September Capital

Who's Your Buddy?

Len Au was good at raising money. He didn’t love doing it. But he knew that money was the life blood of a startup. And he had learned the hard way that running out of money is fatal. So he was determined that no company of his would ever suffer such a fate again. 

Len was the sort of entrepreneur all VCs want to back – a serial entrepreneur with a track record of success and an amazing team that followed him from company to company. VCs know that building great teams is hard. The only thing better than backing an entrepreneur who can build a great team is backing an entrepreneur who has built a great team that is ready to follow him to the ends of the earth (or at least across town). ElectricCity was the third startup that Len and his team had built together. By the third time around, they were faster and smarter and could avoid some of the stupider mistakes they made the first time around (sadly, there are always new mistakes to fill the void left by old mistakes dodged).

Len had been on the road raising money for the last six weeks and was pretty tired of being asked the same stupid questions over and over again. 

“Why wouldn’t Amazon do this?”

“Why wouldn’t Google do this?”

“Why wouldn’t Facebook do this?”

“Sure, it is a lot of traffic, but how are you going to monetize it?”

“Are there any Good engineers in Canada?” 

But he had answered each and every question as if it was pure genius. As if he was hearing it for the first time. As if the question would not only reveal the great unspoken truths of his business, but also demonstrated the incredible wisdom and intellect of the questioner.

Len’s endurance had paid off. He was starting to hear back from venture capitalists. One after the next called and offered to invest in ElectricCity. So it was not surprising at all to Len when his phone rang and the Caller ID read “Jameson Jones.” (In all fairness, Len was a little surprised -- he had no idea that Skip’s real name was Jameson.)

Len liked Skip. He lacked the cockiness and bravado that many of his venture compatriots wore like a uniform. From what Len had seen, VCs fell in three buckets: The Superman, The Tough Guy, and The “Who’s Your Buddy?” Each of these paradigms was easily spotted on the VC websites:

   *  The Superman is always photographed with his hands on his hips, chest thrust forward, chin tilted slightly skyward. If The Superman felt he could get away with it, he would have absolutely posed with a cape. But even The Superman must demonstrate a modicum of humility.

·         * The Tough Guy is always photographed with his arm crossed in front of him. The shot is inevitably taken looking up at The Tough Guy from below in an effort to accentuate his dominance (as if being 6’4” wasn’t dominant enough). The Tough Guy never smiles. After all, smiling isn’t really very tough.

·         * The “Who’s Your Buddy?” is always photographed with a hand in his pocket, sometimes two. He smiles out at you (or at least pulls a Mona Lisa). And even though he himself is over six feet tall, you’d never guess it because he is slouching in solidarity with your average-heightedness. 

Skip was a “Who’s your Buddy?” -- on the September Capital website, Skip stood casually with one hand in his pocket looking more welcoming than menacing. Despite having played football at some Ivy  institution or other, Skip didn’t think that being a successful venture capitalist required intimidation or chest thumping. Len had done some asking around and Skip had a reputation for working his ass off on behalf of his portfolio companies. The more time Len spent with Skip, the more he liked him. 

Len’s phone continued to ring.  <Jameson Jones> <Jameson Jones> <Jameson Jones>  He let the call roll over to voicemail. He liked Skip. But he didn’t need Skip to know that. Yet.