Don't Die

I heard a story about a founder who went from Florida to San Francisco to raise money with nothing but a credit card.

For two months, he kept meeting investors and getting rejected. Eventually, he ran out of money. He couldn't pay the rent anymore and was thinking about moving back to Florida.

In the version I heard, that was when he closed an $8 million round.

I keep thinking about the day before.

When someone tells you a story like this, you know where it's going. You hear about the rejections, the credit card, the rent, and you wait for the good part. The founder living through it doesn't get that reassurance. He has to make decisions without knowing whether there is a good part.

That is a difficult place to be. You've put yourself out there. You've told people what you're building. Now you have to keep believing in something that other people keep saying no to, while the bills continue arriving on schedule.

One fundraising story can't promise anyone the same ending. But it does make me wonder how often we mistake a difficult stretch for the end of the road.

There is an idea from Y Combinator that keeps coming back to me: don't die. Paul Graham wrote about it years ago. Keep the company alive, keep working on it, and keep changing what isn't working.

It sounds almost too simple to be useful. Then you try building something, and you realise how much work those two words contain.

Because what does keeping going actually look like on a Tuesday when nothing is going your way?

Maybe you've spent weeks building a feature and nobody uses it. You can spend another week improving it. That feels productive. You know how to do that. Or you can call the people who tried it and ask where you lost them, knowing you might hear something you don't want to hear.

Maybe you need someone stronger than you on the engineering side. Reaching out means admitting there's a limit to what you can build alone. So you postpone it and spend another evening struggling with the same problem.

Maybe you've decided you're bad at sales. Fair enough. But if the company needs customers, that is now something you have to learn.

This is where commitment becomes real for me. You let the needs of the business change what you're willing to do. You make the call, ask for help, learn the skill, or put your work in front of someone before you feel ready.

You can be incredibly busy while carefully avoiding the one thing that would move your company forward. A full calendar makes that surprisingly easy to hide, even from yourself.

And this is why I'm suspicious of having a plan B and a plan C running in the back of your mind.

There is a particular kind of backup plan that starts taking over before you've properly tried the first one. After a bad meeting, you think about another business you could start. After a slow month, you picture a job where someone else carries the responsibility. Soon you're comparing the hardest part of your current reality with an imagined alternative where nothing has gone wrong yet.

Of course the alternative looks better. You haven't had to do it.

Meanwhile, the difficult customer conversation is still waiting. The product still needs fixing. The person you should have reached out to still hasn't heard from you.

I think we owe the things we choose to build more than that. If you've decided this problem matters, give it your full attention. Give yourself a chance to find out what you can do when you stop negotiating an exit every time it gets uncomfortable.

That still leaves you plenty of room to change your mind about how the business should work.

You might have picked the wrong customer. Your pricing might make no sense. The feature you love most might be getting in everyone's way. You might need to throw away months of work and build something much smaller.

That hurts. Especially when you've already explained your original idea to everyone you know.

But if you're willing to work late for the company, you should also be willing to be wrong for it. Being a founder involves both. Sometimes the most useful thing you can do is admit that the customer understood the problem better than you did.

Airbnb's early story is a good example of how far that willingness can take you. Before the business took off, its founders sold election-themed cereal to help fund it. Later, Brian Chesky and Joe Gebbia went to New York, visited hosts, and took better photographs of their apartments themselves.

Imagine putting together a startup plan that includes packing cereal boxes and photographing strangers' living rooms. Yet those were useful things to do. They brought in money, improved the listings, and got the founders closer to the people they were trying to serve.

I like that version of entrepreneurship. You have a problem in front of you, and you deal with it, even when the solution has very little to do with the job you thought you signed up for.

There is also a less exciting part of staying alive: making sure you can afford to keep going.

The rent in that Florida story matters. Money gives you time to try again. When you reduce what it costs to keep the business running, you give yourself more chances to find something that works. A paying customer can buy you another month of learning. An expense you avoid can do the same.

Moving somewhere cheaper might be the decision that lets you continue. Taking on a piece of work to cover the bills might help, provided you know how much time it gets and when you return to the product. A practical way to keep building deserves more respect than pretending the bank balance doesn't exist.

I want to build a company that can keep going. Getting dangerously close to running out of money isn't an achievement I need to collect along the way.

And while you are buying yourself that time, use it.

If you've spent another month on the company, what do you understand now that you didn't understand before? Can you explain why someone bought? Why someone left? Have you found a smaller problem you can solve well enough that people will pay for it?

These questions give persistence somewhere to go. Otherwise, it's possible to spend a year defending the same assumptions and call it determination.

The encouraging part is that you can become much better at this while you're doing it. The conversation you were scared to have becomes a conversation you know how to handle. You learn enough about engineering to hire more thoughtfully. You read something, try it, get it wrong, and understand it properly the second time.

That changes what becomes possible for the business. A problem that stopped you three months ago might be something you can work through today.

So when I say don't die, I'm thinking about all of this. The willingness to learn. The humility to change direction. The discipline to keep enough money and energy available for another attempt. The decision to stay fully involved when withdrawing would feel easier.

You don't get to know in advance which week will matter. You have to decide what to do with the one you're in.

If you're in a rough stretch right now, look at the thing you've been avoiding. The customer you need to speak to. The decision you keep postponing. The part of the product you already suspect needs to change. Start there, and give it your full attention.

That founder in the story had an $8 million ending. Your next useful step might be much smaller: a customer who comes back, a conversation that changes your understanding, enough revenue to keep building for another month.

Give yourself the chance to get there.

Don't die.