Olly Headey

March 4, 2022

Getting Real with a new job

It’s been six weeks since I officially left FreeAgent and rather longer since my mind started wandering off into the dense forest of 'what next'. After a modest break of trying to do very little (I am very bad at this!) I find myself rolling up my sleeves, ready for something new. But what?

Over the years I’ve come to know a lot of founders, many of whom have sold their business and moved onto new things. I’ve been having a few chats recently, asking for people's thoughts, and unanimously the view is that after selling/leaving your business you should take six months off in order to ‘decompress’ before making any decision on what to do next. You need time to think, to read, to research interesting new sectors and explore ideas to seed your next big thing. This is the default assumption – you’ve been a founder, an entrepreneur, you know how to build successful businesses so you must start something new. It's in your blood!

I’ve thought about starting new ventures a lot over the last few years, ever since an 'exit' (such clinical language) seemed to be on the cards. I have an old Apple note called ‘future bizniz’ chock-full of ideas, some boring, some daft, some potentially interesting, some already done by others. I built a SaaS writing platform (I recently turned it off) which was fun and scratched a programming itch, but it was unpopular and unprofitable. More recently I helped build a prototype B2B SaaS product with a friend which definitely had promise, but a few things got in the way and we both decided to move on. For a successful venture, you absolutely have to be in the right place at the right time.

Timing is everything.

I've also thought about working for other companies but it always seemed such an unlikely outcome. The concept is challenging for a founder. If you've built a company from the ground up the way you wanted, you pretty much believe it's the Greatest Company Ever™, which from your perspective it probably is. Consequently the pool of other companies that you feel you would ever want to work for is pretty shallow, if not bone dry. This is why most founders go and build another company rather than work for somebody else's. When you've presided at the top of the food chain, wouldn't it be too challenging to drop down a trophic level? Far better to take what you've learned and try and improve on it next time?

What if you take what you've learned and use it to help someone else's Greatest Company Ever™ rather than trying to do it all again yourself? If you can get over the ego bruising of diminished responsibility (this is a thing), it's a compelling option. You get to skip all those challenging years of uncertainty and doubt, and focus your energy immediately on helping a brilliant team of people build and scale super-popular products that already have huge numbers of happy customers!

This is the path I have decided is right for me.

There was only ever going to be one company. It's one that I've followed and admired for nearly two decades. I've read their books which inspired FreeAgent in multiple ways (randomly, I'm even quoted in one). I've used their products since 2006, and I love the technology they use (which also happens to be the foundation of FreeAgent). Just before Christmas I got myself into an email conversation with their technical co-founder about a new engineering leadership position that might be opening up. We had some long chats on Zoom and found a lot of alignment. I met some of the team (👋😊) and I wrote a novella on my thoughts on leadership. Then I took a break and waited.

This week I was offered the position and I'm stoked to announce that I'll be joining Basecamp as their Director of Engineering in a couple of weeks. I can't wait to get started! 

Talk about perfect timing.