The Hardest Thing About Being a Second-Time Founder

Going again, and putting myself in the spotlight

I still remember sitting in a boardroom during my first company, PowerLinks, when a big UK institutional investor leaned back and said:

“We’ve built the product now — can’t we lay off the engineering team?”

It was one of those jaw-dropping moments where I realised: this wasn’t my company anymore. I was down to less than 10% ownership, “founder and leader” in title, but not in control. Years earlier, another investor tried to hire a COO on literally ten times the salary of the co-founders — a person who nearly destroyed the business.

That was the hidden tax of dilution: not just financial, but emotional. A slow erosion of control over the very thing you’ve poured yourself into.

Building Differently This Time

At FunnelFuel, I’ve done almost everything the opposite way round.

We’ve avoided the pitch deck treadmill, the endless investor meetings, the false sense of momentum that comes from chasing rounds. Instead, we’ve self-funded, grown organically, and made measured bets. Two small stake strategic investors aside, we’ve kept control in the hands of the people building the company.

It’s meant saying no to “scale at all costs” and yes to profitability. Hindsight is a wonderful thing, but I’m convinced PowerLinks would have fared far better if we’d chased sustainability over speed and scale

This time, we’ve kept control of the clock — the company runs on our timeframes, not someone else’s.

Equity, Teams, and Structure

That decision not to dilute also unlocked something else: the ability to push meaningful equity across the whole team. My view now is simple: if we’re going to spend years building this, the outcome should be life-changing for everyone involved, not just a lucky few at the top. This has checks and balances, against seniority and time in the business, but a scheme that genuinely intends to at least pay significant down payments on homes, not half a pay check in a throw way bonus

In an era where 70% of people say they’re job-hunting at any given moment, equity is a powerful motivator. It creates buy-in, drive, and passion. And it means when exit day eventually comes, it will change lives - plural, not singular. We also live in a world where building a pension pot is dammed hard, even on very good money, because life is expensive. We hope that the FunnelFuel equity scheme will go a long way to setting tens of people up for all stages of their futures

Changing tact, onto org structure, I also learned to separate product from engineering. Or to put it more graciously, my co-founder Dan Shaw led on this, determining we really did need a CTO. In the early days of FunnelFuel, everything technical went through me. All the product questions, all the engineering timeframes, all the delivery pressure. I was too much of a people-pleaser, too optimistic, and it created a gap between vision and reality. The business loses faith in timelines and I was pulled from where I could add value into precisely where I could detract from it. Ouch.

At FunnelFuel, we’ve drawn hard lines: product strategy, roadmap, and vision are separate from day-to-day delivery. It sounds simple, but that clarity is a game changer.

The Emotional Side

Here’s the thing I didn’t expect: the growth this time has been faster than we imagined. If I’m brutally honest, we didn’t think we’d be here yet. We’re maybe even years ahead of plan, operating internationally again — not just in America (where we were bruised before) but in Asia too.

That scale comes with pressure. People always need managing, cajoling, motivating. With a team of 50+, there are more moments of friction, more moments of dissatisfaction, and more moments where you feel the weight of leadership.

The difference is control. Even on the 14-hour bootstrap days, even when it’s lonely working from home, I don’t feel that acute frustration I felt the first time around. The spotlight is always on, but it’s on terms we’ve chosen.

Lessons of a Second-Time Founder

So what’s the hidden tax of being a second-time founder? It’s the scars. The nagging awareness of just how fragile a business is. The temptation to chase a payday after years of commitment, even if the business needs more from you. This is a human trait, we hold losers too long and throw away winners to fast.

In a world that has never changed as fast as AI is changing this one, it brings an old Chinese proverb to mind. When the winds of change come, do you build walls or windmills? In Adtech, this has strong resonance with walled gardens aplenty (think LinkedIn, Meta and co). With all the AI change around, do we back ourselves and our business to thrive, or seek an early monetisation of effort and hard yards already won? any founder would be lying if they didn’t admit they oscillate between these frames of mind. A good, sustainable business means you land on the thrive answer and start building your windmills, even if you keep half an eye on how thick your walls are

But there are advantages too. If I had to distill them, they’d be threefold:

• Experience - You’ve seen the movie before, and you know where the plot twists come.

• Pragmatism - You’re less blinded by hype, more willing to focus on the fundamentals.

• Comfort in footprints - You’ve walked this road once, and while it still hurts, at least the terrain isn’t unfamiliar. First $10k month, $100k month, $1m month, $xm month - they are noteworthy, exciting, celebration worthy but also not an untrodden path - so giddiness can be kept in check, and pragmatism can return. Even with a sore head the next day, because milestones should always be celebrated

And if I could go back and tell my younger self one thing, it would be this:

Get profitable. Control your destiny.