The founder's life for young VCs

December 8, 2010: 3:00 AM ET

Armed with pedigrees and degrees, some entry-level venture capitalists are finding it's more fun and lucrative to be on the entrepreneur's side of the term sheet.

By Jill Priluck, contributor

In early 2009, Bartek Ringwelski was spending his days working at Canaan Partners, a venture capital firm in Westport, Connecticut, where he analyzed pitches and learned startup basics. But after he received 100 responses to a Craigslist post for a cleaning person, he began spending his nights and weekends on an idea: a startup that would rate one-person businesses, which account for at least 15% of the workforce.

In May of this year, after raising $50,000 from friends and family, Ringwelski launched SkillSlate, a site that organizes handymen, dogwalkers, massage therapists and other solos through profiles and ratings the same way dating sites corral singles. This fall, the company announced that it raised $1.1 million in funding from Canaan Partners, First Round and angel investor Jason Finger of SeamlessWeb, among others.

There's an old adage that venture capitalists don't make good entrepreneurs. Historically, entrepreneurs who cash out after years of hard work become VCs, rather than the other way around. But given the financial crisis and the constriction of the venture capital industry, more and more VC firms are "walking dead." The result? Junior VCs are sometimes choosing to flee their plush offices for the rough and tumble world of the startups they used to be tasked with evaluating.

"What's happening to the VC industry is what they've done to everyone else. It's being disrupted," said Chris Dixon, the VC-turned-entrepreneur who co-founded Hunch.com and the Founder Collective, which invests smaller amounts in Internet startups. "The odds of a junior person becoming partner have decreased dramatically," he said.

Instead of contentedly watching founders sweat their way through pitches in sterile boardrooms, these young VCs "pivot," to borrow industry parlance, choosing 15-hour days to grow sites they hope will become the next Craigslist, Twitter or foursquare. The ones who take the leap forgo comfortable salaries to build a company from scratch, even though most startups fail.

Why? In a culture that places the entrepreneur on a pedestal, many junior analysts, whether consciously or unconsciously, are eager to make their own digital mark—preferably with a company that has a billion dollar valuation, although they'd be lucky to get a $50 million deal. As Dan Gellert, an analyst at Time Warner Investments for three years who started GateGuru, a virtual airport field guide, explained: "If you take in $3 million of capital and sell for $20 or $30 million, that's a huge win. People like me don't need ten million dollars to start a business."

The primary forces propelling young VCs to entrepreneurship are, of course, the changing VC industry and low startup costs. On the one hand, there the large $600 and $800 million funds that were raised five years ago, but many have seen fewer exits and poorer returns over the past decade. Beginning in the 1990s, VCs raised bigger funds because of the pay scale, known as "2 and 20," where 2% of the fund size goes to management fees, which acts as a salary for partners, and 20% of the profits (if an investment is successful) goes to the partners. "There's always this incentive to raise bigger and bigger funds. But there's far too much money in the system because companies require less capital to get off the ground, so firms are having trouble finding interesting places to put it," says Dixon.

At the same time, there's too little money. News funds are having trouble raising money. In October, Menlo Partners closed a new fund at $400 million even though it initially projected that it would raise $600 to $800 million. University endowments, pension funds and wealthy families that suffered average or negative returns are pulling back. Moreover, an emerging group of super angels like Dixon who fund companies one million at a time have moved into the space.

By starting in the VC world, these entrepreneurs get the advantages of startup boot camp without the hard knocks. At firms, they get exposed to business trends. In the process, they themselves become walking idea silos. They study enough startups-and enough startup mistakes-that they gain the confidence to try it themselves. "You're watching someone else achieve their dream and you think, 'Wait a minute. Why am I not living my dream?'" says Jordan Cooper, who was an associate at General Catalyst Partners before co-founding Hyper Public, a site that facilitates local connections with strangers.

VCs-turned-entrepreneurs receive perks that they can take with them when they start their own firms. They peek inside the minds of the investors they soon hope to pitch. They know the venture capitalist's preoccupations with the strength of the management team and unit economics. They also know that sugarcoating mistakes is a bad idea. "It's counterintuitive for the corporate world, but you want to be as direct and blunt as possible. Once you raise money and bad news happens, the longer you sit on it, the worse it becomes and if people find out about bad news that happened a long time ago, they are going to think there's bad news happening right now and there's an erosion of trust," said Ringwelski of SkillSlate.

Another reason junior venture capitalists exit is that they rarely get the credit or compensation for their best work. If a junior staffer finds an interesting idea for a VC firm, the partner gets the board seat and if the company sells for a few hundred million, it's the partner's deal. But that might take years. "They don't even know how amazing you are until you've left and gone somewhere else," says Cooper. "It's easier to leave, start a company, grow it, sell it for $50 million and then scale to partner."

This crossover phenomenon is taking place in the freewheeling world of tech startups, but the lesson about the state of venture capital deals is one familiar to every financier and poker player. Junior VCs, paid to consider both the wealth of their general partner-bosses and the fundraising needs and successes of founders they invest in, are starting to consider this: If a deal is being done and it's not clear who the pawn is, the answer might be in the mirror.

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