I Broke Every Money Rule and It Worked
Why the "perfect" financial plan is the one nobody follows
I didn’t follow the money rules.
I partied in college. Bought the car. Took the trip. Lived like it was all figured out before any of it was. I did everything the financial advice industry tells you not to do.
And it worked.
Not because I was lucky. Because every dollar I spent wrong taught me something I couldn't have learned any other way.
The travel gave me perspective. Twenty-plus countries before I turned 30. Culture. Gratitude. The ability to sit across from anyone in any room and connect. The car reminded me what hard work can buy. The parties taught me how to build relationships with strangers, a skill I still use in every boardroom and every investor call. The risks taught me how to bet on myself when nobody else would.
And the debt? The debt gave me discipline. Nothing teaches you the mechanics of money faster than digging yourself out of a hole you created.
The Reality: The money rules everyone follows aren’t rules. They’re defaults. And defaults are designed for people who never plan to build anything of their own.
But here’s what nobody talks about. The people giving you the “safe” financial advice — max your 401K, cut the lattes, wait thirty years — most of them never built anything either. They optimized for not losing. That’s a different game than building.
I did it backward. I did it forward. Right. Wrong. Messy. Expensive. But I did it. And every mistake compounded into something the rulebook could never give me: conviction.
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Conviction is the thing that let me walk away from Apple and seven-figure stock options. Not a spreadsheet. Not a retirement calculator. The accumulated knowledge of having done it wrong enough times to finally understand what right looks like for me.
That’s what motion gives you that theory never will. You can read every book on investing. You can model every scenario. You can wait until the conditions are perfect. But you won’t know what you actually believe about money until you’ve made decisions with it. Real ones. With real consequences.
The path I took wasn’t efficient. It wasn’t optimized. But it was mine. And that ownership is what made everything after it possible. Because when I finally started investing, saving, and building real wealth, I wasn’t following someone else’s playbook. I was running my own.
Now I help others do the same. Not by handing them a rulebook. By helping them build a system that matches who they actually are, not who some financial blog told them to be.
The perfect financial plan doesn’t come from reading. It comes from doing. From making the bet. From learning what your own risk tolerance actually feels like, not what a questionnaire says it should be.
The Bottom Line: The best financial education isn’t a book. It’s the scar tissue from doing it wrong and the conviction from doing it anyway. Most people wait for the perfect plan. You’re learning that the plan gets built through motion, not theory. That’s the difference between knowing about money and understanding it.
What’s the “wrong” decision that taught you the most about money?
If you’re tired of waiting for the perfect moment and want to see what building actually looks like, I’m happy to walk you through how we think about it.
Cheers,
Jon
P.S. I broke every rule in the book. The book didn't build my portfolio. The breaking did.