Welcome to Contrarian Thinking, where we help you think smarter, build better, and live freer.
This week, we share 7 strategies for living a more fulfilling life from one of Codie’s closest mentors.
Let’s dive in…
This is Bill Perkins.
Hedge fund manager. Poker player. Asymmetric thinker. Worth hundreds of millions.
Today, you’ll steal 7 of his principles for living a truly rich life, starting with…
Bill doesn’t do polite encouragement. He does reality checks.
Codie once shared her business vision with him — safe, reasonable, probably doable. He paused, looked her in the eye, and said: “Has small infected your thinking?”
It wasn’t rude. It was a gift.
Sometimes, playing it safe feels smart… when it’s actually just playing small.
Most people don’t have anyone in their life who will call that out. Bill will.
“We’re human beings, not institutions. We don’t live that long,” Bill says.
Rich people aren’t usually much smarter. But they are often much faster. Bill calls it what it is:
While most people are still planning step one, the best have already failed 4 times, maybe even lost money, and figured out the faster, better path to reach their goal.
Bill has a spicy take:
If you’re educated, healthy, and halfway ambitious, you have no actual financial risk. You’re not going to starve or be homeless, he says. You can get a job — maybe not a glamorous one, but a job — any day of the week.
What you probably have is “ego risk.”
That idea hit home for Luke, a veteran and the CEO of our portfolio company, SkyFi:
“People aren’t afraid of failing, they’re afraid of looking stupid,” he says. “That ego trap costs them real opportunity.”
Most people treat risk like it’s binary: you’re either taking one, or you’re not. But that framing is dangerous.
Risk isn’t a light switch. It’s a spectrum of tradeoffs, probabilities, and potential outcomes. The better question isn’t “Is this risky?” but “What kind of risk am I taking?”
When you treat risk as binary, you get it backward. You avoid moves that look risky but are actually rational bets. And you cling to “safe” choices that quietly compound into long-term risk.
Think of risk on a curve:
You probably want to be here. Not playing not to lose. Not swinging blind.
Not too safe, not too reckless, but calibrated. The Risk Ratio Index isn’t about avoiding risk. It’s about taking risk intentionally.
The right level of discomfort, applied in the right direction, at the right time.
That’s the game.
There’s a massive difference between owning a business and that business owning you, Bill says.
The sooner you step back from the oven, the sooner you can start opening more doors.
“I love to fire myself,” he told us. “That’s how you build an empire.”
Bill once lost $10 million on a failed energy project in El Salvador.
“It failed miserably… I lost $10 million when $10 million was a significant portion of my net worth.”
Most would call that a disaster. He calls it part of the process — data collection.
“I’m OK looking like an idiot. And I often do.”
You don’t need to burn millions like him to learn this lesson:
No shot, no progress.
“If I want to go heli-skiing,” Bill says, “it’s not at 86.”
Money has a shelf life, and it expires faster than most people think.
There’s a window when the money actually matters — for joy, adventure, and memory-making. Miss it, and all you’re left with is digits in a bank account.
Timing, not just saving, is what makes money useful.
Bill tells a story about his friend Greg.
Greg took his brother on a ski trip and tried to cover the hotel. His brother refused.
Greg: “If I owned a house and invited you to stay, would you pay?”
Brother: “No.”
Greg: “Then save me the $3 million and let me pay for the hotel.”
That’s the mindset.
Bill doesn’t buy boats or houses to sit in alone. He buys them to share experiences. Not to show off. To create memories.
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The information contained here is educational, may not be typical, and does not guarantee returns. Background, education, effort, and application will affect your experience and the profitability of any business. Individual results may vary.
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