Fred has a great post about track record today.
It got me thinking about my (much shorter) venture career and what some of my most valuable mistakes have been.
The top one is probably getting seduced by traction. Early metrics are good - we all like them. But they de-risk an investment less than commonly presumed. Particularly when customer acquisition is paid marketing and it skews the "true" data you could be getting.
I'd much rather see something grow organically in the beginning, even if that growth is slower than what's possible using paid.
Traction also shouldn't supplant other considerations, like what the market's true prospects are. It's easy to believe that because one company is making this new thing work for a small group of early and passionate customers, it has the potential to be a category-defining innovation. Sometimes novelty is just novelty.
Traction also shouldn't outweigh the team's overall potential. I've compromised on team a few times in my career. Particularly when there was a ton of traction and the idea was really big. Compromising on team has always turned out to be a mistake.
I love audacious people, but there's a fine line that separates it from slightly delusional. Where the vision supplants the details, I am much more careful than previously. A great founder can find the right balance between keeping the big vision and sweating the small stuff.
And finally on team, personality matters a lot. Low agreeability is a trait of a lot of successful founders, but low emotional stability is pretty harmful.
The other lesson is that a geo focus sucks. I invested very widely early in my career - hardware, B2B, marketplaces, travel, mobile apps, commerce... I believed that Europe as a geography had too little depth to really select on anything but people (see above).
I think that is still largely true for the market as a whole. But as an individual or even a firm, there's now enough capital that the huge benefits of thesis-driven specialization outweigh the missed opportunities.
That's why I've been 100% focused on consumer/user-only investing for the past year and a half, and I think that's what I'll want to do for the rest of my career.
I'm sure I've made many other mistakes in the last five years of active venture investing (and ten as an angel). But these are the ones that immediately come to mind as the biggest lessons learned.