Today I’m hugely excited to announce that I’m joining Gautam Mishra at inkl as the Senior Vice President of Business Development. I’m charged with generating revenue across inkl’s news and payments products around the world.

I’ve been fortunate to gain an intimate understanding of this revolutionary venture before accepting this role. In co-leading inkl’s recent financing, I’ve had a unique opportunity to pitch this business to investors around the world and more importantly, understand Gautam’s vision.

Take a moment to think about the volume of information we consume each day. It’s never been higher and whether we comprehend it or not, consciously and subconsciously, it drives the decisions we make.

Fake and sensational information in news is as unhelpful as the way online information and content is currently valued. And as a father and leader I want my children and people around the world to access information which affords them the opportunity to make well-informed decisions.

Inkl’s vision is to create the infrastructure for a new value exchange for online information and content. And the opportunity and positive implications of delivering on this vision are incredibly significant.

This is a major reason I’m bringing 110% to inkl. It’s also a wonderful chance to work shoulder-to-should with some of the best minds in technology, product and journalism that the world has to offer.

So if you want a better information diet, get inkl. And if you write on WordPress, learn about inklPay. These two products are just the beginning so if you’d like to know more, please reach out.

Time to get back to work.


Here’s the punchline: The single most important action you need to take to avoid turning your partner into an entrepreneur’s widow(er) is to over-communicate with them.

This principle is remarkably simple but at first, it might seem counter-intuitive. You might think that entrepreneurs are somehow naturally gifted communicators given the constant practice they have at pitching and selling.

Well, looks can be deceiving. 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 strategise a way thought 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?

Read more



If by reading the title you thought: “We’re different, these near-death things won’t happen to us”, that’s hope talking and it’s time to stop kidding yourself.

1. A key team member will leave unexpectedly

This will be a dark day whether you see it coming or not. And the darkness will be dialled up if the person leaving carries a disproportionate load of one discipline in the company.

The common story here is the CTO moving on and leaving the non-technical co-founder(s) flailing. The same is also true if the business development founder leaves and all that remains is the technical lead.

Speaking from experience, the stress on the day this happens (and days following) is immense.

What will the team think?

What will I tell investors?

What does that mean for traction? 😳 …

Here’s the good news; the age-old adage that “everyone is replaceable” is true. It may take weeks or months to make the replacement but it’s completely doable.

How to minimise fallout:

The immediate action is to negotiate a handover (if possible) and communicate the departure to the team as quickly as you can. Rumours help no one.

Step two is to maintain continuity of mission critical tech with other team members or freelancers until a replacement is found.

Then use this experience as a catalyst to get off your ass and level up your approach to talent. This includes having processes and procedures in place to central store code and other important intellectual property. And from the very, very beginning of each relationship at the company form an alliance with every team member including co-founders.

Proceed without individual alliances at your own peril.

2. Your runway will come within inches of ending

We’ve all been here. But the reality is that you should know months in advance if your burn rate will end in disaster.

However, if your runway is perilously close to ending you’ll need to think seriously about ‘putting everything on ice’ (read: letting your team go) while you get the house in order.

This option will keep you awake at night because you’re responsible for feeding team members and their families. It’s also an option because there will be alternatives like bridge finance from investors, bringing on new investors or on-boarding new customers.

Your mission is to keep the lights on. If that unfortunately means the team needs to move on and the founders need to get paid work elsewhere while continuing to build the company, that’s also an option.

This conundrum is universal to business and it’s tough but rest assured, it won’t happen once, it’ll happen a number of times.

How to minimise fallout:

No one likes surprises in business so maintain regular, high-candour communications with you team and investors about traction and runway. And ensure this is a conversation. It’s essential that founders understand and respond to the concerns of team members, even if they don’t have all the answers.

It’s also important to remember that team members will be trusting founders to navigate through adversity. If it comes to moving team members on, founders should take a leading role in creating conversations and opportunities for each team members’ next play.

3. A cornerstone customer will cancel their contract

This is a bitter blow. This might also feel at the time like it’s game over.

As difficult as it might be, do whatever it takes to understand the dynamic that led to the customer’s decision and what role your team played and could have played differently.

How to minimise fallout:

  1. Rush to understand and document the learnings from engaging with the customer. This includes each milestone that was achieved and each issue that may have led to contract cancellation
  2. Feed ☝ knowledge straight into product and business development team members to help fine-tune the proposition
  3. Try to renegotiate different terms as a means to recover the contract
  4. Report this event to shareholders with a plan to navigate through the uncertainty which they can weigh in on and evolve with you — they are there to help.

4. Key infrastructure that supports your product(s) will fail

It’s bad enough when your website or service goes down. You shouldn’t be left to find out about it from a user.

Always be on the front foot and set up alerts for each online product that you use so you can be ready to proactively reach out to users when the shit hits the fan.

Don’t pretend they won’t notice. They will.

This is as simple as following the support twitter accounts of services you use and making sure notification alerts are turned on (e.g SquareSpace Help if you use them). You can then use insight from these alerts to drive your responses to users. Or it might involve a service like StatusPage which helps you communicate updates on issues directly to people’s inboxes.

How to minimise fallout:

It’s pretty simple. Communicate proactively and consistently until the issue is resolved.

5. A competitor will appear (and freak out your team)

Competitors validate market opportunities. They also force marketplaces to become more efficient. These are the words of a rational person.

Try telling that to a fledgling team who are emotionally tied to their product, fatigued by working 100-hour weeks and who think they are the first to see and capitalise on an opportunity.

This happened at AirShr as we designed a bluetooth button for an in-car use case. When news broke about the Amazon dash button (below) our email went nuts. 

The majority of emails included a link to a press release from people who developed an instant anxiety about AirShr’s future due to Amazon’s new product.

As we moved beyond the headline and image and read the press release, it became clear that there wasn’t a overlap.

How to minimise fallout:

Determine if there is in fact competition.

