5 biggest mistakes I’ve made as a startup founder

No one is perfect and at the pace that startups operate at, mistakes happen often. What makes startups completely unique is that mistakes often mean progress, they mean you are testing the boundaries, trying new things.

Unfortunately, these are not those types of mistakes, they are genuine, straight up whoopsies.

  1. Not holding to my convictions around product/market focus.
    This can be a company killer. You can waste a tremendous amount of time, money and good will with early customers if you make a decision that goes against your thesis early in a company’s life. Every cliché fits here: Don’t try to swallow the ocean, be micro before thinking macro, PMF or bust, your eyes can’t be bigger than your stomach.
  2. Firing too slowly.
    There is a massive difference between having someone in the wrong role too long and having no one in that role for a while. Don’t hang on to people that bring the collective down or clearly aren’t pulling their weight — for any period of time.
  3. Hiring too quickly.
    The exact opposite of #2. Scaling up a startup does NOT mean hiring quickly. Hire, optimize, then hire. You never want to question what anyone is doing in the early stages of a company. That’s a bad sign and bad management.
  4. Assuming everyone has the same vision, understanding of company direction and priorities.
    Things shift often in early stage companies so being clear on what those shifts mean to the team has to be communicated clearly and often. It is all too easy to assume everyone is in your brain. They are not.
  5. Not understanding that cashflow is king.
    No cash? No business. Period. Managing cash is the greatest skill needed to start a business. Bets on direction, customers and people are all determined by the amount of cash you have available. When you are a solopreneur you can bet it all. The rest of the time you need to be measured in your spend, calculated in your ambition and clear on your growth plans.

This list could be endless. As a founder you will make every single mistake on this list because it almost seems to be a right of passage. Just know the signs and react faster and then don’t make the same mistake again.

Making it manual

Senior team updates are important. Strike that. Senior team updates are VERY important. Something of this importance should not be left to automation.

This is a theme that comes up quite a bit as LLMs and AI infiltrate company processes however it isn’t new. In every company, at every stage I hear the same refrain over and over: “why not just export from [[insert software package here]]? It’s easier.”

I’ll tell you why.


It’s too easy to not own your shit. How do you defend a number or think about what the ramifications of including that number in a report is if it is automated? When the senior team meets there should be no speculation about what a number means or is. There should be no unknowns as to why a number changed. There should be complete confidence, with a stamp of authenticity, when a number hits a report that is being shown to the rest of the senior team.

Knowing the numbers means THINKING about the numbers. Automation removes 99% of the importance of what that number means and 99% of the reason for the role…


There is a cost of doing business — any business — and that cost always comes in the form of dilution.

If you trade family for work time, work dilutes relationships.

If you trade time for money, money dilutes time.

If you trade shares for money, money dilutes ownership.

The things we all work for end up being the things that get diluted. Be wary that the price is often high for the things we truly should value.

The Entrepreneur Mindset

I’ve never really thought about what “being” an entrepreneur means. I figured it was pretty simple — you were one or your weren’t.

In my early 20’s I spent time volunteering at our local Entrepreneurship Centre. It was around the time our Federal Government (as a capital city, government is a huge employer) was doing a massive layoff and many of those affected were coming in for advice on how to start their own business.

I was young and had zero responsibilities. They weren’t but they were eager and did have a large buyout while they tested their ideas.

This is where I realized that my thinking was dramatically different from most people when it came to building something from nothing. Everything to them was an obstacle, everything to me was an opportunity. Every challenge made them stop and contemplate if they could overcome/learn it, while I would never give it consideration — I would figure it out.

This trait — or naiveté — is something that can’t be taught and is probably the most important factor in entrepreneurship. You need to be able to ignore the truths of today, to get past the constraints of the way things are currently being done and be able to “see” the other side. Ignorance is bliss and an entrepreneurial weapon.

I still think the same way — even with a house and kids and adult responsibilities. The mindset does not come and go, it simply is there like a superpower or a disease depending on the day.

Startups are hard to keep moving forward

Being a leader of a startup — especially in any operations role — is one of the hardest things to do properly in business.

This is what it typically looks like inside the primordial soup during the early years.

  • The company is still trying to find product/market fit. You think you may have it but “think” and “know” is the same gap between “alive” and “dead”.
  • There seems to be more going wrong than right. Every early stage brings with it a bevy of new growing pains that typically emerge right after the previous problems were solved. This IS evolution and IS good but makes it feel like there is never any progress…but there is.
  • Decisions are fast, furious and frustrating. Being nimble and reactive in the early years means decisions are often made quickly and communicated poorly.
  • Process must be malleable to absorb feedback and lock in P/M fit.
  • There is no HR and morale is very hard to maintain. The work is often repetitive and stressful. This means working in a startup has a very high burnout rate for early employees.
  • Wages are low and benefits often don’t exist.

Founders and early employees are battling on all fronts as they try to figure out where the company fits in the world, how to attract and retain great people, service early customers (if you can convince them to BE a customer), keep rolling out new features and prop up company morale.

It’s an endless cycle and it lasts, in various stages, for years.

Challenge your team

The most important thing that leads to startup success (even more-so than luck, timing, hard work and persistence) is solving a problem in a different way from competitors.

There are very few truly unique ideas, just iterations and evolutions. Success or failure is really determined by the uniqueness of the approach.

This is why it’s important to always challenge your team (or yourself) to go beyond the easy path. For a company like Trexity, it would be easy for us to follow the same path as our competitors and find a warehouse, hire a sorting team and end up looking exactly like everyone else. Trust me, we’ve thought about it, fantasized about how easy it would be to create a mimic. When we start leaning to looking like everyone else, we double-down on going in the opposite direction.

Challenges differ in every aspect of the business. It could be a different business model or a different target market to solve for. It could be automating aspects of the business that are very human-dependent. It may even be finding a way to not hire another person until a certain level of efficiency has been achieved.

Whatever it looks like for you, the main thing to do is to challenge your team to avoid taking the easy path. Every company that failed before you took it. Every company that has succeeded didn’t.

What’s in your control

There are two types of businesses — the one that you control or the one that controls you.

Let me explain.

