The Side-Hustle Into Venture

Last weekend, a number of people shared the first-person account of millennial “side-hustling” that was published in Quartz. You can read the article here. It’s not that great of a piece, nothing new or earth-shattering is revealed, but I’d wager it was shared so widely because people have experienced a dose of this themselves, whether they like to admit it or not.

In the article, the author talks about “side hustles” as a lifeline for many professionals in the economy under 35, coming up at a time after the 2008 financial crisis, after sharing economy networks arose and 1099s took the place of full-time work. Eventually, the author contends, the side hustles run out and folks will be forced to grow up, focus, and take on responsibility.

The article also reminded me I’ve been “side hustling” since high school. If I think through the phases of my life:

8-15: If my work was “school” at the time, there was mowing lawns, shoveling driveways, etc.
16-22: School got more serious and into college, was working in various kitchens (where I developed a passion for cooking).
22-28: This is when the side hustling really started, working nights as a bartender in NYC or working as a bartender for private parties in the Bay Area.
29-33: To defer some grad school costs, I worked as a researcher for various professors across the university and research departments. I would hustle to find pockets of scholarships and hunt them down, a few thousand bucks here, a few thousand bucks there. I finished grad school in June 2008.
34-present: Little did I know The Side-Hustle Muscle would not only help me here in the Valley, it was a critical lifeline for me to survive, stabilize, and get my bearings. It wasn’t paid, but I became a regular contributor to TechCrunch for a weekly column and TV show I started; and I started consulting with a handful of VC firms on Sand Hill Road as a way to learn the business and meet more people. I was lucky that, while I was working at companies, my colleagues not only supported this — they encouraged it.

And, here we are, over 20 years later, and the side hustling mentality isn’t coming to a stop — it’s just now more focused in a particular area (that I really enjoy). Rather than being dispersed, now the hustle remains but is channeled into the pieces of building a managing a small fund — how to find LPs, how to report, how to sift through deal flow, how to work with companies and founders, how to work with new investment partners, and the list goes on and on. The hustle continues, but finally got streamlined.

All this said, I wouldn’t sit here and say “this path led me here!” or recommend it to other people, because there are many downsides to taking this path, too.  I wanted to cut in directly, but that option wasn’t on the table. It’s risky and I’m still paying for it in a way. It was never by design — I was always gunning for a regular full-time job but they never arrived. The side hustle is not one I would openly advocate for, as well. I’m lucky I have a chance to cut into a field I truly enjoy — and I am grateful that hustle provided enough fuel to get this far.