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.

The Bravado Bullshit

There is no part of a startup that is easy. Think about it, you are going against conventional wisdom and hereditary lines. You are sacrificing the now for a potential in the future. You are convinced that your idea is better than what is out there. Hill meets mountain meets Everest.

Why, then, do founders feel the need to gloss over how absurd it really is to start a business? Ask a founder about their business and they will almost unanimously say a variation of the same thing: “We are killing it”.


No founder of an early stage company is killing it. Certain aspects of their business may be balanced, growth may have started, revenue may be rolling in but I can guarantee that they aren’t “killing it”. They don’t have the right talent, they can’t find funding, their top customers are leaving, they have bills piling up that can’t be paid — they aren’t killing it, they are running a company that is most likely killing them. That’s what they meant to say.

Whatever this false pretence is that makes founders hide from the truth and not ask for help is so detrimental. It’s negligent.

I’ve been there before and it happened yesterday. The first time was when I felt I needed to carry the burden and shield my board and my team from the realities of our financial situation which led to layoffs. The most recent time was a co-founder’s candid conversation with an investor who said “it just seemed like you didn’t need anything”.

Bravado is a requirement to step out and do something different but it can also step in the way of success. The next time someone answers “killing it” to your question of how things are going, dive in and find the truth. You may just give that founder their greatest unlock.

Fighting overwhelm

Sometimes it’s not doing too little that hurts a startup. It’s doing too much at the same time.

One thing in common amongst early startup employees is a bias for action. We are the ones that, if you were able to pick us up in one hand, our feet would keep running in the air. Put us down and, boom, we are gone.

This kind of forward motion is perfect for the very early days where things are not settled and if you stand still you fall behind. As the company gets through this stage, this kind of frenetic activity needs to be slowly contained.

If it is not, it can completely overwhelm you.

It’s very easy to work harder and when that doesn’t work, to work harder again. 12 hour days become 14 hours and then 18 hours. Then you realize that there are only 24 hours in a day. It’s untenable to work more and be valuable to your family or the company.

When you reach this point — overwhelmed, fatigued — it’s beyond time to fight back by:

  1. Chunking your functions. You don’t have to execute on everything in real time. Compartmentalize and schedule common things (i.e accounts receivable) to one time per week and do it all then.
  2. Completing a single task at a time. Multi-tasking is bullshit. Simply don’t do it. Choose the task at hand and see it through start to finish. Turn off all notifications and get to focused work. If you can’t complete something from start to finish, don’t start it until you can.
  3. Simplifying what you are doing. We tend to overcomplicate what needs to get done. Overthinking everything means you are stalling on the simplest of things to get moving on. Don’t think about what it needs to look like at the end, just do the first thing that needs to be done now. Then do the very next thing. Motion quells the anxiety.
  4. Building rituals. If you are anything like me you’ve got an endless task list and a full calendar. To manage it all you have to live by rituals. For example my early mornings are for writing and workouts. I wake up and put on my gym clothes right away — this is my trigger. I schedule the coffee maker the night before and when my cup is full I start writing. Another trigger. Every morning. Monday-Sunday. It’s on automatic now.

This is how I started fighting back against my tendency to spend my days completely overwhelmed with activity. Be deliberate and controlling with your time, it’s this discipline that calms.

My worst meeting

It still haunts me.

One of the most important components about being the CEO of a startup is composure. Your team needs to know that you can do the job under tremendous pressure. This does not mean the burden is all yours but the lions share falls on your shoulders and you need to be able to handle it in a humane way.

My breaking point at the time was during our weekly senior team meeting. Sales, marketing, product and finance would meet every Monday morning to pace the week. This particular Monday morning was at a critical point for our company but the banter in the room was anything but focused.

People were late. Tasks weren’t complete. Focus was airy. At that moment, my mood was set and it was not good.

I do believe in a good balance between jovial and serious — it is often me lightening the mood with a dumb joke or poke at myself to lessen the tension — but, for some reason, that morning the meeting was off.

