My worst money move?
I dropped $1,000s into a friend’s “sure-thing” crypto project in my 30s. Slick branding, lots of hype, and a Telegram group that felt like Wall Street with memes. Six months later? Poof.
That loss taught me something I wish I’d known earlier: building wealth isn’t the same as chasing it.
That’s where Barry Ritholtz comes in. In How Not To Invest, he flips the script from “How do I win?” to “How do I not blow it?” And trust me—if you’re the kind of entrepreneur who bets on yourself, this book is a mirror you didn’t know you needed.
Three Traps That Blow Up Portfolios
Ritholtz breaks down investing mistakes into three buckets—and yes, I’ve tripped over all of them.
🧠 Bad Ideas
We love predictions. They give us the illusion of control. But even billionaires get it wrong. Sam Zell predicted a recession in 2015. Didn’t happen. No one knows anything. Not your podcast host, not the guy on CNBC, not your cousin who bought Tesla at $30. Especially not me in that Telegram group.
📊 Bad Numbers
We entrepreneurs live and die by data—but when it comes to investing, we’re great at seeing what we want to see. I’ve cherry-picked crypto gains to justify bad plays more times than I’d like to admit. Ritholtz calls out this BS with examples like the Cisco “must-buy” media hype—right before it tanked. Metrics can be smoke if you’re not watching where the fire is.
😬 Bad Behavior
Greed’s my old pal—I invited it to the crypto party and it trashed the place. Ritholtz doesn’t shame. He just holds up the mirror and goes: “You see this? This is why your portfolio’s limping.” Panic-selling, holding losers, chasing hype—it’s all there. And it’s all us.
The Fix? Chill Out and Stay In
The book closes with ten practical rules—stuff no one wants to hear because it isn’t sexy. But it works.
Index (mostly): Bet on the market, not moonshots.
Avoid dumb moves: The fewer mistakes, the better you do.
Have a plan: And don’t let Twitter threads shake you off it.
Think long-term: You don’t need to outsmart the market—you just need to outwait everyone else.
When Ritholtz says “Index (mostly),” he’s not telling you to be passive. He’s saying: stop pretending you’re a fund manager with a research team and a crystal ball. Play the game where you actually have the edge—patience.
Why This Book Works (Especially for Entrepreneurs)
You might scoff at “just sit still” advice—I did too.
But Ritholtz makes the case: even rebels win by not losing big. We’ve got a secret weapon most pros don’t—we don’t have quarterly reports to impress anyone. That freedom? That’s your edge.
The book hits because it doesn’t just wag a finger. It respects your drive, but reminds you: the market doesn’t care how smart or scrappy you are. What matters is avoiding mistakes that torpedo everything you built.
Should You Buy It?
Absolutely—if you’ve ever:
Bought a stock because of a hot take on YouTube
Bragged about gains, stayed quiet on losses
Thought you could time the market (and got timed out)
Buy it. I’d have saved $5,000 and a bruised ego if I read it sooner. Ritholtz proves you don’t need to be the smartest—just the least dumb.
Entrepreneur-Investing FAQs
Q: I’m already investing—will this feel basic?
Nope. You’ll see new angles on old mistakes. Even seasoned folks need a gut check.
Q: I’m brand new. Is this too deep?
Not at all. Ritholtz keeps it clear, funny, and story-driven. No MBA required.
Q: What’s the biggest shift this book gives you?
Honestly? The freedom to stop guessing. You don’t need a hot pick. You need a solid plan and the will to stick with it.
