In my last post, I talked about The Move from Entrepreneur to VC, and I mentioned that I’d follow up by touching on why I joined the guys at Social Leverage.
One of the key moments that actually drove me to explore a VC career was a conversation with a couple of my closest friends while celebrating Jeremy’s birthday at a Yankee game. Jeremy and Brad were two of my co-founders at Assistly, and they had both recently moved on to head up the technical team at Airtime; so our conversation centered around what I would do next. I told the guys how much I enjoyed working with the entrepreneurs that Alex and I had made investments in and both Jeremy and Brad responded by telling me I should just go off and invest — and given my track record of working with great companies — they were willing to commit to becoming my first Limited Partners (LPs) right on the spot. Wow! I wouldn’t have (necessarily) held them to it, but I certainly appreciated the vote of confidence. I’m happy to say that it didn’t take too much prodding for Brad and Jeremy to commit to Social Leverage and become two of our earliest LPs in our latest fund. That encounter kicked off a flurry of other conversations and thoughts. I considered going out on my own to start my own VC firm. Certainly there are other success stories of individuals becoming first time micro VCs and by all accounts doing extremely well. But Alex made me realize that I’d lose out on two key things; first the camaraderie of working in a team environment and second of learning directly by watching people that had already gone through this journey. I made the decision to only make the switch if I could align myself with the right partnership. Howard was on my call list, as a friend and advisor. I wasn’t thinking that I could join him and Tom at that point, but I wanted to get his perspective on what it was like to be a VC, which groups I should think about reaching out to, etc. I met with Howard at the lounge in the Four Seasons on one of his frequent visits to San Francisco, and when I got there, as usual, Howard was surrounded by no less than four other entrepreneurs from various companies. Introductions were made and the other guys hung around for a bit, but soon left so that Howard and I could chat. I told Howard what I was thinking and the advice I was looking for, and he immediately said, “Why don’t you join Social Leverage — we’d love to have you as a partner!”. It wasn’t exactly where I had expected the conversation to go, but I was certainly flattered — and so we began exploring the potential of the opportunity and how we would work together. A couple of weeks later I took a trip down to Coronado to meet with both Howard and Tom and really get into the specifics — and we quickly solidified the partnership. I’ve known Howard and Tom for about six years now. Howard sold WallStrip to CBS in 2007 and in 2009 moved to Coronado (he recounts that “trade” a few years later), just 40 minutes from where I was then living in San Diego. As Howard was a bit of celebrity in the tech startup world, Alex and I reached out to him and setup a lunch. We enjoyed each other’s company and worked to maintain the relationship on both sides. I met Tom a bit further down the line at one of Howard’s famous Lindzonpalooza events. Tom and Howard have been close friends for 25 years since they met in grad school (ASU). Coincidentally, that’s almost the same amount of time that Alex and I have known each other and it gave me great comfort to come into an environment that’s based on a long lasting friendship. Like Alex and myself, Tom and Howard are great compliments to each other which is probably one of the reasons that they’ve been successful. Howard likes to be in the fray, engaging with as many people as possible, always thinking about how a connection could potential help an entrepreneur get to the next level. Tom is also thinking about how to move the needle for our entrepreneurs, but much more so by bringing his operational and corporate development expertise to bear. While Howard always sees the glass as half full, Tom makes sure that the ship stays roughly on course. Luckily, I fit somewhere in the middle and will be able to help both of my partners, while also learning from each of them. Although I was looking forward to moving into the world of venture capital, I didn’t exactly want to leave the startup world behind. And by many measures (among them lack of existing infrastructure, treating every dollar like it’s our own — because it is, the ability to take charge and make something great happen without asking for permission), Social Leverage is very much a startup itself. Six weeks in, and I’m loving being a part of the team!
Originally published at www.garybenitt.com on January 15, 2015.