Twitter VC Fred Wilson’s first late-stage investment: $25M for Lending Club

Union Square Ventures made its first late-stage investment today, leading a $25 million raise for peer-to-peer lending startup Lending Club.

This was the startup’s fourth round, and it represents a break in Union Square co-founder Fred Wilson’s pre-2008 investment philosophy.

For several years, Wilson, a veteran investor and blogging firebrand, had held the opinion that seed investments were actually less risky than late-stage deals. In 2007, he wrote on his blog, “As a VC making direct investments in companies, I think we take on way more risk when we invest in a later stage company than an early stage company…

“When I go back over time and look at my personal portfolio, some 50-plus companies, I see this fact so clearly. The returns are higher on the seed and first round investments I’ve made… I suppose that’s also an indication that I am better at seed and early stage investing and that there are others who are better at later-stage investing than me.”

Late-stage investment has become something of a trend since the market crash in late 2008. In 2007, early-stage investments were slightly higher than late-stage fundraising. However, the balance has shifted, with slight differences giving way to entirely uneven divisions between early- and late-stage activity.

In 2009, VC fundraising hit a six-year low, meaning there would be less money to go around for the quarters to follow. In the immediate aftermath, early-stage investments, with their smaller deal sizes, were an attractive option for many; but eventually, multi-stage funds became more popular and investors became more squeamish about early-stage funds.

In September of 2009, Wilson wrote about VC investing during a downturn, saying, “Early in a cycle, you want to back young companies at bargain prices… Late in a cycle, you want to back established companies that need a ‘last round’ to get to break even.

“I’ve been in the venture capital business since 1986 (that was a down cycle) and I’ve seen this happen at least three times, probably four times now.”

Then, late last year, Wilson and Union Square Ventures raised $200 million to establish a late-stage fund. The fund’s first deal is the $25 million Series D for Lending Club. The round is small by late-stage standards; it’s exactly the same amount Lending Club raised for its third round one year ago.

Of today’s investment, Wilson writes, “We’ve been interested in peer-to-peer lending marketplaces for about five years now. We’ve studied the category closely but have never found the right entry point. We have watched Lending Club innovate by delivering better risk assesment and mitigation which has led to better returns for lenders.”

In a word, Wilson and Union Square see Lending Club, like most other strong late-stage startups, as a sure bet with a relatively quick return on investment.

Lending Club recently passed $325 million in total loan originations; the startup is currently giving out more than $20 million each month in prime consumer loans.