To be a leader you need to be able to absorb what’s happening around and to you. You need to be able to check your ego. You need to be able to calm your heart rate. You need to be able to control your emotions. You also need to be able to express your frustrations in a mature way.

I did none of that.

By the middle of the marketing overview something tweaked me and pushed me over the emotional edge. Bubbling with frustration I had 3 choices. I could let the person finish and we could have a tough but good conversation in private after the meeting. I could ask the right questions to lead the conversation in the right direction. I could let the team hold them accountable.

I did none of them.

I simply closed my notepad, picked myself up and promptly left the room without saying a word.

I picked up my ball and went home.

My thinking at the time was that the next words out of my mouth were going to hurt someone so I did what I thought was the “mature” thing and I left. The leader just stood up and walked out on the team, mid-sentence.

As you can imagine, in that one swift motion, my actions diminished the value of the person speaking and eroded the confidence my senior team had in me as their leader. One selfish, childish move undid 3 years of building.

I remember feeling like an idiot as I walked to my office. All eyes in that glass boardroom staring at me as I slowly made my way. I knew immediately the damage I had done.

It wasn’t long before that marketing person who I interrupted was gone, what else could they have done?

This happened over 15 years ago and it still sits with me. I’ve made every mistake in the book but this one selfish act at a critical point in the business and all our careers is something that I regret to this day.

Digging holes

For a long time I didn’t really understand what hard work is. Most young people don’t but it’s really not their fault.

I’ve been an entrepreneur my whole life. It wasn’t by choice, it was just something that I was afflicted with really. Because of that, I knew how to work hard in one aspect of my life. I thought, like many, work hard at work and that will provide.

Working hard at work flexes one muscle — similar to doing only arm curls at the gym. Massive arms but the rest of your body isn’t balanced.

So, when I’m getting stuck or my arms are out-sizing my legs, I try something different. Different as in mostly back-breaking, blister-inducing manual labour.

There is something amazing that happens when you take your brain out of your comfort zone and put it to use solving a problem that you don’t normally come across. I’ve built a fence, a shed (the “Shed Mahal”), a 3-season room, a deck and countless other creations. Each time, I’ve learned a new skill and tested the elasticity of my brain and the endurance of my body.

My mind is focused on ANYTHING other than my work work. Maybe this is like a hobby but even a hobby starts to get repetitive after a while. Doing this kind of work brings 100% of my focus with it and is perfect for a short attention span as projects don’t last a lifetime.

Forget about learning yet another language in 30 days. Grab a shovel, start digging some holes and build something new.


Running a start up is full-frontal. Things come at you from everywhere.

You have no money, no time, half the team you need, half the product you need and all the pressure to succeed.

The LAST thing you need is more distraction.

It comes in so many forms — often disguised as “things that could help” but, let’s be honest and clear here, they don’t help. They hurt. That’s why they are called “distractions”.

As a founder, CEO, someone in a leadership position, it is your biggest job to keep everyone focused on the company mission. No side-quests allowed.

As a founder, CEO, someone in a leadership position is it ALSO your biggest job to keep yourself focused on the company mission. You DO have permission for side-quests, as long as they support the mission and don’t distract anyone else from that focus.

As leaders it is easy to send mixed messages about what the focus of the company is. I’ve done it. It started so honestly as a small conversation but there is no such thing as a small conversation in a leadership position in a startup.

We were on the hunt for a series A investment so we let the team know what our plans were. We talked about it at every team meeting, we kept everyone on top of all the pitches and VC meetings we were having. Doing this MADE it important enough to be everyone’s top agenda item. It became our North Star…by accident.


When we realized the gravity of this mistake, we stopped talking about it everywhere.

Then THAT became the topic of conversation. Another distraction.


You can see how this type of distraction can escalate and tower over everything else.

There are so many opportunities to take your eye off the reason for the company. Shiny stuff trumps all here. It is your job to make sure that doesn’t happen.


We recently announced a giveaway. This is a pretty significant kind of giveaway — $100,000 — that will all go to one of our customers.

