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Weekly, someone reaches out to me asking for career advice on the decision to go from being an operator to a VC. Thought I’d memorialize it here in case others are curious:
It’s a big transition. I spent 6 years in VC before joining Pinterest, so when I left Pinterest to join Greylock, I thought it would be like getting back on a bike. Instead, it felt like getting a train back on the tracks one wheel at a time.
Three big reasons:
First, when you’re operating, particularly in a product function, you are always making tangible progress from “Point A” to “Point B”. For example, releasing a new feature.
Every day you make progress towards that goal. E.g., You worked through a big decision with your eng lead, got an experiment out, got a green light in your product review, etc.
Yes, sometimes there are setbacks and frustrations, but you are always making progress towards that tangible Point B, and when you get there, you have the satisfaction of “shipping”.
In venture, you are at Point A, and Point B is this intangible “I want to make a great investment”. You don’t know how you’ll find it, you don’t know if you’ll know it when you see it, and it will take years to really confirm it ("ship").
One of the wheels you need to get on the track: you need to shift your focus to your process and inputs, not the outcome. It’s more like the uncertainty and unpredictability of gardening than building a house brick-by-brick.
Many operators make too many investments their 1st yr bc they are (a) not calibrated, & (b) used to achieving outcomes & therefore focus on the tangible outcome “making an investment”. It takes a while to internalize that the true outcome for VCs is "return capital to your LPs.”
This is part of what makes VC easy to “do” (make investments), and really freaking hard to be great at (generate great returns). So mentally prepare yourself for months of activity and no tangible evidence, and a looooong feedback cycle.
Second, in venture, you make basically ten big decisions a year – ~8 companies that you really dug in on and ultimately passed (or lost), ~2 that you say yes to and invest in. Those decisions are big one-way door decisions. Once you say yay or nay, there is no going back.
And then of course, the feedback cycle on those decisions are YEARS. YEARS! With plenty of ups and downs in between. At Pinterest, I’d ship an experiment and three days later have a good sense for whether the experiment was going to be good or bad.
It’s a crazy transition. Operating, you’re making dozens of two-way door decisions every day. The one-way door decisions are exceedingly rare. The adjustment is another wheel you must get on the tracks.
Lastly, when you’re operating, you feel the stress of execution. As a VC, you trade that stress for anxiety: You have the anxiety of making one-way door decisions on a potential investment, and the anxiety of influencing but not controlling the outcome after you invest.
It’s impt to internalize this last point. Too many operators think they’ll transition to VC and “scratch their operating itch” by working with their companies. NO! That’s a delusion & unhealthy for companies. You’ll need to find other outlets (tweet storms!) to scratch that itch.
So again, it’s a big transition. But once you get that train on the tracks, if you’re someone who loves to learn, is endlessly curious, gets energized by working with & supporting founders, is inclined as an investor, loves to sell, & is competitive: I can’t imagine a better job.
