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Jake Winebaum – Internet Stoic

November 8, 2004

Until you’ve worked at a start-up, you can’t appreciate just how dispiriting life in the entrepreneurial trenches can be. Business models falter, customers go away (or they never show up in the first place), yet you still have some cash on hand and you try to go through the wrenching process of reinvention before the money dries up. It’s a bitch and, most of the time, companies wisely close their doors without much of a fight.
No Pain, No Gain
With these realities in mind, we look at’s recent fund-raising announcement with awe and respect. This venture has always been a URL in search of a business model – and we get the sense that CEO Jake Winebaum, an accomplished entrepreneur, has been back to the drawing board with uncomfortable regularity. But the fact that he’s pulling in $10MM from Benchmark Capital suggests that Winebaum may finally be turning the corner. has experienced compounded annual revenue growth rate of over 150% over the past 4 years coupled with profitability and positive cash flow for the past 18 months.


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