In 1998, Spanx Founder and Executive Chairwoman Sara Blakely cut the feet out of a pair of control-top pantyhose so she could wear white jeans to a party. Starting with only $5,000 in savings and her lucky red backpack from college, she went from selling her pantyhose at Neiman Marcus to selling her shapewear empire to the tune of $1.2 billion dollars.

Since the beginning of her company's success, Blakely, who in 2012 was named the youngest self-made billionaire by Forbes, has pledged to use her platform to elevate opportunities for women and girls around the world. In 2020, she teamed up with GlobalGiving to launch The Red Backpack Fund, which has gifted more than $5 million to women entrepreneurs to help their businesses survive the pandemic. And, in October 2021, the billionaire founder, who had never taken any outside investors, made headlines when she sold a majority stake of her company to Blackstone. To celebrate, she gifted each of her employees two first-class plane tickets and $10,000 to "make a memory that will last a lifetime."

On the heels of the acquisition, Blakely sat down to discuss this milestone achievement and her path from fax-machine salesperson to self-made billionaire with Chief Member Ebony Beckwith, Salesforce's Chief Business Officer and Chief of Staff to Marc Benioff.

She spoke to the intention, authenticity, and humor that's helped her build a legacy as "the girl who made the world a better place, one butt at a time."

On the Gift of Failure

"Perfectionism really can be very debilitating. We all start out mostly wanting to get the approval of our parents, and we want to earn their respect, we want to earn their approval. My dad gave me this huge gift that I wasn't even aware he was giving me at the time: He encouraged my brother and me to fail. So, instead of trying to hold myself back because I was so afraid that if I did it, I wouldn't get on the team, or I might not be good at it, he kind of turned it around. I'd come home from school and he'd say, 'What did you fail at this week, sweetie?' and if I didn't have something, he would be upset. I could come home from something and go, 'Dad, I tried out for this and I was horrible,' and he'd high five me and say, 'Way to go.' He even took it a step further. When something didn't turn out the way I wanted, he would then say, 'Well, where were the gifts in that?' He reframed failure for me. Failure didn't become about the outcome, it became about not trying.

"The two biggest fears humans (have are) fear of failure and fear of being embarrassed, and they're connected. The more that we work to free ourselves up from caring so much about what other people think, the freer we'll be from both. I will intentionally try to embarrass myself. I really don't want it to own me. If I make embarrassing myself the goal, then it just flips the whole thing on its head."

On Bucking Gender Roles and Sharing the Load

"One day, the wheels were falling off the bus for me, and I wrote everything in one column that I was doing to make the household work, and then I put everything that I thought that my husband, Jesse, was doing to make the household work. It was a really enlightening moment for us as a couple. He took it really well, but I wasn't even aware of how much I was absorbing and taking on. I think culturally and societally, we saw what our mothers did. We saw what our mothers were expected to do, and what our grandmothers did and what they were expected to do. Now there's this dynamic that we all have another full-time job because we're working and we're career women as well. That doesn't really work. You've got to really communicate with your partner. Jesse kind of cried a little bit when I showed him that list and thankfully said, 'Wow, let's divide this up differently.'"

On the Blackstone Acquisition

"For me, everything is intuition. People have been trying to buy Spanx for 21 years. I just would always say, 'I'll know when it's right for me, and I'll know when it's right for the business to go to a new chapter.' If I can speak like a mother, my baby was 21. My baby can legally drink now, and my baby not only went to college but is now back at home living with me, so it might be at the point where it's good for the baby to spread its wings and grow.

"[Blackstone] was clearly authentically interested in supporting female businesses, and there was an all-female deal team. They were interested in an all-female board of directors. There was just a lot of synergy between what matters to me and what I built the brand on and what mattered to them. I started this business, and I told everyone it was going to be worth $20 million one day, and they all laughed at me. This was bigger than my dream in so many ways in what it means for women and how I can continue to inspire women."

On the Value of Intuition

"Feminine leadership is, for me, a deep connection to empathy, vulnerability, intuition. I think that intuition is something that really doesn't have a strong place in corporate America. I led with intuition and I gave people around me permission to lead with their intuition… There's a lot of emphasis on data, and I'm really interested in the dots between the data."

On Turning Challenges Into Opportunities

"I always tell people, when your life is really bad and it's really a dark time, that's usually the most fertile time for change. That's what happened to me."