You launched Shoebuy.com at the height of the dot-com bubble, and the site has grown every year, reaching a new milestone recently with more than 600 brands. Why didn't you fail like most other dot-commers?
A lot of businesses had great tag lines, but at the end of the day, the business didn't follow through. We've always run Shoebuy like a value proposition. There is no Catch-22. We set out to have an incredible selection of shoes offered in a convenient manner with free shipping. Now, we make over $1 million per employee.
How did you become a millionaire in your early 20s?
I had the idea that I could identify people who had bought homes in Boston during years of high interest rates in the late 1980s and help them refinance. I ended up going 16 hours a day, seven days a week. I originated more than $100 million in mortgages in one year. I was 23 at the time.
Why are there so few entrepreneurs in Boston?
There are not so many Internet success stories here. Entrepreneurship used to be huge in New England. But sometimes the cost of living can be more expensive. Sometimes access to funding - even though there are very good venture capitalists here - seems better on the West Coast. We need to work with the state to make this a more affordable and exciting environment to build a business.
What's the most annoying shoe fad you've seen?
I've learned to reserve judgment, but there's no reason to be in pain to look good - like 6-inch stilettos.
Are you surprised by the enormous popularity of the totally ugly Crocs?
You have to keep an open mind. But we were hearing early on that the shoes were extremely comfortable and being worn by nurses and chefs. That is why listening to the consumer is so important.
Who's your business idol, and why?
Steve Jobs. He totally gets it. Innovation, technology, marketing, and fun. Plus, I figure if he can make being a computer geek cool, hopefully for my kids I can do the same as a shoe salesman.
If I stole your iPod, what song would you be most embarrassed that I'd find?
Simple, "That's How You Know," the song from Enchanted. If I play it for my 3-year-old, Madison, it is almost guaranteed she will dance with me.
You're turning 40 in October, and you've got a lot of money. What guest would you pay to come to your birthday bash?
I guess Bruce Springsteen. He doesn't seem to get old, and if we get in trouble for noise, his mellower songs are good, too. Bruce, if you are reading this, what do you say?
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