A Bankruptcy Expert Taught Me These 15 Things About What Keeps People Broke

“Your job will eventually make you rich some day”

Tim Denning
The Startup
Published in
7 min readJun 7, 2022


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Bankruptcy isn’t about a bank balance. It’s a mindset.

A friend I’ve written about many times lost his $100m empire more than 10 years ago. He’s still bankrupt today. He and his family live in a single motel room and rely on government assistance.

We regularly chat. His husky smoker’s voice is a clue to his future health. Surprisingly, he still has some of the best business ideas I’ve ever heard.

But he never executes.

Not because he’s lazy. But because he has no energy.

Years of smoking have stripped him of his youthful exterior and replaced his brain with one that can operate for two hours a day at best.

When I tell him to rebuild his empire the same way he did all those years ago, he gives me excuses. He made his fortune in real estate. Real estate hasn’t changed much and probably won’t.

Yet he doesn’t do it — and he loves real estate like Kim Kardashian loves telling us to work harder from the foyer of her mansion.

The reason is his mindset.

Somewhere deep down he doesn’t believe he can do it. The bankruptcy nuked his confidence and wiped out his belief he could do anything.

We must understand how to program our minds to deal with failure.

Here are a few more things an expert who worked with bankrupt people taught me about what keeps society broke.

“Treat your credit card like a debit card”

Credit cards are a trap. Suckers get them to earn worthless frequent flyer points designed as an elaborate scam.

“Just pay it on time and you’ll be fine.”

Sounds simple, except when you’ve got access to an infinite amount of credit, it’s stupidly easy to overspend. Even for a disciplined navy seal. I use a debit card that has rewards. Same benefits, but I only spend money I’ve made.

Too much debt is a tax on your future.

“Your job will eventually make you…



Tim Denning
The Startup

Aussie Blogger with 500M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship — timdenning.com/mb