If you look at the tabloids, we are such a pop culture nation. We love to see which starlet got drunk and went into rehab. We seem to feed off of other people’s failures. In this celebrity environment, lottery winners become D-list celebrities, at least locally. We enjoy seeing their trials and tribulations because it is very easy for us to say, "Boy, I wouldn’t have let that happen to me," in the same way we might say of a celebrity, "I wouldn’t have had to go to rehab," or, "I wouldn’t have had to declare bankruptcy." It has more to do with our society.

A lottery winner’s experience is not that different from that of someone who was at the right dot-com in the late ’90s, and suddenly found himself with great wealth.

You’re absolutely right. We saw a few of those stories when an entry-level employee was at the right place at the right time and drove off into the sunset in a Maserati. But I still think that the same rules apply. Even the youngest person at the little dot-com probably had a higher education level than most lottery winners. The analogy is dead-on, though. New money is new money. It’s a question of how prepared you are to handle it.

You worked in the lump-sum industry for many years. Are there other groups that target lottery winners?

They are the same groups that target any individual who has money. But lottery winners are, in some ways, the perfect target for all kinds of sales people—real estate, financial services, insurance. Whatever you are selling to someone who has access to a big pile of money, lottery winners are obviously a good choice. Sales people are savvy and understand how to close a deal. Closing a deal with someone to whom it is easy to sell a dream, that’s a good client. I’ve been in sales for a long time, and I can sell dreams. Dreams are easy to sell. Reality is a little harder. The difference between most groups that target lottery winners and the lump-sum industry is that if it weren’t for the lottery annuity, there would be no lump-sum industry. While other businesses market very heavily to lottery winners, I don’t think they hold a candle to the efforts of a business that actually eats lottery annuities themselves. It is the epicenter of the business surrounding lottery winners.

You write that on some level you relate to lottery winners.

I was a gambler, and I still am to some extent. Although I come from a well-educated background and a family of educated people, when I was 27 I started working in the lump-sum industry. Within a matter of months, I started making lottery-type money. I had access to the kind of cash that 27-year-olds don’t see. There was the kind of cash flow that allowed me to get away with making a lot of stupid decisions with money, and two weeks later there’s another paycheck, and two weeks beyond that and so on. One of the reasons that I feel I understand lottery winners now, and one of the reasons I was so successful in this industry, is because I felt like I was a lottery winner.

What do you do now?

I am a full-time writer. I’ve finished my first book and I am working on my second now, which is in the development stages. I have made an unbelievable career leap, having gone from the wild world of finance back to my roots, which is one of creativity and humor. I haven’t had any more fun or taken any greater pleasure in my life than in this past year and a half since I left the lump-sum industry. Writing full time has been a life-changing decision—and it’s the best thing I’ve ever done.

Sounds like you won the lottery.

You’re not the first person to say that. It’s more a life lottery than a financial lottery. I hope I’m a little wiser than the average player about what I do with this windfall.