Lessons From 27 Years of Building Companies

I've been building companies for 27 years, across a lot of industries, through a lot of change — from the early days of the commercial internet to the age of AI. Along the way I've had ventures work and ventures not, and I've learned that most of the genuinely useful lessons aren't clever tactics. They're durable principles that hold up decade after decade. Here are the ones I'd hand to a younger version of myself, framed as general truths because that's how they've earned their keep.

Understand the customer before anything else

The very first business lesson I ever learned was at eight years old, selling mistletoe outside a store — I figured out who wanted it, why, and how to present it so they'd choose it. Nearly three decades later, that's still the whole game. Every successful venture I've built started with genuinely understanding a customer and a need. Every struggle traced back to losing sight of that. You can get a lot wrong and recover if you truly understand who you serve. Get that wrong and no amount of execution saves you.

Everything I've learned in 27 years still reduces to what an eight-year-old selling mistletoe already knew: understand who you serve, and make it easy for them to choose you.

Adaptability beats being right

The businesses and technologies I built around have changed completely over the decades. What let me keep going wasn't being right about any one bet — it was the willingness to adapt when the ground shifted. I've written separately about why adaptability beats talent, but the short version is that the world will keep changing faster than your plans, and the founders who thrive are the ones who treat change as the normal condition rather than a disruption to endure.

Focus is a superpower

For years I mistook doing more for progress. It took real maturity to learn that focus — deciding what matters most and pouring your energy there — beats scattering yourself across everything. The most productive periods of my career came from ruthless focus, not from spreading thin. This is true for a solo founder especially, and I dig into it in the discipline of focus. Saying no to good opportunities so you can say yes fully to the right one is a skill worth developing early.

Build things that compound

The most valuable assets I've built weren't the ones that paid off fastest — they were the ones that compounded. Reputation, relationships, knowledge, systems: things that keep paying and grow more valuable over time. Early on I chased quick wins; over time I learned to invest in what accumulates. A business built on compounding assets becomes stronger and harder to compete with every year, while one built on quick hits has to keep starting over. This is the through-line behind the compounding business.

Right-size your honesty about what you can handle

One lesson that saved me repeatedly: be honest with yourself about what you can actually do well right now. Overreaching — taking on more than you can handle, promising what you can't deliver — has sunk more ventures than a lack of ambition ever did. Ambition matters, but it has to be paired with an honest read on your real capacity at this moment. Knowing the difference between a stretch you can make and a leap that breaks you is a discipline that comes with experience, and it's worth developing on purpose rather than through painful failure.

Reinvention is the job, not the exception

Across 27 years I've had to reinvent what I do more than once as the world changed. Each time, the instinct to cling to the old way was strong and wrong. The founders who last treat reinvention as a normal part of the work rather than a crisis. I've written about reinventing yourself every decade, and the core of it is that your willingness to become something new is what keeps you relevant when your old advantages expire. The specific skills change; the willingness to keep learning is the durable one.

The lessons that actually last

If I compress all of it: understand your customer deeply, stay adaptable, focus ruthlessly, build what compounds, be honest about your capacity, and treat reinvention as normal. None of those are tricks, and none of them expire when the technology changes. That's exactly why I trust them — they've survived every shift I've lived through, from the directory era to the AI era. The tactics I used decades ago are useless now; these principles are as true as ever.

I share these not as a guru but as someone still in the arena, applying the same lessons to new ground. If you'd like to talk through applying them to your business or your next move, schedule a strategy session or get in touch, and you can read more of my story on the about page.