Thoughts on people, leadership and tech

Today I turn 39, and I am less certain than ever. I've built companies, led teams, invested in startups, and done more self-work than my 19-year-old self could have imagined. Yet with each passing year, it becomes clearer how much I don’t know. And surprisingly, this uncertainty brings more comfort than certainty ever did.

The rewards for being the best at something are exponentially greater than being ok at many things. Even being just 10% better over time compounds into outpacing the competition dramatically. A few more customers lead to a little bit more money that can be invested into a few more ads leading to even more customers and so on.

The rewards for being the best at something are exponentially greater than being ok at many things. If you've been in business for a couple of years, you’ve probably heard this over and over again in the context of product strategy. But here's what's interesting - these same companies who get it right in terms of strategy can completely miss this principle when it comes to their people.

The team didn’t need me to tell them how to build features. They needed to understand why we were building them in the first place. And as I removed myself from the day-to-day operations, the team started moving faster.

During a conversation with a fellow coach, I had a realization that shook me to my core. For the past five years, I’ve been clinging to an identity as “the person who made it,” and with that, reluctant to put myself in situations where that identity might be challenged.

The team didn’t need me to tell them how to build features. They needed to understand why we were building them in the first place. And as I removed myself from the day-to-day operations, the team started moving faster.

AI seems to be everywhere. It doesn’t matter if you’re working with code, people or biology. The message seems to be the same. If you’re not using AI you’re falling behind. However, I think there is something even more important that is getting lost right now: The craft.

“He was like a brother to me,” he said, tears welling in his eyes as we sat in our weekly 1-on-1. His voice cracked as he described the accident that had taken his family member just days before. In that moment, spreadsheets and project timelines evaporated from relevance. What mattered was the human being sitting across from me.

Just like athletes need recovery between training sessions, organizations need breaks between periods of intense change. Weekends exists, of course. But I think that it’s important to also find a sustainable rhythm in your organization. This is especially important when leading people.

What we often call “perfectionism” isn’t actually about quality at all. It’s about fear. When we obsess over making something perfect in a context where speed and iteration would serve better, we’re not pursuing excellence - we’re avoiding the vulnerability of shipping something imperfect.

The same tools that enable seamless collaboration across time zones—Slack, email, calendar invites—have created an expectation of perpetual accessibility. This isn’t just about interruptions; it’s about the cognitive toll of being always interruptible.

The same tools that enable seamless collaboration across time zones—Slack, email, calendar invites—have created an expectation of perpetual accessibility. This isn’t just about interruptions; it’s about the cognitive toll of being always interruptible.

It’s not so much that we invite complexity into our lives. It sneaks in through the back door, disguised as solutions. A new process here, an extra approval there. Each addition seems sensible. But together they form an invisible web that slowly strangles our organizations.

Your non-decisions are killing your business.

There’s a common challenge I see, especially among new leaders: which team do they primarily belong to - Team 1 (their peer group) or Team 2 (their direct reports)?

2024 is about to end and as always I have earmarked a good chunk of time to reflect on everything I’ve been up to over the year. One of those things is my newsletter.

It took learning how to ride a motorcycle to really understand what a sprint should feel like. And no, I’m not trying to be clever with metaphors here - there’s a very real lesson about tempo that changed how I think about building products.

If you’re a manager you, you should never take the monkey (problem) of the back of your subordinates. Instead you should schedule regular feeding times and make sure your subordinates monkeys are well maintained (by asking questions and giving direction in person).

Most of us dream of unlimited resources and complete freedom, but more freedom isn’t the solution - it’s the problem. When every option is available, decisions become overwhelming. Even worse, without boundaries, Parkinson’s Law says that work expands infinitely.

When it comes to planning, I prefer to optimise for agility more than anything else. Responding to new information over following a plan. Long term vision, yes. But I don’t fool myself into thinking that I can predict the future.

As leaders, we often find ourselves frustrated when our teams don’t follow instructions. We’ve laid out the steps in the process clearly, so why is it so hard for people to follow them?

