I sat down with a Venture Capitalist who dropped out of his PhD and now runs a university entrepreneur program

This gentleman, who will remain nameless, keeps a low profile. (He’s the first person to politely decline my invitation for a recorded podcast interview.) And he was recommended highly by an acquaintance of mine who runs the biggest telecom investment banking practice in the world.

We got together at Bourbon Coffee, and he told me his story.

He studied at the best university on the west coast (in Palo Alto), and then the best on the east coast (Cambridge, MA) — but both were in political science. His dissertation was going to be built around observation of startup companies in a couple of the East Asian Miracle countries. But then a few years in, they exploded in the Asian Meltdown. Economies collapsed, startups closed shop, and all relevant data for his project literally disappeared overnight.

He took a year off to step back and consider his options.

Somewhere in there he called his younger brother, who was working in a vague and little-known profession called ‘venture capital’. Apparently it wasn’t so competitive 20 years ago, when VC firms took (according to him) “any warm body with a college education and their head screwed on right”.

So he ran startup investments for 2 years … until the dot-com bubble burst.

Man, talk about always being in the wrong place at the wrong time.

Over the next 4 years, he worked in finance (M&A / PE) for 2 more Boston firms focused on startup business investing in Asian markets. But then he moved to Washington DC, and this is where the story gets good … So good that I pulled out several the main lessons from his illustrious career.

1. Diversify

You would think someone who lands a ‘safe job’ in university administration after such a hectic career would rest on his laurels, sit back and enjoy life. But not this guy. After having two high-profile jobs vanish into thin air, explainable only by global business trends that few people predicted, it no longer seemed safe to settle for one proven path. Instead …

He landed a gig as director of a startup accelerator … then added on VC investing for a regional environmental fund … then leveraged both of those into being appointed director of a major research university’s entrepreneur program … then used that to win NSF funding … then partnered with the first network-driven venture fund … then leveled up to Associate VP status at the same college as before.
Like my Mom said … “Don’t put all your eggs in one basket.”

2. Tell Stories

Lots of them.

Not lies, not stretched truths, not how-to’s, and not persuasive essays. Just plain-and-simple stories. For every subject that came up at this coffee chat, my guest would tell a story… He told me how Dr. Neal Sikka simultaneously runs a telemedicine center AND an Emergency Room. He told me how Dr. Junaid Shams started a company during medical school and now runs a social fin-tech company for the night life scene. He even told me about the other 2 guys that my I-banker friend recommended getting in touch with:

“Oh, I’m not surprised that Barrientos hasn’t gotten back to you yet. He is heads-down, all-hands-on-deck building an awesome new startup: Brazen chat software. And you’re gonna have a hard time connecting with Aberman too: he’s in super-high demand with the Washington Post & Forward Thinking Radio. Both great guys.

3. “Send Me Helpful Sh*t”

I’ve heard this advice over and over.

Yet it remains one of the most difficult things for young job-seekers to do. But this is basically what he told me was the BEST way to break into venture capital (and probably many other white-collar industries). Don’t ‘APPLY’ to jobs. Start them before you even get permission. As in, before you even get paid to do anything. If you want to work somewhere badly enough, you will make yourself useful, then indispensable, then someone will want you. In other words:

“Send me helpful sh*t. As often as possible.”

Sure, this method is longer and harder, but come on — If you’ve read this far, you have more than a passing interest in VC, and you will regret it if you don’t give this method a shot.

Last thing.

4. Connect & Partner

At the end of our conversation, we discussed the venture program at his university and a new class they were launching that would let STUDENTS become real angel investors.

Warning: this is some of the WEIRDEST charity I have EVER heard of … and I worked in philanthropy consulting for 12 months.

Big-Ticket Donors actually allocated money to this specific college program so that undergrad and MBA students in this specific class could make institutional investments in specific startup companies and (potentially) make real returns that future students can use to do the same thing all over. Cool, huh?

After realizing all the overlap of effort and interest, I offered to connect him with VCIC and InSITE.

The first one is a global venture capital investing competition open to graduate students around the world. And the second (if you’ve been living under a rock is a student-run startup consulting fellowship located exclusively in 6 top academic cities: Silicon Valley, New York City, Philadelphia, Boston, St Louis, and Washington DC.

The conversation ended as quickly as it started.

A smile, a handshake, and “thanks for meeting”.

Onto the next thing: we all have a job to do.

Correction: a previous version of this article incorrectly cited the subject’s annual income as a university VP in the range of $1–2M. That assumption was based (inaccurately) on information in this infographic + article. He is in fact only an Associate VP, and his boss made exactly $574,907 in 2014 (reported in the most recent IRS Form 990 on record), so it might be safe to assume that he makes less than $0.5M per year (from the college position).

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