The pivot was behind us. I couldn’t sleep, couldn’t relax, and was constantly on edge. CircleUp has built transformational tech and the team has helped hundreds of entrepreneurs thrive by giving them the capital and resources they need. 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. Grit (along with undeniable privilege) helped get me to where I am even though I have never been the smartest, tallest, or most skilled person in the room. There was no final straw at work; frankly the company was doing better than it ever had and my job was actually easier than it ever had been. When Dan asked me to step back — even just temporarily — I thought about how I had gritted out making the basketball team as a walk-on at Duke just months after double knee surgery and my doctor saying I needed to give up basketball. I read it on my phone and immediately said, “Damnit!” to my wife. Believing that to attract a great CEO we would need more than two years of runway, the board wanted us to raise a round. 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. 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. We raised the fund. We got the round done for CircleUp. During that time, we pivoted CircleUp away from the original marketplace. But as we pulled up to the hotel and I climbed out, he opened his door, stood up and gave me a hug. I feel thankful for the partnership that Matt, Andy, Dan, and other advisors and investors have given to CircleUp, and to me personally, for years. I feel fortunate to have had the chance to start CircleUp with such a fantastic cofounder, someone who placed our shared values and the Company’s mission above personal glory. I certainly wish I’d had examples to lean on. A redacted email written by CircleUp founder Ryan Caldbeck to an investor board member is the talk of Silicon Valley. Ryan Caldbeck, co-founder and CEO of investment crowdfunding platform CircleUp, recently shared his view on consumer trends for 2015. Sections of this page. I’ve worked on this transition for a while with my management coach, Ed Batista. CircleUp was founded in 2011 by ex-private equity professionals Ryan Caldbeck and Rory Eakin. I have changed nothing in the note (not even a typo) other than redacting email addresses. After more tests, the doctors assured me that this latest symptom was also unrelated to my cancer. He founded CircleUp after seven years as an investor with consumer product and retail-focused private equity firms TSG Consumer Partners and Encore Consumer Capital. I knew it would be a difficult transition for CircleUp, but I also believed it was the right move for the company as much as it was the right move for me. Former CircleUp CEO Ryan Caldbeck shares candid story on stepping down – Business Insider, Your email address will not be published. With limited precedent to guide me, I found the process extremely hard to manage, both logistically and emotionally. Ryan Caldbeck is on Facebook. It felt like that, with no end of dinner in sight and with much higher stakes than awkward small talk. And, for good measure, we had to get all of this done during a global pandemic. I want you to know that there are other founders/CEOs who feel that they have no choice but to “tough it out” in front of the teams, customers, or investors, despite what’s going on at home. Per Crunchbase, Jungju (Jay) Kim was the board partner for Collaborative's Series C investment in CircleUp. 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. I truly feel lucky for their help in steering the ship, particularly through difficult times, with skill, vision, patience, and resolve. In the email, Caldbeck recounts the toxic relationship with the board member that … @ryan_caldbeck 14 Apr For me the hardest thing about being a founder isn’t that any individual decision is complex, it’s amount of daily decisions and emotional roller coaster throughout. Lots of people have to deal with many things happening at once. As far back as college, I’ve made hard decisions with the goal of building a great family. In their minds, we wouldn’t be able to hire a new CEO until that was done, and doing both simultaneously would be impossible to get done in less than a year. I’m so sorry.”. ... SupportEdllc, CircleUp… We hired a fantastic president, Nick Talwar, who became CEO on October 13, the day I became Executive Chairman. And most of all I feel proud of my daughter for speaking her mind. CircleUp is an investment platform powered by technology. 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 … But if there’s any way to make these things worse it’s to ignore the warning signs. This will be the email address for receiving the Ticker emails. I believe hundreds of founders have their own version of this story, but it is rarely told. Maybe my experience means some VCs will not fund me again. If you are in this seat for long enough, it will happen to you. I feel insecure about my answer of “I don’t know” when asked what I’ll do next — that it will be viewed as inadequate. Equity. I don’t blame them. Finally I lost it, shouting, “Why aren’t you just saying ‘I’m sorry’ right now?” It wasn’t fair to them, and I’m not proud of it, but I cracked. We won't share or spam your email ever. Ryan received his MBA from Stanford and a dual BA from Duke. Email or Phone: Password: Forgot account? Accessibility Help. I think an element of my reaction is what Jerry Colonna calls “false grit” in “Reboot.”