  • IF competition equals no, THEN keep pursuing the vision.
  • IF competition equals yes, THEN keep pursuing the vision.

There is next to zero chance that your company is an isolated first-mover and even if you are, expect competition because it’s already on its way.

And before you think there’s a typo in the second IF THEN statement, remember that copying another company’s value proposition will, at best, result in price-based competition and that rarely ends well.

6. Pursuing ‘interesting scale opportunities’ will compromise the core product

Distraction kills. This is as true for texting while driving as it is when building a company. Founders of early stage ventures are exposed to countless suggestions that promise the discovery of product / market fit and scale.

Without a discipline to design, deploy and assess experiments that drive this discovery, valuable time and resources get chewed up, often with very little return on investment. And before long, the core thesis and product gets neglected in favour of ‘interesting opportunities’ to grow.

Less about minimising fallout, more about focus from the outset:

  1. Remind your team to continually ask: ‘Does this activity help us validate [insert core hypothesis]’. If the answer is NO, kill it and move on.
  2. Monitor metrics that reveal the true health of your core product. These aren’t measures only accessible by running a database query that focus only on cohort size or active usage. They are metrics that are one click away and show breadth and depth of revenue, engagement and growth over time.
  3. Share the initiatives you’re pursuing with advisors as a sense-check and listen to their feedback. Given their relationship with you they are likely to call you out on efforts that seem counter-productive.

7. Pivoting a business model will take longer than expected

To ‘pivot’ means to pursue a vision using an alternate strategy. This is simple to say and relies on founders having space to properly reflect on progress and assess pivot options.

The reality is very different.

Pivoting usually happens after the market has responded unfavourably to a version of the product. The almost taboo issue at play in these circumstances is that the organisation has been geared towards a specific strategy for many weeks, months and potentially years. Moving to a different strategy amidst a decreasing supply of capital, increased pressure to achieve traction and fatigue clouds clear decision-making.

The bottom line is that pivoting takes time.

How to minimise fallout:

Ask your team to embrace the idea of pivoting. Give them and yourself a few days to decompress and reflect away from the office. In the meantime, open conversations with advisors and investors to increase your perspective on the situation.

Although early-stage investors and advisors don’t like surprises, there’s a good chance they’ve seen similar situations before. And don’t worry about asking for their perspective and support. They are also incentivised to help you navigate through tricky issues. Remember, you’re not expected to have all the answers all of the time, just most of the time 😉.


Every business has its own language. It’s a mashup of people's past experiences, desire to contribute or a need to exert authority.

In most cases, team members communicate with a clear intent to move their organisation forward. In doing so they look to their CEO or founding team members to calibrate their communication style.

This subconscious exercise takes cues from the tones used in emails to gestures seen in stand-ups to the emoji’s used in Slack. And this is an ongoing process. These recalibration events can occur many times a day as teams focus on iterating quickly in the pursuit of product/market fit.

Unfortunately, a high level of team interaction isn’t a proxy for clarity of mission. In fact, rapid iteration often exposes more questions than it does answers and the reality is team members look to their leaders for clarity (whether they have it or not).

If they don’t have the answers or more importantly a strategy to guide their team through the uncertainty, a leadership vacuum inevitability appears. In these circumstances, it’s not uncommon for team members to project their past experiences into the vacuum as a means to help stabilise the conversation and regain momentum.

I’ve often seen these past experiences manifest as three statements and it’s important to understand why their inadvertent use is potentially destructive.

The first reason is that these statements tend to generate more uncertainty.

And the second is that if these statements become re-used in periods of uncertainty, it becomes more likely that the team will begin using them more liberally or by default in other conversations.

If you’re in a startup more uncertainty is the last thing you need so keep an ear open for statements that begin with…

1. “If we believe…”

There are few statements more destabilising than those which open with “If we believe…” because it contains a troubling undertone of uncertainty.

The very nature of this statement questions the belief system of the team. And whilst the intent is usually positive and designed to elevate the team’s thinking back into the macro, it often precipitates questions which are equally difficult to answer.

The reality is that by the time a product or sales team is sitting in the office they’ve already bought into a belief system around the customer pain-point they are there to solve.

So it’s not about if you believe.

You already believe! You’re sitting around the table!

You just need to negotiate the product or sales challenge that’s in front of you at the moment.

What’s an alternative?

When a team strikes uncertainty try reconnecting them with the experience you’re trying create for someone in your target market.Try briefly discussing how the immediate challenge fits with the company vision and mission. This anchors the team back to purpose and provides perspective on the size of the issue.

Try briefly discussing how the immediate challenge fits with the company vision and mission. This anchors the team back to purpose and provides perspective on the size of the issue.I’ve seen this approach help teams realise that the challenge they were trying to solve was far smaller than first thought. And when more material issues are at play, a reconnection with the big picture has made an issue much more negotiable.

I’ve seen this approach help teams realise that the challenge they were trying to solve was far smaller than first thought. And when more material issues are at play, a reconnection with the big picture has made an issue much more negotiable.

2. “It would be useful if…”

The activity-generating potential of statements that start with this is enormous (and not in a good way). This is because these statements are often opaque information requests that may or may not serve as an input to a future decision.In an effort to gather and make sense of data to support these types of requests, a significant amount of effort and energy can be consumed with little or no payback, not to mention the impact on

In an effort to gather and make sense of data to support these types of requests, a significant amount of effort and energy can be consumed with little or no payback, not to mention the impact on morale of those chasing the answers to ground.

The reality is that it’s up to leaders to be mindful of the effort that can be consumed on opaque requests. Team members can also shortcut these situations by digging a little deeperto understand the request in order to add value.

What’s an alternative?

If you’re a leader who’s contemplating “it would be interesting if…”, reframe it to include the decision you’d like to make. If you can’t articulate why you need the information, hold back from asking until you know.

If you’re on the catching end of a vague information request, share that you’re keen to help nail the request and that by knowing more about the decision, you’ll be able to gather the needed data more efficiently.