I met with another co-founder who had recently raised a Series A investment of $10M. His hardware company was founded in 2016 (8 years ago as of this post), raised a seed round in late 2019 and, despite his business being severely impacted by the pandemic, survived and is now thriving.



He was always in a position to be able to survive. He ran the business very conservatively, knowing that a small wobble in the economy or in manufacturing could kill his business. He built for contingency and that paid off. It always does. He controlled his business.

The founder explained that he always grew from a place of profit — never too quickly as to expose the company to excess risk. When he went to raise his next funding round he didn’t need the money.

Contrast that with many of the businesses that don’t survive despite large investment rounds. Often the founders feel that there is always more investment coming so they build on losses and when the money runs out, the investors do as well.

To build a real business you need to build a real business. There needs to be proof that it can survive on its own and this simple fact often gets lost along the way.

Controlling the growth, the spend, the scope and the scale of the business until it is proven, earning, profitable and can stand alone is how to build a real business that you control.

Reasons NOT to join a startup

Startups are different beasts. If you’ve never been a part of one, it’s really hard to explain just how unique and challenging it is during its early stages. I’ve seen so many people think they want to be involved in a startup only to have the reality punch them in the face when they get what they want.

Here are 5 reasons NOT to join that cool startup (that you think will bring your life excitement and challenge).

  1. You will NEVER get paid a market wage. This is just fact. Startups are broke and their investors are frugal. Take what you are earning right now and halve it for 5 years – that’s probably when you’ll start to see increases, provided the company survives. Don’t bank on an exit — most companies don’t ever see that cash windfall so strike that from your future. You are getting paid what you are getting paid. If something happens beyond that, think of it as a bonus.
  2. More startups die than do survive. To make it 5 years for a startup (or any business) is a miracle. Not just a normal, run-of-the-mill-one-person-survives-a-plane-crash type of miracle, we are talking God descending from heaven and showing herself to humanity type of miracle. Be ready for that to not happen. Also be ready to have to skip pay periods every once in a while.
  3. There is NO advancement, you are already in your role. Don’t expect a promotion or job change in the first bunch of years of life. The role you signed up for is the role you will be doing for years. There is nowhere to move except out.
  4. Don’t expect multi-week vacations. The reality of startup life is that if it can live without you for 3 weeks, you might as well no longer work there. There is not a clearer mismatch than asking for a multi-week vacation while working in a startup. You are not a fit.
  5. There is no HR, no clock and no slow down. You have to understand that the days are long, the weeks blur into each other and the pace is untenable. If you can’t keep up, catch up or stay up, you are not a fit.

If you can stomach these realities and still feel good about startup life, you may be a fit. If not, stop negotiating with the founders and find a job at a company further down its lifeline. You are not ready to join a startup.

Don’t hate the VC

It’s really easy to fall into the trap of hating on VCs if you are a startup looking for funding. It’s easy to wonder how they don’t see the brilliance of your business, the potential of your product. It’s easy to diminish their viewpoint and to dismiss their rejection as idiocy.

It’s easy because they don’t understand what you have. They don’t get it. They don’t see it.

The harsh truth is that for 99.9% of us this is completely wrong. They see it for what it’s worth and, for all but that 0.01%, it is not appealing enough an opportunity to invest.

Your business is either not ready or not a business that most VCs will put money into.

It is not them. It is you. Something is missing. Something is not lining up to their investment thesis or what the market is telling them.

They may have a mandate to invest but they are looking for the best of the best to offer a return to their investors. They invest to make money, not to support destitute entrepreneurs.

To receive money from a VC is to have built something worthy of other people’s money — it is not a right, it is not a requirement and it certainly is not for everyone.

The Founders bluff

When I started my first “real” company in the early days of the Internet era I was traveling with my immediate family to visit my mother in Bangladesh. I remember distinctly the fear I had but it wasn’t about flying or malaria or anything related to the actual journey. It was what my answer was going to be when someone asked me “what do you do for a living?”

I was nervous about a title. I asked my brother and, after looking at me like an idiot, said “you are the founder of a startup.” Period. Full stop. No hesitation.

It has always been an odd role to play because that’s what it seemed like what I was doing back in those early days. I was playing the role of someone trying to build a business. There was no hubris or ego in doing the role but I felt like stating it as a fact — “I am a founder” — wreaked of both.

While it does take a certain type of person to start a new business, my view has always been that it’s an act of insanity rather than a stroke of ego to do it. Who in their right mind chooses this kind of life? That’s why I’m always bewildered by the founders bluff.

This is an affliction that happens all too often. It’s when the founder tries to shield everyone from the truth or tries to take on all the responsibility of success or failure. They won’t admit when it’s not going well but will carry the load and let everyone else carry on. When founder bluffing kicks in it is obvious to everyone except the founder.

There are tell-tale symptoms. Founders are meant to be the most optimistic in the room but sometimes that goes too far and over-optimism means over-compensating. Chalk this down to founders shielding the team from most of the truth or trying to live up to the weight of the title.

Founders play a role in a company, they don’t necessarily play “THE” role.

Founders are also the closest to the dirt and it’s very hard to explain the things they balance every day so often times they don’t. A million great things could be happening but it could look like things are standing still as the founder(s) holds everything close to the chest. This one is more about shielding themselves from the 999,999 things that won’t happen. Managing expectations is fine here but, if there are other co-founders, this cannot extend to that group. Full disclosure is imperative.

The founders bluff is at its worst when it is among founders. No one wants to seem weak or vulnerable so they get in line, speak the words they should — not what they need to say. When this happens the founding team is kidding themselves about the future of their business. How can anyone operate when co-founders don’t feel they can have an open dialog about their changing needs? This is the most egregious display of bluffing — with the most impact, personally and professionally.

If you can’t align with your team and founders or feel like you are all alone in the fight, cut the bravado, open your mouth and start speaking from behind the ego and hubris. Breakthroughs and movement will follow. Guaranteed.

Nurture vs Nature

This is a slight departure but for good reason. Both my kids graduated from high school today with a flourish.

Oddly enough, this is the first high school convocation that I’ve ever been to. I didn’t graduate in the allotted time and had to do an extra semester to finish. I also didn’t think much mattered back then. School and the trappings were not for me.

