This question originally appeared on Quora: What are the most common regrets that venture capitalists have?
Ok, I'm relatively new as a VC partner (18 months), but already have plenty of regrets, or at least, laments may be more accurate.
- Investing in Great Traction but Not Great Founders. Only done this once. I think this can work in B2C but doesn't work in Enterprise. Better risk, other way around (great founders, not great traction).
- Not making a decision in 20 minutes. I fixed this, but when you know it's a great one (or at least could be) -- just make the decision in 20 minutes. I fixed this with Talkdesk, Algolia, Logikcull, RainforestQA, and a few others I did in 20 minutes. This is very hard to do in general ... it's like getting married without even finishing a first date. But with the great ones, turns out it's easy, at least, if you think you have domain expertise to understand what they are doing.
- Not buying more if/when I could have. I wish I owned more of every investment I've made. Turns out it's the same amount of risk and work, less reward, if you don't invest every $$$ you can in early rounds. It took me a while to internalize this. Sometimes you can't buy as much as you'd like, that's fine. But buying less than I could have -- huge rookie error.
- Listening too carefully to others' opinions. The problem in early-stage investing is really, everyone is most attracted to Mr. Paratrooper CEO -- the guy/woman that talks right, looks right, is 6'4? (if male), handsome, trim, whatever -- the CEO that can really sell up -- unless they spend the time to truly understand the company. Just listening to a Monday morning pitch isn't enough if it's early stage for anyone to form an informed opinion. It's enough to help you spot flags and issues -- which is very valuable. But I looked for confirmation on investment decisions. I shouldn't have. No one else can really put in the time to see what you see.
I fixed all 4. But if I'd known this 18 months ago, on paper at least (and only), I would already have paper markups equal to the whole fund.
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