These Co-Founders Insisted on Being Co-CEOs Despite It Costing Them Funding

The co-CEOs of Harper Wilde, an intimate apparel company, share why they stuck to their unusual structure despite hearing they were making a huge mistake.
These Co-Founders Insisted on Being Co-CEOs Despite It Costing Them Funding
Image credit: Harper Wilde
5 min read

In the Women Entrepreneur series My Worst Moment, female founders provide a firsthand account of the most difficult, gut-wrenching, almost-made-them-give-up experience they’ve had while building their business -- and how they recovered.

When Jenna Kerner and Jane Fisher co-founded Harper Wilde, a company that sells intimate apparel through try-on-at-home model, they knew right away they wanted to share the title of CEO. But many people advised them that splitting chief executive duties and company equity would be a huge mistake and deter investors, signaling to the world that there was tension between them and that neither of them were willing to forfeit the role.

Ultimately, they lost funding from one prospective VC for this very reason. But they trusted their intuition that the co-CEO structure would work well for them and help them execute their vision for the brand. They did so despite the need for money and the pervasive wisdom that type of partnership wouldn’t be sustainable, looking to Warby Parker and The Skimm as successful examples. Now, years later, Kerner and Fisher are proud of their equal partnership, which they call a “relationship,”and the healthy debates they engage in to make decisions.

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What follows is a firsthand account of these women’s experience. This interview has been edited for length and clarity.

Kerner: “We were in the office with our team and in good spirits, since the deal was very close to being done. Then the investors asked us to clarify our relationship and responsibilities, which was odd, because that was something we had discussed very early on. We were very open and honest about being co-CEOs.”

Fisher: “Our pitch deck that we shared during the first convo clearly stated we were co-CEOs and how our responsibilities were divided up. It was tremendously hard in the moment to know what was more important to the company: Taking the money so we could ensure the company would continue to function, or not compromising and changing something as fundamental as the way our team worked.”

Kerner: “Looking back, there were signs. VCs had explicitly told us, “You’ll never be able to raise a seed as co-CEOs.” Hearing that there “can’t be” co-CEOs is a common trope. I tend to think that it allows someone to use a crutch without putting in the time and effort to understand what actually makes a particular business tick.”

Fisher: “We took some time to reflect on why were co-CEOs and why it works for us. We had to also take a different perspective and remind ourselves why investors may be pushing the issue, and try to better understand where they’re coming from and their rationale.”

Kerner: Sixty-five percent of startups fail because of co-founder issues. We weren’t going to be a part of that statistic. It drove me mad to think that investors could think that they know more about how our partnership should work than we do. We know it’s important to hear feedback from others, but in some instances, no one understands your situation as well as you do -- and no one is accountable and responsible for what happens to your company except for you.”

Fisher: “We explained to our team that we would wait for the right investor who supported us and what we believe is the best way to run our company. Luckily, even though it was upsetting, Jenna is really even-tempered, so she was able to do a great job explaining this to everyone with a pragmatic approach to the conversation.”

Kerner: “Jane tends to be really emotive, and is great at keeping the energy of the team up so no one gets too bogged down by a setback. I tend to be very rational and often very even-tempered when it comes to both setbacks and successes. We relied on the way we balance each other out to communicate the information to our team. There’s irony in there somewhere, I suppose.”

Fisher: “Even though it is inevitable that deals that fall through, that feeling of frustration can still take a toll on a founder. Being someone who can take a setback in stride and remain calm is one of the best ways that Jenna balances me as a co-CEO, because in that moment I was exasperated that they didn’t accept our team as is.”

Kerner: “For anyone in this position, it’s crucial to be clear on why a particular arrangement works for you. As with any business decision, you should be able to back it up with logic, reason and why it benefits the company overall.”

Fisher: “Only you know your company and relationships best. While there may seem to be a ‘typical’ way to do something, it isn’t always the most effective way for you and your team.”

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