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Summary:

This week’s $250 million funding for vacation home rental listing company HomeAway Inc. was the largest web-related venture capital investment since the bubble days at the turn of the millennium. But it also contained a provision that signals how the lack of venture exits may be […]

homeaway This week’s $250 million funding for vacation home rental listing company HomeAway Inc. was the largest web-related venture capital investment since the bubble days at the turn of the millennium. But it also contained a provision that signals how the lack of venture exits may be causing some entrepreneurs to ask for cash now, rather than waiting for an initial public offering or sale that may never come.

As part of the HomeAway financing, a portion of the money will go toward repurchasing some of the shares held by employees and early investors in the Austin, Texas-based company. CEO Brian Sharples wouldn’t disclose how much money, or what percentage of shares, affected employees would be able to exchange for cash, but traditionally such deals are fairly rare. However, in the last few months I’ve talked to a growing number of entrepreneurs who have negotiated such deals. The fact that they’re becoming more common, especially in younger companies, shows how for some, the economic downturn is spurring a lack of faith in the venture model.

That model is one that rewards entrepreneurs and investors for building up a solid business over a 5- to 10-year period, then selling it, either to the public through a stock offering, or to an acquirer for a sum that makes those years of work worthwhile. It’s the American dream, Silicon Valley-style. But what if entrepreneurs aren’t willing to wait that long? And what if the exit markets aren’t open?

As deals like HomeAway’s show, that’s precisely the environment we’re in now. When a venture-backed company does such a deal it’s generally because employees who have taken a lot of equity in it want to exchange that equity for cash. Usually equity holders get cash after a company exits, via either an IPO, merger or acquisition. With the IPO window shut (so far the total number of IPOs are down by 81 percent this year), and M&A slowing, that’s looking less likely.

Sharples explained the decision to offer shareholders the ability to cash out as a reward for the work employees have put in. The company had planned to go public in 2008, but given the appetite for IPOs, have shelved the idea for at least two more years. This would disappoint any shareholder, but HomeAway is only three years old. For early investors or founders to expect an exit in three years is ridiculous. Other than back in the bubble years, most venture-backed startups don’t achieve an exit for seven years, and in some cases, such as with clean technology, investors are looking at 10 years before a payday.

HomeAway is more of a private equity business model (the company is buying up Internet properties that list vacation homes available for rent in the U.S. and potentially worldwide cities), so perhaps that explains the short time to a planned exit. But HomeAway isn’t alone. Facebook has allowed its early employees and shareholders to sell some of their shares for cash, despite being only four years old. Digg, the news ranking and aggregation service founded by Jay Adelson and Kevin Rose, raised $28.7 million in September, a deal that rumored to have involved Rose taking some cash.

It’s a win when employees can cash out, especially in such dismal times, but raising money in order to buy back shares has the potential to set a lower fair market value for the startup, as well as to dilute the value of shares held by existing shareholders. These sorts of deals are a sign of stress in the venture model, and we’re likely to see more of them if it remains difficult to take a company public in the coming year.

This article also appeared on Businessweek.com.

  1. you don’t know what you’re talking about. cash outs (i.e. secondary purchases of shares) are actually _quite_ common in the VC world.

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  2. So does this mean that Vcs are becoming private equity investors ?

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  3. John "Shadowlayer" Saturday, November 15, 2008

    All I see is bunch of guys obsessed over the idea of being rich before they turn 30, then blaming the market for not letting them get away with it…

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  4. [...] today.  Facebook’s postponement is an understandable bow to market reality — and it prevents the company from setting an official valuation that the social networking site’s inve…. The market is pretty sure the company is worth less  than the $15 billion Microsoft bought into, [...]

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  5. [...] DST is committing to buy out the common stock held by current and former Facebook employees — a trend we noted last year. As Zuckerberg said on the call, the company isn’t anticipating an initial public offering, [...]

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  6. [...] employees aren’t the only ones eager for a payday; Stacey wrote last fall about other venture firms offering employees at their portfolio companies a chance to cash out. Perhaps the drought in IPO and M&A activity makes payday look even further out, or maybe [...]

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