Born Rich: How to Launch a Startup without Really Trying

Startup founder Sam Lessin's reputation as an entrepreneur was already overshadowed by his partying in Cyprus and very wealthy father. Now a key investor has spilled the real reason he invested in Lessin's Drop.io. D'oh.

Reflecting on 16 years in the venture capital game, RRE Ventures' Stuart Ellman explained why he put money into young Lessin's file-sharing service: He's known the guy since he was in like the 6th grade, you see:

My entrepreneurs... are people that I trust...

For a person like Sam Lessin, CEO of Drop.io, who is 26, it is a little harder. I trust Sam but it is helped by the fact that I have known him since he was 12.

Ellman might be trying to make Lessin sound young and energetic, but he's not doing him any favors. Lessin's helpful connections have already attracted plenty of attention. It didn't go unnoticed, for example, that he was written up in the Wall Street Journal by a friend of his girlfriend, who also writes for the business newspaper.

Nor did it escape tech wags' attention that it was at Lessin's investment banker father's vacation home in Cyprus where 19 of his fameballing industry friends made a now-infamous lip-dub video around the pool. Or that he also lapped up the party scene at an ill-timed junket in Playa del Carmen Mexico just a month later, amid an economic meltdown and widespread tech layoffs.

Drop.io might be relatively small potatoes, but obtaining venture backing is further than most wantrepreneurs get. Fair or not, jealous observers are bound to decide Lessin's had it easy, just by connecting the dots: ultra-wealthy dad, likes to party ostentatiously, funded by a guy who knew him since he was 12.

Of course, there's one easy solution for all that, fortunately for Lessin: Making some wealth of his own, either through Drop.io or some followup venture. For a guy as well-connected as Lessin, that shouldn't be too tough.

(Pic: Lessin, by Amit Gupta)