I Sold Drybar for $255 Million... Here's How To Get Rich | Alli Webb

Ali Webb says Drybar grew from a personal need for fulfillment, not from a plan to build a large company or make a fortune. After roughly five years as a stay-at-home mother, she felt intellectually underused and wanted something of her own; she says the later breakdown of her marriage may also have been part of that search for something missing.

Webb had spent years working in salons before starting a mobile blowout business in Los Angeles. She drove from client to client with brushes and blow dryers in a duffel bag, charging about $40 for an at-home blowout when comparable services could cost roughly $150–$200.

The mobile business became Drybar’s proof of demand. Webb became busy so quickly that she had more clients than she could personally serve, but rather than build a network of mobile stylists, she decided the concept should become a physical location.

Her brother Michael became the key business partner and helped finance the first store. Webb describes him as her partner across her ventures; his strengths were finance, leases, negotiations and business operations, while hers centered on the customer and hair experience.

The original concept deliberately separated blowouts from traditional salon economics. Conventional stylists often priced blowouts high because an hour spent blow-drying could otherwise be used for more lucrative cutting or coloring; Drybar instead made blowouts the entire business.

Webb says her naturally curly hair helped shape the idea long before she became an entrepreneur. She had always wanted an accessible place devoted to making hair look good without requiring a cut or color and was surprised nobody had built the concept at scale.

Drybar opened into the aftermath of the 2009 recession with a $35 price point. Webb and Michael calculated that the first eight-chair Brentwood location might need roughly 30–40 blowouts per day to work and could theoretically handle close to 100 at full capacity.

Demand immediately exceeded those expectations. Within roughly a week, the first location was doing around 70–80 blowouts a day, forcing Webb herself into the first chair and leaving the company scrambling for enough stylists.

That early volume was the moment Webb realized the idea could become much larger. Traditional salons usually needed time to build a clientele, whereas Drybar opened to unusually intense demand almost immediately.

Webb attributes part of the founders’ retail instincts to watching their parents operate clothing stores. She and Michael had grown up seeing customer service and physical retail firsthand.

An architect connected to Michael helped turn the service into a deliberately designed experience. He introduced Webb to the idea of “surprise and delight,” and Drybar carefully managed music, décor, transitions between rooms and even bathrooms designed attractively enough that customers would photograph themselves there.

Drybar’s original positioning was “affordable luxury”: premium surroundings without a premium salon price. Webb wanted stores to look expensive and polished while still feeling approachable rather than intimidating.

That positioning was partly a response to Webb’s own discomfort in upscale salons. Having lived in New York and Los Angeles, she remembered feeling judged or insecure in expensive salons and specifically wanted Drybar to avoid making customers feel that way.

The $35 blowout also fit recession-era spending behavior. Webb observed women reducing $300–$500 cuts and color services while still buying smaller indulgences; a good blowout could temporarily make hair look refreshed without the larger expense.

Customer frequency varied dramatically, and the heaviest users became especially valuable. Many clients came every few weeks or once a month, while some visited two or three times a week and effectively stopped washing and styling their own hair.

Webb resisted expanding Drybar into nails, lashes, makeup and other beauty services even when investors pushed for it. By the time the company had roughly six or seven stores, investors saw about 100 women per store per day and believed the audience could support many additional services.

Her reason for refusing diversification was quality, not lack of opportunity. She knew hair deeply enough to enter a store and quickly recognize when a customer was unhappy with her blowout; she did not believe she had equivalent expertise in nails, lashes or makeup.

Webb believed adding services could turn Drybar from exceptional at one thing into merely adequate at several things. She compares the philosophy to In-N-Out Burger: offer a narrow product and make that product unusually good.

She was willing to reject investors who did not accept that focused strategy. If a prospective financial partner kept pushing Drybar toward multiple services, Webb viewed that as evidence the investor was not aligned with the company.

The greatest constraint on Drybar’s growth was labor, not customer demand. The company was perpetually trying to recruit enough stylists while maintaining the quality required to protect the brand.

Drybar built a substantial training operation because many incoming stylists were not immediately ready for the floor. Webb describes an ongoing tension between managers wanting more stylists working to increase revenue and her insistence that nobody serve customers before meeting the company’s standards.

At its peak, Webb estimates Drybar had roughly 5,000 stylists. Elsewhere in the interview she estimates the broader workforce may have reached roughly 5,000–8,000 employees, illustrating the operational burden of a seven-day-a-week service company.