We expected to be able to get broad awareness from a combination of earned and paid for media. Earned for the philanthropic component and the big number, paid for re-engaging and reenforcing our existing relationships.

Our strategy was to pace out the split. First three weeks (1 week leading into and 2 weeks after launch) would be focused on earned and then we would kick in the paid – a combination of SEM and radio in all our markets.

We are 9 days into the earned media as I write this and the biggest lesson we’ve learned to the moment is: Earned media hates the words “contest” and “giveaway”.

This seems obvious as I write it down but it goes to show you how using the wrong word or two can have an impact.

We have always been a company that focuses on the small and medium sized businesses that are being hammered by big box retailers like Amazon. Allowing them to out-compete them with faster same-day, local delivery. We firmly believe that the diversity brought by independent retailers and merchants is what makes our communities and cities unique. We all don’t want to shop at Buy ‘N Large, wear the same clothes and eat the same things. Homogeny in retail is bad for us, bad for the environment and bad for the economy.

We also firmly believe that entrepreneurship is the kindling that stokes the economic fire in our cities and our country. The problem with kindling, while essential, it is the first thing that burns.

I’m explaining this because the $100,000 we were handing over to one of our customers was meant to give them a leg up, to elevate the pressure, the make life a little easier for them to focus on building their business with some breathing room. A luxury most don’t have.

This is also a quarterly initiative. A version of this will happen on repeat every 3 months.

That’s the back story. The reason we are doing this. But then we added “giveaway” and “contest” to the end of the sentence. No one wants to support a contest or help promote a self-serving giveaway.

This is why you, as a founder, need to scrutinize every single word, every single number and be unapologetic about doing so. Slow down. Get the position right. Think from other peoples’ angles. Don’t stop asking questions.

At least we realized this early on in our journey with this program (<– WAY better than “contest”) and have made adjustments in our language and our positioning. Lesson learned.

YOU are the bottleneck

Being a leader doesn’t mean you make all the decisions.

Leading people starts with making sure they are clear about their objectives and then getting out of their way to let them do their work.

If they are unclear about their responsibilities, you haven’t delegated properly.

If they come to you for every decision or permission, you haven’t given them authority.

If you second guess every decision they make, you don’t have confidence in their capabilities.

Your mission

Business is self-serving and this is the problem.

Its (the business entity) goal is to provide a return for investors or shareholders. In fact, as a leader in a venture-backed company, the only goal is a return in a set amount of time. That’s why the investors put money in.

This doesn’t mean whatever you are working on needs to be a soulless shell. Most businesses start with a mission but, somewhere along the way, get lost in the “shareholder” value circle of death.

So many things conspire to erode the company mission it is hard to keep it front and centre. When revenue needs to grow or margins need to increase due to investor requirements (present or future), it tends to supersede the mission. Most of the time these corporate responsibilities are in opposition to the mission.

No one wants to hear about the company’s commitment to fiduciary obligations — outside of the board and investors. This is where steadfast focus on the mission is needed.

To keep it front and centre, ask yourself this sequence of questions and make sure the answers aren’t focused on what the company wants. They should focus on what your customers want.

  1. Why did I (we) start the company?
  2. What was the burning problem we are trying to solve?
  3. Who were we trying to solve the problem for?
  4. What do they need from us to solve their problem?
  5. What has changed since we started the company? Are we still aligned with the original problem?

From there, you should be able to craft a broader mission to build around the company.

For example. Trexity is a last-mile delivery company. Seems so straight-forward. Our mission is to deliver products for our customers. But that’s the same mission as FedEx and Bill’s delivery company. Boring. Uninspired. Commoditized.

Instead, we focused on the problem that our customers were having. They were getting crushed by larger retailers that could get products to customers faster — they were getting eaten by Amazon and WalMart and any other logistically-adept retailers. We set out to level the playing field.

Our mission is to allow your local, Main Street merchants out-compete the big brands that are homogenizing our communities. We are here to support local small and medium-sized businesses in defending and growing their reach in their cities. We understand that SMBs are the blood of a vibrant and prospering city and we are helping them build their business so they can survive and thrive.

