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7 Rules for Turning your Grocery Bagging Skills into a Venture Capital Career

Bullpen Capital is underway on Fund II, and this week I had to update my LinkedIn profile. I’m now a Partner at a venture capital firm on Sand Hill Road. I can’t say I ever expected this, since my career hasn’t exactly followed a normal trajectory. I’ve bagged groceries, mopped bathrooms, and carried golf bags. I had a 3-year stint as a professional poker player. I’ve worked in science, education, and law. But somehow I ended up in Silicon Valley investing in startups.

I keep getting asked “How did you get to be a VC?” and frankly I don’t know the answer to that question yet. This wasn’t some grand scheme culminating in promotion, it was some combination of luck, hustle, and sleep deprivation. What I do know, however, is there are some rules I’ve lived by that helped me get here. If your parents are Stanford business professors or you’re reading this from your country club you probably don’t need my advice, but for the troublemakers out there trying to break into the business, here goes:

Be anything but forgettable:

I missed my high school prom as a punishment for my first computer hack.

I publicly asked an 85-year-old judge from the Federal Circuit out on a date.

I told a dirty joke in an elevator to my future boss (now partner) Paul Martino over a decade ago.

Whatever I was, I wasn’t easy to forget.

It took me 12 years to call up Paul, but when I said “Hey, this is James. We met in an elevator in San Jose in 2001 …” he knew exactly who was on the other end of the phone. Sometimes you’ll be remembered for all the wrong reasons (ask me about my Steve Case story), but when it goes well your network can grow full of powerful people who have your back.

Bring a blue-collar work ethic to white-collar jobs:

When I applied at Bullpen, the team reviewed about 400 candidates for the entry-level analyst job. Some of the candidates had founded and sold their own startups, had 15+ years experience in finance, or were Stanford MBAs with 4.0 GPAs.

I didn’t have that kind of pedigree, and I was frankly just too stupid to know what I was up against — but I did have some grit and work ethic from grinding blue-collar jobs to get through school. So I simply started working for the firm the best I could, without pay and without permission. The team artfully ignored me for the most part, but when the final interview round included an analysis component, the (admittedly inelegant, manually typed) database I built for myself eventually supported the thing that mattered most to the Bullpen guys: “your analysis was simply better.”

So don’t be intimidated by the competition. Work your ass off, mop floors at Sequoia if you have to, and realize that if you play the game right the Ivy League MBAs don’t always win.

Most of your authority figures are wrong:

At every stage in life, there will be pressure to conform. Fight it. If you play it too safe, you won’t create any enemies, but you won’t find your best allies either. Keep being you. Step out of line, be opinionated, be someone that can’t be easily ignored.

Strive to quickly be either glorified or vilified, because that’s the fastest way to find the mentors and career opportunities that reward you for being who you are, instead of trying to beat you into some pre-designed mold.

Spend as much time at the bar as you do at the library:

Education is important, don’t get me wrong, but this is a people-business and your perfect GPA will get stale pretty soon after graduation. Skip enough classes to make an impression on the people who inspire you. Be the person at happy-hour making your colleagues laugh, not grinding away in your cubicle after-hours hoping they notice your hard work.

I’m not saying you shouldn’t work extra to get ahead, but do it when no one’s looking and do it for your own curiosity and ambition, not to gain favor with your boss.

Find opportunities to perform above your pay-grade:

As the junior guy it’s easy to keep the training wheels on and let your partners take the lead (and you usually should because they’re smarter than you) — but don’t get complacent. When you see an opportunity to step up and behave like a partner-level guy, get tenacious.

If you fail, at least you proved you had the guts to take the initiative. If you succeed, you might jump a few years ahead on your career path.

Don’t forget there was a time when you didn’t know jack:

If you work with startups everyday as an investor, you’re lucky to be here. Don’t forget that. The emotional swings facing every entrepreneur are difficult to bear, and when you’re on the side with all the money it can be tempting to become too full of yourself. Don’t be that guy.

Be transparent, make quick decisions, and respect the entrepreneur’s time as much as you respect your own.

Never stop trying to become qualified for the job:

The moment you stop learning is the moment you become obsolete, and there’s a pack of really bright young men and women (and at least one guy I know in his 70s) who will gladly relieve you of your job if you don’t give it the respect it deserves.

Stay hungry, and I’ll see you out there. Let’s do a deal together soon.

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