Don’t Follow the Herd

I hear a lot of young people say they want to go into venture capital these days. It’s a sexy job that sits atop of the startup food chain. But if you’re one of these people thinking about becoming a VC (or any profession for that matter) I think it’s important to ask yourself “why?”

Going into my senior year of college I didn’t know what I was going to do next. Most of my friends were going into investment banking. That was the ‘sexy’ job you wanted if you graduated in 2004. But I was a poli sci major with sub-optimal math skills. There was no chance that I was going into investment banking. Instead, a cabal of my other math-impaired, hippy-dippy friends gathered together one night over beers and we decided that since none of us were destined for Wall St. we’d choose the next most obvious career path: we’d open a youth hostel in Panama.

As you can imagine, our grandmothers were all thrilled with this decision.

As crazy as it sounded, the crazier thing is I ended up getting really close to doing it. We all audited an entrepreneurship course in the business school. We put together a business plan. We even went down to Panama to check out properties. But at the last second I got nervous and chickened out.*

Instead I chose the path of least resistance. I went to law school like every other poli sci major on the planet. I wasn’t 100% sure why I was going to law school. Mostly it just seemed like the thing I was supposed to do. If I wasn’t going to be fancy-pants investment banker, being a fancy-pants lawyer felt like the next best thing.

For the record, this is probably THE WORST way to make a decision. I was choosing a career path based out of fear and ego and other people’s expectations, not because it was something I was super-passionate about.

Fortunately, what happened next, finally set me down the right path. After three years of law school, I failed the bar.

I was pretty devastated. No law firm would hire me, and I had a mountain of debt. It wasn’t the most auspicious start to my fancy-pants lawyering career.

So I went back to the original plan A. I decided to do something I was actually passionate about, not something other people expected me to do. I became an entrepreneur and helped start a company. It was one of the best decisions I’ve ever made.

Eight years later, as I was leaving the company I helped start I found myself in a similar fork in the road. What was I going to do now?

Just like in 2004 when I was graduating college, my decision making process defaulted to fear and ego.

I said to myself, “Okay, I just did this startup thing for eight years. I loved it but don’t have another idea right now or a co-founder to start something new with. I guess, I just have to be a VC now, right? Isn’t that what I’m supposed to do?”

So I decided to explore the world of VC and I asked a friend at one of the top tier VC firms for some help. He ended up giving me some some really honest advice. He said, “why do you want to be a VC?”

I answered that I like helping people.

He responded with a level of candidness that was incredibly helpful. He said something along the lines of:

If you like helping people, don’t become a VC. Our job, at the Series A and B level is not to help people. Our job is to efficiently allocate other people’s money into good investments. The goal is not to find the company that needs help and nurture them along. The goal is to convince the startups that are least likely to need your help to accept your money. In fact, if you’re at the Series A or Series B stage and a company needs a lot of your help, you probably invested in the wrong company. So if you really want to be an investor and you really want to help people, become an angel investor or join an accelerator.

That was a game-changer conversation for me. I took his advice to heart. About six months later, I decided to join Techstars, an accelerator program that focuses on mentorship for early stage startups. I joined about a month ago. I love it so far. It’s a great fit and I get to spend the majority of my days helping others.

If you are at a fork in your career and thinking about what comes next, the best thing you can do is ask yourself what makes you happy. Ignore the temptation to follow the herd. Ignore the easy route down the path of least resistance. Ignore your grandma whispering in your ear about what she thinks you should do. All of that is just noise. Find what it is that is going to make you happy and go after it. You’ll never regret it.

Brene Brown has a great quote in one of her books. She says

Comparison is the thief of happiness

It’s pretty damn accurate.

Stop comparing yourself to others. Do what is going to make you happy. Of course, I’m not saying anything that like a billion people haven’t said before. All of us already know this is true. But we don’t always act on what we know, and so sometimes I think it’s worthwhile to have a reminder.

*For the record, the rest of my hippie-dippy friends from college did end up opening that hostel. They had absolutely no idea what they were doing but they were super authentic and just had fun doing it. I think the authenticity paid off. Eventually, it became the #1 rated hostel in all of Panama and they ended up opening two more hostels, a bar and a super-successful e-commerce site.



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Director @Techstars, LA. Previously Co-founder @GiveForward. Likes burritos. Dislikes injustice.