Startups are hard to keep moving forward

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

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

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

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

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

Challenge your team

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

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

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

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

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

What’s in your control

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

Let me explain.

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



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

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

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

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

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

The Fast No

There is nothing that beats a fast “no”. Doesn’t matter what language, what circumstance, what context — a fast “no” is the greatest gift to receive.

Don’t mistake a fast no with every other type of “no” that is used. There is the “no, but” <– NOT a fast no. What about “not now”? Nope. Not a fast no. Anything without a concrete, 2-letter, hard end or anything remotely sounding optimistic is absolutely, 100% NOT a fast no.

So why is a fast no such a gift? How can that little word, usually the first one out of toddlers mouth or the thing you yell at your dog to stop bitting strangers, be a good thing?

Two reasons.

The first is obvious. It’s the end of a line of conversation. If you’ve ever tried to raise any kind of venture financing you know that VCs are notoriously vague with their answers. Only the good VCs that know and follow their investment thesis say no quickly. The rest string you along for fear of missing something — anything — that pops. They want to keep their options open. Often you’ll hear “let us know when you find a lead” <– that’s a “no”. Or, you’ll hear “circle back with me in a month” <– NO! The fear of that little word is real and sometimes you need it to move on.

The second reason is not so obvious. A fast no is sometimes the real start of the conversation. If someone can say “no” it means they have a line and you are on the other side of that line. A fast no means they can define why “no” makes sense for them. This is glorious. It means you can ask why they said no. It there truly isn’t a fit you are liberated. You are free to move on. There is no more baggage, no follow ups, no awkward emails or calls. But sometimes there IS a fit and the “no” helps clear up any confusion or misconception. Yup, “no” can be a conversation starter. I’ve seen it happen. Often.

Getting to a fast no takes courage from you. YOU need to be able to give the other side the permission to say it. At the end of every optimistic investment pitch or sales call I like to ask a variation of the “asshole” question (nicely, of course): Do you see a fit here? Can we work together? Does this fit your business/investment requirements? We often don’t want to hear no so we avoid asking for it.

Getting to a “no” is a gift — often AS valuable as a “yes” — but anything in between is pure anguish.

Love the work.

I love working. I love that feeling when you know you are contributing to building something greater than just you. Call it work ethic or elbow grease or being reliable — call it whatever you want — but doing the work is what makes me happy.

This wasn’t always the case. I was a terrible student because I didn’t want to do the work. I scraped by with marginal marks the entire time I was in school. I remember the exact moment where I realized effort did not equate to success at school. It was grade 5 math and my teacher said she was generous and gave me a 50 for the term. It was crushing and I explained that I had really made an effort that term and I had. She said that my effort is why she gave be a passing grade but it didn’t necessarily translate into good marks.

I really learned to work when I started my first company. There was no hiding from it then. The need to eat and live under a roof made for enough motivation to put the work in. As most entrepreneurs know, having to run a business and be the business takes an incredible amount of focus and dedication. As Springsteen says, “he don’t work and he don’t get paid.” That forces you to learn to work.

I levelled up again at my work game when I had twin boys. There is no escaping the amount of effort it takes to raise a child but two at the same time means you have to suck it up and get to work. Whatever I thought work was before kids, I was wrong and I needed to get more done in the same time. This is where you really have to love the work or it will beat you down. You need to balance the job of the job, the responsibility of the parent and the commitment to your spouse. An imbalance in any of those and the whole system is off.

There is a lot of wasted space in work. It is this wasted space that makes people hate the work. It can happen when you aren’t focused on doing the right things because of a lack of direction or instruction. It will happen if you don’t like what you are doing. It does happen if you don’t understand the game you are playing and how to win at it. All of these things zap your energy and work becomes work.

As an entrepreneur you can always find things that need to be done but you’ve got to love the grind or you will get tired quickly. As I moved up in my work life into more senior roles I realized that I missed the work. I love being a leader but I love being a leader that contributes by rolling up my sleeves and getting involved. It’s an example I want to set for my kids that despite a title and the prestige that comes with it, you have to work hard to make a meaningful contribution.

You have to love to work or the work eats you up.