The Leap: A Memoir of Love and Madness in the Internet ... (ISBN 0395839343)

Amazon.com Review:
These days, if it isn't a dot-com venture, it's no adventure at all. But in early 1996, when Tom Ashbrook jumped from the world of ink and paper to that of computer screen and mouse, Internet start-ups were largely the domain of computer geeks and 18-year-old whiz kids--not exactly the most obvious place for a journalist with a family to support. But with big dreams and a midcareer itch, Ashbrook took The Leap. The result is a look back at those adrenalin-pumped years that's filled with honesty, humor, and a healthy dose of introspection. Neither a geek nor a whiz kid, Ashbrook was an award-winning writer for the The Boston Globe, where he had worked for 15 years. Shortly after winning a coveted one-year sabbatical in Harvard's Neiman Fellowship program, Ashbrook began talking Net dreams with an old college friend, Rolly Rouse. Their vision was to launch a Web site that would present home-design information and images and enable users to create online idea portfolios and buy quality products for their dream homes. Ashbrook soon quit his job and plunged into the project full time, endlessly revising business plans, tapping anyone and everyone for advice, courting venture capitalists, hoarding free credit cards for backup "security", and forever trying to convince a sane and worried wife that he wasn't zooming headlong over a cliff. As a case study of HomePortfolio.com, it's a story of manic speed and energy. As the story of one man's midlife adventure, it's a tale of trepidation, fear, ambition, love, and wonderment. Ashbrook writes with eloquence. His descriptions are imaginative, juicy, and always dead-on. For example, Harvard Business School "was a gleaming, vitamin-enriched, brick and marble and white-trimmed monument to economic steroids," and its old buildings "always looked next-to-new, like rich, pampered matrons on full-dose nip-and-tuck regimens of estrogen and plastic surgery." And he remembers the Myers-Briggs personality test "smelled a little like horoscopes for eggheads to me, with its big gumbo of letters and pat descriptions." Occasionally, Ashbrook's tendency to spice up his descriptions gets a bit much as he throws in too many metaphors; it's as if his brain is on hyperlink overdrive. Overall, though, his graceful prose flows with alacrity, and the pace is infectious. Forget the quiet comfort of your favorite reading chair; you'll be stomping down the sidelines, hoarsely shouting, "Yes, yes, you're almost there, go, one more push!" For that's what this is, a breathless tale of giving birth, an exhausting, exhilarating play-by-play of sweaty labor and life-changing success. Beware... it'll give you the itch. --S. Ketchum

Fun and Easy Read for An E-Commerce Blank Slate:
"The Leap" is a fun, accessible and page turning foray into the world of e-commerce wannabes, especially if you happen to be clueless but intrigued by the phenomena of web start-ups and the preternatural sums of money required for so many of them. A friend lent me this book unsolicited. More out of courtesy than curiosity, I thought I'd skim the first few pages and return it. Wrong! Until I read it, I didn't think I was particulary interested in e-commerce matters, especially yuppie-sounding ones. But I found instead that Tom Ashbrook's book resonates on multiple levels, so that someone like me who'se not likely to be interested in what goes into starting 'just one more cyber company' is in for a big suprise. "The Leap" is an edgy mixture of personalities, relationships, families, mid-life crises, risk taking, and lots more. It's a quick and suspenseful read. Given the fickle nature of these companies, there's no final ending. Since completing this book, I've found that I pick up on media stories about other similar ventures undertaken by people with little or no capital and have a more fully informed (albeit of a 'cyber start-up 101' nature) idea and appreciation for what's involved. While people like Tom and his partner, Rolly Rouse (the obsessed and original brains behind the entire Homeportfolio venture) may not be entirely like you and me (they are after all Yale educated and know lots of people with potential deep pockets) they and their families are enough like lots of us that their story is simultaneously exciting and frightening. Enjoy your leap into their leap!

Before You Decide to Leap....:
In an article which appeared in FSB magazine, Ashbrook explains "There is a game I call startup solitaire. It doesn't have a rule book. It just comes to you, late at night. It goes like this: You're alone in your bedroom with a tall stack of credit cards. You're slowly spreading them out on the bed, turning the cards over and over, checking them against your monthly statements, looking for a few more dollars to borrow." As he observes in the book, Ashbrook had dreams his life wasn't touching. He heard a clock ticking. He knew the world was changing in ways that obliterated his old assumptions. "Something huge was happening, something on a scale so large that I was lucky to see it even once in my lifetime. It was stirring economies and imaginations and possibilities like nothing I had ever known. And the more I looked at it, the more desperately I wanted to be a part of it." For those who are tempted to make a leap into High Risk/High Reward Entrepreneurship, this is "must reading" because the game to be played -- startup solitaire -- is not for the timid nor for the incompetent. Ashbrook enables his reader to accompany him each step up to his "leap", while he is airborne, and then....The book's subtitle correctly suggests that this is "a memoir of love and madness in the internet gold rush." Like so many others, Ashbrook was caught up in what was the apparently irresistible "fever" of it. What happened to him, to his family members, his friends, and his business associates? What did he learn from his experiences? It's all here, waiting for you to share it...albeit vicariously and perhaps from a position of relative security.

OK, but not as good as Burn Rate:
If you are going to read one book on internet startups read "Burn Rate". This book was interesting in its own way - focusing more on the impact to one's family of doing an internet startup. But I found that story fairly predictable - of course you have to work hard and miss many hours away from home. I found myself wishing the author would get past deciding to commit himself to the venture and tell us more about mechanics of starting the company.

Tom, Thanks for the Ride:
I worked for Tom at Homeportfolio.com. Everyday was filled with passion and gutsy intensity. Thanks for the memories and the education--and sharing your side of things with us from the book.

A disappointing take on the traditional software startup story:
I have worked in the Boston software startup space my entire career. So, when I read that Tom Ashbrook -- who I know as host of the NPR program On Point -- had written a book about his experiences starting up a software company, I was intrigued. I love the "Silicon Valley Startup" style of book. There are so many interesting stories to tell. Stories about success (The Soul Of A New Machine). Stories about failure (Startup: A Silicon Valley Adventure). Stories about the outspoken leaders (The Difference Between God and Larry Ellison) and the unsung heros (Where Wizards Stay Up Late). Stories by MBAs trying to figure out the "secret sauce" of it all (Competing On Internet Time). With so many interesting stories to tell, it was disappointing that The Leap never really found an interesting story to tell. At times, reading The Leap was a bit like watching a tightrope walker without a net -- there is a morbid fascination to see what happens if they slip. But, there is a limit to how many times you can read about *another* failed funding pitch, *another* "last day" before they run out of money, or *another* high stakes credit card gamble, before it just loses its novelty. What really struck me is that I never *really* understood what the company was even trying to do or what Tom Ashbrook's role in the company was supposed to be. Other than raising money, what did he do? I understand that his title was "publisher", but I still don't understand what that really meant. It made me wonder if this is part of the reason they had such a hard time getting funding -- if Ashbrook wasn't able to explain the business value in a 300 page book, how was he supposed to grab the attention of a busy VC with a ton of other deals on the table in a 30 minute presentation? I think this all points to the real problem of the book. Any good story should have a beginning, a middle, and an end. Unfortunately, this isn't *really* a book about creating a software company. Instead, The Leap is really just a story about a beginning -- nearly the entire book is the story of trying to fund the company. And I am just not convinced that, in itself, makes a story. The book feels a bit like a roller coaster ride to nowhere: there are definitely moments of exhilaration and excitment, but in the end, it isn't quite clear if you got anywhere during the ride.