"How Much are you Worth?"

I was at an event in the Midwest recently and was speaking to two local, tech leaders about how many startups had been launched in the last six months when a white-haired gentleman approached us, let’s call him Joe. Joe sidled up to our group with a killer line “are only girls allowed in this conversation?”. Within seconds my two allies headed for the exit and I suspected something was up.

Joe asked me what I did. I explained that I was a VC, located in Chicago but invest across the U.S. and Canada. Immediately, Joe started asking questions about my personal wealth. “How much are you worth? How did you make your money?” When I gave him a couple of non-answers (I rarely tell strange men I have just met about my net worth), he skillfully turned up the manipulation factor. “You know, on the West coast, real VCs talk all the time about where they made their money”.

Joe is right. The VC equivalent of the startup mantra “we are crushing it”, is to be wearing a VC branded vest, give off an air of superiority, ooze affluence, list every well-known startup that you had even one dollar invested in and namedrop like crazy. It is like being the cool kid in high school. Like being an equity trader in the 80s and 90s. Or, like being an investment banker…ever (although that may be changing). It’s why a friend of mine, someone that I think the world of, recently called me the devil. Well, he actually said all VCs are the devil and asked why would I ever want to be a VC.

It’s interesting, being part of a group that you don’t identify with at all. I grew up in a small town in Kansas. I had two entrepreneurial parents, my dad the inventor and my mom the small business owner that she ran out of our home. I started working in the family business at five years old. I grew up thinking it was none of my business what kind of wealth other people had. I went to state school. I worked hard and had some success in my life. It’s not in me to brag about it. Yet, I am constantly being told I should.

It is true that as a VC my first priority is earning a return for my investors. I am unapologetic and aggressive in my pursuit to make MATH a top returning fund. VCs are not evil, it is a successful, proven business model. The reason it is so great for me is that I get to combine two things I love…business and people. The business part is literally in my genes and the people part is what is fascinating, challenging, frustrating, and exhilarating. I get to predict the future, evaluate new technologies and business models, solve problems, coach entrepreneurs, and help others see around corners. If I’m lucky I get to work closely with amazing entrepreneurs building amazing, scaleable companies. Why would I want to be a VC? Because it is the best job in the world!

On the other hand, I don’t actually like SWAG. I prefer approachability to superiority. I prefer humble to showy. I prefer to focus on high capital returning deals versus vanity investments. My relationships, even with the rich and famous, are not something to exploit. I believe my net worth is a personal fact that need not be publicly broadcast. And the truth is, I work mostly with B2B enterprise companies that you have probably never heard of. It’s what I know and where I can add the most value. Maybe those things make me “not a real VC”. Some believe that you cannot attract the “best” entrepreneurs with my approach.  Some believe that you cannot attract the “right” LPs with my approach. Respectfully, I disagree. I think I will attract entrepreneurs that want to build high-growth, scaleable businesses in huge markets with solid unit economics. And, I think we will attract LPs that care more about returns than names.

So, what happened with Joe?

I decided to have a bit of fun with him. I started asking him all sorts of personal questions and when he didn’t want to answer I asked “why, are you ashamed?” He ended up changing the subject and asking me some relevant tech questions and we had a relatively pleasant, short conversation.