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I have sought and taken advice from so many people for so many different milestones over a lifetime of being an entrepreneur and a parent.

A lot of it stuck. The rest allowed self-doubt and fear to creep into my mind — sometimes paralyzing my ability to get moving on things.

Two characteristics of worthy advice is that it comes from someone who has actually done a semblance of what you are trying to accomplish and that you are actually seeking it.

If you are about to embark on your entrepreneurial journey, seek advice and guidance from an entrepreneur (or 10) — preferably someone you’d like to model.

If you are trying to raise funding for your startup, seek advice and a system from someone that has successfully raised that type and stage of funding.

If you are starting a family, seek advice from other modern parents.

Unsolicited or unqualified advice is free but damaging. .

Seeking specific advice for specific things from specific people cuts out the ambiguity and reduces friction — all while crushing the self-doubt.

Money doesn’t buy happiness is bullshit.

This lament is only ever spoken by someone who has money.

There is not a person on this planet that is destitute or struggling paycheque to paycheque who would ever say that more money would not make them happier.

Money removes the fundamental stresses of life.

No more stress about having a safe place to live.
No more stress about eating a healthy diet.
No more stress about ensuring an education for your children.
No more stress about providing for your family and friends.

Remove those stresses from anyones life and, just by default, it is MUCH happier.

When I was twelve I discovered a life-changing album in Nebraska, Springsteen’s 6th studio release sandwiched in between The River and Born in the USA. A complete departure and huge risk at that time in his career, Nebraska is as well-known for the music as it is for the legend behind it.

Springsteen recorded it in his home in Colts Neck, New Jersey by himself. After months of carrying the cassette of his recording around, trying to find the sound that did the songs justice with his band, he chose to release the album using the recording on the cassette itself. I won’t spoil the movie but the legend was created.

In hindsight, it’s easy to see that this record needed to be released as it was. No other combination that I’ve heard recorded or live captures the meaning of the songs with more impact than the originals. What struck me was the willingness to ship what was perceived at the time as an imperfect album.

Entrepreneurs and founders and creatives struggle with this type of decision all the time. We wait, we build, we stall, we add features — we do everything except ship.

Nebraska was released because it was complete from the moment the last track was recorded. It took Springsteen all that time to come to that realization and the rest is history. The album was a critical success and cemented him as one of our generation’s greatest story tellers.

So many of us wait too long to start or release. Something holds us back and it’s only in hindsight after the release or launch that we realize waiting was not necessary, that you/it were ready all along.

We, the people who run operations for companies, are marathon pace bunnies without the ears.

Watch any marathon and you’ll see the ears among the throngs running. They balance the adrenalin of the first bunch of miles with the long run ahead. They don’t let anyone get too far out in front of their feet too early on and don’t let them get too far behind later on. Steady.

You put trust in them. They set the pace. You follow them to hit your goal.

I think of startups and high growth companies as running successive, back-to-back marathons…without stopping…ever. There are tremendous highs and lows along the way and, at each 20 mile marker, you question why you are putting yourself through it. Every time.

This is why setting the pace is so important. Most startups jump too fast out of the blocks or think of the finish line before putting in the work — wasting essential energy on non-essential things.

Pace bunnies lead and encourage everyone around them — often with a smile on their face — but don’t forget, they are running the same marathon as everyone else. It just doesn’t seem like they are and that’s the power of pace setting in action.

Speculation kills startups.

High growth companies need to move quickly. They also need to make quick adjustments if there is no progress. The only way to make these quick adjustments is by starting with the numbers.

Not knowing the numbers means you are speculating. If you hear (or say) “I think” or “I’m assuming” or even the word “around,” it is speculation, numbers are not known and the next decision you make could be fatal.

It only takes a moment for something to become common language. If the owner of the data voices a speculation instead of a fact, left uncontested it almost immediately turns that false data into truth.

My rule of thumb is that if you don’t know the data, don’t say anything. Don’t try to inject yourself into the conversation, don’t offer an insight and certainly don’t speculate. In any stage company one common is truth: Not knowing your business will put you out of it.

Always start with the numbers.

There are two givens operating any business: You get what you can afford and what got you here, won’t get you there.

For some early employees, tenure is fleeting and only during the formative parts of a company’s existence. Those early days require broad weight bearing roles — “fine” is good and “someone” is better than no one.

In later stage companies there is a tendency to hold on to legacy at the detriment of effectiveness.

