Troy Carter on Underdogs: “You've got to convince people to believe.”

This is an episode about an underdog. And, I love an underdog. I think a lot of people do. 

Because they’re the ones who aren’t supposed to win--at work, at life--wherever the odds aren’t in their favor. But they pull it off anyhow.

And once you’ve been the underdog, you understand that the favored contestants don’t always win. This confidence incentivizes you take risks because the stakes are lower if you fail. People assumed you were going to fail anyway.

It makes you believe that you can pull off just about anything if you put your mind to it--because you have pulled off something unlikely before.

And sometimes, it makes you able to see a winner when no one else does.

This week’s guest is Troy Carter, the tech and music entrepreneur who helped Lady Gaga break out. When he met Lady Gaga, she didn’t seem like the kind of artist who was about to become a worldwide sensation. But Troy recognized something special, and he signed her. 

And maybe one reason he could see it is because he knew something about underdogs. He'd been one his entire life. To hear our conversation, you can download the episode here. Then, please, share your own thoughts and tag them #HelloMonday so I can jump into the conversation.

Here are some highlights….

On winning people over: “You've got to convince people to believe in something that sometimes may have never happened before.”

On his education: “I dropped out of school in 11th grade, but I would go to, I would go to the library, you know, a few times a week and just kind of learn about subjects that I, that I wanted to learn about.”

On defending the underdog: “I just naturally fell into that role, you know, as a manager, just being an, an advocate for artists that I, that I cared about.”

On meeting Lady Gaga: “She had just gotten dropped from Def jam records and, and um, she was sleeping on her grandmother's couch for a while in West Virginia.”

On investing in startups: “I know how to pick people better than I know how to pick companies. Pick the right people and they're going to figure it out.”

About last week...

Our culture episode with Ben Horowitz really struck a chord. Our conversation was packed with tips for how to get culture right, as well as many things people do wrong in the name of culture.

Nesa Johnson spoke to the importance of onboarding, writing: "I have long loved the idea of a hiring manager being required to submit a training plan in order to approve a job requisition; however, I have yet to work at an organization where this is a practice." It's something that she'd love to see organization develop more discipline around.

As for whether culture can be fixed once its broken, your opinions were mixed. United Kingdom listener Gary Miller spoke from experience, sharing how his own company had addressed a toxic culture more than 15 years ago. Listener Maria Santacaterina, also based in the U.K., offered up a robust action plan for how cultural change can happen. At its heart is courage.

But nobody suggested the change would be easy. Many people advised that if you're looking at new jobs, you should do your research on the company's culture before you start.

I want to hear from you...

And, I keep thinking about what it means to succeed when the odds are against you. Do you have a great story about someone who has pulled off the seemingly impossible? How? Drop me a line at [email protected] or post on LinkedIn using the hashtag #HelloMonday

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