. I remember no one said, “I’m sorry” — they just processed the logistics with an icy, clinical precision that is probably required for someone to work in a cancer center. Prior to launch, CircleUp raised $1.5 million from investors such as Clayton Christensen, David Topper … But now I’ve now come to understand that persistence is a double-edged sword and my decision not to take a break to not take more off my plate hurt me my family and the company. 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. Press alt + / to open this menu. That’s why I’m writing this blog. So I felt I had no choice but to be a source of energy for potential stakeholders even though I barely had enough energy for myself. I feel appreciative of my family and parents for helping me dream and also pushing me to see that I needed to make changes to be happy. After we bought him out fully in 2019, I sent this feedback email detailing the ways in which he had disrupted our board and company. I’m not here to share a playbook — I don’t think one exists. Maybe it means I now have more empathy for entrepreneurs. One of the better books I’ve read is “Transitions” by William Bridges. There was no way to answer that other than to go by my own feelings. Throughout the entire Uber ride, my driver hadn’t said a word. CircleUp targets consumer facing companies on their platform. Ryan Caldbeck. Co-founder and CEO Ryan Caldbeck … Caldbeck was raising funding and running a startup while hiding his personal battle with fertility and brain cancer, which culminated into a dark period of mental health problems and extreme exhaustion. In hindsight I should have seen a psychologist to process what I was going through — the emotional toll was far worse for me than the physical. I’m not doing so to disparage the individual in question; the only objective is to help others who might find themselves in a similar situation. My personal obstacles were under better control and we now had an infant boy along with our daughter, who was three at the time. On a mission to help entrepreneurs thrive, CircleUp harnesses the power of data to provide capital and resources to emerging consumer brands. I need to come to terms with the end of my time as CEO, though I will still be here at CircleUp. Kim Caldbeck. Ryan Caldbeck, Co-Founder and … Now that I have a chance to reflect, my feelings are complicated. 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. Ryan Caldbeck: We believe strongly in curating the companies that are on our platform. I’m still here, just with far less stress. Facebook. But it was hard to turn away from persistence when it has been so crucial to any success I’ve achieved. I could have made it through for longer had I searched for help sooner — that isn’t bad luck, it was me choosing not to lean on a broader team to get through the hardest periods. This Week in Startups Jason speaks with CircleUp Founder Ryan Caldbeck about why he published a redacted version of an email to a reportedly difficult board member, CircleUp's cap table and timing, filling supply and demand for the fundraising marketplace, pivoting to raise a fund, why Ryan … For me, that happened in the fall of 2019. That’s a lot of one-in-a-million flukes.” I now had a six-month-old boy at home, a relentless fear of whether the doctors might have missed something and an ongoing slew of professional challenges to face. Who wants to invest in an unhappy CEO? 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. 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. Every day, Ryan Caldbeck and thousands of other … 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. I feel nervous about how people will interpret this transition and what narrative they will tell themselves (and others). At the time, I worried that the team would use my diagnosis as an excuse to throw in the towel, that my health would become a distraction, cause the company to fail and make things that much worse. We met with five or six of the best fertility clinics in the country. After the second they said: “Eleven doctors have looked at this and we have determined it is not cancer.” I assure you that wasn’t as comforting as it may now sound as it begs the question, “Why did you need eleven?”. I don’t know when that day will come. After the first MRI, they initially thought it had. Join Facebook to connect with Ryan Caldbeck and others you may know. Further, Collaborative Fund no longer lists CircleUp anywhere on its site. I was doing both — running a technology company while meeting with hundreds of institutional LPs around the world to raise a first-time VC fund. Slowly, reality began to sink in and the enormity of the word “malignant” hit me in full force. 