Sitting in the audience today, watching my kids (twins) walking across the stage, each with a boatload of academic and community building awards, made me question a few things. Before I dive into the questions tho, I realized that I never gave my parents the chance to do this (thankfully they had 3 other kids who did) and that really sucks.

Both of my sons were easy students. They entered the high school system at the height of the pandemic — grade 9 was at home in our basement. The school they went to wasn’t the greatest school academically but they embraced it and completely made their experience there remarkable. They both crafted their 4 years in the way they wanted it to be. They set up clubs, volunteered everywhere, ran tech for the auditorium, sat on student council, joined the band and one sang and acted in 2 musicals.

They did all of this while landing on the honour role and making an impact on their circle of friends and the school. They also allowed their parents to be witness to this and really enjoy brand new first experiences because of them.

I’m not at all sure how they ended up the way they are today — great grades, incredible work ethic, fearless in front of crowds, respected by their peers AND teachers — but, as a parent, to not have to worry about their schooling was a blessing. I can’t imagine what I put my own parents through…

I always figured that my kids would follow in the footsteps of their dad – lazy and low grades throughout public school — but they (thankfully) did not. I joke that I don’t think I actually had a 90 average if you added up every mark from every class I took in high school and they did it with ease.

Work ethic came later for me but we encouraged it every day with our guys and it showed. The discipline and drive they have is something I discovered well into my 20s. We (well, my wife) nurtured the Woodbridge nature right out of them and boy, am I thankful.

Get aligned

Co-founders need to be aligned. Unified. Clear on objectives. To have a voice.

It’s hard enough to run through the gauntlet of a startup but to do it the entire way with co-founders adds so much more complexity. Solo entrepreneurs make the decisions. With co-founders there needs to be consensus and then alignment. Sometimes that means unanimous, other times it means the majority and this is where things get weird.

If it takes 5-7 years to turn a startup into a “sustainable” business, co-founders are committing to a long term, tempestuous, high-stress relationship from the start. To make that work is no different than making any great relationship work — communication, transparency and targets.

Each co-founder needs to be open, honest and clear about their intent, their goals and their vision for their version of the company. Things change, people change, life happens and the person that entered the arena on day 1 is different than on day 1800. Startups grind you down and that has an impact.

The most important part of a partnership of founders is to make sure everyone is still aligned and checked in. So many co-founders think they are saying the same things or going with the flow only to wake up one day and be miles apart.

Talk. Often. Be crystal clear about the outcome you seek. Push the conversation and make sure everyone has a voice.


Choosing the path to start your own company means a lot of things but mostly it means deferral.

Let me explain. If you are a founder, you will understand this immediately.

The general perception about founders is that they are “lucky” to be doing what they are doing. Freedom from the tyranny of “the man”, the ability to chart your own path, the ability to cash out at will — you’ve heard them all, even if you aren’t a founder but work for a startup.

The truth is that for most of us this “reality” is so far from real — tainted by the top of the top companies that we’ve all heard of that have succeeded beyond imagination.

Startups work because everything is deferred.

Founders defer pay.
Founders defer vacations.
Founders defer family priorities.
Founders defer their health.
Founders defer their future.
Founders defer their finances.
Founders defer their friendships.

There is nothing glamorous about founding a company. It requires the highest level of sacrifice in the hopes that it eventually works out.

Faith and deferral is the startup equation.

The best laid plans

Startups, by their nature, are designed to be an uncontainable, uncontrollable and unstructured mess.

The whole idea of a startup means throwing convention out the window. Everything a startup does goes against the teachings of every business book and expert and basic business advice…ever.

That doesn’t mean that planning shouldn’t happen — you always need defined guardrails and a direction — but it does meant that you reserve the right to re-define the direction and expand or contract the guardrails as the company evolves.

It also means there is a lot of ambiguity as well.

Face it, most of us are involved with startups because there is a sense of the possible. This is the allure. To define and build something that wasn’t there before. This adventure, akin to early British or French explorers fearful of sailing off the edge of the planet, is not for a structured mind.

But, there needs to be some planning, it’s just not the same as in established companies.

Startups still need to be aiming for something very specific at all times.
Startups still need to define the benefits their ideal customer will get from purchasing from them.
Startups still need to clearly articulate expectations for the team — down to the person.
Startups still need to set targets.
Startups still need to plan for what success looks like.

The only difference when planning within a startup versus any other stage of company is that all of this can — and is expected to — change in an instant and often.

Instilling structured planning too early in the life of a company can kill momentum. Those nascent moments are really about discovering where/if the company fits where it thinks it does. Exploring with customers can influence its path and founders need to be open to this feedback. Many times when products or services hit the market the plans and expectations are not met and the once-obvious direction is not as clear. The plans need to change.

The entire process of think, plan, test and release must not only be iterative but the outcome may require a complete rethink.

You will drive yourself crazy trying to do long-term structured planning in a startup. Better to be clear on the goals, clearer on the expectations for the team and iterate quickly. Once something has landed on solid ground, plan away. Until then, the only plan to bank on is change.

Should you say yes?

How often do you say “yes” to customer requests?

How often do you say “yes” to win business you have no right to win?

For me it has been all the time. Early in a company’s life “yes” is the word that I think you should use all the time.

Even though I had boundaries on the services offered or the capabilities of the team, “yes” would be the answer to any and all requests. If I didn’t win the business, someone else would.

There have been times that saying “yes” has stretched the team in both ways, good and bad. Sometimes new features were pulled forward that helped evolve us faster and find new customers. Sometimes the requests were so taxing that the strain was unbearable on the team to the point of breaking.

Both instances help define the guardrails of the business — it’s one thing to clearly articulate what you do as a company but it’s as important to realize what you shouldn’t do.

I still default to “yes” — even after 35 years of doing this — and most of the time I don’t regret the decision. The willingness to solve for a customer is too big a lure to ignore it and creates a deep and meaningful and (hopefully) lasting partnership.

The Startup Culture

Lots has been written about the importance of company culture and how to encourage it to develop and flourish in the right way.

Startups and scales ups are unique — especially in our mostly remote work world. They attract a certain type of employee with a different mindset and urgency. From the founders down, the cultural tone takes on an almost quest-like facade.

