
Alli Webb on Building and Selling Drybar for $225M, Founder Evolution, and Building a Second Business
The Dream Bigger PodcastShow Notes
On today’s episode, I’m joined by Alli Webb for an honest, behind-the-scenes conversation about building Drybar from a single storefront into a $255M brand — and what it really takes to evolve as a founder. We break down how Alli identified a white space in the beauty industry, scaled a service-based business at lightning speed, expanded into product, and ultimately made the decision to raise private equity and bring in a CEO. She shares candid insights on fundraising, delegation, leadership growth, and the hard lessons that come with scaling fast. We also explore the emotional side of entrepreneurship — navigating divorce, loss, and personal upheaval while leading a company, the identity crisis that can follow selling your business, and how self-awareness becomes a founder’s greatest superpower. Finally, Alli opens up about starting over with her new brand, embracing natural curls after years as the “blowout queen,” and what she’s doing differently the second time around. Whether you’re building, scaling, fundraising, or redefining yourself after success, this episode is packed with real-world wisdom and founder truth. Enjoy!
To connect with Siff on Instagram, click HERE. To connect with Siff on Tiktok, click HERE. To learn more about Arrae, click HERE. To check out Siff’s LTK, click HERE. To check out Siff’s Amazon StoreFront, click HERE.
To connect with Alli on Instagram, click HERE. To connect with Messy on Instagram, click HERE. To shop Messy at Sephora, click HERE.
This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.
This FREE powerful manifestation guided audio will shift your energy FAST. Get a 14 day free trial and over 60% off for a limited time at www.activations.com/dreambigger. Discount only available through the website, not the app store.
Refresh your wardrobe with Quince. Go to Quince.com/dreambigger for free shipping on your order and 365-day returns. Now available in Canada, too. That’s Quince.com/dreambigger to get free shipping and 365-day returns.
Caraway’s cookware set is a favorite for a reason, it can save you up to $190 versus buying the items individually. Plus, if you visit Carawayhome.com/BIGGER you can take an additional 10% off your next purchase. This deal is exclusive for our listeners, so visit Carawayhome.com/BIGGER or use code BIGGER at checkout. Caraway. Non-Toxic kitchenware made modern.
Get started with the Experian App now!
Text DREAM to 64000 to get 20% off all IQBAR products, plus FREE shipping. Message and data rates may apply.
Use code DREAMBIGGER15 for $15 off first purchase at thirdlove.com
Produced by Dear Media
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
More from The Dream Bigger Podcast
On today’s episode, I’m joined by Colleen Forbes, founder of Linchpin and, more recently, Baloo Talent, to discuss the biggest hiring mistakes creators make and how to build a team that can support long-term growth. We dive into who creators should hire first, why building a strong operational foundation is essential to scaling, and how to identify the right people to help grow your personal brand. Plus, she shares her experience working with creators like Corporate Natalie and Tori Dunlap, why hiring friends can sometimes create complicated business dynamics, and how to approach compensation, contractors, and full-time employees. We also talk about the importance of delegating, creating clear job descriptions, finding the right cultural and behavioral fit, and balancing entrepreneurship with motherhood while running two businesses. Whether you’re a content creator looking to grow your team, an entrepreneur building a business, or simply interested in the behind-the-scenes of the creator economy, this episode is packed with practical advice on hiring smarter and building a business that can scale. Enjoy!
On today’s episode, I’m joined by creator and entrepreneur Tatyana Lafata to discuss the power of a holistic glow-up, building self-worth, and transforming your life from the inside out. We dive into her approach to wellness, gut health, hormonal acne, and the routines and supplements that have become part of her journey. Plus, she shares how navigating personal challenges, grief, and a major life transition helped her reconnect with herself and redefine what it means to truly glow up. We also talk about how she built a successful paid Substack community, why she believes Substack is a hidden goldmine for creators, and how she’s using AI to help creators grow their businesses beyond social media. Whether you’re interested in holistic beauty, wellness, personal growth, or building your own business as a creator, this episode is packed with insights on becoming the best version of yourself. Enjoy!
On today’s episode, I’m joined by celebrity dermatologist Dr. Sheila Farhang to discuss the latest in aesthetic treatments, skincare, and the future of beauty. We dive into how to choose the right laser for your skin, the truth about injectables like Sculptra and Botox, and why you shouldn’t blindly chase every new beauty treatment. Plus, she shares her thoughts on regenerative skincare, exosomes, the skin microbiome, melasma, and some of the biggest skincare trends she’s seeing right now. We also talk about how to approach aesthetic treatments safely, what to look for when choosing a provider, the skincare products worth investing in, and how to care for your skin during pregnancy. Whether you’re interested in skincare, aesthetics, anti-aging, or simply want to better understand what actually works, this episode is packed with expert advice and practical insights. Enjoy!
On today’s episode, I’m joined by Kira Mackenzie Jackson, beauty and marketing expert, to discuss building standout brands, creating strong communities, and the evolving role of influencers in brand building. We dive into why consumers can be your best creators, affiliates, and referrers, how to identify and build around a hero product, and why brands should focus on becoming a leader within their category before expanding too quickly. Plus, she shares her approach to influencer marketing, why creators are increasingly becoming investors in the brands they promote, how to build a strong and opinionated team, and what it really takes to scale successfully in retail. We also talk about using AI to work more efficiently, building a career while being a mom, and why you don’t have to do everything perfectly to be successful. Whether you’re interested in beauty, entrepreneurship, influencer marketing, or what it really takes to build and scale a lasting brand, this episode is packed with practical insights and advice. Enjoy!
On today’s solo episode, I’m sharing my postpartum playbook and taking you through my first month after having Reign. I dive into the systems I put in place before giving birth, from having full-time help and preparing meals to setting expectations with Nish and prioritizing sleep and recovery. I also share how I approached breastfeeding, getting back into movement, supporting my body through nutrition and supplements, and the postpartum routines that have helped me feel more like myself again. We talk about the importance of having a village, asking for help, creating systems that take decision-making off your plate, and giving yourself permission to prioritize your own recovery while caring for a newborn. I also open up about what the first few weeks actually felt like emotionally and physically, what surprised me about postpartum, and why I believe women deserve more support during this transition. If you’re pregnant, preparing for postpartum, or simply curious about what my first month of motherhood has been like, this episode is for you. Enjoy!