Notice that I didn’t mention delivery once? That’s how we make money but that’s not how our customers do. We want to extend THEIR reach. Increase THEIR revenue. Stabilize and grow THEIR business. If they don’t succeed, we don’t succeed.

That’s a mission.

A simple price to pay

When we started Trexity we wanted to offer fair and honest pricing for our deliveries. Other providers over-charged or added surge when things got busy. That wasn’t going to be us. Ever.

We decided on a time and distance model. A customer would only pay for the actual time and the actual distance the delivery would travel. From their store to their customer — nothing else. This would mean that hyper-local deliveries would be very cheap and longer, further deliveries would be more expensive.

Pricing was done in real-time, calculated right when the delivery address was added. If there were more than one deliveries going to the same area, we even calculated the distance between drop offs and only charged for the time and distance between them. It was a thing of beauty, efficiency and honest.

Unfortunately it was killing our business for one simple reason.

When a potential customer asked us how much it would cost to deliver a package, our answer was “it depends”.

“It depends”?!?! That is not an answer to the most important question in our line of work.

Our customers couldn’t budget when we answered “it depends”. Their customers couldn’t understand the cost of a delivery when it was completely dynamic.

The result was we stalled our growth. Merchants that were already with us, stayed because we could provide an “average” delivery cost (even writing this down makes me cringe — how could we not see this was an issue at the moment?).

Our pricing had become too complex and, even worse, against the norm of the how the industry operated. We tried to invent a new paradigm in an industry that would not adjust to it.

We knew we had to change to stop the stall. We had to make it easy to sell but, more importantly, easy for our customers to understand, budget and relay to their customers.

So we took all that dynamic pricing, all that underlying code, all that methodology and tossed it in the garbage and started over again with our customer in mind.

We moved to a simple flat rate pricing. Easy to explain. Easy to understand. Easy to budget for. Easy to sell.

The results were an unlock, and almost immediate. Our monthly volume became our weekly volume which then became our daily volume.

We got too complicated with our pricing. Too sophisticated for our industry. The moment you have to explain how your pricing works is the moment you’ve lost the customer. Over-thinking and over-engineering your pricing will stall your business. Start simple and then get complicated later.

Manual Productivity

New productivity app? I’ve tried it. Things, Twos, Tana, Bloks, Agenda, Routine, Mem, Amie, Evernote, Bear, Fabric, Lazy, Notion, Craft, Reflect, Superlist, Sunsama, Superhuman, Morgen, MayDay, bullet journals, tickle files…endless and exhausting.

GTD? Read it every year. I even interviewed David Allen years ago about how smartphones help/hinder productivity.

I’ve tried automating everything. Star an email in gmail? Send it to my task app. Read later in Slack? Send it to my task app. Tag, star, tag, star, send, send, send.

Has anything worked? Sure…now I have managed to make a list of 1000 things in my task app that I ignore.

For me, the realization was that I will never be the guy that wants my tasks decided for me and added to my calendar — via AI or something else. My calendar is my protected daily operating system — it is up to date at all times with the things I need to get done in the context that they need to get done. Automating this will never happen for me.

I’m a manual and deliberate person and something that lands on my calendar needs to be a manual and thoughtful process.

I’ve taken advice from Dan Martell and chunk my time (read his great book Buy Back Your Time if you are looking for a deliberate approach to running your day/week/month/year). But I do it manually.

My week could look like this:

Mondays: 1:1’s with my team
Tuesdays: Finances
Wednesdays: Product focus
Thursdays: Sales/Marketing focus
Fridays: Executive/working on the business
Sundays: Weekly prep

And I stick to it. Things fall apart when I try to bleed things into other days. My mindset is what dictates my productivity. For example, when I’m in finance mode, I’m in finance mode. Everything else is an alien language to me. Context-switching is a drain and usually doubles the time and effort it takes to complete anything.

