Anger, frustration, fear, confusion — there were so many feelings to contend with. Required fields are marked *, An early bitcoin investor says the best time to buy is when nobodys talking about it – and warns this isnt the first crypto bubble, Demi Lovato & Ariel Pink Take Two Very Different Paths to Ridicule, Biden is an avid Peloton user, but his bike is creating a security headache at the White House – Insider, Snapchat makes overnight millionaires with Spotlight creator fund – Business Insider, Visit Business Insider’s homepage for more stories. 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. On October 13, 2020 I stepped down as CEO of CircleUp, the company I started in 2011 with my cofounder, Rory Eakin. Further, Collaborative Fund no longer lists CircleUp anywhere on its site. Then I walked outside the UCSF hospital, hid behind a concrete pillar, and finally called my wife. 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. 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). By Ryan Caldbeck on July 30, 2020. I told my cancer doctor, “I like data. My only hope is that it might help other founders feel less alone. Ryan Caldbeck: We believe strongly in curating the companies that are on our platform. The highs kept me going even though I knew the downs were unhealthy and untenable. I don’t know when that day will come. The people we let go had joined because they believed in our product and mission. As far back as college, I’ve made hard decisions with the goal of building a great family. This will be the email address for receiving the Ticker emails. Facebook. And if you ask me what’s after that, my answer is … I don’t know. CircleUp was founded in 2011 by ex-private equity professionals Ryan Caldbeck and Rory Eakin. And finally, I am thankful for a wife who encouraged me to follow my dream in 2011 and supported me throughout. 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. It didn’t matter: I could only feel pain. 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. He founded CircleUp after … I disagreed: Even though I knew how difficult it would be to accomplish both tasks at once, I was confident it could be done. For investors, vulnerability or burnout is often conflated with risk. I think an element of my reaction is what Jerry Colonna calls “false grit” in “Reboot.”. I feel excited about our roadmap. We met with five or six of the best fertility clinics in the country. 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. Ryan Caldbeck is planning a quant fund for private markets — a move that could (if they noticed) worry Henry Kravis, Steve Schwarzman, and the pioneers of private equity. Join Facebook to connect with Ryan Caldbeck and others you may know. 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. By the end of 2017, I was completely worn out. Moments of happiness were fleeting. First, I am transferring to a full-time executive chairman role at CircleUp. I only remember a pair of words from the first conversation with my doctor: “two tumors.” I struggled to process it at first. I couldn’t sleep, couldn’t relax, and was constantly on edge. They tried to convince me to stay, but I made it clear that wasn’t an option, that this wasn’t about any issue other than my mental wellbeing. Accessibility Help. The combination of personal and professional stress was far beyond what I could handle. At the time, I told a teammate that it felt like I was playing seven-dimensional chess because of the complexity of the negotiations combined with so many conflicting challenges at work. One of those tests revealed unexpected, terrifying information. I feel frustrated that there are things I could have and should have done differently. Follow me on Twitter @ryan_caldbeck. And, for good measure, we had to get all of this done during a global pandemic. About a year and half ago, Caldbeck … Depression exacerbates exhaustion. 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 … I imagine it was around 2016 or 2017, a period defined by stressful business decisions and physical and mental health issues. 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. 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. Caldbeck signing the offer letter. 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. 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 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. That’s why I’m writing this blog. I hadn’t had a headache in 20-plus years and now I couldn’t go through a full day without experiencing crippling pain in my head. Who wants to invest in an unhappy CEO? 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. @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. 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. It felt like that, with no end of dinner in sight and with much higher stakes than awkward small talk. 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. Eventually I won’t be. I absorbed very little pleasure from our wins, and quite a bit of pain from our losses. I don’t know how we raised a big round from world-class investors right after a pivot, but we got it done. Dealing with the fertility problem, cancer, and issues at work all at once was the hardest challenge of my life. We also had to go through a round of layoffs, the first I’d ever had to navigate as a 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. Read writing from Ryan Caldbeck on Medium. I know I am privileged to be in a demographic, time, and geography that makes starting something this audacious feel possible. They were necessary, but they were brutal. Caldbeck and his daughter. But I tried to put on a brave face to make sure the board felt comfortable. There was no way to answer that other than to go by my own feelings. Primarily, I feel so much pride in what the team has accomplished and have absolute confidence in the company’s bright future. Every day, Ryan Caldbeck and thousands of other … We raised the fund. I truly feel lucky for their help in steering the ship, particularly through difficult times, with skill, vision, patience, and resolve. 