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 prepped for the conversation with my management coach and some CEO friends, but I was still terrified of the potential reaction. Moments of happiness were fleeting. Still, in less than a year we raised a big round (not announced) on terms both we and the board were happy with. I’d never really heard her scared before, and I felt helpless being unable to do anything to change the situation. I later realized that the board interpreted my complaints as “typical founder/CEO exhaustion.” I blame myself for that lack of clarity. 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. We think that the investors that come to CircleUp are looking for really high quality investment opportunities, and we … The board wasn’t happy when I sent that email. In retrospect, I think I would have brought our company closer together by being vulnerable and authentic, and I certainly wouldn’t have felt as lonely. I disagreed: Even though I knew how difficult it would be to accomplish both tasks at once, I was confident it could be done. Conversely, Collaborative Fund led the Series C in November 2015. The people we let go had joined because they believed in our product and mission. 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. The doctors did two MRIs on my brain to see if the cancer had spread there. It didn’t matter: I could only feel pain. I cannot fully express how much I trust Rory and how valuable that trust has been both to me and to the business as a whole. Caldbeck signing the offer letter. Ryan served as CEO from 2012 through 2020. Ryan Caldbeck's stories. For me a perfect storm of personal problems unhappily coincided with some of the most critical business decisions and processes possible. I was losing control, and while she tried to be strong, I could hear the fear in her voice. I am relieved that I’m getting help in the form of a new CEO. Ryan served as CEO from 2012 through 2020. 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. Ryan Caldbeck is the founder and CEO of CircleUp, a San Francisco-based investment platform that harnesses the power of data to provide capital and resources to emerging consumer brands. Founder and Executive Chairman @CircleUp. Read writing from Ryan Caldbeck on Medium. Primarily, I feel so much pride in what the team has accomplished and have absolute confidence in the company’s bright future. CircleUp now boasts a new CEO with an incredibly relevant background and skill set and fresh legs to take the company to greater heights. A redacted email written by CircleUp founder Ryan Caldbeck to an investor board member is the speech from Silicon Valley. And if you ask me what’s after that, my answer is … I don’t know. 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). Caldbeck and his daughter. Two days later, I flew to a work conference in Anaheim, CA, while also trying to schedule further tests and treatment. It was hard for me to measure how much of my pain was because I had young kids at home, the result of specific business challenges or a classic case of founder/CEO exhaustion. I remember crying to the nurse as she drew blood. I even hid the information from all but a few friends, fearing that word might get out. Thread Reader Ryan Caldbeck. But I tried to put on a brave face to make sure the board felt comfortable. Then, suddenly, the major professional challenges were done. On October 13, 2020 I stepped down as CEO of CircleUp, the company I started in 2011 with my cofounder, Rory Eakin. 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. The combination of personal and professional stress was far beyond what I could handle. 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 … I feel fear in that I don’t know what’s next, even though I believe it’s healthy for me not to know. When I’ve talked about my journey in the past, I’ve had similar concerns, but these ones are greater. A few teammates tried to help me focus only on work that brought me joy, but I failed at that task. What is normal? Subscribe @ryan_caldbeck … My wife came in and I cried with her. “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,” he said. Dealing with this issue was one of the loneliest times I faced as a CEO. I am confident some, especially in VC, will inevitably view my story as a lack of grit. Still in shock, and with my hands shaking out of fear, I took the elevator to another floor for immediate tests — before I could even break the news to my wife. I was diagnosed with cancer. I think so, but I can’t know the answer to that any more than I can know how people will react to this account. (Nothing has been removed, including typos, from the email except for names.). She took this picture. 