My productivity stack is minimal these days:

Things for ToDos
SuperHuman for email
Reflect for notes (although I’m currently testing Lazy)
Notion Calendar (love the time blocking features it has for cross-calendar events)

That’s it. I capture tasks as they happen to me in Things (ctrl/space is a miracle). I guard my calendar against useless clutter. I keep church (events) and state (tasks) apart…they are two different things, two different mindsets.

Does this work? For me, right now it does. Keeping it simple is my aim. Productivity has to be done with intent and the only way I can control my time and be at my best is when I decide how to run my own days.

Hiring is lazy

Ok, not ALL hiring is lazy but most of it can and should be delayed for as long as possible in early-stage companies.

People are a headache for startups. More people means more meetings, more complexity, more diversions in a time where companies cannot afford any of that.

MOST importantly is that, with more people too early in a company’s life, things that should get automated simply don’t. They get done by people and then those things that should be automated become a human-led process and part of the DNA of the company. Then that thing becomes a responsibility and then it becomes too unwieldy for one person and a team is formed around it.

Early in the life of a startup every single person on payroll should be bouncing between 90-100% utilization. The difference between 90% and 100% is automation. Only when the company has automated all that it can should it hire for the next phase.

One of my early co-founders said it succinctly: “Wouldn’t it be great if we could run this company with just the founders?” That should be the goal for as long as possible.

The Urgent vs The Important

“We want it now! I want it yesterday, I want f**king more tomorrow, and the demands will all be changed then so f**king stay awake!” – Billy Connolly

If you ask me, this is the biggest stumbling block for early stage companies — the question of what is urgent and what is important.

Urgent = Immediately critical to the well-being of the company, the customers and the team
Important = Necessary and important longer-term building blocks to the stability and longevity of the company, team and customer relationships

Startups run on emotion and the things that are prioritized tend to come from the last conversations that were had. It’s almost the same as going grocery shopping while hungry — you end up making questionable decisions.

The best way to compartmentalize the urgent versus the important is by asking one simple question: “If we don’t do this right now what will happen to our customer/team/service” If the answer is nothing, it is not urgent. You need to be really brutal with this answer. Things tend to bleed into the urgent because of impatience and a lack of clarity when you answer this question.

I’ve been involved in startups for decades (sadly, very true) and I still fall victim to this dilemma. I’ve had great co-founders that keep me in check on this — impatience is a part of being a founder — but if you are your only voice of reason, here’s a sample check list to start thinking about what is urgent and what is important.


  • Critical bug fixes or issues preventing a customer from using your product
  • Responding to a customer support issue, complaint or challenge when using your product or service
  • Resolving any performance issues that impact the stability and/or usability of your product or service
  • Payroll


  • Strategic planning for the business
  • The product/service roadmap
  • Building a robust and scalable infrastructure
  • Funding

Despite the frantic pace of a startup and that feeling that it all has to get done right now or else you are doomed, everything can’t be urgent. Companies that seem all over the place are simply having a hard time distinguishing between urgent and important.

The Founder Origin Story

Every founder has an origin story.

Tobi was trying to sell snowboards online but couldn’t find an adequate e-commerce platform = Shopify
Travis and Garrett were trying to hail a cab in Paris and wondered why it couldn’t be done with their phone = Uber
Brian was trying to make rent and opened up a room to rent during a design conference in SFO = AirBnB

These stories have become legends over time. How far off from the truth is not really clear however what is common among these great stories is that they’ve lived long enough to become legends.

Their products became bigger than their story.

The story is an essential part of building a company. It’s how you find your first investors, convince your first employees to come on board, find your first customers and guides the early version of your product. It is the only asset you have at that stage.

At some point, the story needs to be taken over by results. Growth. Sales. Expansion. A business is born and the story becomes an anecdote.

We only really hear the legendary founding origin stories after the success of the founders and their companies. The stories are not unique but what makes them known is the success of the company. You know Tobi, Travis, Garrett, Brian, Bill, Steve, Larry, Jeff, Mark and many others from their stories, you remember them because you use their products every day.

