How to Lose Investors and Ruin Your Life

In 1998, I started a company making websites for big corporations.

Back then, if you could code HTML, you were basically a wizard—and big companies love wizards.

Suddenly, I was building sites for HBO, American Express, Sony, Disney, Time Warner, and more.

When I sold the company, I was living the dot-com dream.

Money always seemed hypothetical, until I woke up and found it in my account. I went from zero to $15 million faster than I thought possible.

Then, I believed my own hype—that I was some visionary wizard.

I bought the most expensive apartment in New York City. I started investing in internet companies. I was spending about a million a week at one point.

And, it turns out, I really was a wizard. Within months, I magically turned $15 million into $0 and a strongly-worded letter from the IRS.

From millions in my bank account to $143. Literally. A hundred forty-three dollars. I checked twice.

I thought I was worthless. In my mind, net worth equaled self-worth. I didn’t think I was going to survive it.

But here's what saved me: authenticity.

Being honest about how badly I messed up turned disaster into a superpower. The day I admitted my stupidity was the day people began to trust me again. 

Authenticity didn't restore the millions overnight—but it restored something more valuable: my life.

This week, I had a conversation with Sun Yi on his podcast, Authentic as F*ck. 

Authenticity has been an important topic for me for decades. So I was excited to get to talk about it with him.

The Heart of Authenticity

Sun Yi highlighted a common misconception: that being authentic is easy or straightforward.

We talked about the complexity inherent in authenticity—how it often involves navigating conflicting desires and internal contradictions.

Real authenticity means embracing the uncomfortable truth: our identities aren't singular but multi-faceted, evolving, and often contradictory.

Authenticity isn't static.

What feels authentic today might change tomorrow based on new insights, experiences, or values.

True authenticity often involves risking how you're perceived. It's not just saying what you feel; it involves being vulnerable enough to risk losing friends, money, or reputation.

Authenticity has cost me millions of dollars. One time, I returned $500,000 in funding for a dating site on the day of its launch. Why? Because I didn’t think it would succeed.

And when I wrote the article “New York City is Dead Forever,” I wanted to highlight the real problems I saw coming for the city.

Jerry Seinfeld called me a “putz” in The New York Times. HarperCollins, my publisher, called me worried. I guess they were concerned people were going to start burning my books in the streets.

By openly discussing my thoughts and personal failures, I no doubt alienated some friends and acquaintances. Being open about past mistakes is a double-edged sword. While it builds trust with some, it might keep others away.

But, as Sun Yi and I talk about, it’s worth it.

The goal isn’t to appear authentic.

Authenticity is a byproduct of something deeper—being honest enough with yourself to notice when you're lying, humble enough to admit when you're wrong, and brave enough to share it anyway.

Authenticity comes naturally when you stop trying to force your beliefs into neat, consistent little boxes and instead allow yourself to evolve.

Listen to the whole episode with Sun Yi. Learn from my mistakes, then keep making your own. Click here.