3. “From [X]’s perspective…”

If you’ve ever been part of a conversation that starts with “From a [customer / user / supplier]’s perspective…” and ends with vague or confusing observations, this will resonate.

Solving a person’s pain point IS the main game. HOWEVER it’s one thing to make data-driven product and marketing decisions. It's quite another to rely on a vague recollection of insights to make the same calls. The challenge with the latter is that people’s recall is generally poor and when it fails, it often becomes supplemented with people’s own experiences. And this leads to a distraction as the team reorients to solve a different (and unjustified) intent.

What’s an alternative?

The only way to make a compelling statement on behalf a customer, user or supplier is to have corroborating evidence. So the next time someone starts a statement with “From a [X]’s perspective…” ask for the data that supports the point of view and avoid making decisions without it.

Closing thought

There’s little doubt that these statements bring value when testing hypotheses, designing business models and evolving strategy. Outside of these

Outside of these times, their nearly random use creates uncertainty. Don’t underestimate the latent impact this has on your team.

golden rule


People nod in agreement when they hear this rule. It’s because the underlying notion is obvious. In fact, it’s almost expected that people follow this rule to the letter.

But of all the things you need to focus on as a founder — shipping product, generating revenue, managing capital, hiring talent and forging partnerships — this rule is much more difficult to consistently live by.

And it’s difficult for two reasons. The first is that founders are busy and as much as that’s true, it’s a small part of the equation. The second reason relates to the psychology of communicating company progress.

I can tell you from experience that communicating the status of a company involves continuously resolving a mix of competing priorities, the desire to maintain the positive trajectory of their company story, the fear of communicating ‘bad’ news and to some extent, procrastination.

All of this while ensuring that the golden rule is never broken.

golden rule

The intent of this rule is to preserve transparency on strategy and operations. To investors, this means regularly communicating with high-level candour to the people who have a vested interest in your success.

It’s not rocket science. For the most part, this means sending a quarterly email that provides updates on milestones and progress relating to:

  1. Product Development
  2. Sales and Distribution
  3. Partnerships
  4. Capital and Runway
  5. Team and Hiring
  6. Issues and Risks
  7. 3-Month Activity Forecast

This isn’t fancy, it’s an email using Arial font, basic headings and bullet points. And a distilled version of these messages should also be shared with teams, key partners and suppliers because they’ve also bought into helping build your vision. This approach helps avoid this type of question:

“Why am I only finding out about this now?”

If you’re on the receiving end of this question, there’s a good chance you’ve broken the golden rule. And here’s the thing, there’s no reason to be in this position.

In the last decade enough companies have been founded and invested in (and lessons learned and documented) that founders should know what’s expected of them and if they don’t, investors should set that tone.

I’m still surprised when I learn of founders who don’t just break the golden rule but smash it into a million pieces by acting in ways that leave team members and investors unexpectedly scrambling to save a venture. These events damage reputations, sometimes irreparably, and are completely avoidable.

When a founder confides that they’re experiencing challenges in communicating the progress of their company I offer this advice.

In response to: “I need to keep this story positive”

Positive momentum is important but there is no place on earth where a company story is only ever positive. In fact, people grow suspicious when the story is only ever positive.

Investors and entrepreneurs understand that solving big problems involves riding a rollercoaster of wins and setbacks so communicate them regularly in the context of the company mission and strategy. It’s part of the journey.

In response to: “I’ll get around to writing the update”

Bad idea. Just do it and then stick to a quarterly update tempo. At the speed at which circumstances change in startups, a lot can happen in a short time and the longer you procrastinate, the more you’ll need to explain.

This might not seem like a big deal when times are good but that will inevitably change. When it does and you’re left having to explain a series of potentially complex and interconnected events, you may come close to breaking the golden rule. It’s avoidable, so avoid it.

In response to: “But it’s hard delivering bad news”

Yes, it is. It sucks and no-one likes doing it. It also goes without saying that delivering difficult news in a forthright and productive manner is an essential leadership skill and one that gets better with practice.

It’s natural to think that people will be upset on receiving bad news. But what makes the situation worse is a lack of context for why the situation went from normal to ‘bad’.

The clearer people are on context, the more prepared they are to work through challenges with you.

Closing thought

I think about maintaining the golden rule as being as much about respect as it is strengthening trust with allies. Respect and trust with allies is a potent combination. Without them, you’ve got nothing.

It’s Never Been More Important To Ask ‘Why?’ 5 Times

We have a BIG problem.

It affects just about every facet of our lives, from the ideas we foster, to the family we love, to companies we build and to the stories we tell.

We’re losing our grip on the importance of context.

That’s the punchline. And here’s the background.

The circumstances that form the setting for an event (i.e. context) are essential to how we make decisions that affect our family, our teams and many others, in some cases the lives of millions of people. Unfortunately, context gets lost and can disappear altogether when our attention is diverted from diving deeper into an important topic at hand. And it’s easy to add colour to this issue. In 2015 a study conducted by Microsoft’s Consumer Insights division identified that digitalised lifestyles have contributed to the diminishing attention span of humans from 12 seconds to 8 seconds.

Today, nearly two years on, the fight to gain our attention even for a second is fierce. Each day we’re bombarded with ‘headlines’ that feature in news, social media, powerpoint presentations and even in stories told by a friend or family member. Some we believe, some are confusing and some defy belief (and there have been plenty of those lately!).

So what happens when people move away from understanding context and begin scanning and accepting ‘headlines’ as reality?

The answer is many things, none of them good.

And it happens A LOT.

But here’s the good news, there’s a simple way to reconnect with context…

Ask ‘why?’ 5 times.

If this suggestion conjures up a vague link to a motor vehicle you’re on the right track. The idea of asking ‘why?’ five times originated in the 1950’s from the pioneer of the Toyota Production System, Taiichi Ohno. This guy is also considered the grandfather of continuous improvement. Whenever an issue cropped up he encouraged his team to explore problems first-hand until the root causes were found.

