Celebrating 10 Years: 18 Things I Learned Building Woozle

18 lessons on building a company from 10 years experience at Woozle.

Celebrating 10 Years: 18 Things I Learned Building Woozle

In 2016, I left Citadel and started Woozle with £20k. No investors, no safety net. Ten years later, that's still the only capital we've ever used.

Here's what I learned along the way.

1. Know the pain before you sell the painkiller.

Our first clients came quickly. Not because I was a great salesperson. Because I'd been them.

I'd sat in their seat, trying to get answers that didn't exist. Piecing together insights from brokers who were guessing and consultants who'd never run a P&L. I knew exactly what was missing because I'd felt it missing.

When I pitched, I wasn't selling a product. I was describing their problem back to them and explaining what I'd built to solve it.

That's founder-market fit. You can learn an industry. But there's a difference between understanding a problem intellectually and having lived it. If you haven't been the customer, ask yourself honestly: am I guessing?

2. Hire people you'd want on a long flight.

I call it the airport test. Can they do the job? Obviously that matters. But when someone ticks all the boxes on paper, ask yourself: would I want to be stuck with this person for four hours?

We hired someone early on. Talented. Sharp. Also impossible to work with. The kind of person who made every room slightly worse by being in it. We kept them too long because they were good at the work.

The day we let them go, the whole team exhaled.

Culture isn't posters on a wall. It's the people you let through the door. One brilliant difficult person will cost you three good people who quietly decide they'd rather be somewhere else.

3. Work hard. There's no shortcut.

Building a company is a full-time job and then some. You will work long hours. You will think about it constantly—in the shower, at dinner, at 3am.

The problems don't care that it's Sunday. The clients don't care that you're on holiday.

I'm not going to pretend there's a hack. The people who think they can build something meaningful while prioritising balance from day one—I hope it works for them. It wasn't my experience, and I don't know many founders whose experience it was either.

4. Bootstrap if you can.

We started with £20k and never raised a penny. No seed round, no angels, no board, no investor updates. Just clients, revenue, and the freedom to focus on getting the work right.

I've watched too many founders take money they didn't need because it felt like validation. Two years later, they're explaining to a board why growth isn't fast enough, or getting pushed out of their own company because they don't own enough of it anymore.

If you can grow from revenue, do that. The freedom to make your own decisions is worth more than the capital to make someone else's.

5. Beware shiny objects.

You'll get approaches. Investors, advisors, people who want to "explore synergies." It feels good. Someone with money thinks you're worth betting on.

But if you already have enough to grow the business, forget it. Focus on the business.

I've watched startups collapse because they over-promised to people who'd never built anything themselves. They took the meeting because it was flattering, took the money because it was there, and spent the next three years serving someone else's timeline. Flattering? Yes. Useful? Rarely.

6. Kill your darlings faster than you want to.

Our original product was syndicated channel checks. The whole idea when we started. It was also losing a million quid a year.

Did we act fast? No. We convinced ourselves it would turn around. Tweaked the pricing. Changed the format. Told ourselves the market needed time to catch up. Meanwhile, the losses kept piling up.

By the time we killed it, it was losing £1 million a year. That was money and energy we could've put into the things that were actually working.

Problems are like weeds. Pull them when they're small and it's easy. Leave them and they take over the garden.

7. Uncertainty is your friend.

When COVID hit, I thought we were done. The world was shutting down. Budgets were freezing. Nobody knew what was coming.

Then the phone started ringing.

When the world stops making sense, people pay for insight. Every assumption was suddenly up for grabs. Companies were removing guidance because they genuinely didn't know. And when nobody knows anything, the people who can find out become very valuable very quickly.

That year turned out to be one of our best. Not luck—we sell the solution to uncertainty.

If you're building something, ask yourself: does my business get more valuable when things get uncertain, or less?

8. Not all revenue is good revenue.

I learned this the hard way. Chasing deals that looked good on paper but bled us dry. Clients who haggled on everything. Who consumed time and energy and gave nothing back.

Anyone can grow revenue by underpricing. That's not a business. It's a fire sale.

The trick is finding clients who understand the value and are willing to pay for it. Once you find them, everything else gets easier. They refer you to others like them. They don't nickel and dime you. They become partners, not just customers.

Protect those relationships.

9. Learn to switch off.

At previous firms, they forced you to take two weeks off. Compliance requirement. It had a side benefit: you actually rested.

Startups? No one makes you do anything. There's no compliance team. No mandatory leave. Just you and the voice in your head at 2am going over tomorrow's problems.

