VC Lifestyle Myths (in Retrospect)

A great post this week from Susan Wu at Charles River Ventures on the myths surrounding the legendary lifestyle of Silicon Valley venture capitalists:

Susan Wu: VC Lifestyle Myths

I was reading along, waiting for something to resonate, when I saw this screenshot:

Ah yes, it is all coming back to me now. The VC Lifestyle.

Now, let me be upfront about something here. I love venture capital. Honestly, I do. The idea of job where you are striving to know as much as possible about technology, people, strategy, and building businesses is definitely in my sweet spot. Not only that, but I continue to be amazed at the almost accidental set of circumstances that gave birth to the modern venture capital industry in Silicon Valley, and the amazing value that has been generated because of it.

All of that being said, the reality is that the VC lifestyle is not as glamourous as you might think, and definitely has elements to be desired. Susan captures a few key elements that definitely resonated with my memories of being an Associate at a large, early-stage venture fund:

  • Tyranny of Outlook. Meetings, meetings, and more meetings. Easily 6-8 a day, mostly pitch meetings with entrepreneurs & executive teams. The day is blocked off weeks in advance, and as a result, you are constantly moving things around as things come up, meetings go over, and you are trying to meet with just one more person.
  • Miles wide, but inches deep. It’s hard to imagine being lonely when you are meeting literally 20 new people everyday, and your rolodex grows to the thousands. But a vast majority of your contacts are people you meet once. Many others you might talk to once or twice a year. Even fellow venture capitalists and entrepreneurs that you are close too might touch base on a weekly basis. The reality is that the only people you truly see every day are those in your office, and our office was small. At it’s largest, we had two partners, an associate (me), an analyst, two executive assistants, and a receptionist. That’s not a lot of people.
  • Coopetition. Without getting into the nuanced politics of venture capital, it can be draining at times. As a young person in the industry, you are at once trying to build a reputation for yourself and carve out a niche, but at the same time you need the support and assistance of others around you. In the long term, you are judged on your own success, but in the short term, you are judged on your support of the senior partner(s) you are working with.

When I think about my life at eBay, it’s amazing at how much my experience in venture capital has helped me.

First of all, my Outlook calendar still looks like that. 🙂 Maybe that has more to do with growth, drive & Silicon Valley than venture capital itself.

Second, I truly love the number of people I get to work with at eBay. Love it. Not only have I met literally thousands of great people at eBay & PayPal over the past four years, but there are hundreds of people that I now know fairly well. Leading large project initiatives and new businesses at a larger company may be more constrained in some ways than leading a startup, but the counter-balance is the number of people you get to know and work with.

Third, my orientation towards senior executives has shifted. Before venture capital, there was some degree of awe that I felt around CEOs & executives of large technology companies. While I still respect their achievements, I found that venture capital gave me more grounding around the fact that these are, in fact, just people. At eBay, this has allowed me to be more comfortable, in general, around meetings with our senior staff. I still see to this day so many bright people, with excellent ideas, get tripped up the moment they have to succinctly and convincingly present an opportunity to a senior executive.

I’m quite happy with my move back to an operational role in 2003, and I’m extremely happy with the opportunities I’ve been given to help design, launch, and build brand new sites & businesses at eBay.

But some day I’ll likely go back to venture capital. Maybe. Right time, right place, right people. But not yet.

(BTW, If you aren’t reading Susan Wu’s blog, it’s worth bookmarking. I have a special place in my heart for any venture capitalist who actually play World of Warcraft, and can actually comment intelligently on technical issues.)