“Observe the production floor without preconceptions,” he would advise. “Ask ‘why’ five times about every matter.”

This is powerful for one simple reason: Each time you ask ‘why?’ more surfaces about the circumstances that form the setting for an event (i.e. context). And this leads to a clear understanding of the root cause.

Use it anytime but especially when your spider senses tingle.

Asking ‘why?’ 5 times is very useful when something is counter-intuitive or confusing. And while you can do this easily, you should also encourage your team (in particular new hires) to do the same to you. It will help them achieve a similar, if not equal, level of contextual understanding as your own and it might also expose chinks in logic that until this point have been hiding in plain sight.

There have been a number of times when I’ve been asked ‘why?’ 5 times and on the fourth or fifth ‘why’ I’ve had no other option but to say ‘I really don’t know’. This admission has often turned out to be the beginning of very product collaborations because those involved can now start pursuing an opportunity based on shared understanding.

I ask ‘why?’ 5 times:

  • In product development and sales conversations
  • When I learn about Trump’s latest executive order
  • As I forged partnerships at AirShr and today, at Inkl
  • When I learn about Trump’s latest latest executive order
  • In mentoring founders
  • When I learn about Trump’s latest latest… (ok, you get the point)

Knowledge and wisdom do not exist without context. If you feel as though you’ve become good at skimming ‘headlines’ but still feel uninformed, try asking ‘why?’ 5 times and get the context and answers you need. You’ll be surprised at what you learn.



Setbacks come thick and fast in startups.

They can range from minor delays in product development to major issues when key people leave or large customers move on.

At the heart of each setback is an ugly mashup of angst and uncertainty.

The larger the setback, the greater the angst and uncertainty.

In any case and no matter their size, setbacks destabilise teams and the big and unexpected ones can paralyse a young venture.

There’s only one productive way to communicate setbacks

For the most part, experience plays a large role in managing setbacks. The more you see it, the easier it is to manage.

But there are times when large and unexpected setbacks can catch even the most experienced operators off guard. Answers aren’t (usually) immediately obvious in these situations and the pressure on founders increases quickly when teams expect their leaders to have some, if not all, the answers.

Here’s the thing. Unlike wine, angst and uncertainty don’t age well with time.

And I cannot tell you the number of times I have been faced with the frustrating irony that I need more time to discover a path forward. If like me you were born impatient, this situation is particularly testing because as a leader you feel like it’s your job to have answers for your team.

You have three options at times like this:

  1. Present an answer to your team that creates certainty based on what you hope will happen (Pro Tip: Hope isn’t a tactic), or
  2. Say you don’t know what’s going to happen and tell the team you’ll get back to them (which might inspire them to embrace your honesty but it might equally end up costing you credibility), or
  3. Talk with your team about the setback!

I can assure you that the third option is by far the best and here are the three steps I follow to communicate setbacks with teams as soon as possible after they happen.

1. Reintroduce context

In the cut and thrust of building a business, it’s easier than people realise to forget about what attracted them to work together in the first place.

And when stress-induced angst and uncertainty hit a team, they can become myopic and lose sight of the big picture and how much has been achieved.

So open the conversation by reminding them of their collective purpose and how far they’ve come. In these situations, I work hard to position messages in such a way that makes team member’s smile as they reflect on the journey to date.

2. Present the news

The next step is to objectively introduce the events that have led to this conversation. It could be the reasons why a key team member has decided to depart or the change in circumstance that led to the end of a business partnership. Make this a candid and high-level explanation.

Then, present the news.

3. Talk scenarios

There are usually 3–5 scenarios that can play out off the back of any setback.

It’s up to the CEO or founders to come up with, present and discuss the first draft of each scenario with the team.

This part of the conversation lays the groundwork for a path forward and invites engagement from the team to evolve existing scenarios or introduce new ones.

This is THE most important step in short-circuiting angst and uncertainty and in my experience, it’s this step that team members appreciate the most.

The bottom line is that can setback hurt. A lot.

As each setback becomes known always remind the team that they are the same collective of talented and resilient people they were the day before the setback happened. And they will be those same people tomorrow and the next day and the day after that.

The reason this approach works is that it acknowledges team members can sense and be affected by the same angst and uncertainty felt by their leaders.

Facing into setbacks using this approach has been very useful in the past. I hope it’s a big help to you too.

One Sleep Decision That Made Me a Better Entrepreneur

In the early days of a new venture and for some years afterward founders cover every base from building product to selling to hiring and everything in between. And there’s no doubt that getting to market and growing is intoxicating. It’s also physically and emotionally demanding.

Is sleep important? Absolutely, but I didn’t used to believe that. I was the guy waking at whatever time my children woke (anywhere just after 5AM) and then would find my way back into bed at ~2AM. A full agenda demands long days. At least that’s what I told myself and it was folly.

I also knew there were no awards for being awake for 19 hours each day yet trying to crack the cycle of long days seemed like a real challenge.


As founders we create and execute on plans to build and ship products, to acquire customers, to hire great people and to create our own luck. We dedicate 100+ hour weeks to this pursuit to the point of exhaustion and as much as it pains me to admit it, we’re not 100% in control of the intended timing of these strategies. Yet, when it comes to sleep, we compromise.

The irony is that we can control when we sleep. We don’t control much else.

So I made a change. And it worked much, much better than expected. Here’s what I did.

“Hi team, my availability is about to change”

I shared this news with my team during a standup. I reinforced that I was accessible whenever they need me but if that meant a late night product call with our distributed team it would be an exception rather than the rule. I also shared that if they tried to contact me after 9pm they would receive a response the next day.

In bed at 9pm, up at 3am.

Whoa! Hang on, what?