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?”. Sign up for a 60-day trial to receive twice-daily email updates & a weekly Top 20 newsletter. ... SupportEdllc, CircleUp… Again, everyone has their things. Per Crunchbase, Jungju (Jay) Kim was the board partner for Collaborative's Series C investment in CircleUp. There were stretches of time where I felt horrible — lonely; terrified; depressed. Co-founder and CEO Ryan Caldbeck … In the best of times and the worst of times, she has only ever used CircleUp as a positive example for our (now) three kids — to chase their dreams. ... Ryan founded CircleUp after nearly seven years of investing experience in consumer product and retail-focused private equity. In the email, Caldbeck recounts the toxic relationship with the board member that … For me a perfect storm of personal problems unhappily coincided with some of the most critical business decisions and processes possible. I prepped for the conversation with my management coach and some CEO friends, but I was still terrified of the potential reaction. 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. CircleUp targets consumer facing companies on their platform. If you are in this seat for long enough, it will happen to you. 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. Ryan Caldbeck is on Facebook. Prior to launch, CircleUp raised $1.5 million from investors such as Clayton Christensen, David Topper … I’m not here to share a playbook — I don’t think one exists. I need to come to terms with the end of my time as CEO, though I will still be here at CircleUp. Over the past year, when I began telling team members, investors, LPs, and other stakeholders about my transition, their first question was, inevitably, “Why?” I typically explained that the average founder/CEO of a startup is in the seat for less than five years; I had been with CircleUp for nine, and I was exhausted. The doctors did two MRIs on my brain to see if the cancer had spread there. A few teammates tried to help me focus only on work that brought me joy, but I failed at that task. I also hope this piece can help build greater empathy and understanding among the investors, teams, and families that have backed, supported, and lived with founders whose struggles might at first seem opaque or impenetrable but are, in essence, deeply human. Ryan Caldbeck is the founder and Executive Chairman of CircleUp, an investment platform powered by technology. Persistence was my superpower. We think that the investors that come to CircleUp are looking for really high quality investment opportunities, and we … 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 was diagnosed with cancer. Kim Caldbeck. I am confident some, especially in VC, will inevitably view my story as a lack of grit. The cancer diagnosis became even tougher to deal with because I mistakenly believed I shouldn’t discuss it with others. 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. There were so many tests. In the email, Caldbeck recounts the toxic relationship with the board … Ryan Caldbeck's stories. The pivot was behind us. What is normal? Sections of this page. 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. For me, that happened in the fall of 2019. Could I have stuck it out if not for the personal issues? I feel nervous about how people will interpret this transition and what narrative they will tell themselves (and others). 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. I was losing control, and while she tried to be strong, I could hear the fear in her voice. Note that, in Ryan's letter, he cites board issues from 2016 to 2019. But he was. I’m still here, just with far less stress. 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 … I think the investment to build our technology platform, Helio, has set us up to create extraordinary impact and I feel appreciative of the team members that have been here since our first engineer, Bryce, took a bet on us in 2011. Have you ever had to put on a good face when guests come over, even though you’re in a horrible mood? (Nothing has been removed, including typos, from the email except for names.). 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. 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. 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. In October 2019 I told the board that I planned to transition out as CEO. So you can imagine how those fertility issues impacted me and my wife, Kim. 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. 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. I later realized that the board interpreted my complaints as “typical founder/CEO exhaustion.” I blame myself for that lack of clarity. 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. Thread Reader Ryan Caldbeck. Two days later, I flew to a work conference in Anaheim, CA, while also trying to schedule further tests and treatment. That emphasis has impacted everything from which jobs I’ve pursued to what foods I’ve eaten — even before I was married. 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. 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. Slowly, reality began to sink in and the enormity of the word “malignant” hit me in full force. Some were bad for @CircleUp , some were just […]" #Helio. 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