Investing

How to Lose Everything and Keep Going

18 July 2025
Most people think success is about the moment you win. But former UFC champion Miesha Tate—and many investors—learned the truth the hard way: winning doesn’t fix what’s broken inside. In this issue, I share what her journey through loss, depression, and reinvention can teach us about building a stronger foundation—both in life and in the markets.

How I Learned Not to Panic

12 July 2025
When Robert Rosenkranz put 100% of his net worth on the line, he wasn’t gambling—he was thinking clearly. In my latest podcast, we explore how stoicism helped him build lasting wealth, stay calm under pressure, and avoid the panic that ruins good decisions. If you’ve ever judged yourself by outcomes instead of process, this conversation could change how you invest—and how you live.

I Blew $1,000,000 in One Week

6 July 2025
I once blew a million bucks in a week trying to impress people I didn’t even like. Meanwhile, Nomadic Matt spent just $27,000 traveling the world for 18 months—and built a life most people only dream about.

To Win, Just Don’t Die

4 July 2025
I’ve spent decades bouncing between writing, poker, investing, chess—and the quiet misery of failing at all of them. Over 2,000 rejection letters. Empty bank accounts. Eight-hour chess defeats. But through all the pain, I’ve learned something: whether you’re trading markets or taking creative risks, you have to really like yourself to keep going. Here’s why.

Rich, Powerful, and Miserable

30 June 2025
F In 1999, I thought money would solve everything. I was wrong. In my podcast with Marshall Goldsmith—the coach behind Ford and Best Buy’s epic turnarounds—we explored why achievement and happiness have nothing to do with each other. From NFL stars to CEOs, Marshall shows that success is about process, not just results. Here’s what I learned (the hard way) and why you might be chasing the wrong thing.

Not Fame. Not Fortune. Freedom.

26 June 2025
What does real freedom look like? For Gary Vaynerchuk, it’s not about money or fame. It’s about never having to ask permission. In a raw conversation on The James Altucher Show, Gary shares why entrepreneurship is the path to true freedom — if you’re willing to put in the work.

Everything is Rigged… Until You Hack It

23 June 2025
What do The Blair Witch Project and Girls Trip have in common? They didn’t wait for permission. In this week’s podcast, producer Will Packer shares how he hacked Hollywood without connections, a big budget, or even a plan — and how you can apply his playbook to dominate in any industry.

What to do With Your Money Now

21 June 2025
Businesses — both private and public — are where the real money is. You can hold an ounce of gold or a bitcoin from here ‘til kingdom come; you will still just have an ounce of gold or a Bitcoin.