As operators, it is our job to understand when our company requirements have passed the skills and capabilities of our people in those roles.

In both givens, the consequence of no action is to allow it to become part of your DNA. When that happens it defines your culture.

There are 2 incredibly tough aspects of starting and running a business and they are both related to time under tension.

In my life I have not found anything more challenging or stressful than voluntarily starting a business. It is also the most rewarding — but that comes later and always seems to be fleeting before reality crashes in again.

To succeed here you need to build entrepreneurial muscle. This is not a natural act so when we start we are basically all flabby. An idea and a statement of intent does not mean you are in shape to handle the task ahead. Being an entrepreneur IS a muscle that builds over time under tension.

When you use that muscle for the first time and realize it is there, it becomes something you flex for a lifetime. Putting time under tension here is part of your long game. Baby fat be gone, you are learning how to build a business one ripped fibre at a time.

Once you are waist deep in the muck you will experience the other, more visceral, aspect of time under tension.

This is where the real development happens.

Weight lifters use the time under tension strategy to spark muscle growth by slowing down their lifts in order to keep their muscles under stress.

Entrepreneurs are subjected to time under tension as the business requirements grow and the pressure to succeed increases. We are always under a form of pressure regardless of the stage of company. It is a constant and, subjected to it long enough, that muscle grows allowing you to carry more without your legs buckling.

When you get right down to it, success or failure in startups, or entrepreneurship, or business building comes down to how long you are willing to stay under that tension.

Scaling a company does not only mean revenue growth or geographic expansion or hiring or automation. It also means process and management and product diversification.

Early on, the first group gets you leverage, the second group gets you fat.

The most important balance in the early days is to not get in your own way of growth. There are so many false/positives in earlier stage companies that when you think you should add a process, hold off until it is obvious you should have done it months ago.

2 years into my current company we had a clear vision for the product and had determined that we were in need of a product manager to guide us. We promoted from within and set them on what we thought would be the path to product success — for them and the company.

We quickly realized we were WAY too soon for this role.

We almost immediately ran into conflicting processes — we needed to still be moving at a pace that was in conflict with a product management process and methodology. We were still finding our way, our product/market fit and adding a layer and strict process slowed us down to a frustratingly slow pace.

We were not ready.

There are countless moments at this stage in company where you may think you should automate or add process or delegate. Make sure you are doing it for the right reason — to unlock or unblock growth or people.

It particular, hold off on adding fat to:

• Email <– personalized won’t scale but it is how to establish trust. Templates are lazy at this stage.
• Product <– no one knows your product and your customer requirements better than you. Don’t distance yourself from this too soon.
• Marketing <– Grit and grassroots reign supreme over templated initiatives. Visit, call, email, connect instead of broadcast and hope.
• Sales <– Lose the generic patter — you see through it and so will your own customers. Remember why your company exists and put the effort into helping your customers see how you can help them achieve their goals.

We ALL hate receiving generic responses or sales pitches or products that look and taste the same. The companies doing everything the same way have become burdened by process. Trim your fat, stop tipping to laziness and put the work in to stay that way for as long as possible.

To build a startup has no equal when it comes to pressure, strategy, proper execution and hiring (not recruiting — hiring). There simply isn’t a similar experience anywhere.

After product market fit, hiring is the next most important thing to get right because the first hires will always be unique in the history of the company. They will be asked to do things they are uncomfortable doing, they will be stretched to their stress limits, they will have to work with speed and ambiguity and do it all for the potential of a hefty upside while taking home very little actual pay.

The tendency is to paint a picture of a family coming together. The trenches have a way of seemingly creating this familial bond amongst the early team. I look at the first group of misfits at this stage as a team and here’s why:

– YOU choose the team.
– The team has specific skills your company needs.
– You may have to let someone from your team go.
– Your team is aligned with the goals of the company.
– Your team will weed out the weak links.

To go into the startup arena hardens the entire team — it creates a bond that is special in business. The sense of accomplishment and triumph pulls people together. This is part of the startup culture, the team grows together. It breaks down when the company succeeds and that familial bond can’t stretch to new team members. This ends up holding people back and causing stress on them and the company.

Most people don’t switch families every 2 years but it is common for teams to shift as people outgrow the company or gain new skills. As founders and operators our goal is always to find the right combination of people to move everything forward — imagine having that conversation with your family…

Profound change happens in a startup one dollar at a time and it is a founders job to make sure that stays in focus.