For the first three years of Woozle, I couldn't switch off. Dinner, thinking about clients. Holiday, checking emails. Bed, running through the numbers.

It nearly broke me.

Your brain isn't built to be on all the time. You have to create the boundaries yourself because no one's going to do it for you.

10. Watch the downside.

I'm not a natural optimist. I know that's not very founder-friendly. I'm supposed to talk about vision and moonshots. But I spend most of my time thinking about what could go wrong.

Every week: what's broken? What's about to break? Where are we exposed?

It sounds exhausting. Sometimes it is. But if you're always focused on problems, you catch them before they become bigger problems. And by fixing them, you naturally improve what you do for clients and colleagues.

The upside tends to take care of itself when you're not making mistakes on the basics.

11. Letting people go never gets easier.

I wish I had a framework. I don't. It's difficult every time. The night before, you don't sleep. The conversation is hard. Afterwards, you feel terrible for days.

But dragging it out doesn't make it kinder. It makes it crueler. For them, because they're stuck sensing something's wrong. For you, because you're carrying a decision you've already made but won't act on.

When it's time, do it quickly. Be honest about why. Treat them with respect. Make it final.

You'll know it's not working long before you act on it. Trust that instinct. The gap between knowing and doing is where the damage happens.

12. Make mistakes. Learn fast.

You're going to get things wrong. Constantly. The idea that you can plan your way to success is fantasy. You're operating with incomplete information, making bets on things you can't fully understand.

The trick isn't avoiding mistakes. It's making them quickly, learning quickly, and moving on. Speed beats perfection. Make the call. See what happens. Adjust.

The founders who struggle are the ones so afraid of being wrong that they don't do anything at all. Procrastination dressed up as prudence.

13. Wear many hats.

In the early days, you're everything. Sales, ops, finance, HR, IT support, office manager. There's no "that's not my job" because every job is your job.

It's exhausting. It's also one of the best educations you'll ever get.

I learned more in my first year of Woozle than I did in years at much bigger firms. When it's your capital and your name on the door, you pay attention differently. You figure things out because you have to.

14. Align incentives.

We've got analysts who joined dreaming of a hedge fund seat. Others want balance. Others want the title. Some want to learn everything and then go build their own thing.

All of it is fine. All of it is possible here.

My job is to figure out what actually motivates each person and align it with what the company needs. That's not manipulation—it's just smart. When personal goals and company goals point the same direction, you don't have to push. They run.

Have the honest conversations. Ask what they're actually trying to achieve. Then help them get there while they help you build the business.

15. Share the upside.

We do 20% profit sharing. Everyone gets a piece.

When people have skin in the game, they think differently. They care about costs. They care about clients. They're not just doing a job—they're building something they have a stake in.

It's not just about money. It's about the psychology of ownership. When you share the rewards, you're saying: we're in this together. What you do matters. People respond to that.

The best hires are people who want to be part of something, not just collect a salary. Profit sharing is how you prove you mean it.

16. Celebrate the milestones.

The first invoice we sent—I still remember the feeling. A few grand, nothing really. But it meant someone had paid us for something. We were a real business.

The thousandth invoice? Didn't even notice.

Success normalises fast. The first office, the first hire, the first big client, the first year in profit—these moments are special exactly once. They don't come back.

I'm guilty of always moving to the next thing. But every now and then, stop and look around. Take the team out. Acknowledge what you've built. Time moves faster than you think.

17. The best part isn't the P&L.

If you'd asked me ten years ago why I wanted to start a company, I'd have said independence. Or building something. Or probably just money.

That's not what gets me up anymore.

The thing that actually means something now is watching people build lives off the back of what we've created. Paying for someone's CFA. Watching an analyst buy their first flat. Helping someone land the seat they'd been targeting for years.

The P&L is how you keep score. The people are why you play.

18. You'll know if it's right for you.

I was earning good money. Great seat. Interesting work. On paper, no reason to leave.

But I had an idea I couldn't let go of. And I knew if I didn't try, I'd always wonder.

Everyone told me not to jump. Build the idea first. Test it on the side. Don't leave until you've got something.

But I needed skin in the game. I left with enough runway for six months and the knowledge that if it didn't work, I could go back to a fund. The downside was covered.

Here's the truth: if you're on the fence about doing your own thing, give it six months. Either it feels like what you were meant to do, or it doesn't. And if it doesn't, go get another job. You'll be more employable than when you left.

Most people plateau. In a startup, you never coast. Every day is different.

For someone who needs to see the direct results of their work—there's nothing else like it.