I was 24, maybe 25, and I’d raised about two and a half million in angel money for ContentCal. I had no idea what I was doing. But I thought I did.
People were backing me on youth, energy, vibe and sheer will. Which was great. I’d have backed me too. But it only gets you so far, and one investor could see exactly how far.
He’d decided to mentor me, and he wasn’t the arm-round-the-shoulder type. He sat me down and said: you’re not going to get any further on what you’ve done so far. What got you here is done. You need to learn two things. Financial modelling, and the art of corporate finance.
I nodded and privately thought he was wrong.
I was a product guy. Social media, tech, content. Business was about the product, the sales, the team, the space you’re in. Finance was a thing you got someone else to do later, when you were big enough to need it.
He introduced me to a finance director anyway. I thought it was way too early. A finance director for a company our size felt like hiring a head chef for a food truck.
It turned out to be one of the best decisions I’ve ever made. I’ve never started a business since without one.
Me in our Shoreditch office, 2018.
Your company can only grow as fast as you do.
Every startup post-mortem says the same things. Ran out of money. Never found PMF. Marketing didn’t land. Market moved. Someone else got there first.
All true, often. And all beside the point.
That’s the coroner’s report. It tells you what the body looked like, not why it stopped breathing.
After sixty-plus investments through my own investment vehicle and one full founder journey of my own, from quitting Sky in 2014 to selling ContentCal to Adobe and running it inside a company of 30,000 people, I’ve stopped believing companies die mostly because of product or market causes.
They die of founder causes.
The product is just where it shows first.
In The Architecture of Scale I listed what kills companies. I went back to that list and asked a different question. Not “what went wrong” but “who was standing there when it did”.
Lack of focus. Too many markets, too many features, too many bets. Founders call it ambition. I did. It’s usually fear. If you’re doing five things you never have to find out whether the one thing works.
Lack of funding. Obviously. But running out of money is rarely the real problem. Running out before you’ve learned what you needed to learn is. That’s a pace decision, and pace sits with one person. Once the finance director arrived I stopped raising on gut feel. Every round after that was sized against a forecast, and sized to survive the mistakes I knew were coming.
Lack of leadership. Not just at the top. The layer underneath. Founder-led to team-led is where more companies stall than anywhere else, including in my portfolio. It stalls because building that layer means you stop being the answer to everything. Most founders don’t refuse. They just don’t know how to build a team.
Founder who can’t scale. Some founders make great CEOs. Many don’t. The job at 5 people and the job at 150 share a title and nothing else. I’ve employed over 200 people across my businesses and I was a different person at each stage. Not always on purpose.
Not adapting at each stage. Every founder has heard “what got you here won’t get you there”. Few act on it. Acting on it means admitting the way you’ve always done things is now the problem, and that’s a hard thing to admit about yourself.
Unclear on the fundamentals. Market, business model, competition. If you can’t explain all three to a stranger in a minute, nobody else in the company can either.
Not hiring the best talent. Your company is the sum of the people in it. Tolerate mediocrity and that’s your ceiling. Ask who’s tolerating it. It’s usually the person who finds the conversation hardest, or remembers when that person was one of four.
Not letting go. The early calls, the first hires, the original vision. It all feels personal because it all was you. The company can’t let go on your behalf.
Not recognising when it’s not working. Pivot or persist is the hardest call in the game. Founders lean to persistence because it looks like strength. Sometimes the market is talking and you’ve decided not to hear it. That’s not grit. It’s a listening problem.
Read that back.
Nine ways to die, and not one of them lives in the product.
Every single one is a founder who couldn’t see themselves clearly enough to change in time.
The year I learned to pitch
The same investor sent me to see a second person. A pitch coach, basically. A man who taught founders how to raise money.
I went to his house once a week for the best part of a year.
We practised pitching. We role-played investor meetings. He did speech training with me. When to pause. How to answer a question you don’t like without flinching. How to stop filling silence. How to say the number and then shut up.
And somewhere in the middle of all that he said the thing that changed my career. You need to learn corporate finance inside out.
I pushed back. Do I? I’m a product and social media guy. What do I need corporate finance for?
He was right and I was wrong, and I only know that now because I did what he said.
To scale a tech company you have to understand how money works. How to raise it. Equity stakes. Share structures and the differences between them. How different agreements work for different employees. How an angel thinks versus how a fund thinks versus how private equity thinks versus how venture thinks.
None of that was in my head at 24. I thought it was admin. It turned out to be the operating system.
