Designer to founder and back

In 2017, I had been contracting remotely for several years. Some of my contracts were long-running with part-time commitments, others were shorter. While I enjoyed my work and it gave me a lot of personal freedom, something was missing. I was craving something more, something bigger.

That’s when Steve, an old colleague from GoCardless, suggested we start something together. We both felt a need to build something from scratch. We had both been contracting and felt the emptiness of working on something, handing it off, and moving to the next thing. What if we could build a company that would last for at least 20 years?

After a few weeks of exploring potential ideas, we agreed on taking a bet on NDC and Duffel was born. We applied to YC twice, getting accepted the second time round, and raised three rounds of funding from some fantastic investors like Blossom, Index, and Benchmark.

More importantly, we built a great product and a fantastic team.

And just like that, five glorious years flew by. But despite all we had achieved, my life had changed, and it was time for a new adventure. I said my goodbyes, packed up my belongings, and moved to Brazil (for the second time) with my wife and one-year-old son.

Let me tell you what experiencing this huge role change really felt like.

Zero to one

Everyone tells you that being a founder is hard. You shrug it off, but let’s face it, pretty soon it slaps you in the face. You have so many hats to wear. You have a tonne of new things to learn. It can easily get overwhelming. But you didn’t get into it for an easy ride.

I was completely out of my comfort zone, but I was also loving the challenges that came with it. I enjoyed the things that surprised me. Being able to help shape a company’s culture from the start was liberating.

Fuck, you're telling me this place can be anything we want?

The five years I spent at Duffel were full of mistakes, lessons, soaring highs and gutting lows. Looking back is quite painful. Towards the end, I just wanted to be making things rather than being in meetings.

Still, I had a great sense of pride in what we were building, and that bleeds into your sense of identity. I was a founder of something people valued.

We built that. I built that.

So what happens when that part of your identity disappears?

Letting go

My decision to leave Duffel was surprisingly easy to make. It felt clear that it was time for a new chapter. A clean break.

When my son, Rio, was born, I was in the extremely privileged position of being able to step away and take six months of paternity leave (as was our great policy). That meant I could adjust to becoming a father, and it also meant my wife could return to work earlier, as she wanted.

That time with Rio gave me the space to reflect on what I wanted from life, and what I could give him too. During a trip to Brazil to visit family and parade newly born Rio around like Simba, we came to a sudden realisation. Maybe Brasília would be a better place for Rio to spend his early years?

So we set about moving, and within the year we were living back in Brasília. No regrets. Just warmth, green nature, and a better quality of life.

Yeah okay, fine, you’ve twisted my leg. It would be a lie to say this was the only reason for leaving Duffel.

While it was honestly life changing to spend six months with Rio, the truth is that after such a long break from the company, I didn’t really see myself there any more. I felt like it had outgrown me. It had safe hands steering the ship to better things.

Bits of the culture that I loved had shifted. The team had grown a lot, and just like most companies that scaled, so had the number of meetings, structure, and overhead. It wasn’t necessarily a bad thing, but it didn't ignite the same fire that it once had.

I guess, I'm just happier in the uncertainty and mess that is an early stage startup.

To this day, I think about that feeling and wonder. Maybe I failed. Maybe I no longer enjoyed the challenges that come with a scaling company. I don’t regret the decision per se, but I often think, what if I had stayed?

Moving on

After leaving Duffel, I joined a little startup with a huge amount of talent as a design engineer. I had been craving more time to focus on refining my practical skills after a few years of using them less. Fuck yeah, I get to spend all day designing and building great products with amazingly talented people? Where do I sign up?

The change was way harder than I expected.

It felt a bit like starting from zero all over again. But this time, I was playing by someone else’s rules. I had this need to constantly validate why I was no longer at the company I started. Not just to others, but to myself. Had I failed at being a founder?

Probably.

Then the imposter syndrome reared its two-headed self. I was an imposter as an individual contributor, and as a founder. Brilliant.

It took time to get back into the swing of things, but you adjust. The rhythm is different. The remit is different. Sometimes you see problems coming but have no ability to change the outcome, no matter how loudly you ring the bell.

I find it hard to switch off the part of my brain that notices potential issues and without immediately thinking about solving them, but those types of issues are no longer in my remit. I can nudge things until a point, but there are lines I can't cross.

Oh dear, I think you want to start another company.

The journey from designer to founder and back to designer has been rough. But just like becoming a father, it taught me an insane amount about myself and I've re-evaluated that founder part of my identity.

I’ve accepted where I failed. I’ve learnt what gives me energy, and what drains it. I am immensely proud of what Duffel has achieved, but I’ve also accepted that I could’ve done better. Perhaps it’s just hindsight, but there’s definitely a chip on my shoulder there.

More recently, I've realised that given the right circumstances, I might take that journey again.

Actually, fuck it.

I want to.

23 May 2025