From the beginning of 2019, I’ve felt a queasy sense of not belonging at the job I loved. Everything from the mentorship I received, to the people I got to meet, the intellectual nature of the work itself, and the fantastic relationships developed with my coworkers, should’ve created an experience that felt deeply fulfilling. But it didn’t, and I felt stupid for feeling that way.
Given the general zeitgest of working in Silicon Valley, the natural way to deal with existentialism is to pour your hope in to an incredibly romanticized view of starting a company. It’s considered a good enough reason to leave a rare job and still preserve some social status. So naturally that is where my brain started wandering to. I wasn’t totally naive — having gone through the process of being an early employee at a blockchain startup gave me some understanding of the brutalness. But it was a dangerous insight as I convinced myself that I knew what I was doing because I had done it before. I didn’t.
The first sector that consumed my interest was fintech. At Draper Associates, I saw so many fintech companies that were so fundamentally boring, stale, not innovative, and still on paper successful. This perspective was somewhat naive given the regulatory nature of fintech, but I found it baffling. Doing something different in fintech almost felt like an arbitrage opportunity to apply my own creativity. I also felt like it matched what I thought my skills were coming from a business degree, a blockchain background, and my prior job as a venture capitalist. Which looking back feels like such a joke because it’s ridiculous to assume specialization in skills and career at the age of 22. Regardless, I started delving into fintech.
Economic structures and markets always interested me, so I thought I would change fintech by creating brand new financial products primarily targeting low income Americans — conveniently, a demographic I knew absolutely nothing about. What I did know was that they were underserved by institutions today so the revolutionary companies of tomorrow would ideally arise by serving this demographic’s need today. After a depressing, but strangely rewardin trip through the Midwest, I recruited my COO and eventually my CTO. We put out a super great sounding Medium blog post about our vision that got a lot of congratulatory remarks by our intellectual peer group, but was met with confusion among mentors and friends that had actually built products. We were also super rushed to get an idea together so we could have something to apply to YC with. Foreshadowing.
I left my last day of work in nostalgic tears and began working full time on our company with our COO and CTO. All in all, it was a super rewarding process to build out Heroic’s web application, partner with similar companies, and converse with high impact nonprofits about their perspective on innovation. We realized really quickly though that the financial infrastructure costs of making this work would supercede the expected revenue we would be getting from our customers per transaction. Furthermore, making a legally compliant MVP would cost a large investment of several hundred thousand dollars, which we didn’t have. But even outside of all those logistical points, the greatest discovery was that there wasn’t much market demand for the service we were trying to build, and a lot of our ignorance stemmed from the fact that we weren’t building a product that we would use — we were trying to service an abstract customer base that we thought we understood.
This realization really hit us after we got rejected from YC and the On Deck program. Getting rejected hurt, but at this point in each of our very short careers, we were quite familiar with the ego sapping sting of “no.” It did, however, encourage us to look back at what we were trying to do and why we were trying to do it. We were rushed by trying to meet the YC deadline so we put together what seemed like a plausible idea, but no great company was ever formed from a premise of trying to meet an investor’s requirements, and young founders almost always succeed by building products that they would use first. I made so many basic, obvious errors that I thought I wouldn’t.
Over the next week and a half, my COO and I spent all day researching, reading, and prototyping different business ideas for our pivot. It quickly became apparent that sitting in a shitty living room all day trying to come up with business ideas was a poor way to approach this problem. It seems as though the best ideas almost always come from a poised mind observing the catalogue of interactions and individual experiences throughout the day, and playing with the ones that seem like they can be changed. With that realization, we knew that to get our next idea, we had to start actually experiencing life and figuring out different ways we can poke and test it. With that, we officially put Heroic finance on pause.
An important realization that I had was that I didn’t necessarily want to start a company — the source of dissatisfaction was more so the lack of agency, creativity, and authentic work I could produce between the bounds of my job. I used the idea of starting a company as an excuse to leave. For me, work is a deeply personal and emotional thing. At the risk of sounding like the paragon of a snobby Gen-Z, I craved having creative challenges, more immediate accountability, my own brand, and ultimately control over my work. In venture capital, the primary thing you are looking for is profitable businesses, not necessarily the ones that sound the most interesting or feel the most inspired. I was tired of seeing the same SaaS, productivity, or dev tooling companies that, I’m sure have great potential and are incredibly hard to build in their own right, but weren’t the reason why I got interested in technology and entrepreneurship in the first place.
For me, the businesses I get really passionate about are inspired and fresh in nature. Interacting with them feels as fulfilling as listening through your favorite album or hanging out with a group of old friends. It brings joy by creating value that nobody really thought could exist. It’s about the principles, values, and artistic vision behind the product or service first, and its ability to become a billion dollar company second.
I know this line of thinking is dangerous and probably stupidly idealistic. It is why I would have failed as an investor. You get disasters like WeWork or Theranos, but sometimes you get magical websites like Reddit and Spotify. Inspiring and game changing. Even though I know I’m probably being silly and naive, I don’t want to give up on my idealistic vision of technology and the ways it can solve problems without at least first trying to be what I seek.
As for me, I’m going to take the next few months exploring my creative side and diving deeper into my authentic self while building products that I think are useful and beautiful in my own life. A huge part of that is going to be writing more so I hope to put out interesting content in regards to the future of technology and my own creative journey. I’m going to LA in a week to help my aspiring rapper friend Sree record some songs and ramp up his online presence. After that, I hope to go to Seattle to work with one of the first brands that ever got me into fashion. On the side, you’ll see me posting a lot about the future of tech and random products that I am working on.
I’m excited by this new step in my journey and I feel uniquely free in a way I haven’t felt before. Some of the technological themes I am exploring are the future of expression, the passion economy, the intersection of social media from the digital into the physical, decentralized autonomous organizations, and how blockchain fits into the technological world. So if you have any thoughts around that, my Twitter DMs are open! Hopefully by culminating a set of different experiences I can find the thing I want to work on next.
