I Lost Everything in 2008 — Here's What It Taught Me
Draft — pending Dean's review before publishing.
In 2008 I lost everything. Not "had a rough year." Everything. I had my money riding on real estate development because I was convinced it would never end. The boom felt permanent. It always does — right up until it isn't. Then it ended, and I got to learn the hardest lesson in business the expensive way.
I don't tell that story for sympathy. I tell it because it's the reason I coach the way I do. I'm not handing you theory out of a book. I've been to the bottom, and I know what it takes to climb back.
Economies breathe — plan for it
Here's what I understand now that I didn't then: economies move in cycles. Up, down, up, down. They always have and they always will. You don't get a vote on the cycle. The only thing you control is whether you're built to survive the down years so you're still standing to cash in on the up years.
What wiped me out wasn't the crash by itself — it was being concentrated in one thing at exactly the wrong moment. So now I diversify, on purpose. Not because it's exciting, but because diversification is what carries you through the dips. If everything you own rises and falls together, one bad cycle ends you. If it doesn't, you get to keep playing.
Why I like "boring," essential businesses
One reason I point people toward home services is that they're stable in a way flashier businesses aren't. Your roof leaks whether the economy is on fire or in the tank. Your heat or your AC goes out, and you find a way to fix it — because you're uncomfortable, and comfort isn't optional. That's why private equity went after HVAC first. Essential services get paid in good times and bad.
Boring and essential beats exciting and fragile. Every time.
Never quit — change the plan, never the goal
The thing I was told as a kid and never let go of: you never quit. There will be obstacles your whole life. If you believe in what you're doing, you get up and keep going. When the plan you laid out doesn't work — and it won't, at some point — you change the plan, never the goal.
And you don't have to make every mistake yourself. I've made them all, and that's how I learned. But the whole point of putting experienced people around you is so you can skip the ones they already paid for. Their scar tissue saves you money and years.
Losing everything taught me how to build something that can't be taken away by a single bad year. That's the difference between making money and keeping it — and it's the difference between a good run and a life.