I've gotten celebs like Post Malone and DJ Khaled to share stories about being self-made. Here's what they've told me and how I get them to open up. (2024)

That's the whole ethos of my interview series, "Self-Made." I sit down with the person I'm interviewing and we talk about their stories and hopefully motivate people out there to do their own thing. We've had some amazing guests on the show, like Rick Ross, DJ Khaled, and Wiz Khalifa.

My favorite conversations on the show are the most transparent

My first "Self-Made'' interview was in 2017 with Post Malone. He came on the show and talked about how he wanted to be like his father — so in high school, he wore suits everyday to school because that's how his father dressed. People made fun of him but he was in his own lane. I like hearing those kinds of real stories.

I just did an interview with Sean Garrett. They call him "the pen" because he's had so many number one hits, writing songs for other people. He told me his first big song was "Yeah" from Usher, Lil Jon, and Ludacris — everyone knows that song.

He said he'd tried for a long time to get Lil Jon to send him some beats, but Lil Jon's team was like, there's no way we're going to combine Lil Jon with R&B — it's never going to happen. But Sean kept pushing and pushing, and ended up writing one of the biggest songs of all time.

When I interviewed Nipsey Hussle and Nipsey said, "Brett, you know, it's all about popping your trunk," and I don't know what the hell he was talking about, but he said, "You gotta go to the corner, open your trunk, and sell your goods and don't be afraid." And then I got it — I like that. Everybody's got a story to tell.

To have an authentic conversation in an interview, you have to be willing to open up too

As an interviewer, I don't want to know a lot going into the conversation. I like to be surprised and be able to hear the story as if it's the first time. I want to be able to have the most authentic conversation possible —I don't want to hear a canned answer.

I make sure it's a two-way street: I'll often share my own answer to a question, and just be really honest about it. That helps the other person open up. You can tell when you're getting an honest response — you can feel the raw emotion.

I'm intrigued by these 'Self-Made' stories because I have one too

I've been in the liquor business for over 20 years. Not every minute's great. Early on, I put all my money into this business to the point that I lost my house — I stopped paying my mortgage and the bank foreclosed on my house.

I was in trouble with the IRS because I stopped paying taxes to put money into the business. I remember my mom telling me she'll sell her rings for me to put money into the business and keep it going. It sucked. But it was awesome at the same time because look where the business ended up.

The early days for my company were hard, but I learned a lot through the ups and downs

Something I failed at in the beginning was not trusting my gut and instincts. It's good to have people around who challenge you, though.

I argue all the time with my team, and I love it because I need to bounce ideas off of someone and see how they react. One of three things will happen: I'll realize maybe they're right and I'm wrong, or I'll still disagree and go in my own direction, or maybe there's something I learned from that conversation that I should tweak and fix.

At the end of the day, I want to make the decision because I want to be the one who was wrong. That's the key to anything you're doing on your own.