When I started Millennial Masters, I always thought I’d eventually write a book. Somehow, I’ve ended up making a documentary instead. I’m still not sure which would’ve been easier.
The idea came from going back through podcast interviews and pulling together quotes about founders selling their businesses. I started finding connections between their stories and realised I had enough material to bring them together in a film.
By the time I made it, I’d interviewed almost 100 founders and met some amazing people along the way. Thirteen of them tell their stories in their own words in my first documentary, The Exit Files: The Long Way Out.
I think what drew me towards video was what I noticed during the interviews. There’s something about seeing someone’s expression or hearing their voice change when they remember a difficult moment. You can tell when it still affects them, even years later.
I’m pleased with how it’s turned out, and I’m glad I chose video. Some of these stories really are better heard directly from the people who lived through them.
The documentary also became the starting point for my four-part Exit Files written series, which grew out of the research and editing process.
You can watch the full documentary above. If you prefer the big screen, it’ll premiere on my YouTube channel this evening. Both are in glorious 4K.
I hope you enjoy the documentary, and I’d love to know what you think. You can just leave a comment below.
While editing, a few things the founders said stayed with me. Some made me reconsider what a successful exit actually means, even for someone who’s made millions.
I picked out ten of those thoughts below. I think they’re worth reading if you’ve ever considered selling your business, or wondered what life might look like afterwards. 👇🏻
1️⃣ Even with enough money to never work again, you can still be terrified of losing everything
Despite selling three businesses, Luke Tobin still works as though he’s broke. His partner asks him why, and he admits he doesn’t really know another way to live. After leaving home at 16 and losing his mum young, he also went through business failures that left him in serious debt. Even now, he says he doesn’t feel completely safe.
We talk about financial freedom as though there’s a number that makes the fear disappear. Luke’s experience made me wonder how long it takes to actually feel secure after years of having to fend for yourself. Those years don’t just vanish because your bank balance changes.
2️⃣ You can make a fortune selling a business and still wish you’d waited
Matt Watson sold VinSolutions to AutoTrader for a reported $150 million in 2011. Today, he believes the company could’ve become worth a billion dollars if they’d kept going.
He says he doesn’t have remorse about the decision, although he also admits he wishes he’d never sold. I can understand how both feelings could coexist. They made the decision with the information they had at the time, and they’ll never know what would’ve happened otherwise.
There’s something almost cruel about that. You can achieve the kind of outcome other founders dream about and still find yourself measuring it against a future that never happened.
3️⃣ Selling early might cost you more than staying another ten years
Simon Jenner wonders whether he sold his own business too early. He made an interesting observation about the economics of exits: a founder who keeps a profitable company for another decade could quietly earn more from it than someone who sells for an impressive headline figure, particularly once investor dilution is taken into account.
It’s easy to be impressed by a sale price without considering what the founder actually takes home, or how much the business might have paid them over time. It made me wonder how founders decide when they’ve earned enough to walk away, especially when the business is still doing well.
4️⃣ Sometimes the business gets so big that its founder no longer belongs there
At some point, Joshua Dziabiak began to feel as though he was no longer the right person to run the company he’d helped build to a billion-dollar valuation. The business reached a stage where someone else was better suited to leading it. Even though he understood why it was time to step aside, he described a loss of confidence and a feeling of imposter syndrome. He’d spent years creating the company, only to question his own abilities when it no longer needed him in the same role.
I hadn’t considered that handing over a successful business at the right time could still feel so much like a personal failure.
5️⃣ The business can disappear before you’ve had time to say goodbye
Within four months of Luke Tobin selling his agency, the name he’d spent years building disappeared. The business was rebranded as part of a much larger organisation, and the public identity he worked so hard to establish was gone. He knew it was coming, but he didn't expect it to happen so quickly. He described going through a mourning process as he tried to find a new sense of purpose.
I thought about what it must be like to keep turning up to work after the company you created has effectively vanished. Especially when your own identity has been tied to it for so many years.
6️⃣ Having the freedom to stop working doesn’t necessarily make you want to stop
After years of building businesses, Andrew Steele took time away and found himself increasingly dissatisfied. He could earn good money advising other founders while working relatively few days a month, but he missed being involved in the actual building.
Gavin Bell imagined success would give him freedom, then realised that building companies was itself a big part of what made him happy. Nick Holzherr even hired a personal coach after his time at Samsung to work out what motivated him. He eventually found himself drawn back to starting another company.
That building itch seems remarkably difficult to turn off. If the work itself is what gives you purpose, what exactly are you hoping to retire from?
7️⃣ Selling a company can permanently change relationships you thought were secure
After his exit, Matt Watson noticed that people stopped inviting him to their homes. They knew he lived in a beautiful house and seemed uncomfortable asking him over. Even going out for dinner with family came with expectations about who would pay.
He described how some friendships changed and family relationships became strained. Years later, he doesn’t think much has improved. I’d given plenty of thought to how money changes someone’s life, but hadn’t really considered how much it could change the way other people behave around them. Even something as ordinary as being invited over to a friend’s house.
8️⃣ The first successful exit can teach you the wrong lesson about yourself
Success can give you an inflated sense of how much you know. After selling his first company in his twenties, Simon Jenner thought he’d figured out how to build businesses. Surely he could do it again.
The ventures that followed proved much harder, and he eventually realised just how much luck had contributed to his first success. At the time, he’d attributed much more of it to his own skill.
I find that admission revealing. A successful first exit can give you enormous confidence, including confidence in things you might not actually understand as well as you think.
9️⃣ You can spend years building a business and realise you’ve been sacrificing things you never had to
For almost a decade, Melissa Kwan believed founders should be the last to get paid. She lived on very little money and missed important moments in her friends’ lives because the business always came first. Some of those friendships didn’t survive.
She eventually realised that constantly operating in survival mode was affecting her ability to make good decisions for the company. As Melissa put it, “Sacrifice and pain doesn’t mean success. It’s just sacrifice and pain.”
I found that particularly uncomfortable because we’ve almost romanticised this kind of suffering in entrepreneurship. Some of the sacrifices founders take pride in enduring might actually be making their businesses worse.
🔟 The money can arrive on Monday afternoon, and an hour later you’re back in a meeting
When Luke Tobin’s exit money finally landed in his bank account, he was still at work. An hour later, he had to deliver a big presentation to his team, who had no idea what had just happened. After years of building towards an extraordinary financial outcome, the moment itself felt strangely anticlimactic.
I keep thinking about the distance between how we imagine success will feel and what actually happens when we get there. You can spend years believing a particular moment will change everything, then discover that life carries on almost immediately, while you’re still trying to make sense of what’s happened.
After the business is gone, who are you without it?
When Luke Tobin talked about going through a mourning process after selling his business, I recognised the feeling. I’ve lost a business myself, although my circumstances were very different. I remember having to work out who I was without something that had been such a big part of my life for so long.
I think part of what made me curious about these founders’ experiences was wanting to understand what it feels like at the other end of the spectrum. What happens when you sell for millions and get to leave on your own terms? Does having that financial security make it any easier to let go?
Hearing their stories, I was surprised by how familiar some of those feelings sounded. The financial outcomes couldn’t be more different, of course, and I wouldn’t pretend otherwise. Yet even after a hugely successful exit, you can still struggle with losing a business that helped define who you were.
I guess we’re all human, however the business ends.
