Know when to hold ’em, know when to fold ’em.

by | Sep 2023 | Start a Company

It’s now 7 years since I shut down my startup (long story short, we raised $2m but couldn’t find PMF, tried to pivot, failed and shut down. You can read some of the lessons learned here.).

We did a lot wrong, but I think we did one thing very right.

We acted quickly and decisively.


I expect this article might create a mixture of emotions in anyone reading it. We’ve all heard about companies that crept along for a decade before suddenly skyrocketing into the next unicorn, but I’ve yet to experience it myself.

I think, in truth, it’s extremely rare.

Directly and indirectly (as an LP) I’ve invested in around 100 startups. I haven’t seen a single one follow that trajectory. Successes yes, but none that came seemingly out of nowhere.

And I’ve been doing this since 2012.

Have I been unlucky, or is this a myth?

I ask this because I can think of at least 10 founders in my portfolio, who have been creeping along for the best part of a decade, hoping it will happen to them.

But as yet, none of them have broken through.

They remain hopeful, of course, but if they could go back in time, I suspect most of them would choose a different path.

At best these companies look like lifestyle businesses. At least, that’s until you look closely. Then you realise they’re like many other startups: battling to make payroll every month, founders working silly hours, everyone underpaid and nobody having that much fun.

Maybe I’ll wait a bit longer and be proven wrong? I honestly hope so.

But looking back, as a founder who launched a business in 2015, I’m glad we flamed out early.

Of course I’m not happy that I lost other people’s money (that’s another story), but I am pleased I didn’t flog myself stupid for 10 years on a business that never seemed like it was winning.

I really admire the founders who kept going (truly), and some of them have become good friends, but I wouldn’t exchange places with a single one of them.

We shut down our startup after 2 years. Yes, it took me a good 18 months to recover my self-confidence and mojo, but despite that lost time, I’ve since done a whole heap of interesting things, learned so much and am now two years into something a lot more fun and already more successful.

So to any founders out there who are thinking about quitting, please don’t automatically assume it’s the worst possible option for you.

Yes, you should do everything in your power to deliver a good result for your investors and employees, but don’t sacrifice your mental health or your entire career.

Most investors (and I include myself here) want the best for you, but we also want the best for ourselves. We’ll keep encouraging you to battle on, to pivot, to leave no stone unturned. But most of us will do our best to support you no matter what you decide, even if that means giving up.

At the end of the day, it’s you who needs to decide when this chapter finishes and the next one begins. Make sure you leave enough time, and don’t forget to look after number one.

Godspeed.


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– Featured image: Midjourney

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