Troy Carter

Supported by Greenhaven Road Capital, finding value off the beaten path.

Troy Carter joined Guy Raz on the How I Built This podcast to tell his story.

Carter is a high school dropout. Instead of learning from teachers he chose Jazzy Jeff and the Fresh Prince (Will Smith). “They were the only guys from Philadelphia, they were from our neighborhood, they were successful, they were like gods in Philly and they were the way out. Meeting them was plan A, B, and C.” Soon after meeting the duo Carter realized, “I wanted to be less Fresh Prince and more James (Lassiter) and he became my teacher.” It was the manager, not the performer, who Carter wanted to emulate.

Finding mentors is crucial for success. These people, either directly in our lives or in books, have a huge influence in our lives. For Ken Grossman it was the men on his block growing up. For Brian Chesky it was reading a book about Walt Disney. For Judd Apatow it was seeing Steve Martin.

With this choice, Carter moved to L.A. to work for Lassiter and it was great.  “I was having the time of my life.” But he wasn’t getting a lot of work done. “I was taking a lot of shortcuts…I thought I was much bigger than I was.” Carter lacked the rare and valuable skills required for his rare and valuable job.

It’s amazing that he advanced so quickly without experience. Tom Brokaw started building his skills as a teenage disk jockey. Casey Neistat made homemade videos. Bill Belichick grew up in the game of football and has such a deep understanding that coaches say he will spend twenty minutes talking about a single play.

Great jobs require great skills and Carter didn’t have them (yet). He was fired and returned to Philadelphia.

Thanks to some connections via friends and family, Carter gets back in the game by managing Eve. He soon found out that you’re never really ready.

“I had absolutely no clue what I was doing…initially the job was protecting my friend and everything else was learning as I was going along. I remember our first tour was the Cash Money/Ruff Ryders tours. I got on the bus and there was this old bus driver and he said ‘you got the float?’ and I said I’d be right back. So I got off the bus and called one of my buddies who had done touring for a long time and asked ‘what’s float?’ and he said it’s the money you give the bus driver for gas, tolls, and food.”

In his book about Amazon, Brad Stone writes:

“By the first weeks of 1996, revenues were growing 30 to 40 percent a  month, a frenzied rate that undermined attempts at planning and required such a dizzying pace that employees later found gaps in their memory when they tried to recall this formative time. No one had any idea how to deal with that kind of growth, so they all made it up as they went along.”

As Carter cut his teeth he developed his “West Philly Spidey Sense,” a negotiation skill. “Being able to read rooms and read people is very very important and also knowing what’s important for that person on the other side of the table and what’s important for the client. A lot of times it’s not conflicting.”

Through practice, Carter came to the same conclusion as the Harvard Negotiation Project, the book Getting to Yes, and our ideas in How to Negotiate Well.  Carter also learned about how Eve could expand from music to other areas like television, movies, and clothing. Mimicry is a good way to start and Carter copied the Fresh Prince playbook just like Jason Calacanis mimicked Tim O’Reilly.

Carter’s success brought him an acquisition offer and he sold his management company for two million dollars. It sounded great on the surface – Carter had money and a way to scale his business – but it ultimately didn’t work.

“I was dreading getting up and going into the office. I would go in and pull the shades down because I didn’t want to work with people there.” As Mohnish Pabrai and Brian Scudamore noted, if you aren’t excited to go to work something is wrong.

Carter also found out that “Two million dollars isn’t actually two million dollars. You buy a house, pay taxes, a couple of new cars and I invested in the new business.” He didn’t have a low overhead mindset.

Not liking his job he took the money and invested in a new business, taking Eve with him. One year later Eve walked in to explain she’s leaving him for another agent. ‘How bad was this’ asks Guy Raz and Carter says that it was bad, but, “You can’t fall off the floor.”

After this reset, Carter gets introduced to another young, up and coming female artist. She had just been dropped by another label. Her one year experiment to break into the music business was over and her father wanted her to go back to college. Carter says “she was an incredibly hard worker.” That person was Lady Gaga.

Carter and Gaga were an overnight success together… – – wait, wait, wait. You know there’s no such thing as an overnight success.

Raz asks if Carter knew Gaga would be huge. “The real answer is, you don’t know. You think and you hope but you don’t know.” It would take a lot of work and so that’s what they started doing, work. Gaga was a great songwriter and many people wanted her songs – just not her singing them.

Around this time Facebook and MySpace were becoming larger “and we started using those platforms and we were lucky because they were global.” Their shoestring budget was used for tours and costumes thanks to this low-cost distribution blessing.

In tinkering with how to distribute music, Carter started to talk with those technology companies and led to a few investments.

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Thanks for reading,


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