Fast twitch + Slow twitch

Startups are a series of back-to-back marathons. To make it even more challenging, each marathon is made up of 422, 100-meter sprints.

To survive as a founder you need to understand and apply the concept of fast twitch and slow twitch muscles to how you work. Fast-twitch muscles are for endurance, slow-twitch muscles are for short sprints. One is slow to fatigue, the other tires quickly. One is a marathon, the other is a sprint.

Remember those cross-country races in grade school? There was always one kid that shot out of the blocks in a full sprint. I’ll never forget one year this kid, Billy, flew out off the starting line like a bullet. He left the field behind him in the dust and after 100 meters he was 200 feet in front.

Billy ended up crawling across the finish line, in dead last.

Early-stage founders tend to leave the gates fast and furious like Billy, only to end up burnt and exhausted as the rest of the competition — or worse, the opportunity — passes them by. Steady progress and timely, opportunistic sprints builds the momentum and keeps everything and everyone moving forward.

Don’t be a Billy.

Assume it’s no

Raising any kind of investment outside of friends and family is one of the hardest things to do as a founder. It’s an un-natural act to ask strangers for money to operate a business.

There are certain unwritten laws that every founder hunting for funding should acknowledge from the start. These will help ease the pain, the stress and the anxiety that comes with the uncertainty of having other people make a decision about the viability of your company.

It’s really hard to be critical of your own business — you have a slight bias. So keep these in mind as you go down this path.

  • Assume the answer is no. 99.9999% of the time it will be.
  • Do not say anything that isn’t researched or true. NO speculation. NO false projections or results. Just stick to the facts. Do not make stuff up to “win the deal”. You won’t.
  • Investors see 1000’s of business plans, decks, pitches, emails every year. They may invest in 5. It is YOUR job to make your business stand out, not theirs.
  • Warm intros trump cold outreach.
  • Investment criteria will change. Today it might be growth at all costs, tomorrow it will be gross margin, next week it will be EBITDA.
  • FOMO is not a thing.
  • Global, world-altering events are opportunities and threats — even in your small town. Wars, pandemics, inflation all impact the investor psyche.
  • It will take WAY longer to raise than you could ever imagine so brace yourself and your cashflow. Also, see the previous point about the world…when it takes a full season or two to close a Series A, the world sometimes doesn’t line itself up properly.
  • Geography IS important. Investors are looking for the BEST company in your space to invest in with the greatest opportunity to see a return. They have to be able to see the path forward and, unfortunately, you may have the greatest offering but your reach is limited because of your distance to the epicentre of your market.
  • You probably don’t need/deserve funding. This is the hardest to swallow but most companies are not worthy of investment.

So many things need to be aligned in order to raise money from investors. Acknowledging these 10 laws will help as a sanity check if you choose to go down this path. To raise is a full time job — aside from the one you have building the actual business…

Mad startup operating skills

In startups, operating discipline is a muscle but versatility is a skill.

There is a type of person that is built for early stage and growth stage startups. The problem is that it’s hard to define the skills they bring on paper. Even experience is sometimes misleading.

The culmination of all the years, all the ups, downs, successes, failures, scars, product releases, investments won/lost, exits, bankruptcies, hirings, firings, egos, doubt, fear and bravado creates the perfect startup operator.

There is no book that teaches someone how to operate in this environment — one that is like the first day on Mars on repeat. For most, it is overwhelming at the best of times and paralyzing all the other times.

Finding someone that can avoid all the early stage mistakes that waste time and money and effort is an accelerator. That person can see the path that inexperienced or first-time operators will miss. Startups need to cut across instead of going around. Decisions, directions and outcomes are the life source at this stage and the lack of knowledge stalls each.

The skill to fill has nothing to do with book or paper smarts. It is the skill of being a multiplier. A person that brings to bear their culmination of startup operating experience with immediate impact is the secret sauce to startup success.

Any and all advantages are lost by wasting time. Unfortunately that’s what most early stage companies do by not focusing on finding someone with the right skills.