Last year I was considering the next move in my career. I had just stepped down as CEO of oDesk, having successfully merged the company with Elance (now UpWork), and was ready for a change, and a new challenge. Venture capital investing was an intriguing option, but one that would take me out of my comfort zone as an entrepreneur and operator.
A VC friend of mine had counseled me against getting into venture, “don’t do it, it will be a waste of your talents.” He went on to point out that I was most successful and happiest as a “battlefield general, leading troops and taking hills.” I have always loved building and leading teams and executing. I enjoy getting stuff done and seeing the results of these efforts in near real time. All true.
“As a VC you don’t get to do that,” he explained. “You watch your founders do it instead.”
His advice was well-heeded. But I didn’t take it. I joined Polaris Partners in September of last year with, thanks to the counsel I received, a greater sense of the challenges I might face transitioning from an operator to an investor. I knew that to be successful, I would need to give up the general’s seat and find a role that was equally as gratifying and impactful. What I did not know is whether I would enjoy the new gig as much as I did my previous operating roles. As it turns out, my role as a venture investor allows me to do more of what I love, not less. And it’s been an amazing year. Here’s why:
Bigger shoes, larger footprint: Like the athlete who wants to coach, or the actor who wants to direct, being an investor in the same types of companies as those I recently led allows me to make a greater impact across a wider swath of opportunities. My operating experience can apply to many companies and not being in the driver’s seat – but helping to navigate – allows me to scale my contribution across our portfolio. And scaling companies is a sweet spot for us on the Polaris tech team. (Stay tuned for more on that soon).
Different hills to climb: As a CEO, I was always learning. I would estimate (generously) that 40 percent of my job was familiar and 60 percent presented new challenges and opportunities that I needed to figure out. In my role as an investor, I am exposed to verticals – and very smart entrepreneurs in those verticals – where I get to ascend the learning curve more often than not. During those climbs I am able to support companies with many situations that reflect my operating experience, but it never gets stale. There are always new hills to take and I enjoy the opportunity to continue to learn new skills and knowledge.
Keeping it real: At the end of the day, I truly enjoy being helpful. At Polaris, the opportunities to do what I love are plentiful across our portfolio. And even when a company may not be a fit for us, I thrive on offering support as best I can to the entrepreneur who is seeking guidance. It is here that I am most gratified. Today’s entrepreneurs are not looking for just money; they want a partner who will roll up his or her sleeves and work right alongside them when they need it. I have enjoyed being an extended member of many teams and plan do to as much of that as I can moving forward.
Today it was announced that I have become a general partner at Polaris. My past year as a venture partner at the firm has only whetted my appetite to do more. I am thrilled to have found a home at Polaris where we can do great things together with our founders and teams. I am most excited to watch our companies grow and thrive and I look forward to all rising together.
This piece originally appeared on LinkedIn Pulse on September 9, 2015 and can be viewed here.