I know. The wakeup time can seem jarring but after the third day of doing this, the change in energy levels was extraordinary. I tried this approach because I wanted to road-test the idea that one hour of sleep before midnight is worth two hours of sleep after midnight. As current sleep research maintains this is a myth I am at a loss to explain the kick in energy. However, the result was that I could power through three hours of work with hyper-productivity (read: I get 2x done) before 6am, spend time with family and then head to the office.

This is a Sunday to Thursday routine which helped me break a cycle that was unsustainable and impacting my ability to be an effective leader, husband and father. It has well and truly changed the game for me.

Closing Note

The life of an entrepreneur is all in and at the end of the day it comes down to choices. Long hours are part of the job but there’s no accolade for staying up the longest.

Reverse the day to get up early instead of going to bed late. It’s a simple and effective strategy, and one that’s worked well in a household with two young children.



Let’s deal with the context first. William of Occam was an English philosopher and theologian from the 14th century. Building on the ideas of others he formed a razor (a philosophy) that essentially says that when faced with competing hypotheses, select the one that makes the fewest assumptions. In other words:

The simplest explanation is usually the correct one.

It’s a phrase. Use it to remind people that simplicity rules.

Opher was the first person to use this phrase with me. I was sharing a half-formed thought and he capped off his reflection by saying “Occam’s Razor, right?”. Needless to say my half formed thought wasn’t one of my best. I’d forgotten about a product that would do exactly what we needed, there was no need to build it. It saved us a ton of time and effort and it made life simple.

Here’s why you need it more than you think.

When you have an exciting new idea for a feature or product (or anything else for that matter) not only is it half-formed, your mind will naturally start playing out how it will look and feel. Before you know it, and in the space of only a few seconds, a series of assumptions and biases based exclusively on your experience has informed how this ‘thing’ will work. And it’s not only the characteristics of the feature or product that you’ve mentally designed, it’s how you would use it. And let’s not kid ourselves, we also foresee how millions of other people would use it every day.

In this vacuum opportunity is limitless. Existing conventions and constraints don’t feature. The historic profile of the idea (who’s tried and failed or succeeded and what they learned) doesn’t feature either. And even more surprising (or not!) is that the language we use to describe the idea is derived from our own experiences.

But here’s the thing; The true value of an idea (read: new business model) is based on the speed at which it can be validated.

The quicker you move to validate, the faster you learn. The faster you learn, the quicker you can grow OR the quicker you can kill the idea and move to the next one.

Tremendous energy and compounding momentum comes from validating ideas and there’s only one reason why people don’t do it: Fear of rejection and judgement.

It takes courage to present an idea and it takes a mix of compassion and radical candour to effectively respond to one. Here’s how Occam’s Razor fits:

When you present an idea…

Be courageous. Present the idea to five people closest to you. Make sure you give them permission, to be honest about what they think because their first instinct will be not to hurt your feelings.

Here are four additional tips:

  1. The ideal format for presenting an idea is face-to-face/voice. Don’t do this in writing, too much intent can be lost in written exchanges,
  2. Begin the conversation with the expectation that what you’re about to discuss is a half-formed thought,
  3. Pre-reads are not essential but they work. I like receiving a link to the one-page business model canvas — this one, and
  4. Listen and listen carefully. Listen out particularly for this question in response to your idea, “Isn’t this like [insert product name here]?” and don’t dismiss it or provide an explanation that talks around why your idea is different. Acknowledge it and when the conversation is over, look into the product. This is important because your experience with [insert product name here], unless you used it comprehensively an hour ago, is dated. Go back and re-examine it. There’s a reason why this person thinks your idea and [insert product name here] are similar. It’s your challenge to understand why.

When you receive an idea…

Be compassionate and seek to understand the context with which this idea was formulated. It’s also essential to recognise the vulnerability and courage that comes with presenting a new idea, so:

  1. Acknowledge that you know the idea is a half-formed and that you’re excited to listen,
  2. Present analogue products that you think overlap with the idea and ask how the idea differs,
  3. If you don’t see value in the idea, tell them but do so with sound reason e.g. “I don’t think I fit the demographic for this product idea because…”, HOWEVER (and if you’re open to it) offer to be ready to receive and talk about the next idea. and
  4. If you do see value in the idea, ask how you can help.

Remember, the simplest explanation is usually the correct one.



Inspiring teams to go above and beyond is an important part of being a startup CEO. But despite your best efforts, the structures and processes used to drive performance from the founding team will begin to flex under the strain of an expanding one.

Accomplished people and culture specialists usually have an armoury of philosophies to deal with organisational growth.

If you don't have a people and culture specialist in your business, here are three principles that will help.

1. Once purpose and strategy are established, leaders have one job – creating more leaders.

Inspiring others in order to achieve shared objectives – this is leadership. This is as much about coaching and developing people to help them move closer to their hopes and dreams as it is about empowering team members to maintain high-quality decision making.

I’ve seen and led teams of different sizes and one reality has always remained true; A CEO, like leaders at all levels of an organisation, can only be effective when they have a maximum of eight direct reports.

It’s difficult to focus the attention to detail needed to properly coach and develop a larger team, just ask any leader.

There are few exceptions to this rule and as a company grows quickly, the true test of the CEO and her/his direct reports is their ability to create environments where team members at all levels can be effectively coached and developed. The achievement of their hopes and dreams and the companies shared objectives depends on it.

Consider speaking to a leadership development specialist like Melissa Rosenthal if coaching is relatively new to your company. It may prove a critical first step in helping you create more leaders. By the way, you can contact Melissa here.

2. Acknowledge the employee-employer relationship is based on a dishonest conversation. And change it.

This is probably the single greatest people and culture revelation in today’s networked age. Reid Hoffman presented this in The Alliance, a book he co-authored which also presents the idea of employees and employers entering into ‘tour of duty’ agreements as a means to reframe the working relationship.

The underlying philosophy of The Alliance is extremely powerful.

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

This is the essential ingredient to turning employees and employers into allies where they can develop a relationship based on adding value to each other.

