They had done nothing wrong, yet suddenly there was no longer a place for them. I remember a top VC, who was not one of our investors, posted something very positive about me and CircleUp online. On October 13, 2020 I stepped down as CEO of CircleUp, the company I started in 2011 with my cofounder, Rory Eakin. They’ve developed game-changing machine … 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. 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 … By the end of 2017, I was completely worn out. Ryan received his MBA from Stanford and a dual BA from Duke. Again, everyone has their things. 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). My only hope is that it might help other founders feel less alone. 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. Still, in less than a year we raised a big round (not announced) on terms both we and the board were happy with. The board wasn’t happy when I sent that email. I was diagnosed with cancer. Ryan Caldbeck: We believe strongly in curating the companies that are on our platform. Ryan Caldbeck recently stepped down as the CEO of CircleUp after leading the fintech company for almost nine years. Caldbeck signing the offer letter. Two days later, I flew to a work conference in Anaheim, CA, while also trying to schedule further tests and treatment. For me, that happened in the fall of 2019. Co-founder and CEO Ryan Caldbeck … I have changed nothing in the note (not even a typo) other than redacting email addresses. After the first MRI, they initially thought it had. There were stretches of time where I felt horrible — lonely; terrified; depressed. I think an element of my reaction is what Jerry Colonna calls “false grit” in “Reboot.”. I feel sad that my journey as CEO of CircleUp has come to an end. 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. One of the better books I’ve read is “Transitions” by William Bridges. A redacted email written by CircleUp founder Ryan Caldbeck to an investor board member is the talk of Silicon Valley. Former CircleUp CEO Ryan Caldbeck shares candid story on stepping down – Business Insider, Your email address will not be published. Then, suddenly, the major professional challenges were done. But if there’s any way to make these things worse it’s to ignore the warning signs. 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. ... Ryan founded CircleUp after nearly seven years of investing experience in consumer product and retail-focused private equity. When it was time for me to sign Nick’s offer letter, I stared at my computer screen for 35 minutes. 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. 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. For me a perfect storm of personal problems unhappily coincided with some of the most critical business decisions and processes possible. Could I have stuck it out if not for the personal issues? I don’t think so. That group of professional challenges was more difficult than anything else I’ve faced in my career. I’m sure I didn’t do everything right in executing my transition, but that isn’t the point. https://learningleader.com/episode-266-ryan-caldbeck-ceo-circleup I don’t know when that day will come. But he was. 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. Believing that to attract a great CEO we would need more than two years of runway, the board wanted us to raise a round. 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. With limited precedent to guide me, I found the process extremely hard to manage, both logistically and emotionally. After more tests, the doctors assured me that this latest symptom was also unrelated to my cancer. Would their perception of me be better if, instead of helping CircleUp pivot and leaving three years later, the company had failed in 2017? Equity. Dealing with this issue was one of the loneliest times I faced as a CEO. We hired a fantastic president, Nick Talwar, who became CEO on October 13, the day I became Executive Chairman. 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. There was no way to answer that other than to go by my own feelings. 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. Maybe my experience means some VCs will not fund me again. Then we raised our first institutional VC fund (just one of the ways in which we monetize our tech). I certainly wish I’d had examples to lean on. I absorbed very little pleasure from our wins, and quite a bit of pain from our losses. 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. One of those tests revealed unexpected, terrifying information. Conversely, Collaborative Fund led the Series C in November 2015. 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. To this day, I cry every time I go to the cancer center at Stanford. “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. These symptoms were one-in-a-million flukes. I told my cancer doctor, “I like data. 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. 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’d never really heard her scared before, and I felt helpless being unable to do anything to change the situation. There were so many tests. The combination of personal and professional stress was far beyond what I could handle. 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. We also had to go through a round of layoffs, the first I’d ever had to navigate as a CEO. I disagreed: Even though I knew how difficult it would be to accomplish both tasks at once, I was confident it could be done. Eventually, we were blessed with our second child, but it was an extremely painful and isolating process. I’m trying to share my experience — the full and honest version — so that you hopefully don’t feel as lonely on your journey. Subscribe @ryan_caldbeck … Follow me on Twitter @ryan_caldbeck. I’m still here, just with far less stress. 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. 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 feel insecure about my answer of “I don’t know” when asked what I’ll do next — that it will be viewed as inadequate. Press alt + / to open this menu. It didn’t matter: I could only feel pain. 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 feel frustrated that there are things I could have and should have done differently. We think that the investors that come to CircleUp are looking for really high quality investment opportunities, and we … When I’ve talked about my journey in the past, I’ve had similar concerns, but these ones are greater. And finally, I am thankful for a wife who encouraged me to follow my dream in 2011 and supported me throughout. Kim Caldbeck. Leaving the best job I ever had — at the company I helped to create — was difficult and confusing. I’m not here to share a playbook — I don’t think one exists. 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. Depression exacerbates exhaustion. In the email, Caldbeck recounts the toxic relationship with the board … Ryan Caldbeck. I imagine it was around 2016 or 2017, a period defined by stressful business decisions and physical and mental health issues. 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 feel nervous about how people will interpret this transition and what narrative they will tell themselves (and others). We raised the fund. 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. Facebook. Anger, frustration, fear, confusion — there were so many feelings to contend with. Prior to launch, CircleUp raised $1.5 million from investors such as Clayton Christensen, David Topper … I don’t blame them. 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. And most of all I feel proud of my daughter for speaking her mind. Ryan founded CircleUp … CircleUp, an investment platform that targets early-stage consumer product companies, announced on Tuesday it has appointed Nick Talwar as its new CEO. Ryan Caldbeck, Co-Founder and … Contact Email email@example.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 … 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. I know I am privileged to be in a demographic, time, and geography that makes starting something this audacious feel possible. Then I walked outside the UCSF hospital, hid behind a concrete pillar, and finally called my wife. A great board member, Dan, called me to say, “Ryan, I’ve never in my career seen a CEO as worn out as you. 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 am relieved that I’m getting help in the form of a new CEO. Now that I have a chance to reflect, my feelings are complicated. 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. ... SupportEdllc, CircleUp… 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, 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 … Throughout the entire Uber ride, my driver hadn’t said a word. 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. A few teammates tried to help me focus only on work that brought me joy, but I failed at that task. 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. Dealing with the fertility problem, cancer, and issues at work all at once was the hardest challenge of my life. CircleUp was founded in 2011 by ex-private equity professionals Ryan Caldbeck and Rory Eakin. He then said: “Hey, I just want you to know I had the same type of cancer. 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. 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