Years later, when Adobe came knocking, I was in an M&A process for a company I’d built from nothing. If I hadn’t learned how money works, I wouldn’t have known how to sell a business. I’d have been a passenger in my own exit.
Two skills I did not believe I needed. I now think of them as the most important things in a company outside the operations themselves.
And I’d never have learned either if someone hadn’t told me, bluntly, that I’d hit my ceiling.
Self-awareness is the scarce resource
For years I assumed the scarce things in a startup were capital and talent.
It’s self-awareness.
A founder’s ability to notice that the company has outgrown the version of them that built it.
Here’s why it’s rare.
The feedback loop around a founder is broken by design. Your team won’t tell you. Your investors see you sporadically, and need you to be right. Your mates don’t understand the business. Your family just wants you home for dinner.
You run in a vacuum and the only signal that gets through is the lagging one. Revenue dips. A senior person resigns. A customer churns and you find out from a dashboard.
By the time the company is telling you, it’s been true for months.
The company is a mirror. It just runs six months behind.
I got lucky.
One investor was willing to be the mirror in real time, and he was willing to be unpopular doing it. Most founders never get that person. The ones I’ve backed who went the distance went and built one.
The quote everyone gets wrong
You’ve seen the line. Not the strongest that survives, nor the most intelligent, but the most adaptable to change.
It gets pinned on Darwin. He never wrote it. It’s Leon Megginson, a management professor, paraphrasing Darwin in a 1963 paper about businesses and social change.
I like that. The most famous line about evolution was written by a man thinking about organisations, not finches.
And it’s still applied to the wrong thing.
People use it about companies. Market moves, company must adapt. OK. But companies don’t adapt. They aren’t organisms. They’re a pile of decisions made by people, and in the early years mostly by one person.
Adaptability belongs to the founder first.
At 24 I had to become someone who understood a cap table. Not because I wanted to. Because the company couldn’t go where I wanted it to go with the person I was.
Four jobs, same name on the door
Pre-seed to seed, you are the product. I sold it, built it, did the support. Adapting here means being honest about whether anyone wants the thing. Whether they pay and come back, not whether they say nice things.
Seed to Series A, you stop being the product and become the system that makes it. First real hires. First time you hand something you’re good at to someone who’s worse at it, for now. And, for me, the first time I was told the thing I was bad at mattered more than the thing I was good at.
Series A to B, you stop being the system and become the person who hires the people who run the systems. Capital, hiring, narrative, the three decisions a quarter only you can make. If your calendar looks like it did two years ago, you haven’t scaled. You’ve just got busier.
Then, in my case, Adobe. Different job again. Take a product to millions of users inside someone else’s machine.
Some founders become real CEOs. Some become chairs. Some leave and start again. All fine. Pretending is the only version that fails.
How I try to see myself now
Things that worked for me or for founders I back.
Get a finance director earlier than feels sensible. Not for the accounts. For the forecast. You can plan a lot further ahead than your gut lets you.
Write down what your job is, one paragraph, every six months. Compare it to last week’s calendar. The gap is the diagnosis.
Find someone who’ll tell you you’ve hit your ceiling and has no reason to be nice about it. Pay for it if you have to. I spent a year of Wednesday mornings at a stranger’s kitchen table learning to pause and how to answer questions effectively.
Best money I ever spent.
Hire someone better than you at the thing you’re proudest of. Nothing teaches you faster that the company doesn’t need your ego in that seat.
Keep a list of decisions you’ve been avoiding for over a month. That’s a map of where you’re protecting the old you.
None of it is complicated. All of it is uncomfortable. That’s the filter.
Sales still cures all, and that’s on you too
Underneath the nine sits the one that matters most. Revenue solves most problems. A company that can’t sell is dying however good the product looks.
Selling is the first founder skill and the last one you’re allowed to delegate. Early on you sell the product. Later you sell the vision to hires, the story to investors, the change to a team who liked things as they were.
A founder who can’t sell doesn’t have a revenue problem. They have a self-awareness problem. They built a company that depends on a muscle they never trained and told themselves the product would do the talking.
It won’t.
Winning founders, winning companies
PMF matters. Funding matters. Marketing, timing, competition, all of it. I’m not pretending otherwise.
Those are conditions.
The founder is the variable.
Two founders, same market, same capital, same product. One adapts in real time and one doesn’t. The company that survives belongs to the founder who saw themselves clearly and moved before the numbers made them.
Companies don’t adapt. Founders do. Then the companies follow.
I was 24 and I thought I knew what business was about. Someone told me I didn’t, and I was annoyed, and he was right.
The thing most likely to kill your company is the same thing that built it.
You.