Emily Oberg is Sporty & Rich: she owns 100 percent of the women’s athleisure brand she founded in 2018. Products and marketing draw heavily from her Ralph Lauren-esque lifestyle, which has built a loyal following with young, aspirational shoppers.
Until recently, however, the job of actually running the brand was handled by someone else. David Obadia, a Parisian menswear designer, served as chief executive from its earliest days until August, when Oberg replaced him in the top role (her previous title was founder and creative director). His departure was made public in January.
Oberg told The Business of Fashion she felt her brand’s operation needed an overhaul.
The business was in a good place: sales rose 10 percent to hit $35 million last year, spread between a store in New York and wholesale partners including Selfridges, Harrods and Revolve’s luxury arm, Fwrd. But behind the scenes, Oberg said she felt her 25-person team was too focused on brokering wholesale deals and needed to do more to ensure there was enough inventory to supply its growing list of retail partners.
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After consulting industry veterans like Aritzia founder Brian Hill, she felt she was the only person for the job. In an emailed statement, Obadia said he left because he felt that Oberg needed to be in full control as CEO to manage the brand’s growth trajectory.
“No one knows this brand better than I do. The identity is so tied to me,” Oberg told BoF. “It’s my business. I started it alone. I own it alone. It’s on me.”
Plenty of successful brands are run by their founders: Warby Parker is on pace to exceed $800 million in annual sales this year, with co-founders Neil Blumenthal and Dave Gilboa as co-CEOs.
But there are just as many, if not more, cautionary tales. Cami Téllez’s intimates label Parade was at one point seen as a Victoria’s Secret challenger; it sold in 2023 and was shut down last year. Outdoor Voices had a buzzy start under founder Ty Haney, but imploded amid accusations of mismanagement (Haney returned to the brand last year). The list goes on.
“Your vision, conviction and self-confidence is what tends to be the magic for these brands,” said Brandon Yoshimura, managing director in the consumer retail group at investment bank Solomon Partners. “That exact same single-mindedness and relentless pursuit of your dream can make it challenging to take advice or be receptive to outside ideas.”
Oberg’s decision to take the CEO role is all the more unusual in that she’s assuming leadership at the point when many founders step – or are forced – aside. She said her goal is to push Sporty & Rich to $100 million in annual sales within the next five years. That will require a vastly larger and more complex business: she plans to open stores in the US and Asia and introduce the brand’s first year-round collection this autumn.
Oberg knows there’s a high probability of failure in her new role. That’s one of the reasons she’s hired experienced executives from the likes of Aritzia, Ganni and Uniqlo.
“I don’t think the people that get you to $40 million are the ones who are gonna get you to $100 million,” Oberg said. “Now we’re on the right track and we have the proper systems in place, a proper infrastructure, a proper team.”
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Why Some Founders Fail as CEOs
When founders are incorporating their company and assigning themselves a role, many covet the CEO title, said Marissa Lepor, managing director at investment bank The Sage Group. It can also be a practical choice since a new brand often can’t afford to put an experienced veteran at the helm.
But the tenacity and instincts that motivates founders to “build something from zero” with a singular focus can turn into a liability if the needs of the business exceed their leadership capabilities, Yoshimura said.
“When you get to those points in a business evolution after you found your initial success … you either have to start building out skill sets around you to complement what you know, or you have to learn them really quickly,” he added.
Founders who take outside capital in the early stages of their business can also find themselves crumbling under the pressure to achieve rapid growth. Oberg said the potential for a fraught investor-founder dynamic led her to hold off on fundraising, which she hopes will insulate her from the fate of her peers who were ousted from the companies they started.
“Where the issue lies is when [founders] butt heads with the people who invest in the company, and there’s not a shared vision,” Oberg said. “I know we’ll get to $100 million, $200 million … But I don’t want to get there at the expense of not being able to build the brand that I set out to build from day one.”
How Founders Can Succeed as CEOs
When becoming chief executive, founders have to recognise their limitations and build a team to account for those blind spots, including experienced mentors they can defer to in high-pressure moments, Yoshimura said.
“Most of the great CEOs we know have a network of other CEOs, former founders, investors, advisors,” Yoshimura said. “They can pick up the phone and say, ‘Hey, I’m running into this issue. I’m guessing you’ve seen this before. What would you recommend?’”
For Oberg that mentorship has come from Hill, the Aritzia founder, who she connected with last July after he learned that she was a sales associate at the retailer as a teenager. After Oberg shared her concerns about her company’s operations, she ended up visiting Hill in Vancouver where he walked her through Aritizia’s organisational structure and advised her on how to reconfigure her own company, Oberg said.
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In the last two months, Oberg has hired 12 new employees, including a vice president of finance and operations from Ganni and a head of production from Favorite Daughter. Other hires include a head of retail and distribution from Uniqlo, who will spearhead the brand’s retail expansion, including its two-story 5,200 square-foot store in Los Angeles opening in March and a joint venture to open branded stores in China, Korea and Japan. There’s also a new head of merchandising from Aritzia who helped Oberg develop a year-round core collection of knitwear with more subtle logos than those on the brand’s popular fleeces. Those items will be sold alongside the company’s seasonal drops, Oberg said.
Fashion founders can also get distracted by creative elements of the business and fail to nurture and guide the teams responsible for the less-appealing operational parts of the company, Yoshimura said. They’re also their own bosses with a staff who aren’t always incentivised to offer critical feedback.
Oberg’s answer to that conundrum is ensuring she’s present for all staffers and encouraging them to take ownership of their work. Since becoming CEO she’s held daily meetings with all departments to know what they’re working on and how she can support them, she said.
“For me, it’s not getting mad at people or calling them out,” Oberg said. “It’s more like empowering people so they do feel like they have the kind of independence and the power to make decisions and create change.”
The surest path to success for a founder-turned-CEO is assembling all the tools they need and applying the same belief they had in creating their brand to their ability to manage their business long term.
“The common theme is … conviction and knowing where things are, knowing what the future can hold and believing you have a path to get there,” Yoshimura said. “You have to have a very broad set of capabilities, but you also have to want to do the job.”
