Welcome back to Season 2 of The Prosperity Playground Podcast!

We launch Season 2 with Alli Webb who is a visionary entrepreneur, bestselling author and the founder of Drybar, the category-defining blowout brand that grew into a nationwide phenomenon. Today, she’s back in founder mode with Messy by Alli Webb, her newest haircare brand built around embracing the hair you already have.

In this episode, we explore:

  • What happens to your identity after building and exiting a company that became deeply intertwined with who you are
  • Alli’s messy middle where she was experimenting, mentoring and investing before the vision for Messy dropped in
  • What has changed in product marketing, influencer strategy, gifting, PR and customer acquisition since the early Drybar days
  • Alli’s founder-to-founder advice on raising capital, proving a concept, starting smaller and creating real-world experiences that get people talking about your brand

This conversation is such a powerful reminder that your next chapter does not have to recreate your last one. Sometimes the vision becomes clearer when we release the pressure, stay close to what feels true and give ourselves permission to build differently.

If this episode resonates, make sure to share with your founder besties, and we thank you in advance for leaving us a rate & review!

Connect with Alli Webb:

Connect with Anna Lozano:

Founders Retreat in Mexico January 18-23, 2027:
 https://annalozano.com/pages/foundersretreat

Power Hour Business Advisory Session:
https://annalozano.com/pages/power-sessions

AI Employee Bootcamp & Automate to Accelerate Fall 2026 with Callan Faulkner:

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