Download The Podcast MP3

My wife was high from the morphine. And my daughter was passed out. So I left the hospital.

I went to the Mayfair to play poker. But they wouldn’t let me in. “Go back to your family,” they said.

“Listen,” I said. “They’re not awake.”

They let me in. And I played no-limit poker for the first time.

No-limit = you can lose all your money.

I used to play poker religiously. But I quit. And started a business. Which made me lose all my money.


I still play poker from time to time. I like the strategy. I read this book back in 2012, “Play Like a Girl” by Jennifer Shahade, a professional poker player and the U.S. Women’s Chess Champion.

We’ve been playing chess together since we were kids.

And I recently went on her podcast, “The Poker Grid.” And I’m airing it here for you. We talk about my position in crypto, diversifying your investments, side hustles, negotiating and the overall psychology of dealing with high-stakes situations.

Which we all face… often unexpectedly.

So here’s how to get prepared.

Tune in. Subscribe to Jennifer’s podcast. Subscribe to my podcast. And let us know what you learned.

  • 4:22 | Why this episode is special
  • 5:35 | Jennifer Shahade wrote the book “Play Like a Girl.” I appreciated it for many reasons. One is because it’s encouraging for young girls. I gave both of my daughters a copy back in 2012. I also love the book because it gets you to think. And shows Jennifer’s love for the game of poker. (Side note: you can learn more about Jenn’s efforts to empower girls and women with chess at
  • 8:15 | My (many) poker strategies. Including: how to deal with the fear of losing, how to read people, how to bluff and when to bet.
  • 12:36 | The science of poker theory. And how it’s changed and developed over time.
  • 14:33 | The desire to chicken out is huge. So how do you fight that? I tell Jennifer my strategies.
  • 17:39 | My rules for investing. And how poker theory influences my bets.
  • 18:53 | People always ask, “What percentage of my portfolio should I invest in a stock I think is going to go up?” I tell Jennifer my answer. It will probably surprise you.
  • 21:17 | Let’s say crypto gets adopted by the world as a global currency. How much should you invest now?
  • 23:46 | Everything is negotiable. And nothing really has value. It’s all fiction. And bias. Jennifer and I break down some cognitive biases commonly used in poker and how they can be applied to negotiating.
  • 27:02 | The psychology behind anchoring bias. This is why you should start with a high number and allow someone else to negotiate down.
  • 27:41 | My favorite negotiating technique.
  • 29:35 | Try using this tactic to be more persuasive.
  • 33:02 | The mindset of a killer poker player. And the types of side hustles that fit their instincts.
  • 39:01 | How to build your idea muscle. And exercise your ability to execute ideas.
  • 43:20 | Jennifer asks me which one of my books I recommend to people who want to be wealthier.
  • 47:45 | My first 10 ideas list.
  • 48:33 | Why I quit poker and started a business.


Links & Resources