Four Insights from 51 Articles on Breaking into VC Industry

“I didn’t know how to read so I read a book ‘How to Read’ — I couldn’t read it. So then I read a book called ‘How to Read: How to Read’ and I got it.” — Scott Auckerman, Comedy Bang Bang

I’ve read that the total number of VC professionals in the US is nearly identical to that of the number of professional baseball players. So one’s odds of getting “drafted” into VC are just as good as your local little leaguer, who dreams of pitching on Opening Day 2026. To some interested this may seem too daunting, but for others who have done the necessary self-reflection to determine their execution skills and that have started to contribute to the ecosystem, this seems to be par for the course. The difference between my first couple VC interviews (I will have to write about those embarrassing accounts another time) and now, is that I have read some rich articles from venture capital professionals that have given me insights on how to not only get a role in VC but also suggestions on how to have a long career in the risky business.

When I started to seriously look at venture capital as a long-term career path, I would meet with VCs and former VCs for coffee all over San Francisco and Silicon Valley. Many…