3. Create a great culture through routines and rituals

Children learn through routines and rituals. Because they create certainty as they start to understand what life is all about.

Routines and rituals have an identical effect in growing companies. In the face of competing opportunities, resource constraint and evolving information routines and rituals provide a basis for certainty, for things to look forward to.

The idea of introducing routines and rituals is very compelling. The simple truth, however, is that they’re easy to craft but require stubborn tenacity to maintain.

The bottom line is that once agreed, they are non-negotiable and leading by example is the only way to ensure habit is formed around each one. I’ve had positive experience with these:

All Hands — Fortnightly on Fridays with all team members

All Hands meetings are nothing new. It’s the opportunity for all team members to receive an update from the CEO and key others on strategy and operations and for team members to ask questions on any topic.

This is also the ideal setting for leaders to celebrate wins and share their thinking on scenarios if the company is undergoing a change in operating environment like expanding into new markets, acquiring a company or being acquired, to name a few.

This is a relatively simple exercise when a company is small and all team members are co-located. As this changes to include different cities and time zones, consider recording each All Hands on a platform like Zoom and publish each session on your team’s internal SoundCloud account. This ensures team members on leave can catch up on each meeting when they’re back on deck.

Head Space — Monthly on a Friday for all team members

Having time to reflect and decompress is important to each of us. The idea behind Head Space is to provide each team member with time to do whatever they want that helps them reflect and decompress and the vision is that everyone takes advantage of this unique time each month.


This is not like Google’s 20% time. The idea is that every team member is paid to not work for the second half of one day each month.

Obviously, there may be instances from time to time when this is interrupted due to mission-critical activities. If that ever happens the intent is that the company does everything it can to make up that time in the future.

How can you tell if people are taking Head Space seriously?

First, the CEO takes Head Space time and second, there is no activity on Slack.

Stand-ups — Monday, Wednesday, Friday with direct team members

I really enjoy stand-ups. They’re a potent way to update each team member on work in progress at the beginning of the day. Each person has 3–5 minutes to provide an update or let a teammate know that they might need their help during the day or week.

There are some teams that do this daily, as a matter of course or when in intensive pre-launch preparation of a new product. My preference is to have stand-ups on Mondays, Wednesdays and Fridays and to reserve Tuesday and Thursday to get shit done.

One last thing ...

A closing note about “off-sites” or “retreats” where teams visit a different location to do team building activities. These are not routines or rituals. They are important and complementary but certainly no substitute for a routine or ritual. It’s a mistake to believe that big bang experiences will energise teams to ensure they stay on the same page and excited about the future beyond the short term.

By the way, this post builds on How Well Do You Know Your Team and Ever Hired An Intern?


Me: Hey Kevin, quick question. On a scale of one to ten, one being ‘not at all’ and ten being ‘a lot’, how much would you say you’ve learned during your internship?

Kevin: Eleven.

This was a conversation I had with one of AirShr’s interns just before he finished up and it made my day. Kevin graduated with Honours in software engineering from the University of New South Wales, applied online for an intern role and was extremely nervous during the interview process. Since then we witnessed the development of his industriousness, sense of humour and point of view and under Opher and Luke’s expert guidance, Kevin completed his tour of duty having engineered and shipped an impressive product called Search Radio.

Joyce, another AirShr intern, joined us while studying advanced mathematics and computer science at the University of Sydney and she brought an unexpected research and prototyping capability to our business. She couldn’t thank us enough for bringing her on board. The truth is we couldn’t thank her enough for joining us!

I don’t often use AirShr to surface examples in order to make a point. This case is a little different because it highlights a practical challenge that founders often face when trying to hire interns as a means to accelerate the momentum of their ventures.

I’ve heard founders say countless times, “we’ll just get some interns”, as if 1) that task requires no more effort than flicking a switch, and 2) interns come pre-loaded with all the context, knowledge and alignment to strategy and vision required to execute on the milestones they’d be hired to achieve.

This is the strange perceived romance associated with recruiting interns. It’s true that interns are available. They’re typically motivated by an intrinsic desire to learn and gain experience or the need to fulfil a condition of study or a combination of both. However, the supply of interns in no way correlates to how many will be suited to work in your company. In other words, the strategy you employ to hiring the best talent available in terms of ‘fit’, capability and ambition must extend to how you hire interns.

Of course, internships are a different style of employment. Functionally they serve as a time-bound experience to help furnish the future talent pipeline of a company but the reality is that whilst ‘fit’ and ambition can be understood from the outset, the same cannot be said about capability. Why? Because interns usually arrive with no practical experience.

These five steps help address the issue of limited experience and help you understand if your company is intern-ready.

1. Have Coaches and Hire The Coachable

Each intern needs a coach. Period. Look around your organisation. Are your co-founders and team members good at coaching? Which is to say are the people you work effective at building trusted relationships, helping others to elevate self-awareness, and good at challenging thinking and assumptions, being supportive and encouraging to then helping others drive to desired outcomes? Besides the crucial point that a culture of coaching is essential to building a resilient organisation, if the answer is NO, then put simply your organisation isn’t intern-ready. Despite the highest levels of intelligence or motivation interns require regular coaching with teams to understand the context and receive help to focus their developing skills.

If the answer is YES, then determining if an intern is coachable is straightforward for two reasons. Being coachable is somewhat binary. You either are, or you’re not (and yes, I expect that to be controversial). The second reason is that being coachable boils down to whether a person can accept whether they are/were wrong. Understand this in interviews by exploring experiences in the interns past where they accepted they were wrong and they acted to resolve the situation. If you’re convinced of the candidate’s ability to be coached and they do start with the organisation, it’s always prudent to continue looking for signs that support initial point of view. Needless to say, discontinue the hiring conversation if you believe an intern not to be coachable. The unfortunate reality is that this issue will be problematic in the future.

