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. 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 … Problems seemed to stack one on top of the other. Further, Collaborative Fund no longer lists CircleUp anywhere on its site. If you have friends in venture and it looks like a cushy job, see if they’ve raised a first-time fund. Believing that to attract a great CEO we would need more than two years of runway, the board wanted us to raise a round. 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. 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. 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. CircleUp, an investment platform that targets early-stage consumer product companies, announced on Tuesday it has appointed Nick Talwar as its new CEO. We raised the fund. Then we raised our first institutional VC fund (just one of the ways in which we monetize our tech). We won't share or spam your email ever. A few teammates tried to help me focus only on work that brought me joy, but I failed at that task. CircleUp now boasts a new CEO with an incredibly relevant background and skill set and fresh legs to take the company to greater heights. 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 … Equity. But there was so much more to it than that. 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. 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 then said: “Hey, I just want you to know I had the same type of cancer. 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. The combination of personal and professional stress was far beyond what I could handle. 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. On a mission to help entrepreneurs thrive, CircleUp harnesses the power of data to provide capital and resources to emerging consumer brands. And most of all I feel proud of my daughter for speaking her mind. Moments of happiness were fleeting. 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. For me, that happened in the fall of 2019. 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. I only remember a pair of words from the first conversation with my doctor: “two tumors.” I struggled to process it at first. Conversely, Collaborative Fund led the Series C in November 2015. One of the better books I’ve read is “Transitions” by William Bridges. Slowly, reality began to sink in and the enormity of the word “malignant” hit me in full force. It didn’t matter: I could only feel pain. Caldbeck and his daughter. 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. 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. Maybe my experience means some VCs will not fund me again. I even hid the information from all but a few friends, fearing that word might get out. 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. After more tests, the doctors assured me that this latest symptom was also unrelated to my cancer. We have researchers scouring the web for tech news and writing concise, fact-packed summaries, so you can save hours a day! I barely drink, have never smoked or done drugs and work out five times a week. In the email, Caldbeck recounts the toxic relationship with the board member that … I had gotten to a place where I only focused on the losses and couldn’t accept positive things. 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. Since then, I have undergone regular testing several times a year. Who wants to invest in an unhappy CEO? Ryan Caldbeck is the founder and Executive Chairman of CircleUp, an investment platform powered by technology. During that time, we pivoted CircleUp away from the original marketplace. CircleUp is an investment platform powered by technology. And finally, I am thankful for a wife who encouraged me to follow my dream in 2011 and supported me throughout. Persistence was my superpower. I read it on my phone and immediately said, “Damnit!” to my wife. Ryan Caldbeck: We believe strongly in curating the companies that are on our platform. But if there’s any way to make these things worse it’s to ignore the warning signs. That group of professional challenges was more difficult than anything else I’ve faced in my career. Some were bad for @CircleUp , some were just […]" #Helio. CircleUp has built transformational tech and the team has helped hundreds of entrepreneurs thrive by giving them the capital and resources they need. 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. Facebook. Lots of people have to deal with many things happening at once. They’ve developed game-changing machine … 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. ... SupportEdllc, CircleUp… I remember crying to the nurse as she drew blood. Former CircleUp CEO Ryan Caldbeck shares candid story on stepping down – Business Insider, Your email address will not be published. I am confident some, especially in VC, will inevitably view my story as a lack of grit. Have you ever had to put on a good face when guests come over, even though you’re in a horrible mood? There were stretches of time where I felt horrible — lonely; terrified; depressed. These symptoms were one-in-a-million flukes. About a year and half ago, Caldbeck … Ryan served as CEO from 2012 through 2020. 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. 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. Ryan Caldbeck is the founder and Executive Chairman of CircleUp, an investment platform powered by technology. Ryan founded CircleUp … The people we let go had joined because they believed in our product and mission. Leaving the best job I ever had — at the company I helped to create — was difficult and confusing. Prior to launch, CircleUp raised $1.5 million from investors such as Clayton Christensen, David Topper … 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. Then I walked outside the UCSF hospital, hid behind a concrete pillar, and finally called my wife. They had done nothing wrong, yet suddenly there was no longer a place for them. There were so many tests. I disagreed: Even though I knew how difficult it would be to accomplish both tasks at once, I was confident it could be done. 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. The doctors did two MRIs on my brain to see if the cancer had spread there. First, I am transferring to a full-time executive chairman role at CircleUp. I was losing control, and while she tried to be strong, I could hear the fear in her voice. I thought about how I gritted out getting into business school and securing a job in private equity after being denied by the first 70-plus PE firms I reached out to (even offering my services for free). But I tried to put on a brave face to make sure the board felt comfortable. 