Requested by Scott Belsky - and been meaning to blog this at some point
  1. A lot of first dates.
    A lot of them. I underestimated how many times I would meet someone without much context, share my story, hear theirs, and not go on to more conversations until running into them later at an event.
  2. It is never obvious.
    From the outside it sometimes looks like a deal is a no brainer, but every one (on both sides) turns out to be oscillating throughout the process until the very end. There is always less you can really know and stretching (on both sides) on price and dilution/ownership.
  3. It is binary.
    If you believe in a company, you have to do the round that matters. Returns are based in having concentrated ownership in the few companies that win. So if with any deal, you are either the investor with the right ownership for your fund or not. If you think it is a good opportunity, you have to win it over other very smart people and it is more competitive than you think. That final winning is more important than I realized too.
  4. Loneliness is real.
    Sure you have your partners and you have your portfolio companies. But unlike jobs where you are in the same boat with the same people every day, the cadence of weekly partner meetings, board meetings every 6-12 weeks, and other work is so different. And you are on your own the rest of the time.
  5. It is a full contact sport.
    The best deals don't magically drop on your lap. You have to constantly be helping people and start relationships for them to pop at the right time. Thanks Tony Conrad for this advice.
  6. Not surprises: every day is astounding
    As a VC I feel very lucky and privileged to get to have two types of amazing conversations every day: (1) meeting a new entrepreneur who is telling amazing stories about what they have built and how they want to make it into a huge company (2) working with my portfolio with some of the best founders on strategic challenges for their company - product, team, strategy, culture, process, and more