Episode 75: Drybar Founder Alli Webb on How She Almost Lost Herself (and How She Found Herself Again)
Alli Webb is one of the most successful entrepreneurs, who you probably know from her biggest claim-to-fame Drybar, or her other companies such as Squeeze, Canopy, and Brightside. Alli has been named the “100 Most Creative People in Business” by Fast Company, featured on Fortune magazine’s “40 Under 40” list, and Marie Claire’s “Most Fascinating Women." Webb appeared on “Shark Tank” as a guest shark in 2019 and is a New York Times bestselling author. Alli also just released a memoir titled The Messy Truth: How I Sold My Business for Millions but Almost Lost Myself. In this episode, we talk about how Alli built a multi-million dollar company (without a college degree or formal business training), relationship tips and the red flags she wishes she paid more attention to, how she lost herself even when her life seemed perfect on the outside, how she got through the hardest times of her life, and the surprising spiritual practice that she swears by. This conversation is raw, honest, and vulnerable.
SHOW NOTES:
This week’s Ask The Everygirl is a very special one, because in this week’s episode, The Everygirl’s Editor-in-Chief Allyson Trammell joins Emma and Josie to discuss strategies for asking for a raise, as review season approaches. Allyson explains how to approach the conversation in terms of taking your power back and coming to your employer with a strong strategy for negotiation. She gives tips for taking the emotion out of the conversation, and Allyson and Josie discuss why having upward empathy for both your boss and the company itself is important when asking for a raise. Allyson also provides tips for tracking your own achievements throughout the year in order to prepare for your review and present a strong case as to why you deserve a raise. She advises seeing your request as a sales pitch and explains how to present yourself as an invaluable asset to the company. Then, the interview with Drybar founder Alli Webb begins with Alli sharing her own entrepreneurship story, including how she hopped from job to job in New York City and South Florida in her twenties before starting Drybar with her brother and her now ex-husband. Josie and Alli discuss what set Drybar apart during the first few days of the business when Alli and her team were just getting started. The two also have a conversation about what it has been like for Alli to be a woman in business and to be a female founder. Alli explains why she thinks being a woman in business has actually played to her advantage: She discusses why it’s actually just harder to simply be a woman than it is to be a woman in business. Then, Josie and Alli move on to discussing the subject of Alli’s memoir, The Messy Truth: How I Sold My Business for Millions but Almost Lost Myself. Josie asks Alli to explain what it really meant for her to “lose herself.” Alli dives into what it was like to go through a divorce while her teenage son was entering rehab, and how that changed the conversations she was having in her day-to-day life. Josie asks Alli if there were signs that her marriage was not right for her before the divorce—Alli explains that there are always signs, but they are extremely easy to purposefully ignore. She provides advice for tapping into your intuition in relationships and explains what she would have changed if she were to go back in time. Alli also dives into the self-care and meditation practices that she used when it felt like her entire world was falling apart. Then, Josie asks Alli a follow-up: After she lost herself, what was it like to find herself again? Alli explains her reinvention process, her evolution of self, and the joy of having a beginner mindset. The episode closes with rapid-fire questions for Alli.
Must-Listen Moments:
[1:29] Ask The Everygirl: My end-of-year review is coming up, any tips on asking for a raise?
[29:19] Alli Webb’s journey to entrepreneurship, from the odd jobs she picked up in various industries throughout her twenties to founding Drybar
[38:23] The Drybar co-founder’s perspective on being a woman in business, and why her femininity is actually a strength
[44:30] How did Alli Webb “lose herself” when she went through her divorce, and how did she cope with the feeling of everything falling apart?
[55:21] How Alli found herself again, from having a beginner’s mindset to reinventing herself entirely
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