Founding CEOs Join the Great Resignation

Ryan Williams announced late last week he will step down as CEO of Cadre, the New York City-based real estate investment platform he founded in 2014. He’ll become executive chairman, chairman of the board, and co-chair of the company’s investment committee. His replacement is Jared Kaplan, who most recently served as CEO of OppFi, a fintech platform that provides credit and lending products to banks.

Williams, 34, who appeared on Inc.’s 30 Under 30 list in 2017, says he’ll remain deeply connected to the company–he plans to work on expanding partnership opportunities like the ones recently inked with his alma mater, Harvard University, and BlackRock, for instance. He also plans to launch a foundation that he hopes will accelerate diversity in Cadre’s investor and partner base. The latter initiative sprang from Williams’s effort to cope with, and spur change, after the murder of George Floyd. Still, the decision to cede the CEO role, optically at least, is a big one–and few founders relinquish the title lightly.

“Look, I’m a hundred percent all in and focused,” says Williams, who seven months ago became a father for the first time. “Cadre is a huge part of my legacy, and I’ll be coming in every single day, when I’m not traveling, to meet with partners, and executing, hopefully better than ever before, to fulfill the promise to the business. That’s what it’s about.”

Williams is the latest in a string of entrepreneurs to give up the CEO title in recent weeks. Emily Weiss, 37, and Ryan Petersen, 41, both stepped down as CEOs of their respective beauty and logistics companies, Glossier and Flexport.

Petersen, on June 8, tweeted his reasoning behind hiring Dave Clark, formerly Amazon’s worldwide consumer chief, as the San Francisco-based company’s new CEO: “I’m now to the point where the only fear I have left for Flexport is that we’re not living up to our potential.” In a blog post on May 24, Glossier’s Weiss, who was preparing to go on maternity leave at the time of the announcement, said she plans to shift back into creative and brand strategy, which she sees as her strengths. She’ll cede the top job in the New York City-based company to Kyle Leahy, Glossier’s former COO. “With this CEO evolution, I’ll be able to focus more of my time as I did in the earlier days,” Weiss wrote.

Yes, these founders lassoed top-tier executives to help their companies scale, and they’re all becoming executive chairs of their respective companies. But they’re also doing so after two years of running companies during what can only be described as a universally dreadful pandemic that’s still spewing consequences across industries and locations. And it may be taking a toll. In the latest Small Business Index from the U.S. Chamber of Commerce, 50 percent of small-business owners say they are working more hours now than they were a year ago. Just 30 percent of business owners reported as much the last time this question was asked in 2017. 

Jeff Carr, a clinical professor of marketing and entrepreneurship at New York University’s Stern School of Business, suggests the stress of the pandemic has exacerbated issues that may have been present in the past but hadn’t surfaced before now. “I wouldn’t be the least bit surprised if over the past two years an awful lot of CEOs have realized they don’t have the skill sets necessary for keeping [their companies] growing, which is also why they’re working 50 percent more,” Carr says, and adds: “When things are going good, it doesn’t matter. When I don’t have all these big PR crises and supply-chain issues, you can always get around it; you’re growing, you’re building.”

Williams says his decision to relinquish the day-to-day reins comes down to divide and conquer. “I can’t do everything myself. I have learned no person can scale [an organization] based off self-determination alone,” he says. His successor Kaplan is a proven CEO who has inhabited various leadership roles including as co-founder of small-business insurance provider Insureon, which was acquired in May.

“I believe there are different archetypes of CEOs. There’s the big-picture, visionary builder archetype, and then there’s the more in-the-weeds tactical operations, scale archetype,” Williams says, noting that Kaplan is a unicorn in the sense that he fills both roles. “I’m thrilled and excited that we’ll have the operator and partner that we deserve.” 

One key focus area for Kaplan is Cadre’s plan to allow retail investors to tap into its network of commercial buildings and multi-tenant homes. The effort, which a source familiar with the company’s plans says could kick off as early as 2023, will expand Cadre’s addressable market from 15 million or so to a hundred-plus million. Currently, only accredited investors and institutions may invest in properties on the platform.

But that’s just part of the pie, says Williams. “We have an opportunity to transform hundreds of millions of people’s lives,” he says, nodding to Cadre’s mission of improving access to an entire asset class–real estate investment properties–that most people typically can’t touch. “I didn’t grow up owning real estate; I always rented. And I didn’t really understand the difference between renting and owning until I got to Harvard, which was a huge change and inflection point for me … I saw that there were so many people who had built wealth through ownership of real estate.” Which consequently made him wonder: “Why isn’t real estate a part of people’s 401(k)s?” It should be, along with other alternative assets, he adds.

And if Williams is not necessarily the only person responsible for making that happen, all the better, he says. “I want to ensure I can actually focus on delivering. I’m just not equipped to do that today. I just don’t have the bandwidth,” he says.