And on top of all that, it’s not fair to criticize

9 min readDec 6, 2020

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.

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.

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.

It’d be easy to end on some cliche like, “You can’t teach anyone how to love you.” But that’s wrong. That’s exactly what dating is — teaching. You’re showing someone how to love you, and they’re showing you. Be a good teacher. Be a good student.

Here was a fanless, highly optimized computer with a chipset said to allow for comically robust battery life — Apple claims 18 hours, and many reviewers have gotten close to that. How’d it do? Well at first, I thought it was holding its own. However, I soon noticed that Dropbox was taking up three-quarters of my RAM, and that my swap file was reaching 10 gigabytes in size. Even after letting it sit around overnight to sync, it still wasn’t done — and worse, I started seeing beach balls.

Dropbox traditionally has not handled lots of small files particularly well. And in the past, my Dropbox folder has brought computers large and small to their knees… and made them kick up the fans.

I’m not a video editor, but I’m pretty sure I brutally slayed the M1 MacBook Air I just bought (8 GB RAM and a 512 gigabyte SSD, in case you were wondering) in less than a day of use.
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.
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.

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.

So, here’s the deal: For a number of years, the content management system I used for my newsletter was based on Node.js, which generally stores its many parts inside of folders called node_modules. Any small Node applet inside of the primary Node app can also have a node_modules folder. These apps basically build on one another, creating a Russian nesting doll of sorts, each folder filled with its own tiny folders, of which there can be thousands included in a single directory.

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?”
The culprit? All those dang node_modules folders. I would keep these old folders of my CMS around as backups of local installs on the off-chance something would break. (Eventually, I started compressing them.)
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.

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.
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.
At some point, it sucked up so much power I decided to unplug my laptop to see how fast it would drain the battery. In about two and a half hours, I managed to knock out two-thirds of the computer’s battery life, by which time I had made a point to remove syncing capabilities on every folder with node_modules as a subfolder. It seems on track for about four and a half hours while plugged into a monitor… even after all that.

I’m a special case. I experiment a lot with random things, and my Dropbox folder is like a storage locker that’s never been organized. It is totally unfair to Dropbox to blame them for my bad storage habits.

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.It comes down to two reasons, really: The lack of an Apple Silicon-optimized Dropbox app (it’s coming), and a solid decade-plus track record of bad habits in terms of how I store my old projects.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.

And on top of all that, it’s not fair to criticize

Written by moxced