There’s a point in every business journey when you stop charging forward and start asking the bigger questions. For me, that moment came after losing someone close. It shook my sense of invincibility and forced me to think about time, how finite it is, and how often we act like it isn’t. We plan exits for our businesses but rarely for our lives. So I built a timeline for mine, mapping it like a business plan. I started with my drop-dead date and worked backwards. Morbid, maybe, but it gave me a clarity that decades in business hadn’t.
Watch the whole recording here.
I’ve come to see life in three stages. The go-go years are when you’re full of energy, building and breaking things just to see what happens. The slow years are when you start consolidating, mentoring, and finding rhythm. And then there are the no-go years, when you release your grip and pass things on. My parents are there now, and watching them has reminded me that all the titles, deals, and deadlines we chase eventually fade into something much simpler. Those reflections shaped much of what I shared in my Masterclass, not just about business but about living with intention.
One story I told was from my first partnership. I thought I owned the business. In reality, I only owned half of it. When my co-founder and I parted ways, I had to buy her out, a painful but necessary lesson in understanding the difference between being an owner, a shareholder, and an employee. For years, I’d underpaid myself, convincing myself it was for the greater good. When it came time to split, all that sacrifice counted for nothing. That experience changed how I mentor young founders. I always tell them: value your time, even if the business can’t yet. Respect the employee as much as the owner. It will save you heartache later.
That lesson also taught me focus. Someone once told me you can’t sit on two toilets at once. Crude, but true. For years, I was juggling ideas, new ventures, and distractions that made me feel productive but really just diluted my energy. Focus is what builds momentum. It’s not about saying yes to everything; it’s about saying no to almost everything so the right thing can grow.
The early years of my company were a blur of strategy decks and business plans, fifty-three of them to be exact, before I even spoke to a customer. It took me years to learn that strategy without execution is just theatre. These days, I tell people to get out of the building, talk to customers, and test in the real world. The market will tell you the truth faster than any spreadsheet.
Another insight that’s stayed with me is about simplicity. I love complexity, systems, integrations, and global teams, but I’ve learned that simple businesses often outperform the clever ones. A mate of mine runs a business that, on paper, looks dull. But it’s tidy, profitable, and predictable. I used to think that was boring. Now I think it’s brilliant. There’s a generation of solid, well-built companies about to change hands as their owners retire. Some might look uninspired from the outside, but they’re goldmines for people who can see the value in steady, well-run work.
Of course, I’ve said yes to the wrong customers, too. Every business owner has. You know it’s a bad fit from the start, but you convince yourself it’ll be fine. It never is. The wrong customer drains your team and your morale. These days, I live by a simple no dickhead policy. It sounds blunt, but it keeps things clean. Be upfront about who you work best with. Clarity saves everyone time.
Money’s another area where I’ve learned to swim against the current. I’ve never taken outside capital. For 25 years, I’ve bootstrapped, not because it’s easy but because equity is the most expensive money you can take. Every dollar you raise comes with expectations you might not want to meet. I’d rather build something slower and keep control. The best investors I’ve ever had were customers who paid us to build what they needed.
Somewhere along the way, I stopped thinking of business as a race. It’s a marathon. The people who survive are the ones who keep showing up. They absorb the knocks, learn, and move forward. Resilience is underrated. It’s not glamorous, but it’s what gets you through.
That resilience also comes from dropping the ego. I used to think I had to have all the answers. Now, I’m happy to admit when I don’t. When we had a hack attempt on a client site recently, I called the CEO myself, explained what had happened, apologised, and told them we were on it. It wasn’t a comfortable call, but it built trust. People respond to honesty more than polish. Vulnerability isn’t a weakness; it’s what makes leadership real.
I’ve also learned the power of surrounding yourself with people who love what you hate. I thrive on ideas and energy. Detail drives me mad. Luckily, my operations manager, Karen, eats detail for breakfast. She saves me from chaos every day. Building a great team isn’t about hiring clones of yourself; it’s about balance. The people who got you to one stage might not be the same ones who’ll take you to the next, and that’s okay.
If there’s one thread that ties all of it together, it’s time. Time is the only resource we can’t earn back. I once heard about a billionaire who stopped an airport so a helicopter could take him straight to his yacht. At first, I thought, how arrogant. Then I realised he just valued time more than anything else. We don’t need private jets to do the same; we just need to decide what we’ll spend our hours on and who we’ll spend them with.
Running a business for 30 years has taught me that the real win isn’t scaling faster or raising more money. It’s designing a life where the business serves you, not the other way around. That’s what I wanted to share in the Masterclass, not theory, just the stuff I wish someone had told me at the start.
If any of these reflections hit home, I’d love to keep the conversation going. Maybe we can swap notes over coffee sometime. After all, these lessons aren’t really mine alone; they’re just the universal ones every business owner eventually learns, one hard-earned chapter at a time.