I’m 28 and I’m on track to own part of thousands of companies in my lifetime. I’m one of a handful of investors in a school for entrepreneurs, a school where the tuition is a piece of ownership in the company itself. The entrepreneurs receive office space, classes, mentors, access to investors, web design, photography, and a Demo Day to show off their businesses to several hundred investors in the city. Despite this success, graduating with honors from a top 25 business school, and my unwavering passion for creating jobs and technology–I’m best known for my exploits on MTV. Go figure.
People think that my investment career and my MTV persona require two different brains, and in a lot of ways they’re right. But both of these things have helped me acquire a great deal of pattern recognition–the ability to see good and bad decisions before or as they’re being made so investors can either fix them or get out of the deal.
1. Investing in the team is most important thing you can do
Almost every startup investor says the same thing: invest in the person, not the company.
The company changes so much over the first years of its life that it’s more important to have good leaders at the helm of the boat, than it is to have a good boat. What’s important to note about a good team is they aren’t just duplicates of each other. They need to have extreme specialties. I like to invest in two-person teams where one person is great at content (programming) and one person is great at form (selling). A startup needs to be good at a lot of things, not great at a few of them.
The same thing goes for creating a great alliance on a game show. If you form it with all the jocks then there’s gonna be a lot of pissed off people who don’t outweigh your athleticism, but instead outnumber you in votes. So I diversify. I want lookers, losers, athletes, partiers, and talkers. I need a representative from each one of these skill sets, and I demand that they all live in different rooms from one another.
The idea is to be a part of every conversation and outsource the variant jobs to the person with equivalent skill set.
2. Being “normal” is bad for your career
I have an in-person meeting with just about every would-be entrepreneur that applies to be a part of our school. I’m looking for home-runs. Average doesn’t score home-runs. Insane scores home-runs. Insane works harder and longer, and is fueled by different motivators than the average person.
The same thing goes for MTV. They don’t cast average people. They cast geniuses, crazies, politicians, Ivy League graduates, loud mouths, millionaires—interesting people go far, “normal” people don’t. I don’t care if you have dread locks, are four feet tall, dropped out of college, or you were on a reality television show–are you pitching a revolutionary concept, and is there something special about you that the world will take notice of?
If you’re just like everyone else, what reason would anyone have to invest in you, over anyone else?
3. Travel and extreme situations make you more innovative
My passport is completely filled with stamps and visas to foreign countries. I’ve lived on both US coasts, the south, and now the Midwest. This was fun, but more importantly as an investor this has given me the ability to empathize better than anyone I know.
I “get” how people consume products and services differently from state-to-state and from country to country. I don’t want to invest in anything that can’t eventually be an international giant, so if the leader of the company hasn’t traveled, it’s a red flag. They don’t have the ability to empathize with the various types of customers they’ll be selling to if their company grows.
4. You learn more from failures than you do from successes
I won the biggest cash prize to ever be given out on MTV, in the history of the channel. I’ve forgotten most of what it took to win that title, but I haven’t forgotten the mistakes I’ve made that are brought up daily from both my inner game footage and my fans.
My entire life has been filmed and put in front of the masses. I allow myself to make mistakes, and fortunately, I’m punished for them more than the average human. This means I learn more, faster.
The most important question I ask new entrepreneurs is “what is your biggest failure?” I want to know what happened. I want to hear the shit. I want to hear that they have used that failure and learned from it in a way that will be a competitive advantage for their business moving forward.
5. Don’t judge a book by its cover
The path that I’ve taken throughout my career in entertainment has helped fund a program that creates jobs that are used to feed families in the worst economy of our generation. It’s a program that turns dreams into reality, and most importantly, solves a problem that has ailed the world in some way. So laugh, insult, swoon, or whatever actions your emotions call for as you’re watching TV, but don’t jump to conclusions about what kind of people we are behind closed doors. We might very well be the kind of people that fund your first company.