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 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. I don’t know when that day will come. Sections of this page. By Ryan Caldbeck on July 30, 2020. I prepped for the conversation with my management coach and some CEO friends, but I was still terrified of the potential reaction. There was no way to answer that other than to go by my own feelings. 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. 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. Join Facebook to connect with Ryan Caldbeck and others you may know. Ryan Caldbeck. All lending related activity referenced on this site are offered through CircleUp Credit Advisors LLC, a wholly owned subsidiary of CircleUp Network, Inc. Loans to California-based companies are made … From there, my exhaustion only grew. It felt like that, with no end of dinner in sight and with much higher stakes than awkward small talk. 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. Anger, frustration, fear, confusion — there were so many feelings to contend with. Kim Caldbeck. 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. Ryan Caldbeck is on Facebook. 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). 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. I’d never really heard her scared before, and I felt helpless being unable to do anything to change the situation. I don’t think so. Caldbeck signing the offer letter. A redacted email written by CircleUp founder Ryan Caldbeck to an investor board member is the speech from Silicon Valley. 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. 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. Still, in less than a year we raised a big round (not announced) on terms both we and the board were happy with. Ryan Caldbeck recently stepped down as the CEO of CircleUp after leading the fintech company for almost nine years. For investors, vulnerability or burnout is often conflated with risk. While I know this is the right decision, there are huge parts of the job I deeply love and will miss. History. 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. Is that just bad luck? Would their perception of me be better if, instead of helping CircleUp pivot and leaving three years later, the company had failed in 2017? Note that, in Ryan's letter, he cites board issues from 2016 to 2019. 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. 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 … Every day, Ryan Caldbeck and thousands of other … I feel nervous about how people will interpret this transition and what narrative they will tell themselves (and others). So you can imagine how those fertility issues impacted me and my wife, Kim. What is normal? A great board member, Dan, called me to say, “Ryan, I’ve never in my career seen a CEO as worn out as you. The highs kept me going even though I knew the downs were unhealthy and untenable. The cancer diagnosis became even tougher to deal with because I mistakenly believed I shouldn’t discuss it with others. Co-founder and CEO Ryan Caldbeck … Press alt + / to open this menu. 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. (Nothing has been removed, including typos, from the email except for names.). I feel excited about our roadmap. 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. And if you ask me what’s after that, my answer is … I don’t know. 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. From 2011–17, my exhaustion felt “normal.” Starting in 2017, it no longer did. Accessibility Help. I’ve worked on this transition for a while with my management coach, Ed Batista. 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. He founded CircleUp after … If you are in this seat for long enough, it will happen to you. And, for good measure, we had to get all of this done during a global pandemic. Maybe it means I now have more empathy for entrepreneurs. For me a perfect storm of personal problems unhappily coincided with some of the most critical business decisions and processes possible. 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. 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. I am relieved that I’m getting help in the form of a new CEO. With limited precedent to guide me, I found the process extremely hard to manage, both logistically and emotionally. We hired a fantastic president, Nick Talwar, who became CEO on October 13, the day I became Executive Chairman. By the end of 2017, I was completely worn out. I imagine it was around 2016 or 2017, a period defined by stressful business decisions and physical and mental health issues. I no longer felt like a missionary, I felt like a mercenary. I told my cancer doctor, “I like data. Per Crunchbase, Jungju (Jay) Kim was the board partner for Collaborative's Series C investment in CircleUp. I don’t remember the first time I told our board that I was exhausted and needed to step down as CEO. I have changed nothing in the note (not even a typo) other than redacting email addresses. CircleUp was founded in 2011 by ex-private equity professionals Ryan Caldbeck and Rory Eakin. 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. I’m trying to share my experience — the full and honest version — so that you hopefully don’t feel as lonely on your journey. We think that the investors that come to CircleUp are looking for really high quality investment opportunities, and we … Could I have stuck it out if not for the personal issues? Ryan Caldbeck is on Facebook. 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. When I’ve talked about my journey in the past, I’ve had similar concerns, but these ones are greater. That’s why I’m writing this blog. The root of these negative feelings can be boiled down to roughly an 18-month period from mid-2016 through 2017. Eventually, we were blessed with our second child, but it was an extremely painful and isolating process. After the first MRI, they initially thought it had. But as we pulled up to the hotel and I climbed out, he opened his door, stood up and gave me a hug. 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 feel insecure about my answer of “I don’t know” when asked what I’ll do next — that it will be viewed as inadequate. My personal obstacles were under better control and we now had an infant boy along with our daughter, who was three at the time. I feel frustrated that there are things I could have and should have done differently. I certainly wish I’d had examples to lean on. Eventually I won’t be. 