In Emotional Twitter Thread, CircleUp CEO Reveals ‘Burnout’ Is Behind His Decision to Step Down

“It has felt like bone on bone,” says CircleUp co-founder Ryan Caldbeck.

Ryan Caldbeck (Demetrius Freeman/Bloomberg)

Ryan Caldbeck

(Demetrius Freeman/Bloomberg)

CircleUp co-founder Ryan Caldbeck has opened up about the emotional hardship driving his decision to step down as chief executive officer from his firm, which backs consumer companies.

“Much of this I have never talked about,” Caldbeck, who is now executive chairman of CircleUp, said in a thread of Twitter posts Thursday. “Over a 12-18 month period that ended in late 2017 I ran my tank far beyond empty for far too long,” he wrote. “Worst year of my life. Since then it has felt like bone on bone.”

CircleUp had announced just two days earlier that Nick Talwar, who joined the San Francisco-based firm as president in July, would replace Caldbeck as CEO. Talwar was previously a partner at growth equity firm Apis Partners.

Over Twitter and in a Medium blog Thursday, Caldbeck described personal trials far tougher than the professional challenges of building a startup seeking to bring quantitative investing to private markets. He cited “brutal fertility issues” that he went through with his wife as well as a diagnosis of cancer that doctors, after “crippling headaches” and an initial MRI, worried had spread to his brain.

Fortunately, after a second MRI, the doctors determined it had not, according to Caldbeck, who wrote in his Medium blog that his cancer operation was successful. But by the end of 2017, the “normal” level of exhaustion he had found “exhilarating” as CEO had turned into “burnout and depression,” according to the Twitter thread and blog.

“Leaving the best job I ever had — at the company I helped to create — was difficult and confusing,” Caldbeck wrote in his blog. “I found surprisingly few first-hand accounts from founders or CEOs transitioning from their initial role, and even fewer that shared their full, authentic story of what really happened when they left and how they truly felt about the process.” Caldbeck said he chose to share his “experiences and vulnerabilities with full candor” to give other founders a resource he lacked.


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In December 2018, Institutional Investor reported on Caldbeck’s efforts at CircleUp, founded in 2012, to bring systematic investing strategies to private equity. The following year, he hired Neil Constable from GMO, the Boston-based investment firm co-founded by Jeremy Grantham, to help with its quant push. In February, Constable told II that CircleUp expected its systematic private equity fund to complete a first closing of $100 million before the end of June.

Constable left CircleUp in July to become of head of quant research for asset management at Fidelity Investments in Boston, according to his LinkedIn bio. CircleUp’s systematic fund will now become a “sleeve” in the firm’s second venture capital fund, which aims to raise $275 million, CircleUp CEO Talwar said Thursday in a phone interview with Institutional Investor. The systematic sleeve will represent 20 percent of the fund’s assets, he said.

Having worked with Caldbeck now for three months, Talwar described Caldbeck as “a very heart-centered person.”

“His leadership comes from a place of authenticity and courage and vulnerability like almost no one I’ve ever met,” Talwar said. “It challenges us all in our own way at the company to go to our edge and to reveal what is most authentic about us.”

In Caldbeck’s view, the future of CircleUp remains bright.

“CircleUp now boasts a new CEO with an incredibly relevant background and skill set and fresh legs to take the company to greater heights,” he said in his blog.