Risk and Reward Are Not Obvious

I went to business school in the mid 80s. Investment banking was hot. The leveraged buyout craze was on. Junk bonds were hot. Everyone wanted to work on wall street.

I was obsessed with venture capital and had worked in a small venture firm the previous summer and had gotten an offer to work full time in venture capital for $60k per year with no bonus and no incentive comp. I also had gotten a job offer from an investment bank at $125k per year with a bonus opportunity of $250k.

Those investment banking job offers were all over the business school and almost everyone I knew took them. They all went on amazing summer vacations and showed up on wall street in September 1987. In October 1987 the stock market crashed and by December many of my classmates were out of work.

I took the VC job, made basically enough to live and work in NYC for ten years (subsidized by The Gotham Gal's income), but I did set myself up for Flatiron and then USV.

I told this story in a comment to my MBA Tuesdays post and figured it was worth posting as a full blog post. Risk is not obvious. And reward is not obvious. Don't do the obvious thing. Because I can assure you it rarely works out as planned.