Founder, author, and beauty trailblazer Alli Webb built Drybar from a simple blowout idea into a $255M beauty empire that transformed the industry.
In this episode of The Burnouts, Alli sits down with Phoebe Gates and Sophia Kianni to share how she went from doing hair in her living room to leading one of the most recognizable service brands in the country. She talks about the explosive rise of Drybar, selling the company for hundreds of millions, and the personal challenges that followed at the height of her success.
Alli opens up about losing her sense of identity after the sale, navigating grief and motherhood, and rebuilding her life through her new brand, Messy. She reflects on what the beauty world gets wrong, the lessons she learned as a female founder, and the real cost of fast growth.
Whether you are building a brand, growing a service business, or figuring out the next chapter after burnout, this conversation is a powerful look at resilience, reinvention, and finding purpose again.
Chapters
00:00 – From stay-at-home mom to mobile blowouts
02:30 – The idea that sparked Drybar
05:00 – Opening the first Brentwood studio
07:00 – When Drybar went viral overnight
10:00 – Raising capital & navigating hypergrowth
13:00 – The truth about selling a company
15:30 – Alli’s personal life falls apart
18:00 – Losing her identity after the exit
21:00 – Rebuilding from scratch & finding purpose
23:00 – Launching her new brand, Messy
26:00 – Advice for founders rebuilding their lives
29:00 – What Alli wishes every woman knew about success
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Phoebe and Sophia aren’t just your hosts — they’re the founders of Phia, a new fashion-tech app helping shoppers find the best prices across retail and resale. Try it now for free in the App Store.
About The Burnouts
The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond headlines to explore the real stories, breakdowns, and breakthroughs that define your 20s.
Past guests include Paris Hilton, Tommy Hilfiger, Kris Jenner, Karlie Kloss and other entrepreneurs redefining our generation.
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