Drybar’s Gen X founder’s success story

Webb, the 48-year-old founder of blowout empire Drybar and author of The Messy Truth, went straight from high school to New York, where she jumped from job to job until she landed on styling hair, a career she never left.

After getting married, moving to Los Angeles, and having two kids, Webb began traveling to clients’ homes and styling hair on demand—a service that quickly blew up among busy women in the Brentwood area. Alongside her brother and then-husband, Webb spun the concept into Drybar, which has since become a household name and destination for on-the-go reliable hairstyles across the U.S.—and a venture capital darling.

It wasn’t always easy, and in her new book, Webb is open about her mistakes and regrets. Namely, she struggled with severe burnout, especially balancing difficult family issues, including the death of her mother and her older son’s time in rehab. 

In an interview with Fortune, Webb—a self-made multimillionaire—walks through building her brand from scratch, establishing herself in a crowded field, trusting her instincts, and taking money off the table with each VC round—despite what popular wisdom might recommend. The following has been lightly edited for clarity.

Can you tell us a little bit about where you grew up and what your childhood was like?

I was born on Long Island, New York, and I grew up in South Florida. My parents were entrepreneurs, not a big surprise there. That’s really where I got my entrepreneurial spirit. I grew up watching my parents operate a business and learned firsthand how to do it, and how to bend over backwards for customers. It was an upbringing that would turn out to really serve me as I got older and started Drybar, but one that I didn’t even really pay attention to as a kid.

What was life like growing up financially for you? Did your parents teach you about money management?

They did not. I’ve never managed money well. I watched my parents run their…