Thank you to everyone who contributed to this post including Ed Batista, Emma Stubbs, Grace Gellman, Henry Davis, Jordan

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.

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.

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published a story about a few lessons I learned from my millionaire CEO. I’ve known him for 3 years now, and he recently sold his company after 10 years of hard work, becoming a multi-millionaire in the process. In my previous article, I emphasise how he’s always been easy to talk to and down to earth. Funny enough, I happened to have lunch with him a few weeks after writing the piece. He was sitting alone at a canteen table watching a video on his phone. You would have never guessed this guy had just sold his company for tens of millions of dollars. I sat next to him and waited until he popped out his AirPods.

Primarily, I feel so much pride in what the team has accomplished and have absolute confidence in the company’s bright future. CircleUp has built transformational tech and the team has helped hundreds of entrepreneurs thrive by giving them the capital and resources they need. CircleUp now boasts a new CEO with an incredibly relevant background and skill set and fresh legs to take the company to greater heights. I feel excited about our roadmap. 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 thankful for the partnership that Matt, Andy, Dan and other advisors and investors have given to CircleUp, and to me personally, for years. I truly feel lucky for their help in steering the ship, particularly through difficult times, with skill, vision, patience and resolve. I know I am privileged to be in a demographic, time and geography that makes starting something this audacious feel possible. I feel fortunate to have had the chance to start CircleUp with such a fantastic co-founder, someone who placed our shared values and the Company’s mission above personal glory. 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.

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.

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. And finally, I am thankful for a wife who encouraged me to follow my dream in 2011 and supported me throughout. 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. And most of all I feel proud of my daughter for speaking her mind.

The problem with object-oriented languages is they’ve got all this implicit environment that they carry around with them. You wanted a banana but what you got was a gorilla holding the banana and the entire jungle.

Imagine you’re setting up a new program, and you’re thinking about designing a new class. Then you think back to a neat little class that you’ve created for another project, and you realize that it would be perfect for what you’re currently trying to do.

By encapsulating data and methods, object-oriented programming made software development more human-centered. It matches human intuition that the method drive() belongs to the data group car, but not to the group teddybear.

It can corrupt your entire code. You might not even have touched it. But one day your project works like a charm, the next day it doesn’t because somebody changed a minor detail in the base class that ends up being crucial for your project.

Except for the fact that this class may actually be a subclass of another class, so now you need to include the parent class too. Then you realize that the parent class depends on other classes as well, and you end up including heaps of code.

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 again that I feel as passionate about: being the Founder and CEO of CircleUp is the greatest job I’ve ever had.

Again, everyone has their things. I’m trying to share my experience — the full and honest version — so that you hopefully don’t feel as lonely on your journey. 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. For me a perfect storm of personal problems unhappily coincided with some of the most critical business decisions and processes possible. Is that just bad luck? I don’t think so. Lots of people have to deal with many things happening at once. If you are in this seat for long enough, it will happen to you. But if there’s any way to make these things worse it’s to ignore the warning signs. 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.

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.

This sounds like a powerful machinery. The problem, however, is that programmers who only know object-oriented code will force this way of thinking on everything they do. It’s l