When I was a green founder trying to balance the early stages of a company and the needs of early stage employees, I visited other founders to understand their company culture. At my company we had all the “culture building” trappings — a foosball table, birthday celebrations, catered lunches and even a garage door that split our board room and kitchen (it was a thing in the 90’s — really).

The other startups that I visited over the years had distinct cultures that attracted their right employee type. Shopify attracted a type of employee where having tapped beer kegs that were flowing at 10am and a slide was appealing. Lyft’s culture was the most empathetic and welcoming of all the companies that I’ve seen and it attracted the same. TripAdvisor was totalitarian in culture — silent and intense — and visiting some of their offices was like entering a library.

Now, for early stage companies that are just trying to establish themselves, culture is a hard thing to build with intention. It’s ok to not “have” a culture at this stage — in fact, culture will get in the way. As the company grows and the team expands, culture will break and rebuild many times over. Instead of establishing a culture in those early days, I tend to think of it as a building a quest.

This startup quest will attract the right people for the right time and, slowly, human by human, company culture will emerge and only then will it require intentional nurturing and guidance.

What do you do for a living?

This is the hardest question to answer for founders.

I’ve always struggled with it. Mostly because of the perception of being a founder. Imposter syndrome is rampant when the answer is “I started a company” or “I’m the CxO of the company I started”. How arrogant and unreal does that sound? The role wasn’t “earned” in the traditional sense. It was taken, not bequeathed. Anyone can start something and name themselves king.

When anyone asks that question I will most often demur to the fact that I was unqualified to do anything other than to start a company.

I will diminish the value and experience that starting a company gives its founders.

I will try to change the subject as quickly as possible so I don’t betray the real struggle that comes with building something from the ground up. No one wants to hear the real parts.

I will listen to them talk about starting their own company and how much freedom that would bring. Like it’s the easiest thing in the world to do and success is guaranteed.

I will listen intently (and many times with envy) as everyone else details their elaborate vacation plans.

I will question every decision that I’ve ever made that led to where I am at that moment.

Most founders aren’t creating the next Shopify and that’s what a startup founder means to most people.

No one has ever heard of the companies I’ve started.

They won’t understand when I say the greatest accomplishment has to be that we haven’t missed payroll in 4 years.

It is a loaded question because most founders and entrepreneurs do what they do JUST to make a living.

Politics is a dirty word

As the US and potentially Canada gear up for elections, the ideological divisions are obviously quite deep. Each side feels that theirs is the righteous one and their party alone is the one that speaks the truth.

A simple fact is that, since the invention of politics in prehistoric times, it has been on a slow (but rapidly increasing) run to bankruptcy and the way that politicians operate has followed suit. To cast a vote today means assuming a baseline of bullshit from both sides and then understand what their vision is for the country. What will it look like on their last day in office, not their first.

It may be cynical to think this way but to be a politician you say what is needed to get where you need to go. If that succeeds then the real agenda can be implemented — for good or bad, depending on your viewpoint.

Left or right, an ideological vote is more powerful and spreads faster than an educated vote. Just don’t be fooled by the facade on either side.

From anarchy to…less anarchy?

“Just f@cking do it.”

No phrase better summarizes the early days of a startup. If something needs to be done, there are likely very few people (if any) to delegate to. It just needs to happen so the person that says it, does it.

If you are reading this, you already understand that startups require a different breed of human that can survive in a high stress amorphous blob with little direction, no tools, zero established processes, non-existent hierarchy that pays less than minimum wage.

This is the beauty of a startup. That anarchy is what draws people in. For most of us, the allures are the undefined walls and the open possibilities. The business or industry, while important-ish, is secondary to the pull of the build.

The problem is after the startup starts and when any sort of success follows. There is no way to operate the same way as before. Every new customer, every new employee, every new release changes the company and starts adding boundaries. Those anarchistic leanings are still there but instead of them being the spark that gets things moving, if left completely unchecked they will be the reason that the company is flailing.

Anarchy is the source of life and death for startups.

Slowly but surely the ground starts to settle under the business. Quarterly planning, employment contracts (beyond those found on the Internet), bookkeepers, code repositories, HR (GASP), processes, hierarchy. You get the picture. At some point the anarchy cannot be the primary source of energy.

It still needs to be there in some shape, just less of it and it can’t be the primary source of energy.

Anarchy can manifest in product thinking. It can be present in marketing initiatives. It should be a constant in outbound sales. If the company falls into a predictable rhythm in any of those categories — doing the same as everyone else — the results will be the same as everyone else.

It is a rebellious act to be a founder and that rebellion can never get buried while building a company.


Title or outcome.

For a long time in my career I was governed by my identity as a role. I am a founder. I am the CEO.

This is an easy trap to fall into. We all grapple with the need to fit into whatever box other people understand and a title sums everything up pretty neatly.

I’ve spent most of my life starting with a big title and then spending the years in it earning it.

Today I choose to be identified by outcomes of the work I do.

If the results I produce are worthy of a title, so be it but the title is not what I’m looking for.

Titles are bequeathed. Outcomes are earned. Identity is forged from progress. I’d rather be known for the things I’ve done and not the title I carry.

High effort or none at all

What gives a startup the highest chance for success?

There are obvious things that check the typical “startup” boxes but those are all detailed in retrospect. Most of us don’t hear about companies until they are well past the startup mode, then we study them and try to apply what we learn from them to our context.

The real stuff that most don’t see is what makes or breaks an early stage company.

Effort. Very high effort.

Before the viability of the company.
Before product/market fit.
Before investment.
Before customer personas.
Before word or mouth or earned media or any awareness.

The only determining factor for early startup traction is the amount of energy that is injected into it.

Everything is high effort and low impact to begin with. The startups that succeed are the ones that continuously apply high effort to a specific problem until the impact starts to increase.

It’s only at that point that the founders can decide if the velocity is there to warrant continuing to pursue the idea or to pivot.

This is the startup grind where sustained high effort is most often the differentiator.

Embrace the silence

Great interviewers know that silence is a tool. They don’t feel the need to fill the space left by a question or an answer. They soak in it and keep their mouths shut.

