During that time, we pivoted CircleUp away from the original marketplace. For investors, vulnerability or burnout is often conflated with risk. I worry about whether I will ever do anything again that I feel as passionate about: being the founder and CEO of CircleUp is the greatest job I’ve ever had. A redacted email written by CircleUp founder Ryan Caldbeck to an investor board member is shining light on a dark corner of the venture world. 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. They had done nothing wrong, yet suddenly there was no longer a place for them. Who wants to invest in an unhappy CEO? This will be the email address for receiving the Ticker emails. Ryan Caldbeck is on Facebook. But as we pulled up to the hotel and I climbed out, he opened his door, stood up and gave me a hug. Eventually, we were blessed with our second child, but it was an extremely painful and isolating process. Could I have stuck it out if not for the personal issues? Would their perception of me be better if, instead of helping CircleUp pivot and leaving three years later, the company had failed in 2017? I thought about what I had said to Rory in 2011 when we were discussing the possibility of launching CircleUp: “I need you to know that I never give up.”. Eventually I won’t be. One of the better books I’ve read is “Transitions” by William Bridges. The highs kept me going even though I knew the downs were unhealthy and untenable. It didn’t matter: I could only feel pain. In a 30-minute Uber ride, I told my story multiple times over the phone to multiple administrators at multiple hospitals (for reasons that aren’t relevant to this blog post, my medical case was uniquely and extremely complex). The doctors did two MRIs on my brain to see if the cancer had spread there. I wasn’t misleading them about my belief in the business or my intentions going forward, but I was trying to mask the depression I felt. I explained that he couldn’t possibly know enough to mean these positive things, and his comments only made me wish that he genuinely did. One of those tests revealed unexpected, terrifying information. She turned to me and said, “I took this job over something that paid more, and now what should I do?” These agonizing decisions kept me up at night for weeks, and I know it was much harder on those affected. I even hid the information from all but a few friends, fearing that word might get out. Ryan served as CEO from 2012 through 2020. We think that the investors that come to CircleUp are looking for really high quality investment opportunities, and we … I wish I had found other stories about how the transition actually went and what it felt like. At times I thought I was sending up big red flares that I couldn’t sustain my pace, but others were just seeing the normal ups and downs of a founder. I feel nervous about how people will interpret this transition and what narrative they will tell themselves (and others). Ryan Caldbeck is the founder and Executive Chairman of CircleUp, an investment platform powered by technology. I truly feel lucky for their help in steering the ship, particularly through difficult times, with skill, vision, patience, and resolve. I told the board and my cofounder about my diagnosis, but no one else at the company knew. But I tried to put on a brave face to make sure the board felt comfortable. Ryan Caldbeck recently stepped down as the CEO of CircleUp after leading the fintech company for almost nine years. 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. Facebook. I barely drink, have never smoked or done drugs and work out five times a week. Ryan is the founder and CEO of CircleUp, an investment platform that provides capital and resources to innovative, early-stage consumer brands. He was named a “Titan of Retail” by Bloomberg, won the 2013 40 Under 40 M&A Advisor Recognition Award, and was a 2014 40 Under 40 San Francisco Business Times Honoree. I feel sad that my journey as CEO of CircleUp has come to an end. I hope that my candor helps others to feel more comfortable than I did asking for help and more willing than I was to confront feelings of loneliness and weakening stamina before they reach a breaking point. Persistence was my superpower. Once again, I’m not sharing this information because I think it was the perfect way to handle the situation, but so others might be able to learn from my experience. As far back as college, I’ve made hard decisions with the goal of building a great family. These symptoms were one-in-a-million flukes. Ryan Caldbeck, co-founder and former CEO of consumer-brands-focused investment platform CircleUp, recently published an email he’d written to a former director on the board of the … On a mission to help entrepreneurs thrive, CircleUp harnesses the power of data to provide capital and resources to emerging consumer brands. ... Ryan founded CircleUp after nearly seven years of investing experience in consumer product and retail-focused private equity. But he was. Still, in less than a year we raised a big round (not announced) on terms both we and the board were happy with. I only remember a pair of words from the first conversation with my doctor: “two tumors.” I struggled to process it at first. The job itself was nowhere near as difficult as it had been in the past, but depression and burnout can make even small challenges feel like a big deal. 17 min read On October 13th 2020 I stepped down as CEO of CircleUp, the company I started in 2011 with my co-fou n der, Rory Eakin. I don’t know how we raised a big round from world-class investors right after a pivot, but we got it done. I’ve worked on this transition for a while with my management coach, Ed Batista. The board wasn’t happy when I sent that email. The cancer diagnosis became even tougher to deal with because I mistakenly believed I shouldn’t discuss it with others. There were stretches of time where I felt horrible — lonely; terrified; depressed. And, for good measure, we had to get all of this done during a global pandemic. I imagine it was around 2016 or 2017, a period defined by stressful business decisions and physical and mental health issues. CircleUp had just gone through our pivot and we were in the middle of raising that first fund and the parent company round. Ryan Caldbeck. So you can imagine how those fertility issues impacted me and my wife, Kim. I don’t blame them. In it, he talks about becoming comfortable with living in the “nothingness” and saying, “I don’t know” when asked, “What’s next?” A successful and healthy transition requires one to live in the nothingness between the end of one period and the beginning of another. I had gotten to a place where I only focused on the losses and couldn’t accept positive things. By the end of 2017, I was completely worn out. I told my cancer doctor, “I like data. The people we let go had joined because they believed in our product and mission. Per Crunchbase, Jungju (Jay) Kim was the board partner for Collaborative's Series C investment in CircleUp. In the email, Caldbeck recounts the toxic relationship with the board … When I’ve talked about my journey in the past, I’ve had similar concerns, but these ones are greater. Ryan Caldbeck: We believe strongly in curating the companies that are on our platform. Subscribe @ryan_caldbeck … I prepped for the conversation with my management coach and some CEO friends, but I was still terrified of the potential reaction. After the pivot, after the layoffs and after raising that $125 million fund, we raised a meaningful round for the parent company from Temasek and TPG. What is normal? For years I did a poor job of communicating the depth of my stress and exhaustion, a problem only compounded by the fact that, at times, I wasn’t even sure of my own feelings. Then we raised our first institutional VC fund (just one of the ways in which we monetize our tech). Ryan Caldbeck's stories. CircleUp co-founders Ryan Caldbeck and Rory Eakin San Francisco-based CircleUp got started as a crowdfunding platform connecting food and beverage start-ups with accredited angel … To be clear, this email is unlike anything I’ve sent in my life, and I’ve thought long and hard about the decision to share it. CircleUp has built transformational tech and the team has helped hundreds of entrepreneurs thrive by giving them the capital and resources they need. They’ve developed game-changing machine … But 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. Please, you need to take a sabbatical — at least six weeks.” He, and other board members, tried so hard to do the right thing and convince me to take care of myself. best @Jason, founder, LAUNCH Ticker, Apple’s first VR/AR headset will be a high-price product aimed at a select market, according to Bloomberg sources; the company does not anticipate it will sell many units but will instead position it as a product intended to prepare developers and consumers for more mainstream devices in the future; Apple is set to launch the headset next year, with a primary focus on VR features; the company is also developing an AR-only device, but it’s not expected for several years -, One or several email addresses are invalid. I disagreed: Even though I knew how difficult it would be to accomplish both tasks at once, I was confident it could be done. I feel fear in that I don’t know what’s next, even though I believe it’s healthy for me not to know. Moments of happiness were fleeting. 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