How did get your start in the venture capital community?
After Stanford, I worked for the leading boutique investment bank in Silicon Valley (Hambrecht and Quist). They had a venture fund, and as a research associate the partners would call on me to do due diligence for them. As opposed to the transactional world of banking, I found working with entrepreneurs exhilarating. One night I ran into a friend from Stanford who worked for NEA, I told him of my desire to work in Venture and as good fortune would have it, he happened to call the founder of Oak Investment Partners the next day about a new catalog as a possible joint investment, Victoria Secrets. The founder of Oak wasn’t interested in investing in a catalog (clearly he missed a great opportunity!) but asked if my friend knew of a research analyst they could hire… That would be me! I packed up and moved to the sleepy suburbs of Connecticut, built my career at the firm which led to working with many great entrepreneurs, board memberships, successful deals and exits, and ultimately to the launch of Oak HC/FT, an independent entity of which I am one of three founding partners.
What’s a day in your life as a VC like?
It is totally unpredictable, which is why I love it. While the bulk of my time is spent in board meetings, meetings with entrepreneurs, and speaking at industry events, I never know what issue will arise or what amazing entrepreneur with the next incredible idea will walk through the door. Every day is an adventure in venture. It’s about problem solving and exercising your brain, so it never goes stale.
How many companies have you invested in and what is your overall investment?Since Oak HC/FT’s inception in June 2014 we have invested in over a dozen companies with about half of our fund’s capital left for future investments. We’ve led most of these financings providing check sizes ranging from $1 million to $30 million per company. In my career I’ve led over 40 investments with board seats at most of these companies.
What stage do you focus on and how much capital do you look to deploy for each portfolio addition?
Our focus is about 25% of venture investing and 75% growth stage investing. We prioritize opportunity over stage to stay flexible in different market cycles. We invest in earlier-stage companies and entrepreneurs with outsized potential to offset later stage pricing pressure, as well as companies at an inflection point to increase the odds of success.
What matters to you most when evaluating a company as a potential fit for your firm and how does that relate to the ambitious companies that you have worked with in the past?
First and foremost, we invest in exceptional entrepreneurs and category-leading companies across the healthcare information and FinTech industries. Whether a company is early stage or more mature, what matters most to us is the passion the team exhibits and the nature and importance of their mission. You don’t get into venture for the sole purpose of making money; we are VC’s because we believe that investing in innovation makes a positive contribution and that will lead to outsized returns for your investors.
What advice do you offer to a first time founder?
Your team will be the key to your success. Never compromise on people; surround yourself with A+ thinking, people you like, trust and respect. Apply the same rule to your investors. Venture is a two-way street: the VC chooses the entrepreneur and the entrepreneur chooses the investor. Don’t be seduced by an investor who will pay up, but has no appreciation for you and your business. Never make short term decisions that will compromise your long term vision or integrity.
What is the one common denominator that stands out to you across all great investments your firm has made during its history?
Management teams that are resourceful, resilient and relentless in attacking large, important problems.