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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode, we sit down with Alli Webb, the powerhouse entrepreneur, New York Times bestselling author, and founder of the $100M+ brand Drybar. Alli opens up about her early struggles, what led her to build a beauty empire from a simple idea, and how she's now channeling her energy into her new venture: Messy — a platform all about life's beautifully imperfect journey. From single motherhood and burnout to scaling a household name and rediscovering herself, Alli's story is a raw and inspiring masterclass in resilience, reinvention, and living life on your own terms.
Follow Us: 📲 OMAR's IG: https://www.instagram.com/omar_therockstar/ 📲 ALLI's IG: https://www.instagram.com/alliwebb/
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Timestamps: 00:01:47 – Omar introduces the amazing founder of Drybar and Messy 00:03:05 – How Drybar Was Born 00:06:20 – Childhood, Creativity & Family Lessons 00:08:45 – From Stylist to Startup Founder 00:11:50 – What Made Drybar Take Off 00:14:30 – Juggling Marriage, Kids & Business 00:17:10 – Her Take on Being a Female Founder 00:20:40 – Co-Founder Dynamics & Divorce 00:24:15 – Therapy, Self-Discovery & Rebuilding 00:27:25 – Lessons From Scaling Drybar to $100M+ 00:31:00 – Why She Stepped Away From Drybar 00:34:40 – Rediscovering Herself & New Joy 00:38:20 – Parenting Teenage Boys in a Digital Age 00:41:00 – Dating, Remarriage & Evolving Identity 00:45:00 – Alli's Take on Burnout & Boundaries 00:48:35 – Biggest Misconceptions About Success 00:52:10 – Alli's Advice to Entrepreneurs 00:55:20 – Learning to Love Again After Divorce 00:58:10 – How Alli Found Her True Self 01:01:15 – Lessons From the "Messy Middle" 01:04:50 – On Building Empathy & Leadership 01:08:05 – Her Daily Habits & Wellness Routines 01:11:40 – What Alli Would Tell Her Younger Self 01:15:00 – On Legacy, Motherhood & Mentorship 01:18:10 – Rapid Fire: Love, Growth, Faith & Failure 01:21:55 – Outro & Thank You
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