2. Always go paid

If you don’t pay interns and then at some point (inevitably) they start adding value to the company, you’ve just crossed the line into exploitation. It’s as simple as that and in many countries, this is the principle that drives industrial relations law relating to paid versus unpaid work. Beyond this, there are two important and very human reasons to ‘go paid’. The first is that everyone needs money to live. If an intern is going to deliver value, help them create value in their life so they can live and have fun — simple. And the second reason is based on the old adage that you value what you pay for. An intern not receiving the coaching they need to thrive during an internship because they are a ‘free resource’ simply isn’t right. You’re wasting their time and in any case, paying an intern reminds the company that every investment should come with a return. In this case, the return starts with coaching.

3. Expect the internship scope to change

There is only so much you can learn about someone through interviews. As trust and a sense for what an intern is truly capable of become clearer, there is every chance the scope of the internship will change. This might be less true in large organisations with structured intern programs but in new ventures, this is almost always true. Set the expectation with intern candidates that this might happen. Also, be open to guidance from interns on what they think they can work on after being with the company for a couple of weeks. Kevin and Joyce came to AirShr with very different initial scopes compared to what they ended up working on (which was largely driven by them). It was a win : win, they thrived and we benefited!

4. Have an intern interview an intern candidate (if possible)

In every interview process involving high calibre candidates there comes a time when the conversation turns from interrogation to sales. The company becomes convinced there is value in the candidate joining their team and now it’s time for the company to its best to bring them onboard. This ‘selling’ often focuses on remuneration, career development opportunities and the promotion of culture and sense of purpose. It’s expected that company leaders do this each day and do it well but there is nothing more authentic than an intern candidate having a candid conversation with a future peer, intern to intern.

Obviously, this is potentially a double-edged sword.

However, if leaders have created an environment where team members are inspired to do their life’s best work, this conversation will not only demonstrate the trust you have in your intern and empower them, it will take your intern value proposition to the next level.

5. Understand how interns want to grow during their internship

I recently wrote about knowing your team which focused on understanding the hopes and dreams of your team. This philosophy applies to all team members, interns included.

One last thing...(that doubles as a red flag)

If the solution to an issue is just hire interns, the issue isn’t well understood which means the solution will be ineffective. Be real about whether you’re intern-ready or not.

Hiring interns is about creating value, for you and for them. Do it poorly and consequences await. Do this well and it’s win : win.



Each team is unique and its ability to thrive depends on a range of factors – capability, collective tradecraft and industriousness, compassion and humour to name a few.

As leaders, we are charged with inspiring others to achieve shared objectives. And beyond the intrinsic motivation of team members to bring their A-game, it’s on us to understand what makes each team member tick.

Knowing your team doesn’t mean being able to recall the specifics of their role, their tenure or whether you think they deliver value. When the going inevitably gets tough recalling any other surface-level fact will do little to help lead them through difficult waters.

Play this out a little further. How will this basic knowledge help if a team member suffers a personal tragedy?

It won’t.

Exercising empathy and compassion, two essential behaviours which need to be available at full volume during times of adversity is nearly impossible, in the absence of knowledge about people you lead.

Understanding Each Team Member

When I build teams my mental model is to create an environment where I can help each person achieve their hopes and dreams. This is my cultural true north which I marry to the companies vision. The payoff in my experience is a virtuous cycle of strengthening contribution over time.

This ambition is not as lofty as it might seem because at the end of the day it comes down to learning more about each team member outside of the work context.

This doesn't mean becoming intimately involved in their life. It does, however, mean knowing more than they would expect you to know or even care about. And this begins with demonstrating that you’re worthy of this knowledge.

It’s also important to recognise that for some revealing what they want to achieve personally and professionally (if they know, and many don’t) may make them feel vulnerable at work. For that reason, I approach it carefully.

Here’s what I do. My mentees have also enjoyed success with their teams.

Collect gradually and apply thoughtfully.

If this isn’t already part of your every day, start actively listening and looking out for insights that help you better understand each member of your team.

The three arenas below make up the framework I use to start learning about team members.

I usually end up committing this information to the team member's profile that lives in my address book alongside their contact details.

Arena 1: Birthdays! 

From the moment as children we become aware of this occasion it’s deeply cherished. Its relevance may lessen as we grow older but for a large portion of our life this one day a year is rightly a celebration.

Dates of birth are simple to find, just take a look at HR records or simply keep an eye on LinkedIn or Skype (they’ll tell you on the day).

Whether it be a loud, whole-of-office affair or discrete and just involves the delivery of a cupcake, every birthday must be paid attention. Make them count.

Arena 2: Family

The desire to be present with family has almost always been traded off against professional pursuits. Understanding who is part of that trade-off is important.

If 'family' is a:

  • Spouse or partner, know their name,
  • Spouse and children, know their names, or
  • Pet, know their name.

Get the gist?

Gone are the days where work and life can exist in a kind of balance. Work and life integrate with one another and do so through the setting to boundaries. Checking in from time-to-time to see how the family is responding to work commitments is important. It establishes the basis for an authentic conversation, one which might reveal ways to make life at home and at work more enjoyable.

Arena 3: Interests.

“If you had a day to do whatever you wanted, what would you do?”

Ferris Bueller knew. If you don’t know how each team member would respond, perhaps it’s time to ask.

By way of example and from working in software I’ve come to expect that engineers work on side-projects. I’ve not yet had anything but fascinating conversations about what they work on in their spare time. In fact, it’s provided incredible insight into their potential and their desire to work on other interesting problems — win:win!

One last thing ...

These three areas are a starting point. It’s not rocket science to collect or act on this information and as you do other important themes will begin to reveal themselves.

However, if you choose to stick to surface level facts about your team you’ll deny yourself the opportunity to unlock potential and create a true basis for compassion, support and ambition. All of which is essential to achieving greatness as a company.



Not so long ago I fell in love with the idea of owning a Mini Cooper S. At the time (even at 6'5") everything about them appealed to my sense of style and adventure. Soon after that love affair began whenever I was out and about I started to see more Mini Coopers on the road, parked on the street and even for sale. Even though I was in the market for a car (any car!) I kept collecting more information about model types and pricing before ultimately making the purchase.