Silence is the most powerful tool to harness but the hardest to resist. It is uncomfortable and cries for us to end it.

Don’t. Embrace the silence.

Every word that comes after the silence will have the most impact. It will be the thing that everyone remembers so choose those words wisely.

If you are letting someone go from their job, don’t end the silence by saying “you were a great employee”

If you are admonishing someone for missing their targets, don’t end the silence by letting them off the hook with “I know you tried your hardest”

It is human nature to relieve the silence with throw-away words to get closure. Resist that temptation.

Is your story better than your product?

“We need you to remove your product right away. It is hurting our business.”

A year before those words were uttered to me, I had been blown away by the co-founders of Gymtrack talking about their automated exercise tracking platform.

I fell in love the first time I heard the story.

The crazy thing was that it worked. I saw it in action in the gym they had set up in their office. Lift the weight (plate-loaded, selectorizer or dumbbell) and there it was, a rep and the weight recorded.

So how did I end up in Minnesota, face-to-face with their lead customer, asking me to remove the Gymtrack product from their gym a year after meeting them?

I was so in love with the Gymtrack story that I found myself the CEO of the company. That day in Minnesota I had realized very quickly that the story outshone the offering.

It was a time before the smartwatch and the Internet of Things was in its true infancy and this company had the greatest story to be told in the gym industry.

The problem, as the co-founders later revealed, was that the business had been conceived with the sentence “wouldn’t it be cool” and then the story was built from there.

Their story was incredible. The product, while functional, didn’t match it but they still managed to secure a hefty seed round of funding and a marquee lead customer.

Then the wheels fell off.

In the end, the product could never live up to the story.

There is an incredible balance that needs to be considered when crafting a startup story. If it’s too fantastical, no one will believe or invest in it. If it is too underwhelming, no one will believe or invest in it.

That fine line where a little imagination and a spark of potential is the aim. It has to sound plausible and unique not insane and unneeded.

For Gymtrack, the possibilities were there but the story was just way too good and way too big to ever achieve.

You can’t aim to sell

It is every startup team’s hope — that they are building something that puts them in front of someone else that wants to buy their company.

What they aim for will determine if that will ever happen.

If the goal is to have an option to sell, there is only one way to make that happen and that is simply to build a business or product that has a chance to get bought.

The difference between selling and getting bought is a mile wide and 1000 miles deep.

Selling as an aim means the work hasn’t been done well enough to gain the right attention to get bought.

Getting bought is the culmination of finding the right product, solving for the right customer at the right time while building a real business.

Selling is not a strategy, it is the outcome of the strategy.

THE decision-making framework

Shane Parrish is a writer and podcaster (catch him on the Tim Ferriss podcast). He has spent the better part of the last 15 years studying high-achieving people and has tried to capture it all in his most recent book called Clear Thinking. One of the most salient and simple approaches he articulates in the book is about decision making. Some of us have a hard time making them. Period. We like to analyze options until we’ve backed ourselves into a corner and all of them have expired.

Here’s his simple framework. There are 2 principles that resonated with me: The ASAP Principle and the ALAP Principle.

The ASAP Principle: If the cost to undo the decision is low, make it as soon as possible.
The ALAP Principle: If the cost to undo a decision is high, make it as late as possible.

This is a very simple approach to the hundreds of decisions we make every day — most of those are done on auto-pilot. Making decisions can be paralyzing but Shane’s approach takes the burden and cognitive weight off the “easy” decisions while freeing up time to think about the tougher, more impactful ones.

The secret to scaling is stopping

I’ll never forget the day it sunk in. I was on the road doing deliveries, on a conference call with my co-founders who were also out doing deliveries when one of them said the sentence we all needed to hear:

“Instead of racing out and doing the deliveries that are piling up ourselves, we need to spend that time getting other drivers online so we don’t have to do it anymore.”

We were like all other founders — eager to solve the immediate problem (lack of drivers) by doing whatever was needed to solve it right away (get on the road and do the deliveries). It’s what founders do. Work hard to scale.

Does this sound familiar? For us, we explicitly told our team that if things got backed up, start giving us routes. We made it our process so it became our process. And there we were, on the road hours per day doing thousands of deliveries instead of really moving the company forward. We even had a leaderboard for team deliveries!

We needed to stop or there was no hope of scaling properly.

There are 100’s of these side quests that early teams institute to move the company forward — guaranteed. They seem so innocuous at the time but eventually become the things that hinder real scale.

Side quests fall into three categories but don’t be fooled, they are all equal in their ability to derail growth:

  1. Internal processes
    These are dead end points that need solving but are lower priority so the team finds a way to solve them manually. Those manual processes get handed down to new employees, become instituted and the next thing you know they are part of your DNA and very hard to extract.
  2. Product development
    Gaps in the product lead to bad behaviour with good intention. It’s hard to polish product features in the early stages so often times good enough is good enough. The gap between where a feature is currently and what the completed feature should be is where side quests begin.
  3. Customer expectations
    Early in any company’s life it is your obligation to say yes to a customer request in order to win or keep their business. You will do anything and everything for every customer and this is clearly the hardest thing to scale. The expectations you set for your customers needs to be crystal clear for the service you are offering. Any variance is now a branch that you have to maintain.

Exceptions and side quests are a killer feature for early stage companies — this flexibility is often why a customer chooses one company over the other — but they are never sustainable.

To scale properly you need to hunt these down and stop them at their roots or they will continue to hold you down.

Your Situation Room

After the disastrous Bay of Pigs invasion in 1961 — attributed to a lack of up-to-date information — President Kennedy ordered the creation of the Situation Room in the basement of the White House. Its sole purpose was to bring together the right people and information at the right time, mostly during a crisis, to make the most right decision available.

It has been the backdrop to some of the most consequential and historic moments since. Kennedy’s own assassination, The Vietnam War, President Reagan’s assassination attempt, 9/11 and we’ve all seen the photo of President Obama watching the raid on Abbottabad to subdue Bin Laden. All things actioned and monitored from the Situation Room.

Today, this “room” is in continual use — not just in a time of war or crisis but to hopefully avoid both.

Most companies convene a “war room” during times of crisis or major initiatives. We did it at Lyft during major holidays or social events like New Year’s Eve. We would pull together our key teams leading into the day, execute on the day and then disband — only to fire it up again when needed.

