Dealing with the fertility problem, cancer and issues at work all at once was the hardest challenge of my life. I couldn

e people want their hand held while they learn a skill. They don’t want anybody else to teach them except you. Coaching is a business any writer can start. If you can schedule a weekly Zoom call, send a PayPal invoice for ten lessons paid for in advance, and come to each coaching call prepared, then you can be a coach. A coach is a paid teacher with one student in the classroom at a time.

I feel unsure about how others will react. In venture, doubt isn’t respected. I am confident some, especially in VC, will inevitably view my story as a lack of grit. Would their perception of me be better if, instead of helping CircleUp pivot and leaving three years later, the company had failed in 2017? Maybe my experience means some VCs will not fund me again. Maybe it means I now have more empathy for entrepreneurs. Could I have stuck it out if not for the personal issues? 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. My only hope is that it might help other founders feel less alone.

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.

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.

Still, in less than a year we raised a big round (not announced) on terms both we and the board were happy with. We hired a fantastic president, Nick Talwar, who became CEO on October 13th, the day I became Executive Chairman. While I know this is the right decision, there are huge parts of the job I deeply love and will miss. When it was time for me to sign Nick’s offer letter, I stared at my computer screen for 35 minutes. My wife came in and I cried with her. She took this picture.

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.

Raising a round and hiring a replacement in parallel was emotionally draining, in part because I had to show passion and excitement even though I was personally exhausted. 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. Who wants to invest in an unhappy CEO? For investors, vulnerability or burnout is often conflated with risk. 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. Have you ever had to put on a good face when guests come over, even though you’re in a horrible mood? 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.

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.

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.

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.

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.

More than a few people have asked me what comes next. First, I am transferring to a full-time Executive Chairman role at CircleUp. I’m still here, just with far less stress. I’ve worked on this transition for a while with my management coach, Ed Batista. I’ve also talked with countless CEOs (including my LIT group), friends and advisors. One of the better books I’ve read is Transitions by William Bridges. 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 need to come to terms with the end of my time as CEO, though I will still be here at CircleUp. Eventually I won’t be. I don’t know when that day will come. And if you ask me what’s after that, my answer is… I don’t know.

Now that I have a chance to reflect, my feelings are complicated. I am relieved that I’m getting help in the form of a new CEO. I feel sad that my journey as CEO of CircleUp has come to an end. I feel fear in that I don’t know what’s next, even though I believe it’s healthy for me not to know. I feel nervous about how people will interpret this transition and what narrative they will tell themselves (and others). When I’ve talked about my journey in the past, I’ve had similar concerns, but these ones are greater. I feel frustrated that there are things I could have and should have done differently. 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. I worry about whether I will ever do anything aga

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