I'm a very commonsense guy - I just look at the viability of the idea, if I feel the team has the ability to execute the idea. I also look at the investment syndicate, the size of the market, and then a lot of gut married on top of it.
If you look at a company like Uber, a company that so anti-establishment that cab companies are trying to find ways to shut it down, one could compare that to how Public Enemy and NWA went after then-modern society in hip hop.
Actors play different characters, so you have to build a new base around each new movie - with few exceptions, most actors don't have a fan base that just follows them around. With musicians, the fan base just goes everywhere they go.
As we look at Hollywood and the controversy around the Oscars, it goes back to the voting block and the lack of people who come from that culture. For example, the NWA movie is a fantastic, fantastic movie. You need people who can look at a piece of art like that and understand the artistry in it.
So many black kids aspire to be entertainers or professional athletes because those are the only role models they see that look like them. There are only 300 jobs in the NBA but an endless amount of opportunities as an entrepreneur. With enough hustle, entrepreneurship opens doors to a world of opportunities.
Being born in the adolescent years of hip hop helped us learn about flux. And when you're in an industry that is constantly growing, changing, maturing... you get a chance to try different things out and a chance to fail.
I like to compare the attitude and energy of an emerging start-up to that of the early hip-hop era. From working at labels like Bad Boy and Ruff Ryders, walking into the Def Jam offices, A Touch of Jazz and things like that, the vibe is that off making something out of nothing and making things work, and that's what I love about start-ups.
When we look at transportation in America, there's going to be companies like Magic Bus, where you have these private bus fleets. You're going to have carpooling; you're going to have these different types of transportation. It's going to be a full ecosystem, but it's not going to be a winner-takes-all.
I invest in black-led startups not because of a sense of charity. I make those investments because of the basic principle of supply and demand and the reality that black entrepreneurs typically lack the network to have their deals become bid up and overvalued.
When we're looking at strategic partners, it may be that they're larger partners or big corporations or start-ups. But, when you look at Gilt and places like Amazon and Starbucks, they're all places where it's a lot of foot traffic or digital traffic.