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Look Before You Leap, But Leap
Tom Ashbrook Shares A Tale Of Love And Madness In The Internet 
Gold Rush

(Washington, DC -- June 22, 2000)  Every entrepreneur has a story to tell; most have a lot of them.  The outcomes may be different and the details may vary, but they’re all full of adventure and emotion and lessons learned.  Tom Ashbrook’s story may not be entirely unique, but he is more eloquent about it than some others.  Before co-founding, the leading Internet destination for premium home design products, he left a long and successful career as an award-winning journalist and editor for the Boston Globe to tackle the high risk world of the netpreneur.

I knew I had dreams my life wasn't touching,” said Ashbrook of why he took the leap into entrepreneurship.  “I knew there was a clock ticking.  I knew the world was changing in ways that meant I shouldn't count on old assumptions any more, but I didn't know if I could act on that with kids and a mortgage and all the habits of a familiar life.”

Ashbrook, who is author of the new book, The Leap: A Memoir Of Love And Madness In The Internet Gold Rush, attracted more than 300 pre-, post- and mid-leapers to hear his tale at this morning’s Coffee & DoughNets meeting.  More than war stories, however, he focused on the human side of the risks and rewards, including the emotions, anxiety and effects on family.  Maybe it was that he expressed many of their own personal experiences with humor, style and an almost confessional intimacy, but Ashbrook clearly built a bond with the audience, and they responded with an energy and camaraderie uncommon in such a group.


The journey toward HomePortfolio’s success was full of lean times and tension, bizarre hours, a strained marriage and having to say no to things like movies and soccer for kids who had come to expect such things.  As a 40-year-old husband and father, some might say that he went too far by dragging others into the risk¾people who depended on him.  Ashbrook, however, knew he could always go back to his previous, if no longer enthralling, career in the publishing world: “Part of my motivation for doing this was to be the right kind of model for [my kids].  I don't know about ‘new economy’ and ‘old economy’¾I think the wall is disintegrating between the two¾but the winners in this new century will be people who are willing to envision and take risks.  I wanted to be a model for my children in that way.  I didn't want to be someone who clung to that desk as the industry eroded underneath it just for that weekly paycheck.”

In fact, his greatest fear was not failure itself, but that if his children saw him fail they might react by becoming too skittish about taking their own risks later in life.  While many people consider entrepreneurship a young person’s game, it could be that having more to lose may make an older entrepreneur more determined to succeed.

If the early days of HomePortfolio were “like 40 years in the desert,” as Asbrook described them, the arduous journey of finding funding, developing a business model and launching a company had its pay-off.  The ordeal toughened Ashbrook and his partner, validated their idea, helped them build a network of contacts and made them more likely to be able to compete successfully against bigger, stronger players.  It may be a less risky venture now that the company has customers, advisors and over $60 million in venture funding, but it isn’t any easier.  There are always new challenges, new milestones and new sets of expectation.  The passion that sustained them during the tough times is still there, but at least the Ashbrook children can play soccer again.

Listening to Ashbrook, passion may be the key characteristic necessary in a successful entrepreneur.  In the face of inevitable obstacles, set-backs and naysayers, an entrepreneur needs determination, confidence and perseverance to follow their dream.  Certainly it’s not passion alone.  Your idea must have profit potential; you must ultimately be able to convince customers, partners and perhaps funders of that fact, and you must prove to them that you are the ones to pull it off.  Without passion, however, the obstacles will drive you out early, and that’s why VCs will often test your commitment as part of the process.


It’s more true now than it was even a year ago.  While tremendous opportunity still exists for netpreneurs, the heady mania of “anything goes” is over.  Funders are becoming more sober and realistic about their investments, according to Ashbrook, which means they scrutinize companies, models and teams more carefully. founder Mario Morino, a technology entrepreneur, advisor and investor, has observed the same thing.  He wrapped up the meeting with his perspective on what it takes to be successful entrepreneur and what life is like after the leap.  He also offered his insight into where the Internet market is now and where it is going.  He agreed that investors are more diligent and said that it reflects a much needed and ultimately positive return to business basics--you have to make money.

That notwithstanding, he said that there is actually more money chasing Internet opportunities than ever before.  “It means you are going to have to do your homework better,” he advised, “but the chance of succeeding is still remarkably high.”

For a first-timer, Ashbrook compared taking the leap to throwing yourself off a cliff and building your wings on the way down.  That may seem crazy, but, he said, “If you are really creating something new, you are going to wonder sometimes if you are crazy.”

There’s no doubt that it’s a risky proposition, one you can only accept with both eyes open.  Luckily, there are more and more successful entrepreneurs like Asbrook and Morino who have already built their wings and are ready to share their knowledge.

Ashbrook advised, “Be visionary, be brave, and be sure you have a new idea¾as sure as you can be anyway.  There is opportunity.”  Morino went further, acknowledging that taking the leap is a tremendously difficult decision, especially at certain points in one’s life, but he urged, “When you have a dream and the opportunity to make the leap, you have to do it.  You don't want to wake up 20 or 30 years from now and say, ‘If I only had done it.’ Woulda, coulda, shoulda doesn't count. Did does.  If you want to do something in your heart, and you have the opportunity to do it, you take the leap.”

Copyright © 2000, Morino Institute. All rights reserved.



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