What Building Three Companies Taught Me About Backing Founders

Operator experience isn’t nostalgia. It’s a filter.

I founded Supply Chain Connect in 2000, Wonga in 2006, and co-founded Tide in 2015, funding it from the start. That’s fifteen years of building: through a dot-com hangover, through a consumer-credit business that in 2011 topped the Sunday Times Tech Track 100 as Britain’s fastest-growing technology company, and through the moment when a regulation opened up a whole new category. Each one taught me something specific about why companies survive their early years and why most don’t. Backing founders today is mostly applying those lessons before the founder has had to write their own.

What follows is the portable version: the three lessons that come up in almost every conversation I have with a founder who’s about to make a first cheque’s worth of mistakes. The full version is longer, more boring and more about logistics than philosophy.

Lesson one: the founder is the company

The founder is the unit, not the market and not the category. Almost every other decision a company makes is downstream of who they are and what they will and won’t tolerate.

Supply Chain Connect taught me this from the wrong direction. The market shifted, the cycle turned, and the people in the building responded according to what they’d been hired for, which wasn’t always what the business needed. The lesson wasn’t “hire better”. If you don’t select for founders and senior operators who’ll rewrite their own job description when the market rewrites the business, you haven’t selected for the one property that matters at the bottom of a cycle.

Wonga taught me the same lesson the right way round. The people we hired in the early years built what became the world’s first real-time AI system in consumer credit. That came down to who we’d selected at the start and almost nothing else.

Tide taught me the constructive version. We hired into the regulated-business reality from day one, because we knew what was coming. That’s what having founded before actually gives you: calibration, rather than a deck of slides.

So when I sit across from a founder now, the question that dominates the first hour is who they’ll hire when the market punishes them for being right too early, and whether they can already name that person from relationships they’ve spent the last decade quietly building. What they’re building comes second.

Lesson two: speed and honesty are the same skill

The most common early-stage failure is substituting motion for honesty about what’s actually working. Companies fall behind because they can’t tell themselves the truth fast enough about which motion is producing results.

Wonga, in its fastest years, was moving extraordinarily quickly: building product, hiring, expanding into adjacent categories. The speed was real, and it was producing results.

Tide, in its first two years, had to make the opposite trade. Building a regulated financial business is slow by nature, and the honest thing to tell the team was that the regulatory side would set the company’s calendar. The way to make speed visible was to build the operating muscle around it (the legal, compliance and policy work) so that when the permissions cleared, the rest of the business was ready to run. Speed without that honesty would have been a press release; honesty about the real constraint was the speed.

The short version I give portfolio founders: most early-stage companies don’t have a speed problem. They have a feedback problem. They can’t hear what the customer, the regulator, the team or the cap table is telling them quickly enough to act on it. Fix the feedback first. The speed shows up on its own.

Lesson three: the cheque is the smallest part

This is the one I underestimated for longest. As an operator I assumed the most valuable thing a board member contributed was their time at the table. As an investor I’ve learnt that the cheque is the smallest part, and the table isn’t far behind. The hours that compound are between the meetings.

In practice it’s a late-night call when a founder is rehearsing tomorrow’s board update and needs somebody who’s been on the wrong side of that exact conversation. Or an introduction made before it’s asked for, because the operator knows the founder will need it three weeks before the founder does. Sometimes it’s the willingness to take a hard call about a co-founder split and stay in it long enough for the right outcome rather than the comfortable one.

None of that is in a term sheet or on a deck, and it’s the difference between a cap table that exists to optimise a portfolio and one that exists to get this particular company across the line.

For founders choosing investors, the corollary is simple: ask the portfolio, and ask for evidence rather than testimonials. Nobody keeps a record of the hours between the meetings, but the founders on the other side remember exactly who was value-add and who wasn’t.

What stays the same

The companies were different. Supply Chain Connect was hosted, cloud-based supply-chain software in a category that has since become unrecognisable. Wonga was a consumer fintech built on real-time decisioning. Tide, a small-business banking platform, was built in the gap between two waves of banking modernisation. The categories and the cycles were different each time. The pattern wasn’t.

Pick the founder, fix the feedback, do the work between the meetings. Everything else is downstream.

The more than seventy-five first cheques I’ve written since 2011, across fintech, AI, health-tech and enterprise software, haven’t changed the pattern either. Different markets, different geographies, different decades, and the same three lessons. If they stopped working we’d notice. They haven’t, so we keep applying them.

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