One post from Matt Bertulli, called Live 50 Lives, hit close to home for me, and I want to work out why. Motivating, aggravating when I think of the opportunities I passed on, and ultimately thought provoking.
Bertulli is the co-founder and CEO of Pela Case and Lomi, a co-host of The Operators podcast, and the author of a free weekly newsletter for founders called No Competition. On his website he says he sold his first company after bootstrapping it past 100 employees over ten years.
The post in question is called Live 50 Lives. It’s free, though you’ll need to subscribe to his newsletter to open it. I’m not going to reproduce it. I’ll give you the gist, then spend most of this post on what I think about it. This came to me through his email list – one of the few I actually read – but I wanted to find the actual post to share with you. So I recommend putting in your email address…
The Idea in Brief
It opens with one line: “Be the 85 year old who’s lived 50 lives.” His argument is that most people get life backwards. They choose a lane in their early twenties, hold it for the next sixty years, and call that discipline. What they end up with is one life stretched thin, when they could have had many distinct ones stacked on top of each other. His alternative is to treat a life as a series of seasons, each different from the last, and to be willing to trade the comfort of the current season for the unknown of the next.
He adds two things I found more interesting than the headline. First, he thinks this is the best time in history to be a builder, because AI has cut the cost of starting things so sharply. Second, he says the only reason that holds up over decades is curiosity. Not hustle culture, not whatever an algorithm happened to reward, not an idea of what successful people do. Money, status, and even a big sale eventually stop being enough. Curiosity doesn’t.
Why It Landed
This site’s tagline is Build Wealth. Build Optionality. Build a More Sovereign Life. Seasons are optionality across time. Flag theory is optionality across geography, the idea that where you live, bank, and do business can each be a separate choice. The components of personal sovereignty are about the same thing from another angle: having enough control over your own life that you can say yes to the next door when it opens.
The default Canadian script is a single lane: school, a career with one or two employers, a mortgage, a pension, and a retirement date. Nothing about it is wrong, and plenty of people are happy in it. But it’s a lane you were handed, and Bertulli’s point is that you can choose differently, and more than once.
What the Seasons Look Like Here
This publication has been through a few seasons of its own over the past several months. Looking at the publishing calendar, it runs from tax and registered accounts, to foreign real estate and medical tourism, to flag theory, to buying a business, to country-by-country expat guides, and lately to Canadian stocks. The cottage is the clearest personal example. I put it on Airbnb and wrote up what the first summer looked like. If you want a map of the business-building seasons, the closest thing here is the post on whether to optimize, acquire, or build a side hustle, along with the comparison of buying a business versus real estate.
Ask Yourself
Bertulli’s claim that the excuses are gone is strong. AI really has lowered the cost of making things, and I have no quarrel with that. But has it lowered the cost of earning trust, finding customers, or carrying a mortgage while you try? The same technology has a (albeit much overblown) darker side too, which I worked through in Will AI Kill Us All? Bertulli also writes as someone who has built and sold companies, so risking everything costs him something different than it costs a professional with one income, kids, and a house. The usable version, I think, is to risk what you can afford to lose so you’re still standing for the next season. Fifty lives requires surviving the first ten.
That’s why I like having a floor under the risk. A coast FIRE number, which I covered in Coast FIRE in Canada, is the closest thing I know to one. Once your retirement is mostly funded by compounding alone, you can take a lower-paid or riskier season without borrowing against your future.
Fifty is a number, not a plan. By his own account, Bertulli’s first company took ten years of bootstrapping, and he’s now leading two companies at once. Some of his seasons are evidently long and deep. That’s an important qualification to the slogan. Depth in one thing is how most people build the capital that lets them try the next, so I read the idea as permission to change rather than a quota to hit.
A third thought is a Canadian one, and it’s the part a post aimed at a global audience wouldn’t cover. Stacking lives gets expensive if the structure is wrong. If one of your seasons ends in a sale, the lifetime capital gains exemption can make selling shares of a qualifying small business very different from selling a stock portfolio, which means a decision made in season one can change what you keep in season three. If you buy rather than build, the difference between an asset purchase and a share purchase matters on both sides of the table. And if you run more than one venture, it’s worth understanding holdco and opco structures before you need them. None of that is exciting, and all of it is cheaper to sort out early.
The Part He’s Most Right About
Curiosity is the only reason that survives a long run. Hustle burns out, status shifts, and a big exit leaves you asking what’s next. A season you entered because you wanted to know what was behind the door is one you can keep going in when it gets hard.
He’s also right that the permission problem has largely disappeared for media. You can reach an audience without asking anyone. The Canadian version of that season is something I looked at in the post on faceless YouTube channels in Canada. The cost of a failed season is low when you’ve kept your fixed costs and debt under control, and that’s the quiet link between the exciting part of this idea and the boring financial work underneath it.
What I’d Actually Do
- Name the current season in one sentence and write down what would end it. A season with no exit condition quietly turns into a lane.
- Build the floor before the leap. Know the number that lets me take a bad season without panic, and keep fixed costs low enough that a failed experiment is a lesson and not a crisis.
- Sort out structure with a Canadian accountant before the first real profit, not after a sale. Corporate structure and share ownership are hard to fix retroactively.
- Price buying against building before committing to either. They’re different seasons with different risks.
- Keep one small, cheap experiment running at all times, so the next season has something to grow from.
- Read the original and treat it as a prompt, not a plan. Decide which door I’d actually walk through, then work out what it costs to enter and to leave.
Seasons are a good way to think about a long life. The Canadian addition is to pay attention to what each one costs on the way in and on the way out.
This post is personal documentation of how I think about my own situation. It is not tax, legal, financial, or career advice. Corporate structure, capital gains, and business acquisition rules are complicated, change often, and apply differently to every case. Confirm anything here with a qualified Canadian accountant or lawyer before you act. Claims attributed to Matt Bertulli come from his own newsletter and website and have not been independently verified.