I still wake up every day amazed at the entrepreneurial possibilities that have unfolded over the last 20 years. It’s never been easier to start something new but it’s never been harder to contain the breadth of the idea to see it through to a business.

Great operators know that a business without focus is a doomed one. There needs to be a relentless fixation on the problem they are trying to solve and for whom. I frame it as remaining as close as possible to the dollar.

Staying close to the dollar means really understanding what your ideal customer will pay for that helps them solve a real problem right now. Business is not complicated: Other companies have a problem that needs to be solved. You have devised a way to solve it for all of them.

The focus muscle comes in when you have collected that first dollar. The temptation is to branch from your core and try to solve another problem for the same customer instead of finding more customers that have the same problem. This is where startups fail.

Three really relevant examples come to mind around focus — these are things that I see companies doing too early and at their peril.

1. Expanding too quickly into new markets (that could be new cities or new verticals)
2. Building features that are only impactful for a small percentage of customers
3. Spray and pray marketing initiatives

The closest path to revenue is selling your existing product to more customers. The focus and discipline it takes to do this is what differentiates great operators and companies from the rest.

Nobody makes a purchase after 1 call.
It takes seven (ten? twenty?) interactions to create some sort of brand awareness.
Kids need 5 wake up calls before getting out of bed.

The hard truth is that things don’t happen by saying them once…or twice…This is as valid in business as in the rest of life.

Startups move so quickly that things often get overlooked, forgotten, deprioritized, re-evaluated or simply disregarded.

Operationally exceptional startups focus on easy to digest priorities and then set them on repeat until they are part of everyone’s conversations.

It is not good enough to write them down, talk about them once in a meeting and then assume everyone understands and will execute.

Repeat them everywhere.
Repeat them every time.
Repeat them until you hear them coming back to you from everyone.

The best advice I’ve ever read about starting a company is to not over-engineer the offering.

I think of startups as rockets trying to get into orbit. The challenge is so complex that most don’t even make it to the launchpad properly ready for launch.

To get a startup 1 inch off the ground so many things need to go right. It needs to be built for purpose, proven in the market to make a different to someone, fabricated (or coded) to work, packaged, sold and shipped.

Building too much, too soon is the same as trying to move a rocket with less fuel than required.

Building too little burns out before reaching the needed velocity.

Physics and friction are constant drags on a company’s velocity and nothing is more important than getting the mix right for that first inch of motion.

The hardest part of early startups is how to clearly know if you’ve found product/market fit. It’s an elusive term with even more elusive definitions — only really understood when you actually find it.

I’m so tired of trying to “be the aspirin, not the vitamin” thinking, it is killing ingenuity and innovation and the messy part of being an entrepreneur. This truth is that building a business is hard, it’s dirty, it’s lonely and every thing is stacked against you. It is unconventional to want to do this and it is next to impossible to get right.

Being perfect is not an option. Stumbling in the dark, blindfolded but finding your way is where most of us end up. But that’s ok.

I like to think of business building as looking for a hole and trying to fill it. Thinking this way means you are looking for an existing problem in need of a fix — instead of wasting time building something no one needs now. It also makes it clear that this journey will not be easy.

It’s not fancy but neither is building a business.

When a startup moves to scale up, the biggest blocker happens to be the people that actually made that happen.

Early leaders that don’t build for their future team are doomed to becoming the leader that “got them here but won’t get them there.”

Moving from a doer to a delegator means knowing that the work may not be done the way it was intended right away. The work may suffer. It may take more time. But more work will get done once the responsibility of ownership is shifted.

This transition doesn’t mean that quality should suffer long term — never settle for “ok”.
This transition doesn’t mean the abdication of responsibility — outcomes are still owned.
This transition doesn’t mean it will work with the current team — leading means monitoring and adjusting constantly.

The hardest thing to do is to trust that the work will get done without you actually doing it. The worst thing to do is make this leap and fall back to old habits because it isn’t happening fast enough or the way it was done before. Have faith in the team, give it a time limit, don’t revert and always move forward.

Stalling at this moment most certainly is the inhibitor to growth and for a company at this stage that cannot happen.

On March 17, 1845 the elastic band was patented by Stephen Perry.

179 years later a simple use of Perry’s invention makes for a powerful example of customer service.

