Drama, Health Challenges Revealed in CircleUp’s CEO Switch-Up

CircleUp, a fintech company that’s raised more than $250M between debt and equity, saw a change in leadership last week, with more than a fair share of transition drama. Co-founder and CEO Ryan Caldbeck stepped down, giving way to President Nick Talwar. 

After stepping down, Caldback took to Twitter and Medium, opening up in a 41 tweet story about why he chose to leave. A scathing private letter from Caldbeck to an unknown investor and chair of the board at CircleUp also circulated social media.

“I made many mistakes during this time, thinking I could just grit it out alone,” Caldbeck wrote. “I thought keeping everything to myself would allow me to handle the professional challenges more effectively. My approach was wrong.”

CircleUp is a tech-driven entrepreneurial investment company, known for supplying funding to consumer firms like Halo Top Ice cream. Caldbeck founded the firm in 2012 with Roy Eakin, as a platform to connect entrepreneurs to investors.

On Twitter, Caldbeck shared his internal hardships during the C Series pivot. Facing immense stress at work while his company pivoted, fertility troubles at home, and cancer diagnoses beginning around 2017 and continuing into the present, Caldbeck went from burnout to drawn-out depression.

“There’s no doubt my mental health was suffering during that period,” Caldbeck wrote. “Some think they have no choice but to ‘tough it out’ in front of the teams, customers or investors, despite what’s going on inside their heads because doubt isn’t respected in venture.”

Caldbeck said that the “normal level” of CEO exhaustion was something he thrived on, including catching sleep in the restroom in the spare minutes he had before board meetings. But when his fertility testing found cancer, and his stress brought headaches that were feared to be brain cancer, Caldbeck said even a papercut would set him off. 

Simultaneously, a board member at CircleUp was acting so disruptive that Caldbeck later complained that he was throwing the entire team off. Just this past week, Caldbeck sent an email that got shared all over the internet to that board member as advice, and in part retribution for how the investor acted.

According to Caldbeck’s letter, the disrupter invested their way onto the team and treated the rest of the board with disrespect. They talked down clients, disrupted meetings, projected insecurity and paranoia, and forced the sales team to market their stake when they wanted out.

“The data suggests that venting doesn’t actually help mental health- it hurts,” Caldbeck said. “I’m not writing this to vent, I am writing this because I am hopeful it will help future entrepreneurs you invest in.”  

While Caldbeck was facing cancer, the board member was reportedly putting down the entire company. Caldbeck said he should have seen a red flag that he didn’t even meet the investor before they were sitting on the board and that many other executives share his negative opinion. 

“Your involvement was incredibly difficult for all of CircleUp and our board,” Caldbeck said. “My hope is that over time you can process some of this information below and make the necessary changes if you decide to stay in venture.”

Luckily, his brain scans came back negative, and his cancer was removed by operation, and Caldbeck and his wife had a secound child. However, the 12 to 18 month period of exhaustion had taken its toll. Caldbeck had reached the end of his rope, signified when his five-year-old daughter said, “Daddy, you always look sad.”

In 2019, Caldbeck sent a letter to his board explaining his intent to step down, after serving as CEO since founding in 2012.

After a long transitionary period waiting for a replacement, Caldbeck finally shared his story, hoping to inspire other leaders to be open about their struggles and feel less alone. Nick Talwar, a 20-year industry vet, was hired as president of CircleUp in July. Caldbeck wrote that he is excited for the CircleUp team despite his time of struggle as he becomes the Executive Chairman.

“I feel immensely proud of what we have built at CircleUp,” Caldbeck wrote. “The team is truly extraordinary, and I think the technology (Helio) will transform consumer and private investing. We’ve helped hundreds of entrepreneurs to thrive, and we will help thousands more.”

Kevin Travers was a Reporter at deBanked.