Webb considered creating a dedicated school to train Drybar stylists from the beginning. Bureaucracy, regulatory red tape and limited organizational bandwidth prevented the idea from becoming a major initiative.

The inability to open stores quickly enough helped create Drybar’s product business. Webb realized customers without a nearby location could buy the same tools and products used in stores and learn to recreate the looks themselves.

Her first book, The Drybar Guide to Good Hair for All, was built around that same idea. It offered tutorials on techniques such as styling bangs and recreating Drybar looks at home.

Webb says raising outside capital was necessary to exploit the opportunity quickly enough, but she now wishes she had retained more equity. She does not describe the fundraising strategy as a mistake, but the eventual sale made the cost of dilution much more tangible.

She and Michael repeatedly debated the tradeoff between owning a large percentage of a smaller company and a smaller percentage of a much larger one. Webb contrasts Drybar’s capital-intensive expansion with founders who remain more heavily bootstrapped and hold their businesses for much longer.

Copycat blowout businesses were a major reason Drybar felt pressure to raise money and accelerate expansion. Heavy press coverage created both enormous demand and many competitors, and the founders feared a better-funded imitator could open locations faster than they could.

Webb believes organic expansion would have taken roughly twice as long. Early stores cost around $500,000 to build and later locations could approach $1 million, making rapid national growth difficult without substantial outside capital.

The founders initially hoped to raise roughly $10 million to $15 million, but their first major financing became about $26 million. Webb says the private-equity investors wanted to deploy more capital; some of that money was also earmarked for the product business.

The founders used to talk about selling within three to five years, but the company remained under their ownership much longer. By year seven they were still building, and the eventual exit occurred almost exactly a decade after Drybar began.

Webb’s attitude toward copycats changed substantially over time. Initially she monitored them closely, lost sleep over them and became angry when people copied the concept.

One customer learned extensively about the business directly from Webb and then opened a similar operation outside San Francisco. The woman later emailed Webb to disclose what she had done, which Webb remembers making her extremely angry at the time.

Webb eventually concluded that Drybar’s real protection was execution rather than the basic idea. Competitors could copy the concept, but she believed they consistently missed details such as stylist training, lighting, music, service and the overall customer experience.

Customers themselves reinforced that conclusion. Webb says clients sometimes told her they had visited “the copycat” when Drybar was fully booked but found the experience inferior; she could usually identify why based on the competitor’s execution.

Copycats eventually became useful in markets where consumers did not yet understand what a blowout was. Competitors entering those cities first educated customers and changed behavior, allowing Drybar to arrive later with an already-developed market.

Webb still drew a line at businesses using Drybar’s name, identity or her own image. She says numerous cease-and-desist letters were issued, and some operators went so far as to use Drybar-related names or photographs of Webb on their sites.

Webb views obsessive attention to detail as one of Drybar’s strongest competitive advantages. Her operating philosophy was that taking a customer’s hard-earned money created an obligation to make every part of the experience as good as possible.

She argues that a strong concept can still fail through weak execution. Dirty spaces, bad music, disengaged employees or neglected details can undermine an otherwise attractive business.

Drybar ultimately used both company-owned locations and franchises. The early Los Angeles stores were corporate-owned, while markets including Dallas and Arizona used franchising to expand the brand without Drybar funding every location itself.

Franchising solved a capital problem but created a control problem. Franchisees were entrepreneurs with their own ideas, while Webb wanted them following Drybar’s established operating method; she describes managing corporate stores and a franchise system as effectively running two different businesses.

At the time of the sale, Drybar had about 150 locations, with Webb estimating roughly 70 company-owned stores and the remainder franchised. The company was more willing to franchise isolated markets such as Louisville, while dense strategic markets such as Los Angeles—where it had roughly 25 locations—received greater direct attention.

Site selection became more difficult outside markets Webb knew personally. In Los Angeles she intuitively understood customer behavior, but expansion required local real-estate knowledge and detailed understanding of how women moved through each neighborhood.

A Long Island location became a costly lesson in seemingly small accessibility differences. Drybar chose between two shopping centers and picked the one that proved harder to reach and park at; despite the alternative being nearby, customers naturally preferred the easier location, making the Drybar store much harder to grow.