Have you ever bought blueberries — or any berries — from a grocery store only to get home to find them free and loose at the bottom of your grocery bin?

One of my local grocery chains has solved this with a simple elastic band, wrapped around the plastic berry container. Problem solved. No crushed berries, no spillage.

This small attention to detail at checkout won’t change the world but focusing on things like this will change your business.

Balance in a startup has nothing to do with work or life.

Balance is the time between an ask and an answer.
Balance is the moment between realizing a strategy isn’t working and what’s next.
Balance is knowing when a person is not a fit and having that conversation.

Balance in a startup has everything to do with progress and action.

Do you know when you are going to die? To most of us, the answer is no (unless you’ve been to the crossroads like Jimi Hendrix, Kurt Cobain and Jim Morrison).

For startups the answer needs to be yes.

A startup has one foot in the grave the day it is born — and it stays that way until it graduates to becoming a business or the other foot drops.

At the startup stage a precise death date is easy to figure out: Take what’s in the bank, what’s coming into the bank, and subtract what’s leaving the bank. That gives a simple runway and when the runway runs out, so does the startup.

Personally, I like to share this date with the entire team for 2 simple reasons: (1) It level-sets to where/what we are as a group. (2) It (should) motivate the team to focus on the most important/impactful things.

No one in a startup should be surprised if things don’t go as expected. A death date brings unbelievable and ruthless focus — also known as the discipline a startup needs.

His wife was a week away from giving birth, she was unemployed and I had to lay him off because I didn’t see the obvious.

It was 2009 and I was the CEO of a small software company and we were starting to feel the effects of the banking crisis. Our top customer was a bank and they were slowing their spend, reducing their team and that was hurting my business.

I thought, like many inexperienced younger CEOs, that it was my responsibility to shoulder and shield. Shoulder the weight of the crisis and shield the team from the reality. The opposite is true. By keeping anything from the team it robbed them of their ability to make any decisions — especially about their own future.

When I finally explained our situation to the team it was too late to save 7 employees, including the soon-to-be father. After the dust settled and the wounds were healing, the remaining company took me to task for not letting them be a part of the solution. They were there for a reason. They believed. They just needed to be included in the good and the bad.

Laying people off because of something out of your control is one thing. Doing it because you didn’t adjust is something completely different. It took me until that day in 2009 to realize that business is not a solo mission.

There is a misconception that you work FOR a startup. This gives it a persona as though it is a real business — one with process and hierarchy and a cadence that allows everyone to breathe. This is simply not true.

To be a part of a startup you need to think of yourself as a group of renegades trying to prove that the idea — whatever it may be as the sands shift beneath everyone — is something WORTHY of becoming a company.

You don’t work FOR a startup, you work ON a startup.

The business of baseball and the business of technology are, in many ways, alike. Both types of organization are trying to assemble a balanced but elite team that ultimately dominates their industry. Each pays the “appropriate” amount for the talent that could get them there. The simple difference is the number of humans that can hit an 84MPH curveball after seeing a 100MPH fastball or throw that 100MPH fastball are scarce. That makes them a sought-after prize. Where else can you get paid an average annual salary of $4.41 million?

Compare those elite 975 employees that play for the 30 Major League Baseball teams to the millions of tech workers on the planet. At one point, their skills were needed – necessary even — and they were swallowed up into companies like DoorDash, Twitter, Facebook and Shopify. Assembled into teams, paid well in cash and options and sent on their way to help contribute to the success of the company.

The biggest difference is their approach to winning:

Baseball organizations — for all their faults — have a recruiting process that mostly works. It limits the number of players in the pool and, each year, forces ball players to be better and better to achieve stardom. Tech casts a wide net, over-hires and hopes.

Baseball nurtures their talent if you make the cut. Tech cuts the talent when times are rough.

Baseball builds teams with a cause but are only allowed a certain number of people per team. Tech hires everyone and hopes.

Baseball doesn’t lay off their team during an economic downturn. Salaries don’t go down. Ex team mates don’t share condolences on LinkedIn for other players who have been fired. No docs circulate with “great and talented” people for consideration.

You see where I’m going here — it may be far-fetched to compare baseball teams and tech companies but how can we be ok with 10’s of thousands of people being considered “extra” to their companies and being laid off? Without remorse. Without penalties. When a baseball team fails to live up to their promise, the leaders get fired. How do we not hold up our tech leaders to this standard? While it isn’t criminal to hire too many people, it is a complete failure on the management that did this. Think of all the wasted time, money and effort (and more money on gracious exit compensation) all for zero value to the company?!?

