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Green Grass and the Ego


close photo of green grass
In February of 2023, I ran away from home. I didn't run out of fear. I didn't run because I wanted to. I ran because my ego told me I was about to do something massive, world-changing. So I packed my knapsack, slung it over my shoulder, and hitchhiked my way from the place I'd help make home to somewhere new.

In December of 2022, an executive at ClickUp reached out to me interested in a blog post I had written when I was working on Graphite. The executive wanted me to come and lead the engineering efforts to do something similar at ClickUp. However, I wasn't interested in writing code for a large(ish) company. I decided a while ago that I am happy writing code for myself and for small, nimble operations. Undeterred, ClickUp decided they were interested in me running product around ClickUp Docs. The idea was I could drive the engineering improvements and the feature development.

I was not convinced.

Let's rewind, though. In 2015, I was working at a small EdTech startup in Dallas. Shortly after the Ethereum blockchain launched, we ventured into a digital credentials project for universities to issue certificates, diplomas, and more on both Bitcoin and Ethereum. This was my indoctrination to blockchain technologies. Less than two years late, in 2017, I began work on an app I had conceived to replace my usage of Google Docs. I wanted a storage backend that I controlled and an account system that I could not be locked out of. Graphite was born.

Not long after that, I quit my day job and went fulltime on Graphite. I would later start another company in the nascent Web 3.0 space before eventually landing at Pinata as their first employee. I helped build Pinata from a pre-investment company to a Series A startup with strong revenue in a space that struggled to monetize without a token. By February of 2023, I had been there for nearly 3 years, and I loved it. It was home.

Now, here was ClickUp, a company marching towards an IPO, trying to pull me away from not just Pinata but from web3. And I was not convinced. But they persisted. The CEO of ClickUp got on a call with me. Zeb was very kind and didn't pressure me at all, but he did offer something that was hard to say no to.

ClickUp had done a great job competing in the project management space, but they had fallen behind on the Docs side of the house. Zeb and ClickUp wanted to change that, and they were offering me the opportunity to take on a massive challenger head-on. I'll let you all figure out the challenger on your own, but this got my attention.

What was on the table:

  • Build a product used by hundreds of thousands of people

  • Build a Docs product (a category I love)

  • Take on a darling in the SaaS space and try to make ClickUp's product number 1

That kind of opportunity is hard to say no to. Was the grass greener on the other side? Was I chasing that green grass? Not exactly. I loved Pinata and did not want to leave. The grass was plenty green there. But my ego nudged me. It told me this was a massive opportunity. To have my name associated with what I was convinced would be a flipping of players in the Docs market was too much to say no to.

And so it was in February of 2023 that I had the hardest phone call of my life. It felt like a part of me was dying when I told Kyle, Pinata's CEO, that I was leaving. The news came as a shock to him and the whole team.

Ego had won.

But here's the thing about ego: sometimes it's right and sometimes it's wrong. Had I taken this role and been able to take ClickUp Docs and turn it into the number one collaborative document editor on the market, my ego would have been right. Yet, even if the ego is right, the soul pulls in another direction.

In my case, the ego was wrong and my soul was constantly pulling me back to where I had left. ClickUp is not a bad company. Not by a long shot. They ship incredibly fast considering they were at 1000 employees when I was there. They have some of the sharpest engineers I've ever met. However, I discovered something while working at ClickUp, something I had long suspected about myself. I'm not the right fit for organizations of a certain scale. I fit best in the 0-1 and even 1-2 stages of startups.

I'm a tinkerer. I'm a builder. I need to see immediate impact, so waiting for results or bartering to ship and iterate is something I can't stomach. On the flip side, as a company grows, you simply can't expect to ship and iterate at the same speed. Breaking things at $300m ARR is a big difference from breaking things at $3m ARR.

While at ClickUp, I had a chance to step out of the web3 world—something I was honestly sort of excited to do. It had been so long, I wondered if I had forgotten how the "real" world worked. What I found was that while web3 is an echo chamber, the non-web3 world is boring. Boring businesses make a ton of money, and innovation happens at the pricing and packaging level more than at the product level. The things that had excited me about web3—the product innovation, the creativity, the cutting edge can-this-actually-fucking-work feeling—still excited me and my inability to experience them in the more traditional startup world brought me down.

As I realized this a mere five months into my time at ClickUp, I knew there were only two paths forward for me:

  1. Start my own company again in web3

  2. Go back to Pinata, a place I loved and a place I considered home

Fortunately, I had stayed close with everyone at Pinata. In fact, it felt like I was still there in many ways. I met up with people from Pinata, had constant text conversations, and most importantly, Kyle and I stayed close. So, it was with extreme serendipity that Kyle playfully text me asking if I was ready to come back to Pinata on the same day I had decided I was going to ask if he'd have me back.

I spent just five months at ClickUp, but it was enough to learn some lessons that I have been able to apply to Pinata, and, more importantly, it was enough time for me to realize I need to be working at the edge of innovation. Crypto has many faults–and I call them out frequently–but it also has some of the most creative builders.

I've come home, and it feels right. My ego and my soul are aligned on this one now.