There’s a rhythm I’ve noticed in effective leadership - a pattern that emerges when building high-performing teams. I call it the 90/10 rule: spend 90% of your time pulling people forward gently, and 10% pushing hard enough to break patterns.

The best hire I ever made took no more than a handful of days. Not because I rushed. But because I knew exactly what I needed - both for now and for the future.

Each day brings fresh crises. (If it doesn’t then maybe you’re not moving fast enough) This means that you need to prioritise and pick your fight for the day.

Kevin Kelly puts it well: “I don’t think to write, I write to think. When I write, my mind clears up. But why write as a leader?

My three favorite frameworks for getting delegation right.

If you’re like most people, you’ve probably been taught to delegate, trust your team, and avoid micromanagement at all costs. That’s all good in a normal company. But what if that advice is dead wrong for startups?

Your team needs to know where they're going, how to get there, why it matters now, and what their part in it all.

As a startup you want to be running as fast as possible. Doing to much up front slows you down, which means you need to wait with everything until the last possible moment.

Your product tells a story about how many problems you're trying to solve at the same time.

when it comes to finding Product Market Fit, “AND” is a red flag. What you really want is a big, bold OR!

Spending a little bit of time thinking about how your management systems influence both culture and results is not just nice, it's necessary.

Startups often begin in a state of organised chaos, rapidly testing hypotheses to find their footing. As a company matures it needs to start looking at strategy as more than just a buzzword.

Once upon a time Netflix looked at expanding to Canada. Should be simple, right? Wrong.

Everything in life moves in Seasons. Season has its theme, and when a Season has passed it never comes again. Use fact in all areas of life to give yourself superpowers

Rewriting a piece of software is a daunting task. And sometimes straight-up dangerous. In this post, I explore the pros and cons of a rewrite, and share some examples along the way.

Selling to everyone means selling to no one. The Ideal Customer Profile is a tool you can use to gain clarity about who you are selling to.

Don't get caught up in perceived unfair advantages. The only thing that matters is doing quality work.

Building a company is hard. Building a company while obsessing over competition is even harder. Stop competing and build something different!

Have you ever experienced days where you've been mostly responding to other people's requests and by the end of the day you're not sure if you've gotten any work done? Then this post is for you!

Angel investing is about making good decisions. The right decisions will give you money to last a lifetime and the wrong decision can lead to losing a lot of money. Having been angel investing for over four years now, I’ve made quite a few mistakes.

Throughout a startup's journey, the role of the CTO goes through four different stages, and each stage requires different types of leadership. Knowing what stage you are in and where the focus should lie is key for both CTO and founder.

My first two blog posts on angel investing were about getting into deals. This one is about how you get money back.

Angel investing with other angels is a great way to manage risk and increase the likelihood of getting into the best deals. In this post, I try to explain why.

Writing is editing. If you're having trouble writing something good, start by writing something bad.

Angel investing has gained a lot of popularity. Here is my attempt to write the introduction post that I would have wanted to read when I started out almost four years ago.

If someone had given me ten cents every time I heard the sentence in the title, I would be a very wealthy man. However, that sentence is a perfect example of the worst type of feedback you can give someone.

Life is cumbersome when you work on other people's plans.

Focusing on the right thing is hard. In his book, The One Thing, Gary Keller argues that you can use a single question to find actionable insight about where to direct your energy and focus.

Most people I speak to have experienced some form of burnout. This is my story of the day that it happened to me.

Managing is hard. Managing when you can't see your team every day seems even harder. Covid forced the and of many companies and the genie is not going back into the bottle.

I have finally decided to start putting my ideas where other people can see them. In this post I try to reason about why I do this in the first place.

As covid hit and people who were used to working in an office had to start working remotely, Slack (and similar tools) became the de facto standard for communication. However, bad practices quickly lead to availability stress followed by burnout. This is a collection of rules that I use to avoid this.

One thing that I have been thinking a lot about lately though is the misuse of the word velocity. When most companies and teams say that they are measuring velocity they actually mean speed. But as it turns out, direction matters!