Megan Thee Stallion's Biggest Career Mistake: Not Asking Questions

By Nathan Brooks

In 2024, Megan Thee Stallion signed a deal with Warner Music Group that gave her full ownership of her masters and publishing — a structure she built only after admitting her biggest early-career mistake: she was scared to ask questions about her contract.

The three-time Grammy Award winner, whose real name is Megan Pete, laid out the story at Entrepreneur's Overcoming Impossible event last week. Her first record deal, she said, was one she knew was flawed at the moment she signed it.

What did the first deal actually cost her?

Pete entered the music business with a simple picture of how it worked. Before she made it big, she saw rappers on social media showing off new cars and fancy clothes. She assumed they made a tremendous amount of money, and she couldn't wait to become one and take care of her whole family.

The reality, she said, was that she wasn't getting paid what she was worth. She signed anyway, because the money let her take care of her mom and pay the bills. She was excited, in her words, to "take care of her people."

The gap widened as her profile grew. The bigger she got, the more she realized how much her likeness and sound were worth.

"I started realizing I'm not making as much money as I should be making because I kind of just gave my life away to somebody else," Pete said. "I had to take a step back and think, Okay, let me see what's going on with my contracts. Let me figure out how I can be my own boss."

For founders and creators negotiating their own deals, that's the practical lesson. The cost of a bad contract compounds precisely as your brand appreciates — the asset you signed away cheap becomes the most expensive line item in your business.

Why she didn't ask questions

Pete was direct about the root cause.

"I was a little bit nervous about asking questions," she said. "I feel like that is one of the biggest things that hold people back, being afraid of sounding stupid."

Her fix is blunt: now, if she doesn't understand something, she asks about it. No clause survives unexamined.

Ownership, not fame, became the priority. She said she didn't just want to be famous; she wanted to own her own music, because she was putting in all the work and felt like she wasn't receiving anything back.

The Warner Music Group deal reflects that. Pete retains her independence as a musician while tapping Warner for promotion and marketing — effectively keeping the upside on her catalog while buying distribution muscle as a service.

"I do own my masters," Pete said. "It was important to me, coming out of a situation where I didn't own anything and I didn't have control of my career. I just didn't want to ever be in that position again."

What drives the decisions now

Only one topic made Pete tear up on stage: her "North Star," the guiding light she uses to stay focused. For her, that's family — her mom, dad, grandmother and great-grand-grandmother are her foundation.

"I do things that I feel like they would have wanted to see me do," she said. "I just keep them in mind, and I just know that my mom is proud of me, my dad is proud of me."

Wiping away tears, Pete said her responsibility is bigger than herself. She wants to give her fans "little pieces" of herself to incorporate into their everyday lives, and she filters business decisions through how her family would respond to them.

Her advice for anyone on any career path comes down to one principle: be true to yourself.

"When they're being authentic to themselves, that's when they win," Pete said. "That's when they're most successful."

For practitioners, the takeaway is structural, not sentimental. Ask the stupid question before you sign. Price your likeness before someone else does. And if you've already signed badly, know that restructurings like Pete's 2024 Warner deal show there's a path back to ownership — as long as you're willing to renegotiate from a position the first contract helped you build.