Investing

I Blew $1,000,000 in One Week

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

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.

I Flew 4,000 Miles to Say “Be Stupid"

I flew 4,000 miles to say “Be Stupid.” Then I sat down with chess legend Vishy Anand to learn how to stay relevant when everything changes. The lessons? They apply to any game you’re playing.

How to invest in OpenAI and SpaceX as of Monday

Two of the most attention-grabbing companies in the world right now are OpenAI and SpaceX. I think if you casually mention these companies to most…

Rich, Powerful, and Miserable

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.

Interest Rates, Observed

Lower interest rates encourage borrowing. That’s the whole idea. Debt goes up. Spending goes up. The feds ‘print’ more money to cover their deficits. Prices rise further.

Not Fame. Not Fortune. Freedom.

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

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, Part II

Commercial real estate is a very local matter. If you can find a good building, in good shape, with a reliable tenant, and decent cash flow, it could be a good place for your money.

What to do With Your Money Now

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.

The “altstock boom of 2025” is taking off

Forget altcoins — public “altstocks” are where the action is in 2025. From Circle’s IPO to stablecoin-powered toy companies, the crypto takeover of public markets is here. Here's how it's playing out… and where the biggest profits may be hiding.

Shoveling Sh*t and Finding Gold

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.

I Visited Google. AI is Just the Beginning

Years ago, I visited Google with some friends and, after almost getting arrested, my mind was blown… First, we wandered into the garage where they…

The “Sleep Well at Night” Portfolio

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

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