When Tyra Banks retired from her iconic career as a supermodel, she turned down a lucrative three-year contract with Victoria’s Secret, opting instead to focus The Tyra Banks Show, a move she describes as her “biggest risk.”

“I wanted to have a talk show, and I felt like I couldn't have a talk show if I was still a model,” she recently told Chief Members at ChiefX New York. “If I'm talking about self-esteem, gender stereotypes and body image and all of these different things, I want my words to be trusted. So I walked away, and that was very risky, because that was my money, my support and everything I was known for. And I wasn't proven as a talk show host.”

In the end, it paid off. The Tyra Banks Show aired for five seasons, winning two Daytime Emmy Awards, and Banks told the audience it was one of her best decisions. But it’s also why Banks thinks it’s a myth that women should persevere no matter what. ”I'm a serial entrepreneur because I have failed,” she continued.

“As women, we get coached that you don't give up, you keep going, you don't let anybody tell you no. And that's true in the beginning, to get in and get past difficulties,” she explained. “But there comes a point where a lot of things come to an end, and it doesn't mean it's a bad thing. It's OK to pivot and do something else.”

Her latest pivot is launching an ice cream venture, inspired by the scoops she shared with her hardworking mom on Friday nights. The company, Smize & Dream, recently launched a pop-up shop in Washington, D.C., counting Vice President Kamala Harris among its first customers.

Banks credits much of her business savvy to the years she spent building her personal brand. Early in her career, she realized there weren’t many Black models who marketed themselves as the “girl next door”, so she crafted an image that took advantage of the “white space” in the industry. Since then, she’s sharpened those instincts thanks to mentors like the late Zappos CEO Tony Hsieh, executive coaching, leadership courses at Harvard and her own hard-earned experience as a business leader.

Don’t be Afraid to Ask for More

Banks encouraged the audience to ask for what they want — whether it’s mentoring or more money. She famously cold called Hsieh after reading his book on company culture, and asked him to mentor her. “Slide into the DMs,” she suggested. “It is the easiest way to ask for mentorship.”

“As a business owner, I’ve noticed women don’t ask as often as men do for a raise or promotion,” she observed. “And when they do, their voice shakes. But I’d rather their voice shakes than they didn’t ask.”

Her hilarious tip for asking for what you want? She tells her staff to look at her (ahem, famously generous) forehead instead of her eyes, when they’re feeling nervous.

Giving Feedback Is Essential

Banks may be known for dishing out critiques on her former hit show America’s Next Top Model, but in reality, she admits she has had to learn how to share feedback over the years, a skill she believes is essential for good leadership.

When she was hosting The Tyra Banks Show, a 360 assessment revealed that her employees weren’t always sure of their footing with their iconic boss.

“I cried myself to sleep when I got the results. What the [junior staffers] said is we don't feel comfortable, because when we mess up, she keeps smiling, and that’s scary,” she said. “I was so scared to give feedback, it was backfiring.”

She once was given the advice, “Feedback on the run is better than none,” and learned to embrace it wholeheartedly.

“I always compliment feedback. I always say, ‘Thank you for that,” she says. “It gives them the courage to speak up.”

Now, Banks admits, she has the opposite problem, describing her leadership style as “too collaborative.”

“I want everybody to be excited. I want everybody to have an idea. And so I do so much collaboration to the point where I think sometimes it can kind of upset my team a little bit, because at times they just want me to make a damn decision and tell them what to do.”

It’s a balance Banks said she’s learning to navigate — along with the newfound challenges of menopause, which she is trying to embrace, especially when hot flashes keep her awake.

“I'm in Australia and the world is asleep, but New York and D.C. are awake, so I take advantage of that flash, and I email teams,” she said, offering a bit of her classically funny and forthright advice: “If you are flashing and you're suffering, just do a little work. Because you’ll get ahead of the younger women that are not flashing.”