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Drybar Founder Alli Webb On the "Messy Truth" About Marriage and Entrepreneurship
The article features an interview with Alli Webb, the founder of Drybar, discussing the complexities of balancing a successful entrepreneurial career with personal life, specifically marriage. Webb, who built a multi-million dollar blow-dry bar empire, candidly shares her experiences with two divorces, her self-help journey, and the insights gained from these challenges.
Webb recounts a period in her life where she reached a personal rock bottom. Her 16-year marriage to business partner Cameron Webb was ending, her then 16-year-old son was entering rehab, and her role in the company she founded was undergoing significant changes. This confluence of events led to immense pressure and a feeling of being lost. To cope, Webb immersed herself in self-help, attending therapy three times a week, meditating, and reading extensively. This period of intense self-work was crucial for her to regain her footing.
Following the sale of Drybar in 2019 for $255 million, Webb continued her entrepreneurial endeavors, co-founding Squeeze (a massage concept) and Becket + Quill (a jewelry brand) in 2021, and becoming president of Canopy (a clean humidifier brand) in 2022. She also co-founded The Blueprint Mastermind to mentor aspiring female entrepreneurs. Despite her professional achievements, her personal life presented new challenges. She remarried Adrian Koehler, an executive life coach, but they are now divorcing after less than two years, a situation she addresses in her new book, *The Messy Truth: How I Sold My Business for Millions but Almost Lost Myself*.
Webb emphasizes the continuous nature of self-awareness and personal growth. She reflects on how easily individuals can lose and find themselves throughout life, particularly when navigating demanding careers and relationships. When questioned about her book's assertion that a booming business and a happy marriage cannot coexist, Webb expresses a desire to believe she was wrong, but acknowledges that in her experience, her first marriage wasn't the right fit. She admits to becoming too focused on building her business and raising her children, which led to the neglect of her marriage.
She also discusses the delicate balance of working with a romantic partner, drawing from both her own experience and that of her parents. She believes it can work with strong boundaries, but highlights the risk of the relationship becoming solely about the business, leading to a lack of individual connection. Webb advocates against settling for a “mostly happy” life, asserting that fear often prevents people from seeking more fulfilling relationships. She made the difficult decision to leave her first marriage, driven by a realization that she deserved more and wanted to model a healthier relationship for her children.
Webb touches upon the unique challenges successful female entrepreneurs face in dating, noting that some men may feel emasculated by a powerful woman. She recognizes the need to balance her masculine professional energy with her feminine personal energy and seeks a strong partner who is not intimidated by her success. Ultimately, she believes that "doing the work" on oneself directly contributes to being a better entrepreneur, fostering qualities like softness and reducing reactivity. The "messy truth" for Webb is the importance of openly sharing personal struggles, as it allows others to feel less alone and helps normalize the imperfect realities of life, even amidst outward success.
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