Brilliant story. I call the "Funemployed" window "the After Party" - I'm older so at 56 I'm avoiding the word retirement. Living a plural life creating, collaborating, coaching and deploying capital. My 4 Cs. They keen my fizzing. Thanks for sharing this story 🤓
Love this - I sold my "boring bootstrapped" business for £45m in May last year and retained majority shareholding in exactly the same way as Spencer. Started my business in 2005, so two decades is my timeline too.
I didn't make the news either, and other than close friends and family I'm completely under the radar.
I'm also early 40s, have taken funemployment (love that term), building a car, flying planes, playing music in a couple of bands, travelling and doing whatever the fuck I want without ever worrying about money again.
All eerily similar! Perhaps I should also go to burning man :)
Simon, congrats on your success! I love a great founder story. Maybe I can have you on my podcast season 3 which I'll start recording soon. It's called ProfitLed, and this season's theme will be about the intersection of passion, profit, and purpose, and how those things shift as founders come into success. DM me if you're open to it, we can keep you anonymous if you like! PS. YES, you should absolutely go to Burning Man. You can fly your plane in :)
This framing matters more than people realize. The "boring" exit to a strategic is also usually the cleanest one legally. The diligence is shorter, the working capital and escrow fights are smaller, and the founder actually walks with most of the headline numbers instead of watching it get clawed back in earn-outs or recap math. The quiet 13-year build to a best-of-category sale is the version where the cap table, the contracts, and the founder's life all survive intact. Thanks for telling this one. There are way more of these out there than the headlines suggest. I wish these stories would get more airplay so entrepreneurs see a different and better path to an exit!
I’m 25 years self funded to the bottom line. My model - be simple, sustain, and accumulate until the next big opportunity. Patience combined with ambition.
I’ve just started #2. This time around we’re redesigning and rearchitecting a dissonant $3.2T market in need of creative destruction.
The stories that aren't talked about are usually the best ones. I believe building - and retiring from - a "lifestyle business" is the goal of most people.
What stands out is time horizon discipline. No VC clock. No performative growth. Just building something useful for a decade. That’s how optionality is actually earned, not tweeted about. :)
Brilliant story. I call the "Funemployed" window "the After Party" - I'm older so at 56 I'm avoiding the word retirement. Living a plural life creating, collaborating, coaching and deploying capital. My 4 Cs. They keen my fizzing. Thanks for sharing this story 🤓
Thanks for taking the time to read this, Chris!
Love this - I sold my "boring bootstrapped" business for £45m in May last year and retained majority shareholding in exactly the same way as Spencer. Started my business in 2005, so two decades is my timeline too.
I didn't make the news either, and other than close friends and family I'm completely under the radar.
I'm also early 40s, have taken funemployment (love that term), building a car, flying planes, playing music in a couple of bands, travelling and doing whatever the fuck I want without ever worrying about money again.
All eerily similar! Perhaps I should also go to burning man :)
Simon, congrats on your success! I love a great founder story. Maybe I can have you on my podcast season 3 which I'll start recording soon. It's called ProfitLed, and this season's theme will be about the intersection of passion, profit, and purpose, and how those things shift as founders come into success. DM me if you're open to it, we can keep you anonymous if you like! PS. YES, you should absolutely go to Burning Man. You can fly your plane in :)
This framing matters more than people realize. The "boring" exit to a strategic is also usually the cleanest one legally. The diligence is shorter, the working capital and escrow fights are smaller, and the founder actually walks with most of the headline numbers instead of watching it get clawed back in earn-outs or recap math. The quiet 13-year build to a best-of-category sale is the version where the cap table, the contracts, and the founder's life all survive intact. Thanks for telling this one. There are way more of these out there than the headlines suggest. I wish these stories would get more airplay so entrepreneurs see a different and better path to an exit!
These stories do get more airplay! I just launched Season 3 of ProfitLed Podcast today: https://www.melissakwan.com/p/profitled-season-three
Also check out Greg Head's podcast, Practical Founders. One story a week there :)
Thanks for taking the time to read this, Josh! Appreciate it.
That's great to hear! I'll check those out.
I’m 25 years self funded to the bottom line. My model - be simple, sustain, and accumulate until the next big opportunity. Patience combined with ambition.
I’ve just started #2. This time around we’re redesigning and rearchitecting a dissonant $3.2T market in need of creative destruction.
I love your take on this Melissa and this line is on point! - "The media fucks up our idea of success."
I do uncover truths about business that people aren't aware about and help explain it in a direct manner - Please do check it out :)
The stories that aren't talked about are usually the best ones. I believe building - and retiring from - a "lifestyle business" is the goal of most people.
Yes, it should be! Not chasing unicorns!
What stands out is time horizon discipline. No VC clock. No performative growth. Just building something useful for a decade. That’s how optionality is actually earned, not tweeted about. :)
The most successfully companies I know build in silence. No need for external validation. Just focus on the business and customers