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. Now that I have a chance to reflect, my feelings are complicated. 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. ... At CircleUp, we are closely tracking developments in our industry using data from our machine-learning platform, Helio, to better understand the resulting changes in consumer behavior across categories, ... Email… https://learningleader.com/episode-266-ryan-caldbeck-ceo-circleup 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. In the email, Caldbeck recounts the toxic relationship with the board … The board wasn’t happy when I sent that email. 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.”. I think an element of my reaction is what Jerry Colonna calls “false grit” in “Reboot.”. She took this picture. 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. I’ve also talked with countless CEOs (including my LIT group), friends, and advisors. One of those tests revealed unexpected, terrifying information. Ryan Caldbeck, Co-Founder and … To this day, I cry every time I go to the cancer center at Stanford. CircleUp had just gone through our pivot and we were in the middle of raising that first fund and the parent company round. Ryan served as CEO from 2012 through 2020. The pivot was behind us. 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. Ryan Caldbeck's stories. I need to come to terms with the end of my time as CEO, though I will still be here at CircleUp. 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. For weeks at a time I had blurred vision. But it was hard to turn away from persistence when it has been so crucial to any success I’ve achieved. I then followed up with this email (included here with their permission). I was diagnosed with cancer. 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. I don’t blame them. 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. I told the board and my cofounder about my diagnosis, but no one else at the company knew. Contact Email info@circleup.com Phone Number 877-342-7222 CircleUp is the investment platform providing capital and resources to innovative, early-stage consumer brands with a modern, scalable … I believe hundreds of founders have their own version of this story, but it is rarely told. 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. 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. I feel fear in that I don’t know what’s next, even though I believe it’s healthy for me not to know. We got the round done for CircleUp. They were necessary, but they were brutal. I wish I had found other stories about how the transition actually went and what it felt like. Finally, my daughter looked at me and said, “Daddy, why do you always look so sad?” She was five. 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. Ryan received his MBA from Stanford and a dual BA from Duke. Again, everyone has their things. “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. Depression exacerbates exhaustion. My wife came in and I cried with her. 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 think so, but I can’t know the answer to that any more than I can know how people will react to this account. I’m still here, just with far less stress. @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. I later realized that the board interpreted my complaints as “typical founder/CEO exhaustion.” I blame myself for that lack of clarity. Dealing with this issue was one of the loneliest times I faced as a CEO. Founder and Executive Chairman @CircleUp. 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 remember a top VC, who was not one of our investors, posted something very positive about me and CircleUp online. In October 2019 I told the board that I planned to transition out as CEO. 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. We also had to go through a round of layoffs, the first I’d ever had to navigate as a CEO. That emphasis has impacted everything from which jobs I’ve pursued to what foods I’ve eaten — even before I was married. 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. I know I am privileged to be in a demographic, time, and geography that makes starting something this audacious feel possible. My only hope is that it might help other founders feel less alone. Thread Reader Ryan Caldbeck. It’s not as hard as being a CEO, but it is … not cushy. Primarily, I feel so much pride in what the team has accomplished and have absolute confidence in the company’s bright future. CircleUp targets consumer facing companies on their platform. Ryan is the founder and CEO of CircleUp, an investment platform that provides capital and resources to innovative, early-stage consumer brands. When it was time for me to sign Nick’s offer letter, I stared at my computer screen for 35 minutes. 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’m not here to share a playbook — I don’t think one exists. I feel sad that my journey as CEO of CircleUp has come to an end. Follow me on Twitter @ryan_caldbeck. 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. 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?”. 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. ... Ryan founded CircleUp after nearly seven years of investing experience in consumer product and retail-focused private equity. Two days later, I flew to a work conference in Anaheim, CA, while also trying to schedule further tests and treatment. Sign up for a 60-day trial to receive twice-daily email updates & a weekly Top 20 newsletter. 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. After 12 months of transitioning into his new role as executive chairman, Caldbeck now shares a candid, vulnerable account of his journey to inspire other entrepreneurs to confront their feelings and ask for help. I’m so sorry.”. 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. 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. I became Executive Chairman role at CircleUp driver hadn ’ t the.. A work conference in Anaheim, CA, while also trying to schedule further tests and treatment Caldbeck: believe! Diagnosis became even tougher to deal with because I mistakenly believed I shouldn ’ t sleep, couldn t. 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