Seeking Serendipity

As I was giving some career advice recently to a college class, I realized there was one important piece of advice that I never received, but now preach and try to practice:  as busy as you may be, always carve out the time to take random meetings.  Simply put, it pays on occasion to take meetings with high-quality people, even though you have no idea who the person is that you’re meeting with and why.

I have learned that in the world of VCs and start-ups, those somewhat random meetings with high-quality people can lead to interesting outcomes.  In fact, my career has been shaped by VCs I didn’t know reaching out and having random meetings with me, leading to interesting outcomes.

When I was a student at Harvard Business School, at a time when I didn’t even know what venture capital was, a VC firm called Greylock invited me to a dinner meeting on campus and, later, was kind enough to introduce me to one of their portfolio companies, Internet commerce start-up Open Market. I ended up joining the firm after business school and had the privilege of riding the Internet 1.0 wave as an executive there for five years, through an IPO and many exciting ups and downs.

In the middle of my time at Open Market, I got a random phone call from another VC I didn’t know, David Fialkow from General Catalyst, who wanted to have breakfast with me. I wasn’t looking for a job and didn’t really have any reason to meet with him, but I enjoy meeting interesting people and so took the meeting. Another interesting person was at that breakfast – a great marketing entrepreneur named Michael Bronner. Michael had an idea for a new company:  helping families save money for college by redirecting the billions of dollars they spend on marketing programs into tax-free college savings plans. I thought it was a brilliant idea and immediately agreed to jump on board to help found the company and serve as president and COO. Today, Upromise has over $18 billion in college savings plans under management across 8 million households in America. Sallie Mae purchased the company in 2006.

Three years into my tenure at Upromise, I got a random call from another VC – this time one I knew.  He and another friend were starting a new venture capital firm and wanted me to consider joining them.  I told them I wasn’t interested in becoming a VC – just like I wasn’t originally interested in a job at Open Market or helping Michael Bronner start Upromise – but they were interesting people that I knew and respected, and so took the meeting.  Shortly thereafter, I joined my partners Michael Greeley and Chip Hazard in starting a new venture capital firm, IDG Ventures Boston.

And now I’m the one on the other end of the phone calling up people I don’t know, and who don’t know me, and asking them to take a random meeting that may lead to an interesting outcome.

Everyone is super-busy and over-programmed, so it’s hard to maintain that discipline, but I’ve always been impressed with those that block out the time to take a few random walks and seek out serendipity.

6 thoughts on “Seeking Serendipity

  1. I’m a huge fan of random meetings. I will definitely meet with the next VC/Entrepreneur that randomly contacts me. The problem is that that has never happened.

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  2. interesting! But note this doesn’t happens to everyone! my be you are genuinely precious to VC’s!
    don’t know but somehow I have got a feeling that many harvard guys get into VC firms quickly, may be VC’s feel to use harvard’s brand name as a part of their marketing to entrepreneurs and second they think harvard people has / can get good contacts all around

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  3. This is how I feel about blogging. Engaging with people online (via blogging and commenting on others blogs) is a very time-consuming process, the the unpredictable benefits easily outweigh the time cost. It’s a more efficient (albeit, sometimes less personal) way of networking… and online version of what you’re describing.

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