If you’ve followed me a while, you know my story includes big wins, painful losses, deep depressions, big comebacks, and more reinventions than Madonna.

Between all of it, I spent a lot of years trying to understand how success and self-destruction can live so close together.

Recently, on the TruthWorks podcast with Jessica Neal and Patty McCord, we went straight into all of it.

My full story.

The real arc:

HBO → $50 million → $46 → depression → rebuilding → repeat.

And the most important things I learned through it all.

If you’re new here—and even if you’re not—this is me getting back to the basics. The things that saved my life over and over again.

My First Big Break

In the ‘90s, I started my career in the least respected department at HBO: IT.

Back then, maybe five people in New York knew how to build a website. We all knew each other. We all started companies.

I started one called Reset.

I built HBO’s website by day then built websites for American Express and movie studios and record labels by night.

After 18 months, I left HBO.

I kept building Reset until I finally sold it. Suddenly, for the first time, I had generational wealth.

And then I made the classic mistake: When you’re good at one thing, you assume you’re good at everything.

I thought making money meant I understood investing.

It doesn’t.

Making money, keeping money, and growing money are three completely different skills.

I only had one.

My First Big Lesson

I didn’t just lose money.

I lost:

• My house

• My family

• My identity

• My sense of who I was

And the worst part was the shame.

I lied to a friend when he saw my house listed in the New York Times. I couldn’t admit I was collapsing. That’s how strong shame can be.

Shame is heavier than bankruptcy.

And it comes back in cycles. 2009. 2015. You don’t “graduate” from vulnerability.

You learn how to manage it.

The Four Bodies

One of the core ideas we discussed is something I’ve written about for years. It’s one of the big insights that helped me come back from rock bottom.

We all have four bodies:

1. Physical

2. Emotional

3. Creative

4. Spiritual

Each one has circulation. Energy flows inside them and between them.

When something blocks, you don’t just get tired.

You get a creative heart attack. An emotional heart attack. A spiritual heart attack.

You can’t ignore one dimension and expect the others to thrive.

Founders especially think: “If I just work harder, everything else will stabilize.”

It doesn’t work like that.

Sleep. Relationships. Creative practice (writing 10 ideas a day). Meaning.

They compound just like money.

The 1% Rule

At the end of each day, I still ask myself: What did I do today to improve my life by 1%?

Not a grand plan. Not a five-year vision.

Just 1%.

Physical.

Emotional.

Creative.

Spiritual.

1% compounds faster than ambition.

Failing Fast (Without Drama)

One of the biggest problems ambitious people face is holding onto dead ideas too long.

If a bird falls out of the nest and doesn’t survive, the mother bird doesn’t hold a ceremony.

She builds another nest.

Abundance mindset doesn’t mean you’re blindly optimistic. It’s knowing you can generate another idea.

If you can create, you’re never bankrupt.

If you haven’t failed yet, borrow someone who has.

Get mentors who:

• Have scars.

• Have lost.

• Stayed in the game.

The key to investing and entrepreneurship is simple:

Stay in the game long enough. You can’t win if you’re wiped out.

Why I’m Careful About AI Investing

Speaking of investing, they asked me about investing in the AI age.

Here’s what I said, broken down simply:

Large AI models are becoming commodities. Commodities become price wars. Price wars destroy margins.

The real leverage is:

• Proprietary data

• Hard-to-access datasets

• Physical AI (humanoid robotics)

• Hardware

The world is built for humans. The infrastructure assumes two legs, two arms.

Humanoid robotics is an engineering mountain. Mountains create durable companies.

The next wave of millionaires won’t emerge from copying GPT. They’ll emerge from owning what can’t be replicated easily.

As always, my team and I are on the hunt for the BIGGEST opportunities throughout all of our letters.