Don’t Break In to VC But Wait for the Best Opportunity for You

How ‘Oceans 13’ inspired my 33 Month VC Job Search

Earnest Sweat
The Importance of Reading Earnest
15 min readApr 25, 2018


Over the last 15 months the most common question I’ve been asked through email, twitter, in person, and smoke signal has been “How did you break in to VC?” Each time I’m asked this question it reminds me of two things: 1) how eager I was to find any nuggets of advice that I could utilize from individuals’ journeys into VC and 2) that I should really write my story down because each passing year, month, day, and minute it gets a little fuzzier on how I got to my current role at [Redacted] Ventures.

I’ve finally decided to write my story down so I can respond with a link when people ask me that broad question in an informational interview. Just kidding, I will still answer the question, but now I’ll have this post to fill in the gaps.

My Career Before VC (Before Aug ’13)

If the influx of super hero movies has been an indication of anything about the human psyche, it’s that people don’t really like origin stories. No one wants to hear about how Peter Parker lost his family or what Darth Vader was like as a pre-teen. People generally don’t want to use up the limited film of movies for this background — we yell “Get to the spider bite” or “Hurry up and choose the dark side.” I say this because you probably don’t care about where I was born, who I was born to, or what my high school and college experiences were like.

I’ll get right to the facts that provide the context for what shaped my job search into VC. In 2013, I finished business school, and found myself headed west to San Francisco to start my “dream job” at Bridgespan, a leading nonprofit consulting firm. Prior to business school, I spent four years working in investment banking at BMO Capital Markets where I served as an equity research associate and focused on the exciting world of real estate investment trusts (or REITs). The final two years at BMO, I started to get more fascinated with the idea…