"I Made $6 Million at Age 26—and Lost It by 28"

My career accelerated quite a lot at that time. I was the youngest guy at Exodus Communications, a $36 billion company.

I was in charge of due diligence for our mergers and acquisitions department. So, when we wanted to buy a company, I was the guy who'd go in and say, 'Is this technology going to work for us? Yes or no?'

I attended board meetings. And because of that, I knew all of the upcoming acquisitions. So, I was blacked out [of trading stock he had received as part of his compensation]; it was illegal.

When those stocks started to teeter, what I should have done was quit my job, sell all of my shares and retire. Instead, I said, 'I can't do that. I might lose an additional $4 million in uninvested equity or something.'

So I stayed at the company. And the stock dropped from $60 a share to $5 a share.

In retrospect, I should have thought, 'I have enough money. I can do whatever I want. I should just walk away today.' I could have done that. But for six months, I didn't walk away.

Every day, I was worth less and less in the bank account. And that was a grinding down, horrible feeling.

And there's another thing. I don't think I've ever talked about this: I was with some online broker—going back 15 years. It was a very cutting edge broker that let me do options and all this stuff.

Based on the reports it seemed like I had a couple hundred thousand grand in the account, at least enough to take care of my basic expenses. But there was a margin on that account that I didn't even know about because I wasn't managing the stuff tightly. I was too stubborn and fearful to hire someone to help me manage it. The margin ended up consuming most of the account before I even noticed.

Today, the advice translates to: Hire a professional to pay attention to the stuff that you're not paying attention to."