The company preferred locations embedded in customers’ ordinary routines rather than pure destination sites. Webb wanted Drybar near businesses such as grocery stores, nail salons and fitness studios so customers could incorporate a blowout into activities they were already doing.

Webb treated investors as long-term operating partners rather than interchangeable sources of money. She compares taking investment to a marriage and says misalignment on the fundamental vision could become disastrous.

Drybar abandoned one financing deal at the eleventh hour after a trusted insider warned the founders against it. Their lawyer and friend Jeff, who with his wife was involved with the Dallas business, sent what they called a “Jerry Maguire” message arguing that the prospective partners were wrong for the company.

Walking away meant restarting a long and exhausting financing process, but Webb believes it was preferable to accepting the wrong partner. Drybar subsequently completed its roughly $26 million financing with the private-equity partner she identifies in the interview as Castanea, later Stride.

A later investor brought specific franchising experience through work with scaled concepts such as Orangetheory. Webb viewed the different investors’ skills as complementary rather than choosing purely on who offered capital.

Webb initially felt intimidated in private-equity boardrooms despite being the founder whose idea had created the company. She says she grew up in an era with relatively few visible female entrepreneurs and had internalized the idea that men were the people who ran major businesses.

Michael actively encouraged her to speak in meetings instead of deferring to financiers and executives. Webb sometimes texted questions to him under the table, and he would tell her to ask them herself.

Investor Steve Berg also explicitly reminded Webb that everyone in the room was there because of her idea. She credits that kind of support with helping her become more confident about asserting her knowledge and authority.

Webb says supportive men were important to her leadership development rather than describing her experience solely as conflict with male executives. She specifically mentions Michael, investor Steve Berg and later CEO John Hefner as people who encouraged or respected her leadership.

That confidence issue resurfaced when Webb started her new hair company, Messy. She initially expected Michael to be CEO and told a female-founder friend she did not think she was suited to the role because she was not strong at numbers and spreadsheets.

A friend challenged Webb on why she should not be CEO of the company she was actually leading. Webb says this contributed to a broader shift in which she recognized that some of her hesitation came from ingrained assumptions about who a CEO was supposed to be.

Webb and Michael ultimately became co-CEOs of Messy. She says it took years to fully “step into” her authority and hopes other women and girls see that they can occupy the top role themselves.

The hosts describe Webb’s Drybar exit as a $255 million transaction, which she accepts in the conversation. The sale occurred almost exactly ten years after the company started.

The business sale coincided with an extraordinarily difficult period in Webb’s personal life. Around years seven and eight, her marriage was ending, her 13-year-old son was struggling and entered rehab, and her mother died while Drybar was simultaneously considering outcomes including an IPO or private sale.

Those personal crises meant Webb was less involved in the sale process than outsiders might assume. The board, CFO, CEO and Michael largely drove the transaction, while Michael kept her updated on developments.

Webb estimates the sale process itself took about a year. By the time it closed, she felt emotionally ready to leave after a decade of building the company.

The transaction closed around the end of February or beginning of March 2020, immediately before COVID dramatically disrupted normal life. Webb says the timing intensified an already difficult transition.

The unexpected consequence of selling was a major identity crisis. She remained Drybar’s founder, but losing her everyday connection to the company left her asking who she was and what she should do next.

Her second book, The Messy Truth, became a way to process both the business and personal experience. Webb never attended college or earned a degree and felt that building Drybar had effectively given her a practical graduate education in business, so she wanted to document what she had learned.

Webb spent roughly five years trying to find the right next chapter after Drybar. She experimented with other businesses and joined boards, only to discover that hours-long meetings dominated by numbers did not play to her strongest skills.

She ultimately concluded that customer experience, product and brand building were her real strengths. That realization helped lead her back into hair with Messy.

Webb strongly prefers the operational structure of a product company to running 150 physical stores. Drybar’s thousands of employees and seven-day operations meant her phone was almost constantly active; a product company can scale without the same labor burden.

She had already discovered during Drybar that she loved building physical products. Product development turned out to be a capability she did not initially know she had, and Messy lets her return to that work with a much smaller operational footprint.

The name Messy combines Webb’s personal story with a major change in how she treats her own hair. After publicly discussing divorce and family difficulties, she increasingly embraced imperfection and found that women responded strongly to the honesty.

Webb intentionally wrote about her son’s difficulties and treatment despite initially feeling ashamed that her successful public image did not match what was happening privately. She says he spent almost two years in rehab, and the family went through extensive turmoil and therapy.

