Out of the Ashes – Something Isn’t Quite Right

“Customer Development” was born four years earlier and 200 miles away on Sandhill Road.  I was between my 7th and 8th and final startup; licking my wounds from Rocket Science, the company I had cratered as my first and last attempt as a startup CEO. I was consulting for the two venture capital firms who between them put $12 million into my last failed startup. (My mother kept asking if they were going to make me pay the money back. When I told her they not only didn’t want it back, but were trying to see if they could give me more for my next company, she paused for a long while and then said in a very Russian accent, “Only in America are the streets paved with gold.”  It was a long way from Ellis Island.) Both venture firms sought my advice for their portfolio companies. Surprisingly, I enjoyed seeing other startups from an outsider’s perspective. To everyone’s delight (and my surprise,) I usually could quickly see what needed to be fixed. At about the same time, two newer companies asked me to join their boards.  Between the board work and the consulting, I enjoyed my first-ever corporate “out-of-body experience.”

No longer personally involved, I became a dispassionate observer. From this new vantage point I began to detect something deeper than I had ever seen before: there seemed to be a pattern in the midst of the chaos. Arguments that I had heard at my own startups seem to be repeated at others. The same issues arose time and again: big company management styles versus entrepreneurs wanting to shoot from the hip, founders versus professional managers, engineering versus marketing, marketing versus sales, missed schedule issues, sales missing the plan, running out of money, raising new money. I began to gain an appreciation of how world-class venture capitalists develop pattern recognition for these common types of problems. “Oh yes, company X, they’re having problem 343. Here are the six likely ways that it will resolve, with these probabilities.” No one was actually quite that good, but some VCs had “golden guts” for these kinds of operating issues.

Yet something in the back of my mind bothered me. If great venture capitalists could recognize and sometimes predict the types of problems that were occurring, didn’t that mean that the problems were structural rather than endemic? Wasn’t something fundamentally wrong with the way everyone organizes and manages startups? Wasn’t it possible that the problems in every startup were somehow self-inflicted and could be ameliorated with a different structure? Yet when I talked to my venture capital friends, they said, “Well, that’s just how startups work. We’ve managed startups like this forever; there is no other way to manage them.”

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One Response

  1. I recently found your blog through the “Secrets of Silicon Valley” series — I greatly enjoy your articles here. I have been working on getting a startup to revenue for a while, and while this is my 4th iteration and I have not yet succeeded, I’ve been learning new things every time. Your blog post has provided a lot of useful insights for me which I’ve been implementing.

    Do you have thoughts on specifically how to restructure startups? Would you mind sharing them? I’m a software engineer by trade, so I’m always interested in some better way to do things, whether they are in software or in business processes or organizations.

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