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Drybar Founder Tells ALL Her Secrets! “Trusting My GUT Made Me $255 Million” | Alli Webb

Today, I have the pleasure of hosting the remarkable Alli Webb as we delve into her journey to becoming a successful entrepreneur.

Alli WebbguestJay Shettyhost
Nov 10, 20231h 27mWatch on YouTube

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At a glance

WHAT IT’S REALLY ABOUT

Alli Webb on gut instinct, messy success, and staying whole

  1. Alli Webb describes her path to founding Drybar as an “unlikely entrepreneur,” starting with a mobile blowout side business that grew through word-of-mouth and led to opening a first location.
  2. She distinguishes intuition from delusion by emphasizing the importance of getting quiet, noticing bodily signals, and not ignoring red flags, which she says later become key lessons.
  3. She argues that entrepreneurship is inherently messy and requires taking practical next steps, accepting uncertainty, and embracing imposter feelings as a sign of growth and beginner’s mindset.
  4. She shares how learning to receive feedback—especially uncomfortable feedback about her leadership presence—helped her mature personally and professionally and build healthier dynamics.
  5. Alongside business lessons, she discusses relationships, divorce, shame, and grief, explaining how success can coexist with personal unraveling and how she is working to stay whole while pursuing love and purpose.

IDEAS WORTH REMEMBERING

5 ideas

Intuition is listening; delusion is overriding red flags.

She described intuition as a clear internal “ping” you can sense when you get quiet, while delusion shows up as pushing forward despite warning signs. She also reframed mistakes and ignored red flags as “gifts” that become lessons in hindsight.

Big outcomes can come from small, practical next steps.

She emphasized that Drybar began as a small next step from a mobile blowout service, not a grand plan for “world domination.” She framed the early mindset as focusing on what felt right, learning as she went, and trusting she’d figure it out even if it didn’t work.

She credits passion and service—more than money—as the fuel that sustained the business.

She said she didn’t build Drybar by chasing money, and noted that for years she didn’t take much salary because she simply loved the work. The internal driver was enjoyment and service, with money as a secondary result rather than the primary goal.

Imposter feelings can be evidence of growth—and a cue to stay teachable.

She explained that feeling like an imposter often means you’re in a new environment where growth is happening, and that she routinely took roles where she felt underqualified and then learned quickly. She also highlighted the freedom of saying “I don’t know” and asking others what they think to build a healthier culture.

Feedback reveals blind spots that passion and perfectionism can hide.

She shared a painful piece of feedback from her brother that “people are scared of you,” rooted in how she would enter stores and immediately notice everything wrong. Over time she learned to take notes, avoid “ruining everybody’s day,” and value feedback as a gift even when it stings.

WORDS WORTH SAVING

5 quotes

I think delusion is maybe ignoring red flags.

— Alli Webb

I'm a little bit of like the ignorance is bliss mentality because I feel like the less you know about what you're getting yourself into...

— Alli Webb

There's so much freedom in saying, "I don't know."

— Alli Webb

No one's gonna die if this business doesn't work.

— Alli Webb

I don't think it's mathematically, spiritually, emotionally possible for someone to master every area of their life perfectly at all times.

— Jay Shetty

Read the available transcript
Starting small and taking the next stepMobile blowout business to first locationIntuition vs delusion and red flagsMoney vs passion as motivationImposter syndrome and beginner’s mindsetReceiving feedback and leadership presenceDivorce, shame, grief, and identity

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SPEAKERS

  • Alli Webb

    guest

    Founder of Drybar and New York Times bestselling author of "The Messy Truth."

  • Jay Shetty

    host

    Host of "On Purpose," author and former monk who interviews guests on wellbeing and purpose.

High quality AI-generated summary created from speaker-labeled transcript.

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