One of those tests revealed unexpected, terrifying information. I was diagnosed with cancer. I only remember a pair of w

But he was. 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. Slowly, reality began to sink in and the enormity of the word “malignant” hit me in full force. I remember crying to the nurse as she drew blood. Then I walked outside the UCSF hospital, hid behind a concrete pillar, and finally called my wife. I was losing control, and while she tried to be strong, I could hear the fear in her voice. I’d never really heard her scared before, and I felt helpless being unable to do anything to change the situation.

Two days later, I flew to a work conference in Anaheim, CA while also trying to schedule further tests and treatment. 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). 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. 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. For the next several months, my emotions would sometimes pour out in a tidal wave of tears and yelling. Anger, frustration, fear, confusion — there were so many feelings to contend with. Throughout the entire Uber ride, my driver hadn’t said a word. But as we pulled up to the hotel and I climbed out, he opened his door, stood up and gave me a hug. He then said: “Hey, I just want you to know I had the same type of cancer. I’m so sorry.”

The cancer diagnosis became even tougher to deal with because I mistakenly believed I shouldn’t discuss it with others. CircleUp had just gone through our pivot and we were in the middle of raising that first fund and the parent company round. 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 told the board and my co-founder about my diagnosis, but no one else at the company knew. I even hid the information from all but a few friends, fearing that word might get out. 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.

The board wasn’t happy when I sent that email. I don’t blame them. 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. 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.

A few weeks later, I started peeing blood, repeatedly. After more tests, the doctors assured me that this latest symptom was also unrelated to my cancer. These symptoms were one-in-a-million flukes. I told my cancer doctor, “I like data. 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 me, that happened in the fall of 2019. 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. It didn’t matter: I could only feel pain. Finally, my daughter looked at me and said, “Daddy, you always look so sad”. She was five. It was the push I needed to change.

By the end of 2017, I was completely worn out. Then, suddenly, the major professional challenges were done. We got the round done for CircleUp. We raised the fund. The pivot was behind us. My personal obstacles were under better control and we now had an infant boy along with our daughter, who was three at the time. A great board member, Dan, called me to say, “Ryan, I’ve never in my career seen a CEO as worn out as you. 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. But after a lifetime of gritting things out, I told myself I didn’t need to take a break. I think an element of my reaction is what Jerry Colonna calls “false grit” in Reboot.

In October 2019 I told the board that I planned to transition out as CEO. I prepped for the conversation with my management coach and some CEO friends, but I was still terrified of the potential reaction. I then followed up with this email (included here with their permission). I have changed nothing in the note (not even a typo) other than redacting email addresses. 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 certainly wish I’d had examples to lean on.

After several discussions, the board became aligned with my decision but felt I wouldn’t be able to transition within 12 months. Believing that to attract a great CEO we would need more than two years of runway, the board wanted us to raise a round. 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 disagreed: even though I knew how difficult it would be to accomplish both tasks at once, I was confident it could be done.

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dn’t maintain my balance in our conversations now. I was so used to keeping the peace but I was tired. I decided to risk it all, like in the song. Say it all. I was numb to risk now; we either fell or we worked out how to get off the tightrope safely. Either way, things had to change.

But it was hard to turn away from persistence when it has been so crucial to any success I’ve achieved. 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. 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 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). 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.” Persistence was my superpower. 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. That was the biggest mistake of my career.

Dealing with the fertility problem, cancer and issues at work all at once was the hardest challenge of my life. I couldn’t sleep, couldn’t relax, and was constantly on edge. For weeks at a time I had blurred vision. The combination of personal and professional stress was far beyond what I could handle. 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. The doctors did two MRIs on my brain to see if the cancer had spread there. After the first MRI, they initially thought it had. 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 had a successful operation. Since then, I have undergone regular testing several times a year. To this day, I cry every time I go to the cancer center at Stanford. 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’ve eventually realized that for far too long, I wasn’t clear — with myself or others — about what I wanted or needed. 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 believe hundreds of founders have their own version of this story, but it is rarely told. 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.

From there, my exhaustion only grew. 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. Problems seemed to stack one on top of the other. Moments of happiness were fleeting. A few teammates tried to help me focus only on work that brought me joy, but I failed at that task. I absorbed very little pleasure from our wins, and quite a bit of pain from our losses. I remember a top VC, who was not one of our investors, posted something very positive about me and CircleUp online. I read it on my phone and immediately said, “Damnit!” to my wife. 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 had gotten to a place where I only focused on the losses and couldn’t accept positive things.