Alli Webb | “The Messy Truth" from Founding Drybar to Finding Myself

If you love the look of a big, bouncy blowout... chances are you’ve heard of Drybar, the salon that revolutionized the industry with its exclusive focus on blowouts. Loved not only by women across America, but also by celebrities like Julia Roberts, Zooey Deschanel and Jennifer Garner, Drybar became a sensation.

But the story behind this $255 million idea might surprise you…

Alli Webb, Drybar founder, recounts her path from starting out having no clue what she wanted to do to twisting-and-turning her way through various job possibilities to embarking on the journey to launch this ground-breaking business.

(Lest you feel like you should have it "all figured out" right away... think again!)

The part of her story you may have heard before is the "female founder finds the white space, builds an empire, and makes an epic $255m exit" story. The part you may not know.... underneath it all, there was the realization that her marriage was failing and her teenage son was battling drug addiction.

Alli shares her story, including the dark, messy truth about the parts that didn't look "perfectly coiffed." 

If you're struggling with life feeling less-than-perfect these days and wondering where to find the strength to keep going... tune in to hear Alli’s gems, including: her advice for other entrepreneurs, how she overcame challenges like imposter syndrome, and how to find gratitude for both the obstacles and wins you’re bound to face.

IN THIS EPISODE:

[00:09] Jamie introduces Alli Webb. 

[04:02] Alli begins to talk about her childhood and feeling like a late-bloomer.

[05:43] Alli shares her experience moving and living in New York City to finding her way to beauty school. 

[07:59] Alli talks about motherhood and the itch to do something for herself.

[09:57] Alli recounts how her business started and developed which led her to address a hole in the marketplace.

[14:48] Alli describes where some of the defining details of Drybar were inspired by. 

[17:03] Alli talks about what drew celebrities like Zooey Deschanel, Julia Roberts, and Jennifer Garner to Drybar.

[23:04] Alli opens up about her marriage and the realization that it wasn’t going to last forever. 

[26:04] Alli shares her teenage son, Grant’s, experimentation with drugs and her reckoning with how to parent him. 

[31:29] Alli describes Grant’s turnaround and reveals her biggest lesson as a mother.

[32:23] Alli explains her identity crisis during her second marriage and divorce. 

[35:28] Alli talks about what’s next: new projects, mentorship, and dating. 

KEY TAKEAWAYS:

[14:58] Alli shares her advice for all entrepreneurs to “build something that you want.”

[31:50] Alli reveals the shift in her parenting approach, crediting “getting curious” to her and her son’s healthy relationship. 

[36:50] Alli describes her gratitude for the little things, such as no longer being heartbroken or in pain from grief.

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Make sure to follow Jamie @jamiehess on Instagram for news & updates, and visit our companion Instagram account @gratitudeology for a sneak peek into the personal moments discussed on the show.

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Thank you to Alli Webb for sharing your truth with us today. Follow Alli on Instagram @alliwebb.

Check out more about Alli: 

https://www.alliwebb.com/

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The Gratitudeology Podcast theme music is by HYLLS, performed by Nadia Ali @thenadiaali 

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Alli’s Bio:

Alli Webb is the Founder of Drybar, N.Y. Times Bestselling Author, Co-Founder Squeeze, Brightside and Becket + Quill. After spending 15 years as a professional hair stylist, Webb left the hair industry in 2005 to start a family, but after being a stay-at-home mom for 5 years, Webb decided to find a way to continue pursuing the creative side of hairstyling at a new-mom pace. She began offering affordable in-home blowout services to her mommy friends, which quickly expanded into a mobile operation by 2009. In 2010, Webb opened the first Drybar in Brentwood, CA. 10 years later and over 150+ locations across the U.S., Webb’s Drybar has exploded into a nationally recognized and highly sought-after brand. 

Webb diversified the Drybar brand, creating a line of products and tools sold at popular retailers such as Nordstrom, Sephora, and Ulta, recently selling this product division to Helen of Troy for $255 million. Webb has been on the cover of Inc Magazine’s “How I Did This” issue, named the “100 Most Creative People in Business” by Fast Company, featured on Fortune magazine’s “40 Under 40” list, Marie Claire’s “Most Fascinating Women” and recently Inc. magazine recognized her as one of “The 100 Women Building America’s Most Innovative and Ambitious Businesses.” Webb appeared on season 10 of ABC’s Emmy nominated hit show “Shark Tank” as a guest shark in 2019. 

Webb currently serves as an Advisor and Investor in The Feel-Good Company’s newest brand, Brightside - A brighter take on infrared yoga & saunas. Brightside brings the well-researched benefits of infrared yoga & saunas. Brightside combines the well-researched benefits of infrared yoga and sauna, and modernizes them with thoughtful technology in just the right places. The gorgeous custom space will teleport you to the brightside, the moment you walk through the door, and the incredible services make every interaction personal and meaningful. Brightside’s flagship location is now open in Culver City, CA.