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. I absorbed very little pleasure from our wins, and quite a bit of pain from our losses. What she didn’t know — and what most people didn’t know — is that during that same 18-month window, I was also juggling personal challenges that were far more stressful than the hurdles at work. If you have friends in venture and it looks like a cushy job, see if they’ve raised a first-time fund. I barely drink, have never smoked or done drugs and work out five times a week. I remember a top VC, who was not one of our investors, posted something very positive about me and CircleUp online. They’ve developed game-changing machine … I’m trying to share my experience — the full and honest version — so that you hopefully don’t feel as lonely on your journey. Ryan Caldbeck. I don’t think so. But there was so much more to it than that. In October 2019 I told the board that I planned to transition out as CEO. Persistence was my superpower. For weeks at a time I had blurred vision. I want to share my experiences and vulnerabilities with full candor in the hope that other founders can have a resource that I lacked; that they can learn from my experience and feel less lonely than I have through this process. 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’ve also talked with countless CEOs (including my LIT group), friends, and advisors. Is that just bad luck? He then said: “Hey, I just want you to know I had the same type of cancer. So you can imagine how those fertility issues impacted me and my wife, Kim. Eventually I won’t be. Then we raised our first institutional VC fund (just one of the ways in which we monetize our tech). History. Since then, I have undergone regular testing several times a year. Could I have stuck it out if not for the personal issues? I told the board and my cofounder about my diagnosis, but no one else at the company knew. A great board member, Dan, called me to say, “Ryan, I’ve never in my career seen a CEO as worn out as you. CircleUp had just gone through our pivot and we were in the middle of raising that first fund and the parent company round. Another who gravitated to Latta’s vision was Ryan Caldbeck, founder and executive chair of CircleUp, which he described as an investment company powered by technology. But he was. Ryan Caldbeck is on Facebook. This Week in StartupsJason speaks with CircleUp Founder Ryan Caldbeck about why he published a redacted version of an email to a reportedly difficult board member, CircleUp's cap table and timing, filling supply and demand for the fundraising marketplace, pivoting to raise a fund, why Ryan stepped down as CEO, more - Link, 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 - Link, Creator support platform Patreon is considering an IPO as soon as this year, according to a source for The Information; the firm has had discussions with some blank check companies but would prefer to handle its own listing; Patreon’s annualized revenue has reportedly passed $100M - Link, UK-based IG Group (~$4.5B market cap) acquires online brokerage platform Tastytrade for $1B cash and stock; Tastytrade provides trade and investments content; IG Group notes the deal will help its expansion in the US - Link, The Bombay Stock Exchange and the Securities and Exchange Board of India (SEBI) say they do not object to a $3.4B arrangement that will see Future Retail sell assets to Reliance Industries; follows moves by Amazon to block the deal, citing its own agreement with Future Retail - Link, This Week in StartupsJason speaks with Frame.io CEO Emery Wells about how distributed work is changing the film industry, how production companies work, transitioning from filmmaking to running a software company, pitching to VCs for the first time, fielding a pre-launch acquisition offer, more - Link. Some were bad for @CircleUp , some were just […]" #Helio. I told my cancer doctor, “I like data. Eventually, we were blessed with our second child, but it was an extremely painful and isolating process. ... Ryan founded CircleUp after nearly seven years of investing experience in consumer product and retail-focused private equity. One of those tests revealed unexpected, terrifying information. CircleUp, an investment platform that targets early-stage consumer product companies, announced on Tuesday it has appointed Nick Talwar as its new CEO. 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. I’m sure I didn’t do everything right in executing my transition, but that isn’t the point. I don’t remember the first time I told our board that I was exhausted and needed to step down as CEO. Thread by @ryan_caldbeck: "1/ In honor of all the CEOs who have told me they are "crushing it," and that they “can’t keep up with the growth”ard just some of the many many mistakes I’ve made as CEO. And finally, I am thankful for a wife who encouraged me to follow my dream in 2011 and supported me throughout. Depression exacerbates exhaustion. He founded CircleUp after … They were necessary, but they were brutal. 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. The highs kept me going even though I knew the downs were unhealthy and untenable. 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.”. Ryan founded CircleUp … I only remember a pair of words from the first conversation with my doctor: “two tumors.” I struggled to process it at first. 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