The Look After 'The Leap'

Tom Ashbrook, a former reporter and deputy managing editor at The Boston Globe, is a co-founder and vice chairman of HomePortfolio.com Inc. in Newton, Mass. The founding of HomePortfolio, and the changes it caused in Ashbrook's life, are chronicled in his book The Leap.

In 1996, Tom Ashbrook left a lengthy career as a newspaper journalist, hooked up with a longtime friend and plunged into the then-fledgling world of e-commerce. After more than 15 years in "old media" as a foreign correspondent, then as deputy managing editor of The Boston Globe, he saw the promise of "new media" in what became HomePortfolio.com Inc. in Newton, Mass., which helps homeowners furnish their homes and links them with suppliers of the products they need.

In Ashbrook's recent book, The Leap: A Memoir of Love and Madness in the Internet Gold Rush (Houghton Mifflin Co., 2000), he paints a dramatic portrait of how the struggles of launching a Web-based business in the early days of the Internet strained his family life. There were long days at the office that sometimes ended at midnight, months of forgoing a salary as the new company sought venture capital funding and even an emotional e-mail from his wife, Danielle, wondering if HomePortfolio - and the Ashbrook family's finances - would be able to ride out the storm. In one telling paragraph, he writes of how he walked away from a potential $1 million in stock options he would have received had he stayed at the Globe just one more year. When Danielle read that in the book's galley proofs, she "was not a happy camper," he told Computerworld's Rick Saia in an interview.

But in 1998, the venture capital money came in and HomePortfolio's fortunes, as well as life at the Ashbroook home, began to turn for the better. As for those stock options, Ashbrook says, Danielle has "developed a sense of humor about it."

Q: If someone came up to you today and said, "I'm gonna launch a Web start-up," what would you tell him?

A: First, I'd sit him down for a long talk. I would say, No. 1, "Know your personal tolerance for risk." When you walk away from that last paycheck [at the job you're leaving] to start something brand new, the vulnerability hits you like ice water. And you better assess before you take the leap what your capacity for risk-taking really is. No. 2, I'd say, "Don't get involved in any kind of copycat Web play at this point. The me-too era is over. . . . Be sure that you've got a fresh and singular idea."

On the personal front, I'd advise them to brace their love life .. . because the stress to the system of launching a start-up can be enormous, and it comes right home with you. It tends to take over your life for awhile. So batten down the hatches at home.

Finally, don't do it just for the [big] money. You may make it and you may not. So get involved with an effort that you have a passion for. That passion will carry you through the rough patches and will bring you satisfaction, whether you become a billionaire or not.

Q: With the clarity of hindsight, what would you have done differently?

A: I'd like to say that I'd pick my timing better, that I wouldn't have dived in so early, because diving in as far ahead of the market as we did made a long walk in the desert almost inevitable. On the other hand, we had no special lock on this home-design industry, and if we hadn't dived in early, we wouldn't have been able to sew up the many advantages that being early brought us. So it was painful, but maybe that pain was necessary, given where we were starting.

Q: You endured financial challenges and family stress that would have caused others to throw up their hands and walk away from this dream. What was the No.1 factor that kept you going?

A: I know that pride is a sin. But once I cast my lot with this wild idea, it became kind of a do-or-die challenge to me. Maybe there are times in life when, for the health of your soul, you've gotta commit to something all the way. Now, that kind of talk made my wife crazy, but this became my odyssey, my personal life challenge.

In retrospect, you can see that we were really all caught in a gold-rush fever, maybe even a kind of millennial madness. . . . The whole experience made me think about my [English and German]immigrant forbears. What was it that made them, instead of their neighbor, climb on the boat and sail out into that big ocean that they had never crossed before? I don't know. But some certain people and most Americans who are the offspring of such people cannot resist a sexy frontier. I guess I was just one of those people.

Q: So, would you do it all over again?

A: I would devoutly hope and pray that if I did it again, I would be smart enough and now experienced enough not to have to attack so many elements of a start-up with a brute-force approach.

My understanding of what it takes to create a successful business model is much more lucid. . . . So, would I want to do it again, the way I did it the first time? Oh God! Please! No! But would I consider doing it again with the benefit of the experience I gained? Don't tell my wife, but I might.

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