This concept always made me feel uneasy. I was of the mind that we should diffuse these “festivals” by doing our jobs every other day. This would make those huge days less risky and flow easier instead of putting so much emphasis on them.

This is where your company Situation Room could help.

If you are running a tight ship, nothing happening inside or outside your company should be a surprise. The data is all there. The people running everything are accessible. Your customers have more ways to be vocal about your offering than ever before. Market information is public. Most companies are building in the open.

Your obligation is to take all that information and balance it against what you are — and should be — building while at the same time monitoring for any threats.

These threats come in different forms:

Industry Threats
At Trexity we noticed an alarming trend that our competitors, once fierce and full of investor cash, started wilting and dying. This perception that the industry was stagnating or in decline was the threat. Those competitors took all that money and invested in warehouses and robots and not in their core product so we took a different approach. We went assetless and, while they were all selling for parts, we accelerated our growth.

External Threats
When I was running a company called Rove (remote IT administration from smartphones), our high-value customers were international banks. It just happened to be 2009 and the world was about to be hit with a global banking crisis that would hobble the economy. This had nothing to do with our product offering and everything to do with an external threat that was out of our hands. Seeing this in the horizon helped us make key decisions that allowed us to shift course and avoid (most of) the carnage that followed.

Internal Threats
This is much more day-to-day and involves true product/market fit (are your customers staying or churning), product scope creep (are you building the right features/services) and processes (are your people doing the right things consistently).

That pulse is your Situation Room — a continuous flow of information that helps you make key decisions, avoid surprises and normalizes the heartbeat of the company.

*This post was inspired by The Situation Room: The Inside Story of Presidents in Crisis by George Stephanopoulos. A great read.

How patient is too patient

How much patience should you have with employees in an early stage startup?

It takes a certain type of person to thrive in the mud and muck that is a startup. They have to remain unfazed by undefined roles. They have to accept there is little to no work/life balance. They have to realize that the earn is in the outcome, not in the salary. They must realize that there is no place to hide and it could all end tomorrow (or later today).

Who would do that? Who would give up salary, stability, freedom for a shot at something big?

Very few people.

Startups pose a real challenge when it comes to human rights and, for some reason, those of us that do it accept this willingly. But…it isn’t for everyone.

Great founders move people out that don’t fit and they do it quickly. There is very little room in the early stages of a company to carry people or help them progress to an acceptable level of production. There simply isn’t the time. If someone is not making an outsized contribution there can’t be a seat for them at this stage. Period.

I’ve been on both sides of this conversation — hired at a startup that worked, let people go at a startup that weren’t working out and have been the one let go at a startup because there wasn’t a fit.

The pace won’t relent and if there are people that can’t pull the company ahead, they have no place in it at this stage.

Pull the future forward

Adult Mayflies live for 2 days. They spend a year as larvae, burst onto the scene with the sole purpose of mating and then, 2 days later, dead.

In an infinite time horizon, Mayflies and startups are basically the same. Startups spend the majority of their lives building, incubating like the Mayfly larvae. After they launch there is a limited amount of life left in them to succeed and most won’t.

I picture those Mayflies cramming their entire life into 48 hours. They know their task at hand, throw caution to the wind, do not worry about 1 minute beyond the 2880 they are given — they pull their entire future forward.

This is where startups need to learn from nature.

The very limited timeframe a startup has to establish itself means that they need to focus on the efforts that will make a difference right now. Not one minute past the end of their bank balance.

This doesn’t mean planning is excused. There could be a 3-year plan in place but things that move the needle need to be front loaded in that plan. For example:

  • Build the lowest lift features into the product/service that captures the broadest appeal among customers.
  • Leverage third-party tools to speed up development (do NOT rebuild things that are already built by others).
  • Focus efforts on a single customer pain point to be the best at solving that for now.
  • Market a single message — don’t get complicated.
  • 80% complete is 100% good.

There is a visualization that I like to share with my team that cements the process for me. I ask everyone to picture all of us sitting on a patio the day that some significant milestone has happened to the company — a successful raise or an acquisition or a bankruptcy. The LAST thing we should be talking about is regret that we didn’t try something or change something or do something differently.

We should feel that we’ve left everything we had on the field, that we did everything we could to succeed, that we pulled enough of the future forward to feel good about where we were — even if the company didn’t survive. The last thing you want to hear is “we should have” or “why didn’t we” or “I wish we did this”.

We should have no regrets.

Startups have a short life before they are expected to transition so why do anything at all that doesn’t make that happen? If the purpose is survival, pull that future forward and get to the destination. Don’t be a Mayfly.

Real VCs make decisions and move on

The all-too-common knock against venture capitalists is that they never make up their mind. They lead founders on, always asking for more proof points only to disappear or finally say no months too late.

Although it may feel this way while you are in the middle of a raise, this is not entirely true and, as a founder, this is your fault if it happens.

It all starts with how you are connecting with the investors. A cold list and prayer is not the answer here. You can write the most compelling intro email with the most compelling numbers and get shut down or ghosted 100% of the time.

There just isn’t enough time in the world for VCs handle the volume. They don’t know you. They’ve never heard of your business. They see 100’s of deals per year (or month or day depending on their fund). When you send a cold email, just know that you are being relegated to their junior associate, 8 days out of B school.

No decisions are even being considered.

There are really only 2 ways to get in front of the right person with the ability to make a decision:

  1. A warm WARM intro. Not just an email “meet so and so” email but a deep, “I understand their business and they are someone you should look at” intro. The best example is a referral from an existing investor (angel or otherwise).
  2. Having an investment bank or the equivalent on your side. Time burns money so cutting through to the crux is essential for startups raising (series A and beyond — including operating debt).

Good VCs through warm intros say yes or no right away — because you are connecting with one of the decision makers.

Once you’ve established yourself — raised already and (hopefully) had a positive exit for your investors — this becomes reputation based. Until then, you are spinning your wheels and hoping without a strong endorsement.

Regardless of the path you are on to raise your funds, the common factor amongst all investors is that your business needs to be sound and growing. Investors won’t invest unless you’ve done the work on the business and you’ve earned the introduction.

