As disparate as styling hair and making music videos may seem, both fields are highly competitive and high glam. It’s tough to make it, and even tougher to make it big. But improbably, that’s exactly what Alli Webb and Damian Kulash did, and in a similar fashion.
Webb is the founder of Drybar, a salon where you can buy just one service—a blowout—and Kulash, front man for the pop rock band and viral YouTube sensation OK Go. Their secret? Each honed an unusual expertise while surrounding themselves with a close-knit team, all of which enabled them to break through and realize success on a scale neither had ever envisioned
Recently, as part of a series of conversations between successful entrepreneurs called “Dreamers and Doers,” the powerhouse changemakers convened at Webb’s house in L.A. to discuss their unique and, at times, counterintuitive approach to their work, the need for continual risks, and the importance of having a trustworthy band of collaborators.
Mastering The No-Frizz Biz
South Florida’s suffocating heat and humidity made Webb’s childhood difficult in a way that only curly haired children know: frizz. “I always hated my curly hair and was mystified and obsessed with how anybody got soft, bouncy hair,” she recalls with a laugh. When she mastered blowing out her own hair into long, straight locks, she found a vocation that doubled as an obsession. Later, after becoming a hair stylist, she says, “blowing out hair was still the thing that was most exciting to me even when I was cutting hair.”
After settling in L.A. with her husband Cameron, she started a mobile styling service, Straight At Home, which was meant to keep her busy while allowing enough freedom to raise her two young sons. Webb was no stranger to entrepreneurship. Growing up, she had learned customer service dynamics and more at her parents’ clothing store. And she was good at it, which served her well as an entrepreneur. After word-of-mouth about her talent spread like Oscars gossip, Webb posited that women would like to come into a luxe environment to get their hair blown out instead of some strip-mall salon. She went to her brother Michael Landau and pitched him on creating a brick-and-mortar location.
Landau was all in and her husband signed on as creative director. With seed money from friends, family, and other angel investors, the trio opened their first salon in Brentwood in 2010. Customers loved the single-service approach and the luxurious feel of their yellow, creamy white, and gray décor palette. There was free champagne and 1980s comedy flick screenings overhead, and in no time Webb knew she had a hit. The overall salon experience was just as important as the stylist’s skill. As the volume for the hair-volume business increased, Drybar spawned several locations around L.A.
Next, Webb and her co-founders sought outside investment to grow faster. But those first venture capitalists and private equity investors dismissed the concept. “I remember thinking, “These guys do not get it, and this is not going to work,” she says. “[But] I always stuck to my guns. We do one thing really well, and that’s been the guiding light from the beginning.”
The key, she says, was seeking out investors who “got” them. She found that match in Castanea Partners, which had backed the edgy makeup brand Urban Decay. After that, Drybar really blew up. Webb, whose first location opened in 2010, now oversees a national chain of 100 salons that do more than 1 million blowouts a year.
Related Video: More with Damian Kulash and Alli Webb
In Tune With His Creativity
Growing up in Washington, D.C., Kulash had eclectic musical and artistic tastes. He was into bands from the city’s hard-core punk scene as well as Prince and Depeche Mode. But visual arts were also a passion. As a kid, he’d happily lose himself designing Lego structures. After college, in the early days of OK Go, he worked as a graphic designer at a digital advertising agency by day and a budding rocker by night. Since forming in 1998, the band has released four albums, but it’s best known for its innovative music videos.
In 2005, on a lark, Kulash shot a grainy video in his L.A. backyard of the band performing a complicated dance choreographed by his sister, a dancer, for their song “A Million Ways.” After sending the clip to a few family members and friends, he didn’t give it much thought. Eventually, though, he logged onto YouTube only to discover that their DIY video had racked up more than 4 million views. In an era where established artists still spent millions on an elaborate video, the band’s “happy accident,” as Kulash calls it, had attracted a huge audience without spending a penny.
Sensing an opportunity, Kulash and the band strategized their next creative move. Clearly, goofy choreography and dancing could help them get noticed. So for their next video, with the help of Kulash’s sister, they incorporated an unlikely dance partner, treadmills (to date, 2006’s “Here It Goes Again” has more than 50 million views).
The trick for Kulash and the band was avoiding a gimmick. The point, he says, wasn’t actually the dance. It was the joy and surprise they evoked by seeing the potential for choreography in unusual places (onboard a zero-gravity plane, 12 million views) and with unusual partners (a Rube Goldberg machine, 59 million views). Their videos attracted a loyal fan following that showed up for live shows where some of the choreography has become an integral part. “We realized that those little platforms for having fun were part of the job and, in fact, kind of the entire art form,” he says.
The Company They Keep
Of course, even mavericks can’t go it alone. Webb and Kulash both surrounded themselves with people they trusted—their family members and bandmates, respectively. But history is littered with ventures that failed because such groups couldn’t work together harmoniously. Keeping everyone in sync isn’t always easy.
Making it work has been a delicate dance at times for Webb. “I would lose my temper when I would go into a store and things weren’t the way I wanted them to be,” she admits. “I’ve been through a lot of coaching and conversations with my brother, who told me I needed a better way to deal with the things I was seeing. Because nobody sees the things that I see. Which is a great thing, but it’s figuring out how to make those changes more impactful versus making everybody crazy.”
While letting go took some work, each of Drybar’s founders largely sticks to their own areas of responsibility, she says. She manages the style decisions. Landau handles business operations, and Cameron is the creative mastermind. Having boundaries helps them avoid stepping on each other’s toes.
As for Kulash, he had to know that his bandmates were comfortable with the offbeat video routines and incorporating them into the band’s concerts. While auditioning new guitarists at one point, more than 30 candidates showed up. Most thought Kulash was kidding when he asked if they could do complex choreography while playing. The one who didn’t flinch, Andy Ross, is still with the band.
Now, Kulash spends time brainstorming pie-in-the-sky ideas and then marrying them with a methodical approach to production to ensure that the band doesn’t go bust. “You have to be ridiculous enough to be like, ‘Yeah, of course we can find a zero-gravity plane and get access to it for a month,'” he says.
For both Webb and Kulash, surrounding themselves with trusted squads has helped them make bold decisions that turned longstanding passions into wildly popular endeavors. At their core, both haven’t lost their dark-horse mentality, the opportunistic streak that created their first break.
“The model I used early on and basically still do, is that in the music industry and any creative industry, there are a million people wanting to do it for every one who gets to,” Kulash says. “So you definitely cannot miss any of your chances. Every opportunity you have, bring your A game and make something awesome.”
This story was created for and commissioned by Dark Horse Wine.