My Messy Founder Story

If you looked at my journey from the outside, you’d probably assume it all happened in a straight line. I built things, they grew, I kept going. But living inside of it has never felt linear. It’s felt chaotic in small ways and big ways, full of detours, false starts, and constant improvising.

A lot of the “mess” in my own path shows up in the day-to-day. Some days I’m bouncing between ten different tasks, or even different projects, trying to keep momentum across worlds that don’t neatly fit together. Other days it’s the ideas. I get flooded with them. I try them quickly, build the first version, get it out of my head and into reality. And then, often within a week or two, I feel done. Not because I’m bored. But because once I can finally see the idea, I realise it’s not something I want to take further. Those little experiments look flaky from a distance, but they’ve always been how I think. They’re how I separate impulse from intuition.

There’s also the unglamorous, invisible work no one ever sees: endless admin, finances, operations, content scheduling, team logistics, contracts, planning, and all the maintenance work required just to keep things running. When you’re building something mostly alone, you eventually become the person responsible for every spinning plate — and there’s no one there to catch them if they fall.

When it first felt real

There were a few big milestones along the way, but one stands out more than the others. It was when I had a team — a real team — and suddenly I wasn’t just building things for myself anymore. I can still remember the feeling of leading those early weekly meetings. Something that began as a scrappy idea I explored on the side had somehow become a proper company with other people relying on me to make decisions, set direction, and keep everything moving.

It’s funny: there was no checklist moment, no “now you are officially a founder” ceremony. Just the quiet, almost mundane realisation that other people were now inside something that once lived only in my head.

A moment I’m not proud of

I’ve abandoned projects before, and not the quick one-week experiments. The long ones. The ones where I invested months of time, money, and mental energy, and so did other people.

Notify was the biggest example. It was an email API for developers, something they could integrate into their software to handle transactional email. We spent more than six months building it. The team did great work. The product functioned well. There was a real need for it. But as we approached launch, I could feel the gap between us and the existing players. Other companies were doing it significantly better, with more polish, stronger infrastructure, more resources, and a head start that mattered.

I could have pushed on. I could have convinced myself that six months of work meant we had to keep going. But that would’ve been pure sunk-cost thinking. Continuing would have meant more payroll, more technical complexity, more marketing spend, and honestly… more denial. My gut said, “If you keep going, you’re doing it for the wrong reasons.”

Telling the team we were stopping was awful. It didn’t feel like leadership. It felt like failure. I wasn’t proud of that moment — even though, deep down, I knew it was the right call. That’s the part of being a founder that no one romanticises: you’re sometimes the one who has to say, “This isn’t the path,” even when you’ve already walked halfway down it.

A moment I am proud of

One of my proudest moments is tied to something that also feels strangely small and private: the first couple of payout months from Medium.

Back then, In Plain English wasn’t a “company.” It was something I built to simplify technical topics for developers and to document what I had been learning - a publication that grew into multiple publications with different verticals. Medium launched a partnership program to support high-performing publications, and In Plain English joined.

The first month’s payout was big enough that I quit my job as a senior software engineer. The second month’s payout was even bigger, more than my full-time salary. I can still picture opening that dashboard and feeling this mix of disbelief and validation. It wasn’t luck. It was years of teaching myself how to code, freelancing before I felt ready, taking jobs that stretched me, writing endlessly, building publications, curating content, and slowly attracting an audience.

It deserved a celebration. But I didn’t really celebrate it. I was living abroad, mostly alone, not yet surrounded by people who understood what I was building. I think part of me didn’t know how to pause and acknowledge it. But it was the moment that confirmed I hadn’t been delusional. The work I had done in the dark had actually led somewhere.

The emotional thread

Looking back, the thread that runs through everything is this:

• I’ve always started before I felt ready.
• I’ve built a lot of things alone.
• I’ve kept going even when no one saw any of it yet.
• I’ve doubted myself constantly, sometimes loudly, but always created anyway.
• I rarely knew where the path was leading — but I walked it anyway, trusting that clarity comes from movement.

That’s my messy founder story. Not the polished one. The real one. And if you’re reading this because you’re on your own messy path, I hope you see pieces of your story in mine.