Investing

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.

Shoveling Sh*t and Finding Gold

13 June 2025
Most business books suck. But Shoveling Sht* doesn’t pretend. Mike and Kass Lazerow built, broke, and rebuilt their way to a $700 million exit—together. On my podcast, they open up about failure, therapy, ramen dinners, and the real cost of entrepreneurship. It’s raw, hilarious, and exactly what founders need to hear.

The “Sleep Well at Night” Portfolio

2 June 2025
In this piece, James Altucher shares the investing insights he’s learned over two decades of wins, losses, and hard-earned lessons. From market history to real diversification and the power of moonshot opportunities, this is a deep dive into what it actually takes to succeed—and sleep well—while investing.

How to Escape Prison

22 May 2025
Most people will never see a prison cell. But most live behind invisible bars—trapped by fear, routine, identity, or shame. On this week’s podcast, I sit down with Damon West, a former college quarterback turned inmate who rebuilt his life inside a maximum-security Texas prison. What he shares isn’t just a survival story—it’s a manual for mental freedom, forgiveness