She included that experience because she believed other families were suffering through similar issues in silence. The large number of messages she received from women and families reinforced her belief that discussing difficult subjects openly was useful.

COVID also changed Webb’s relationship with her naturally curly hair. Staying home led her to stop getting blowouts, experiment with her curls and eventually embrace a looser, “messier” appearance; she says she no longer gets blowouts herself.

That overlap between an imperfect personal life and less-controlled natural hair became the conceptual basis for Messy. The brand is meant to give women permission not to look perfect and to work with the hair they already have.

Webb took the Messy concept directly to Sephora. She pitched products and education centered on embracing natural hair and imperfection, and says Sephora agreed there was an underserved opportunity.

At the time of the interview, Messy had just launched and was exclusive to Sephora across its stores. Webb identifies the brand’s social handle as “itsmessy” and says Messy is her main current project, while also mentioning other projects that were not yet ready to discuss.

Webb was invited onto Shark Tank through an unsolicited call rather than through her agent. The showrunner, Clay, had seen her on the cover of Inc. and told her the program wanted more female sharks.

Her first reaction was to decline because she felt intense impostor syndrome. She worried about appearing alongside experienced investors and specifically doubted her ability to calculate valuations quickly on camera.

The production reassured her that she could sit beside Mark Cuban, and observing the set changed her confidence. Webb found the other sharks welcoming and concluded she was capable of doing the job.

She was explicitly told that succeeding on the show required interrupting and speaking up. Webb replied that strong opinions would not be a problem, and off camera she sometimes asked Cuban to help her quickly work through the numbers before responding.

Although the interview asks what Webb specifically looked for when investing on Shark Tank, her answer never develops into a clear set of investment criteria. The discussion instead focuses on how she was recruited, overcame intimidation and operated on set.

Webb believes family and close-friend partnerships work when responsibilities are clearly divided. At Drybar, Michael handled numbers, leases and negotiations; Webb handled the customer-facing experience, products, training and service; her then-husband was the principal brand and creative specialist.

When the founders disagreed, the person whose area of expertise was involved generally received the final call. Webb believes partnerships become much harder when several partners want the same role, status or responsibilities.

She also rejects “yes-man” cultures. Webb recalls employees withholding bad news because they wanted to protect her and told them she needed the full reality of the business in order to lead it properly.

Webb now has zero involvement in Drybar and says she was not invited to remain involved after the sale. She admits feeling hurt or offended by that, even while recognizing that a buyer has the right to change a company after acquiring it.

She says she receives frequent messages from customers telling her Drybar is “not the same anymore.” Webb believes some change was inevitable once a highly founder-driven business was no longer led by its founders, though she still wants the company to succeed because it remains part of her legacy.

Webb has not entered a Drybar location in roughly five years, including newer international locations. She says she does not think she could comfortably watch details being handled differently when she no longer has the authority to correct them.

Her perfectionism around store execution was intense even when she still owned the business. CEO John Hefner sometimes had to help her moderate her reactions when she entered a store and immediately noticed dozens of details that did not meet her standards.

Webb prefers to remember Drybar at its peak rather than closely inspect what it has become without her. She describes herself as emotionally detached while still loving the brand, taking pride in it and wanting it to prosper.

The decision to hire professional CEO John Hefner originally came from Drybar’s private-equity investors, not from Webb. During the first major financing they told Michael that a company becoming this large would probably eventually need a more experienced professional CEO.

Webb initially fought the idea because she feared an outside executive would destroy the company’s founder culture and diminish Michael’s role. She later says that fear proved wrong.

Hefner won her over because he understood founder-led organizations rather than approaching Drybar as a conventional corporation. In his early conversations with Ali and Michael, he described the three of them as a “three-legged stool” and consistently respected Webb’s vision.

Webb’s main leadership advice is to “lead with kindness.” She says early in Drybar she thought leadership required having every answer and projecting strength, but later concluded that treating people well and caring about the mission mattered more than appearing all-knowing.

She explicitly rejects money as the ultimate purpose of entrepreneurship. Her view is that if founders do not love the work, the mission or the people around them, financial success by itself is not enough.

Webb says she wants to be remembered first as a great mother. Beyond that, she hopes her business legacy is helping create a path for more female entrepreneurs and being a strong female leader who was willing to take the risk and build something new.