Over hiring can happen but if you have to fire over 88000 people collectively in one moment to correct it, that is not over-hiring, that is bad management.

Can you imagine your favourite team, in any sport, reading the Wall Street Journal and then deciding to fire 13% of their team like Facebook did in 1 day? Nope. The behaviour of boom and bust that we’ve become accustomed to in tech is NOT normal but we’ve normalized it. How can we accept that humans have become the collateral damage of bad management?

We shouldn’t.

I always take a window seat when I travel on an airplane — even if it means denying my kids that very joy. I love seeing the grind of the plane as it rolls down the runway, lifts off the runway and barrels towards the heavens as the earth gets instantly smaller. It is never lost on me — the miracle of flying is so cool.

There are those days, tho, when the plane is sitting in the middle of a rain or snow storm and the windows are thick with precipitation and it’s cold and dark. These ascents are the bumpy ones and I always think “this is what’s it’s like to be in an early stage company.” <– really, I do.

Let me explain.

Early stage is hard. Not just notionally hard, I mean physically, emotionally challenging. The kind of stress on the system that is unique and acute. Going through those early days/months/years is akin to that plane barreling down the runway in a rain storm. Every bump felt, every drop hitting getting harder and harder. With every meter movement forward the stress gets worse and worse. Getting off the ground takes absolute power, strength, planning, commitment and, in the case of a startup, great timing and tremendous pain.

Then come the thick blanket of storm clouds that the plane rolls through. Turbulence. There’s a reason you keep your seatbelt on during ascent. The plane bounces and heaves as it makes its way up, up, up. For a startup, once off the ground, the real work begins. It is this real work, through those storm clouds and gravity trying to bring you back down to earth, that makes or breaks it.

Once the plane cracks the plain of the cloud cover it becomes a different world. The sun is shining, the air is clear, no more storms, no more bumps, just miles of visibility. It almost feels like there is nothing else up there but the airplane. This is where great companies end up when they’ve hit product/market fit, built the right technology that solves that elusive problem for the right customer, lined up the right financing, built the right team and are growing in the right way. You have the wind at your back and momentum in your favour.

When a startup is in that rarified air it can do no wrong. It is the talk of the town, the media is glowing, the CEO is everywhere, investors want in, people want to work there, customers refer customers because that startup at that moment owns the air. Owns the conversation. Owns the momentum. As a startup, this is what you’ve fought for the entire ride.

The problem is that, just like being in an airplane, all things must land.

As with every trip, eventually the plane must descend back through the clouds and land. The momentum for startups is fleeting and It is this brief time that good companies become great companies by leveraging momentum and bad companies listen to their own press and miss their moment.

To make momentum work is hard work. Harder yet is to use the momentum to turn the startup into an actual company.

Pandemic supply-chain issues aside, closing the loop is the ENTIRE goal of e-commerce: To enable customers to find and purchase product. Dollars spent in building, promoting, staffing, warehousing and fulfilling are directed to one thing: Closing the sale. Here’s a tale of two e-commerce experiences that show both sides of closing the commerce loop — I’m not sure which is worse…

The “we’ll take your money” approach

Do you want to buy those Edmund dining room chairs? No problem. Expected delivery date is 3 weeks? Sounds good. Just pay now.

This is a grab. Those chairs were ordered in March, delivered in August. Not 3 weeks. Not even close. The delivery date simply kept on slipping. No note or apology from the merchant until a text came letting me know that my blessed day had arrived. 3 weeks to 6 months in incremental time increases plays on the sunk cost fallacy because if they had said 6 months from the onset, the likelihood of an order would have been 0%.

The “we won’t take your money” approach

Do you want that Lindbyn mirror? Sorry, out of stock. Can’t have it. Can’t order it. Can’t preorder it and certainly can’t have it shipped from another store that has it in stock. It MUST come from your city.

This is the other extreme. Those companies that have inventory elsewhere but don’t seem to have unified logistics or simply don’t have inventory at the moment. Even if they anticipate inventory in the coming weeks, we the people cannot reserve or pay for it. Just a “please come back later” note and be off.

Two extremes: We’ll take your money and you’ll eventually get the product (capture) or we won’t take your money but please please please come back and check regularly (release). Both fail to close the loop.