How startups can save $100,000

Early days in startup life feels like David Allen’s GTD on amphetamines.

Every day is a series of tasks that ends with the founders saying “we’ll deal with that later”.

But they never do.

There are 4 things that founders can do from the start that will save them hundreds of thousands of dollars — if the company makes it to its second birthday.

Pay to have up to date and sound employment contracts.
Startups hire and fire people all the time and the only thing between fair and ruin for it is the employment contract they have employees sign. If you don’t want to pay someone that you fired more than they deserve, be great at this part. It is worth it 10X over.

Keep your minute book current
The moment you add “inc” to your name is the moment that you’ve committed to keeping a log of your business transactions, loans, shareholder ledgers, board of directors, investors, records of board meetings and resolutions — everything.

Have a financial reporting process
Finances are loose during the early early days but this is one of the first things that should be professionalized. Finances are the foundation of a business — regardless of the stage. Best practices from the start are crucial down the road to file taxes, find investors and read the company’s future.

Sign a founders agreement
Founders should not just shake hands and carry on. Every one should sign an agreement as soon as possible and in that agreement there needs to be covenants to protect the business and the founders. Two HUGE covenants you need to have are an equity cliff (no shares issued if a co-founder leaves within the first year) and a buy/sell agreement (a way to establish how/if/when shares of a departing founder can/will be bought back by the company or the other founders).

There are MANY other things that will cost you money but these 4 are the ones that I’ve seen founders ignore at their peril over and over. In the companies that I’ve come into, my first 100 days are usually spent fixing these issues and spending dumb money to do so.

What you don’t pay for now, you will later and at a premium.

Fighting Fiefdoms

This happens all too often in early stage companies.

You think you’ve been clear on direction.
You think you’ve been clear on initiatives.
You think you’ve been clear on requirements.

Everyone thinks they are clear on direction.
Everyone thinks they are clear on initiatives.
Everyone thinks they are clear on requirements.

But somehow everyone is moving in the opposite direction of each other but thinking they are in tandem.

This happens when responsibility is misdiagnosed as ownership.

Product doesn’t own a release. The entire company does.
Marketing doesn’t own an initiative or program. The entire company does.
HR doesn’t own hiring or the first day experience. The entire company does.
Sales doesn’t own the customer. The entire company does.

Delegating or abdicating ownership creates fiefdoms and finger pointing, wastes time and slows growth.

Options in tandem

The answer will be no.

It sounds crazy to go through life thinking that everyone is going to say “no” to you but that’s just reality. The first word you learn as an infant? No. The first word your infant learns? No. The first word you scream at your dog? No. The first word a VC says to your pitch? No.

Prepare to hear it on repeat but have a great story and a plan to fight it.

You need to have options and attack them in tandem. Putting all the effort into one outcome is a sure sign you will fail. Your simple goal is to move as many options forward every day so that you are not starting over after every time you hear the word “no”. As one option falls, another should take its place.

To do this you need to produce. Good options are only available to those that are worthy of them and to be worthy of them you need to be able to show a great story. This means hitting your growth numbers, showing the results that you promised, demonstrating traction, you know…building the thing you said you were going to build.

Controlling your own destiny means always working options in tandem. The last place you ever want to be is out of them.

Earn your views

I love the simplicity of this statement: Earn your views. Views can mean something different to everyone but it’s the “earn” part that hits for me.

Somewhere in my 20’s, when I started my first business, I fell in love with the work. Doing the work was the differentiator for me. I knew that if someone was starting a business in the same space that I would simply outwork them. Grind more. Do more.

Success or failure for me was about how much effort was put into the work. Lots = success. Little = failure.

During that time in the heyday of the Internet, magazine covers and news outlets praised the exact opposite. People were rewarded for getting to the starting line, not finishing the race. The world got caught up in the celebrity of the startup.

I didn’t. I always focused on earning my spot. This meant that I could back up the praise with the work. My thinking was that I would get the results to get the views. I would earn them.

This stubbornness has downsides. I certainly did miss out on the quick wealth as we’ve seen in every technology shift in my lifetime. There are always people that are able to sniff out opportunity at the start of the “thing” and be in and out before everyone else. The Dotcom boom/bust, the mobile era, social media, cannabis, and now the AI race are full of entrepreneurs with little expertise reaping rewards from capitalizing on the trend.

No shame at all in doing this if you can. Capitalism is capitalism. I just couldn’t justify doing it that way.

An outsized motivator was the consistent hum of imposter syndrome that most (all?) entrepreneurs suffer from. Doing the work, validation from the effort and being able to defend the outcome helped ease that voice of discontent in my head.

I’m motivated by removing the tenuous nature of success by putting in the effort all the time. You can’t go wrong always asking yourself if the view you are seeing was earned or absconded.

*The title of this post is from Dan Martell who consistently posts about earning his views. I love the simplicity, the focus and the broad application of it. Thank you Dan for distilling the complex to this simple powerful statement.

The alignment meeting

Remember that old adage that to assume makes an ass out of you and me? That’s cute but in startups, assumptions derail initiatives and kill momentum. Nothing cute about that.

I’ve been in so many companies, run so many programs or initiatives and still I am baffled by the lack of the simplest of thing — the alignment meeting.

You can have the perfect launch playbook, have everyone responsible for its success sitting in the same room, take questions, get heads nodding, FEEL aligned, send everyone out to get the job done and then be completely gobsmacked when the wheels fall off.

People hear things at different decibels.

THAT’S why the alignment meeting is so necessary. I can’t believe I’m even writing about this simple, yet often overlooked step.

Pick a number of days into the initiative to have a quick regroup with the same team as on launch. If whatever the thing is lasts a month, regroup a week into it for example.

Structure the meeting in these 3 sections:

  1. What is each person currently doing FOR the initiative. Ask for specifics (i.e. I’ve adjusted our email flows to incorporate this, or Every time I call a customer I mention it)
  2. Ask for feedback on how [target] is reacting/responding/converting. What are your customers saying?
  3. Ask what else can be done to boost/augment this initiative. What are we NOT doing that we should be doing?

