Why Success Gurus Die in Debt
Everyone you grew up admiring—the authors, the speakers, the celebrities, the viral sensations—are either broke, divorced, in therapy, or quietly Googling “how to declare bankruptcy without anyone finding out.”
They checked all the boxes. The degrees. The experience. The speaking gigs. The bestsellers.
They were qualified.
Guess what? Didn’t save them.
Last week at the Full Stack business conference, Peter Saddington put me on the spot: “How do you succeed when you’re not qualified?”
Maybe that’s the wrong question.
Because the most successful people? Weren’t qualified at all. They were just too stubborn, too weird, or too unemployable to quit.
- Steve Jobs dropped out of college after six months.
- Richard Branson never finished high school.
- James Dyson failed 5,126 times before inventing his vacuum. No engineering degree.
- Quentin Tarantino worked in a video rental store. Never went to film school.
- Walt Disney was told he “lacked imagination” and got fired from a newspaper.
Every time I was too naive to know it was supposed to be impossible, I pulled it off.
The moment I started listening to the experts — believing I needed permission, credentials, qualifications — it actually became impossible.
Here’s what I told Peter—with the biggest secret (the one that changed my life) at the end.
Secret #1: Being Unqualified Is a Superpower
When you have zero qualifications, you’ve got nothing to protect—no title to cling to, no reputation to uphold.
You get to ask dumb questions, try crazy things, break rules, reinvent the rules, and then eat lunch alone because everyone thinks you’re weird.
That’s the edge.
The people who “know better” are often trapped by their expertise. You? You’re free. You’re dangerous. And you’re going to surprise everyone—including yourself.
Example: I started a web company in my 20s with no clue how business worked. No business plan. No suits. Just pure, dumb enthusiasm. Somehow, we landed HBO as a client and eventually sold the thing. Why? Because I didn’t know I couldn’t.
Secret #2: Rational Optimism Beats Everything
Not delusional optimism. Not “The Secret” vision-boarding-manifest-a-Lambo. Rational optimism.
I was broke, depressed, and living in Airbnbs I couldn’t afford. But I’d ask myself: What tiny action can I take today that makes tomorrow slightly less awful? That’s rational optimism. You anchor your hope in reality. Then you do something about it.
Every success in my life started with one optimistic thought—and then one uncomfortable action.
Secret #3: Exercise Your Idea Muscle
Feeling unqualified often means feeling idea-less. Solution? I write down 10 ideas a day. Every day. Even when I don’t want to. Especially then.
Most of the ideas are garbage. Doesn’t matter. The process works. You get more creative. You build confidence.
One of those dumb little lists turned into a company I sold for $10 million. Another turned into a book that sold 100,000 copies. Most? Trash. But trash is compost. And compost grows things.
Secret #4: Choose Yourself
Stop waiting for someone to pick you. The college, the boss, the publisher, the investor. Forget them. They don’t know what they’re doing either.
Start a blog. Launch the podcast. Write the book. Sell the thing. The tools are free. The gatekeepers are gone. The only permission slip you need is the one you write yourself.
Secret #5: Make Yourself Useful
Hate networking? Me too. So don’t “network.” Be useful. Send someone 10 ideas for their business. Introduce two cool people. Post something helpful online. Show your work, don’t just talk about it.
When you’re useful, people remember. And when people remember, doors open.
Qualifications Are a Lie
Everyone’s winging it. Everyone’s scared they’re about to be found out. So here’s the truth: You’re already qualified.
Because you’re willing to try.
That’s rare.
So raise your hand. Start the thing. Say yes, even when your brain screams “Who do you think you are?”
You’re someone who’s doing it anyway.
And that’s exactly how people succeed.