Sound familiar?

In cognitive science, this is an everyday example of confirmation bias, the tendency to search for or interpret information in a way that confirms one’s preconceptions.

The key issue with confirmation bias is that it narrows the way we think about particular topics, usually to the exclusion of other alternatives, without providing a sense of whether preconceptions are valid or not. This, in turn, can lead to preconceptions becoming reality in the mind of the person with the confirmation bias and this inevitably leads to errors of judgment.

The notion of confirmation bias (and the myriad of other bias humans possess) is not new and I’m not the first to write about it. I’ve suffered from

I’ve suffered from it, like I imagine most have, and I’m seeing it play out more and more with my mentees. When it comes to startups, running out of cash is terminal. Confirmation bias can be just as fatal and it can play out in many areas, I’ve seen it play out more commonly in product development and in co-founder relationships.

Take product development. First-time entrepreneurs often hatch a solution to a problem that they have experienced many times. In doing so they develop fierce conviction to solve the problem in a way they believe it should be solved and do so under the belief that they are best placed to bring that solution to market. This can be a mighty power for progress. However, it can be an equally destructive force because a founder’s confirmation bias can reduce their acceptance for feedback and interest in pivoting to an alternative strategy. In this scenario, running out of cash soon becomes the inevitable reality.

This can be a mighty power for progress. However, it can be an equally destructive force because a founder’s confirmation bias can reduce their acceptance for feedback and interest in pivoting to an alternative strategy. In this scenario, running out of cash soon becomes the inevitable reality.

So how can confirmation bias affect co-founders? When it comes to the relationship between co-founders, trust and clear communication are the currencies of progress. At AirShr Opher and I consider these qualities essential to our success and it makes us a potent partnership. But when trust and communication breakdown, ventures tend to die, quickly. To be fair it’s not uncommon for things to get lost in translation as new ventures move quickly from nothing to their first meaningful milestones. However, as stress and fatigue start to become part of every day, frustrating behaviours begin to have a higher than normal impact.

A number of my mentees have experienced this and the first symptom we talk about is recurring behaviour they’ve noticed in their partner. In a recent example the person who was observing this behaviour started to build a bank of evidence to support his hypothesis for why his co-founder was acting the way he was.

The formulation of this hypothesis, which ultimately proved to be untrue, and the subconscious evidence gathering he was undertaking (to the exclusion of other points of view) was having an enormous and exhausting emotional toll. Not surprisingly this hindered clear communications and began eroding trust between the two people who had solved the unsolvable and were on track to growing an incredible venture.

Thankfully, this issue has since been resolved and the upside of these situations is that when you know what to look for confirmation bias is relatively simple to identify. But here’s the thing, just being aware of it isn’t a solution. The solution is to have compassionate conversations that increase understanding and remove bias. This may be easier said than done but in each of the instances I have seen this play out for the better the person who developed confirmation bias:

  1. Made the conscious decision to understand why they began collecting evidence that fuelled their bias in the first place
  2. Confirmed a time to meet with the other person concerned and in doing so suspended any bias until that meeting
  3. Set the tone for the meeting by opening with a compassionate message similar to “I’ve noticed some things recently that I don’t fully understand and I’m concerned about how they might be affecting you. Although I could be wrong about what I’m seeing, I’d like to share them with you”

The outcome in nearly every case has been an increased understanding and empathy for each persons circumstance and as a result the confirmation bias significantly decreased or was dismissed altogether.

The bottom line is that confirmation bias, left unchecked, becomes an counter-productive obsession, the byproduct of which can devastating for founders and ventures.

It also goes without saying that startups are hard work. They’re also the place to have fun and do your life’s best work so if you suffer of confirmation bias at any point take active steps to resolve it so you can get on with building a great business that confounds the critics and puts a dent in the universe.



Last week we closed AirShr’s seed round. It’s a terrific milestone for our team and we couldn’t be happier with the investor group.

Anyone who has raised seed financing will tell you it’s an unavoidable part of the new venture roller coaster. It involves selling a vision and that usually translates to countless conversations, multiple pitch-deck iterations and barrages of questions as prospective investors size up the proposition and the team who claim they will deliver. This is par for the course.

We spoke to angel investors, VCs, media industry heavy-weights and friends and family. There were over 40 parties in total and we met with each party on average three times.

I’ll never forget the interactions we had with two very experienced angel investors very soon after we opened our round. They didn’t invest and in hindsight, they were the most valuable to us for three simple reasons.

1. They Were Quick To Say ‘Thanks, But No Thanks’

This message can be hard to receive but don’t underestimate the value of a quick decision. The longer it takes to determine the interest of prospective investors, the longer you (and your co-founders) will be distracted from the main game — building a great business. The worst case scenario which we experienced more than once was this statement: “We’re excited about your product and interested in making an investment”. This comment is brilliant if the sentiment is genuine. However, if this response is used as a means to avoid a slightly more confronting conversation, it has real potential to waste the already precious time and bandwidth of founder(s).

2. They Were Genuinely Excited To Share Their Venture Investing Knowledge

For us, the knowledge came in two forms. The first was feedback relating to the milestones they thought were important for AirShr to achieve quickly based on their venture experience. The second type of knowledge came in the form of anecdotes about strategies that had worked (and hadn’t worked) for other ventures they were involved in. This helped validate and challenge our priorities and path to market which at the time was immensely useful.

3. They Were Keen To Help

And they did. ‘You should talk to …” was quickly followed up by introductory emails and as a result our network of prospective funders, suppliers and customers grew.

Not all ‘thanks but no thanks’ investors act this way although, in addition to these two angels, some do. Oh, one last thing. We’ve stayed in touch with these angels since their initial decline because we hope to work with them in the future and, well, because we believe that being told ‘no’ doesn’t mean no forever.

Time to get back to work.