Yes #1:

I wish I had never started a business, to be honest.

Here’s the results of my first business:

My partners (one sister, one brother in law) no longer speak to me.

I lost all the money I made from that business.

I gave up on my dreams of launching a TV show. I was in the middle of pitching two shows to HBO at the time I left to do my own business.

I gave up on dreams of writing a novel.

I stopped sleeping from 1995 to 2010. 15 years of little to no sleep. My brain is now damaged.

I learned fear, hate, anxiety, stress and poverty from that first business. I wish I hadn’t said “Yes” to it.

Yes #2:

I wish I never started in the financial industry. I ran a hedge fund for many years. I have nothing really to show for it. I learned a lot about business.

But I also gave up on doing what I was good at. I was good at building websites.

I started my first fund around 2003, after being a solid day trader for the prior two years.

I read 200 books on finance, I wrote software modeling the markets, I started networking with other hedge fund managers, I started writing about finance.

I really became an expert in the entire field of trading and stock markets, etc.

You know what… Wall Street is mostly BS and a scam. I really despise almost everyone in that industry.

Whereas when I finally started building websites for people again, in 2006, I quickly got over a million users a month on the first site I released to the public. And I sold it a few months later.

I wish I had said, “No” four years earlier.

Yes #3:

Then I wanted to be on TV.

Every time CNBC called I would say “yes”. I would drop everything, and sometimes travel 70 miles so I can go on TV for three minutes.

Here’s what would happen.

I’d be sitting next to the anchor. She’d stare at her notes until 5 seconds before we were going live.

She’d say (It was always a “she”), “How do I say your name again?”

I’d look at her and say, “I’ll… touch… her. But fast. I’ll-touch-her”. And the she’d still be laughing when we’d go live.

I went on twice a week for years. Each three minute visit was about five hours door to door including preparation. So about 1500–2000 hours of wasted time because I couldn’t say “No”.

Here’s the only thing I learned about news TV. “All we are trying to do is fill the space between commercials,” one major news producer told me.