These 3 questions will give you a sense as to what is actually happening (of course) but also how everyone interprets their part in this initiative. You’d be surprised at how different the launch conversation was interpreted by each person.

The last thing is to schedule a quick follow-up huddle 3 days after this meeting to get an update. This will tell you if you are on the track or not and if there is complete buy-in.

This small, simple step will make sure you aren’t wasting the initiative. There is NOTHING worse than sitting back in a post mortem and hearing “I didn’t know” or ” we should have done this” or “I didn’t realize it was that important.”

I’ve actually spent my last penny

When I started my first real company — a web development company called Thunder Rd — I was broke.

I borrowed $5000 from a great friend and his dad to start the company, which was enough money to buy a computer and to print business cards. They were also my first customer and referred me to my second.

One of those customers contributed a significant amount to my well-being, financially and physically it would turn out.

I’ll never forget this act of complete faith.

I was working on a training module for a local company that was being produced for the web. It was a significant project at the time with a significant impact to my finances. I had done the naive thing as a young entrepreneur and agreed to bill upon completion (NEVER do this…ever). I submitted my final invoice and a quote for another project together, in one email, in the SAME document (NEVER do this…ever).

Then I got the email letting me know that I should receive payment in 45-60 days.

It was early December and my bank account was empty. Christmas was around the corner and no presents were purchased. Nothing.

I donned my only suit, grabbed the last of my pennies and took a bus to the office of my client to beg for a faster turnaround. They agreed and said they would issue a cheque that week and send it by mail.

It arrive the following week and…it was almost double the correct amount. They had combined the invoice and the quote and issued a cheque for that amount. I called in a panic and they asked me to return it to them so they could issue another one with the correct amount this time.

I once again donned my only suit, dug up enough cushion money for bus fare to get me there and made my way back to their office. This time they said it would take until after the Christmas break to fix because the person whose signature graced the cheque was gone for the holidays.

That broke me inside. She must have noticed because her tone changed, her demeanour was concern and she started calling around to see if there was petty cash she could give me to help me through the holidays. Or, most likely, just to help me get home.

Then she produced a miracle and said I should take that original cheque and cash it. She’ll call it a pre-payment for the work I would be doing for them in the new year. I know she saw the tears in welling in my eyes. This act of faith did more than she would ever know. At that moment she saved my business and gave me the ability to move forward.

Cheque in pocket, bounce in my step, I made my way into a snow storm with literally no money in my pocket and a 6km walk in my best suit.

Ahhh, my first taste of real entrepreneurship.

This is the unglamorous part of entrepreneurship where the start is being broke, the middle is struggling to reach broke and, in the end you are broke.

When do you add an operations lead

This is a question that not enough founders ask. The simple answer is right now.

Let me explain.

Most companies are built on tomorrow’s hope and are generally operated that way. The thing that triggers a focus on today could be the first bunch of customers, a potential expansion to a new city or a round of funding.

At that point there is a scramble to get finances up to a level that are readable, sales and marketing aligned and product in check to the next phase (while also backfilling to make sure it can scale).

My first 100 days in a company are usually clean up. Forget about setting direction and a roadmap, most of the time is making sure we can report on the things that are moving the company and the things that are putting it in jeopardy.

What I’m not saying here is that this role needs to be a C-level hire, that’s not necessary at this stage. What is required very early on is someone that can cut through the learning curve most founders go through. Speed is what you are bringing on.

I see it every single time. Founders need to focus on scaling the business without a shred of focus on the operations of it. So they let that slide, manage by the balance in the bank account and delay the decisions that move the business further and faster.

Now. The answer is now.

Why you aren’t growing

This is a quick reminder of the simple principles that govern startup business life.

Humans and startups need to grow. If either are not growing, it’s not them, it’s you.

If you feel you have hit a plateau or aren’t able to perform beyond that level in your role, it isn’t right for you.

If your business is having a hard time finding or keeping customers, it hasn’t found the pocket (also known as product/market fit).

Both require SERIOUS contemplation and even more serious action.

A ball player has a hard season, underperforming at every level. He is traded to another team or signs for a below-average 1-year deal then lights up the league the following year.

A company struggles to survive for years only to pivot into a new approach or model or vertical and becomes a household name.

There is only so much pushing and prodding and self-delusion that can be masked before reality sets in. Nothing grows by force and sheer will for long.

Are you in the right role but the wrong company? Find the right company.

Is your business fighting in a market of 1 or 1000? Pivot to where the demand has been demonstrated or specialize in a vertical.

Growth will not come to those who settle and wait.

Kill the (be)cause

Most of the challenges of building a business are a direct result of ignoring the “because”.

No one is buying your product or service because you haven’t solved product/market fit

Your product keeps failing because you haven’t built it to scale.

Your team is leaving because you haven’t given them clear goals.

During the early stages of a company’s life, speed is emphasized. Run. Fast. Faster. This leads to cutting corners. You tell yourself and your team that you will come back to that later. But you never do.

These become the causes of failure and they will become ghosts in your machine if left unchecked.

When these finally show themselves, don’t ignore them, solve them. Scale-up companies don’t build scaffolding around a weak model or the wrong offering or the wrong people.

You can run for a while, you can ignore the truth for a little longer but you cannot hide from the obvious.

The lost art of resilience

Nobody explains resilience better than Rocky:

“But it ain’t how hard you hit; it’s about how hard you can get hit, and keep moving forward. How much you can take, and keep moving forward. That’s how winning is done.”

Building a company is an intense life sprint that tests resiliency every single day.

It wasn’t too long ago that starting a company required a business plan, a bank loan and a full-time commitment. None of those are necessary today and that makes for a diminishing amount of resilience in the entrepreneurial wastewater.

It is easy to start something today. The infrastructure and the playbooks are right there. Everyone is building in the open and ideas flow at breakneck speeds. Start a store on Shopify, sell subscription boxes, become an influencer, write a newsletter, become a coach, the “things to start” stack is endless.

The hard part is sticking with it. Most ideas aren’t worth the effort and those that are worth it are hard to get going so most people give up on them too easily.

Resilience is a muscle reserved for belief and commitment. No part time founders succeed. You can’t be one foot in or it’s just a hobby.

Stepping in the ring is easy. Getting hit repeatedly isn’t.