Dues paid, lessons learned and life as a founder

Running a startup for the past three years has been the hardest journey I’ve ever taken professionally by far and ranks among my biggest personal life challenges as well. In late 2020 when I was considering a few business ideas to kick start with my ex-co-founder, I had already been progressively gaining experience, expertise and a reputation among peers in the cryptocurrency industry since 2014.

My fascination and love for crypto had begun when I was on a sabbatical in South Korea teaching English to kindergartners after spending my 20’s dealing with the great recession, bouncing around jobs trying to make financial ends meet. After a failed remittance which caused me to miss one of my student loan payments, I researched frantically to find a way to use Bitcoin and my Coinbase account to circumvent the SWIFT payments system and get money to my home bank more reliably. My writing and learning journey would eventually open doors for me to work with major projects at Consensys (Metamask, Infura and more), Lunie.io, Blockdaemon and more. I built one of the first support practices for non-custodial wallets and services and absolutely loved the intersection of technical support, content creation and community enablement I was able to achieve in my jobs.

To be honest, when I was watching projects launch ICO’s in 2015-2017 in the early days of Ethereum I was extremely excited to see the success that some were able to achieve in terms of funding. I was reading all of the whitepapers as they came out and trying to participate in the communities early on - well before the potential promise of airdops and pump-and-dump schemes really started taking hold. I was inspired by the boldness of the founders, the mootshot-like vision conveyed in the whitepapers. I was like a kid the night before Christmas that couldn’t wait for the dapps to launch so I could use them.

Funny enough, and maybe naively, the prospect of getting financially rich off of any of these projects seemed remote to me - maybe my world view or lower-income upbringing didn’t quite let me believe that I’d ever accumulate a significant amount of assets through my interests, let alone get out of debt and start saving money for once. But as one year after another passed I found my personal interests in crypto intersect with my career and things started to get better. Over time I would eventually get married, have a child, buy a starter home and go down a path more focused on family and personal wellness - both of which I felt were out of reach for me given the financial burden I had brought on myself with student loans and other poor choices in my 20’s.

So when I was faced with the idea of starting my own business, something I had loosely toyed with before but never seriously considered beyond a few semi-successful solopreneur ventures, I was excited but nervous at the prospect. I always felt like someone on the outside mingling among high powered founders that I met - whether it’s my socio-economic background, my mediocre college degree or just lack of good ideas, imposter syndrome was already messing with my head.

I had already experienced several market cycles in crypto - boom and bust over the course of 6 years and my expectations that crypto or anything else would go up-only were tempered dramatically. In 2020 we saw DeFi Summer, FTX, SBF and other high profile rises to fame really getting traction and suddenly it was clear that there were opportunities to get funded given my and my ex-co-founder’s backgrounds. He wanted to build an esoteric crypto-trading firm and I wanted no part in that. I idolized projects like MakerDAO that leaned into decentralized governance and real-world uses of crypto so much I pushed back hard with everything I had to create a protocol that matched my world view in crypto - that there were people in the world who needed to use financial tools that couldn’t access them through traditional means and that was a worthy pursuit.

We settled on building a borrowing and lending protocol on Solana. There was so much activity early on with hackathons, VC’s funding the winners and seeing how projects on Ethereum had shown some promise with DeFi primitives like lending - we wanted to be first to do this on Solana. By the grace of some higher power a friend of mine who happened to be an experienced attorney in the crypto/fintech space was in between jobs and he jumped in early to help my ex-co-founder and I get the business spun up and ready to raise capital.

The whole process was surprisingly fast and resistance-free once we committed to doing it and we had no idea whatsoever how lucky and how good our timing was. Despite all this, just before I had decided to quit my job with Blockdaemon, which was a great place to work, I had a talk with my wife about whether she’d be comfortable with me trying to do a startup. We settled on the idea that if I was willing to de-risk my financial portfolio (I was far too overweight with crypto-assets up until that point), we’d be in a position to weather any period of time where I wasn’t able to pay myself a salary, should that day come. Today I’m so glad I did this because this enabled me to make more rational and grounded decisions when things started to go poorly for us and I wasn’t able to pay myself anymore.

I wouldn’t say financial uncertainty was the hardest part about my startup experience - we raised a lot of money for what we planned to build from some great investors that I am eternally grateful for. What was more difficult was the mental toll of seeing our focus as a company wane, the relationship and friendship with my ex-co-founder fall apart to the point where he quit the company with zero notice and having to try to keep the team together and rally through a bear market where we had little chance to raise more capital as the bank account got closer to zero without us having many users of the product.

Throughout the three years, both before I had a co-founder and after I worked a lot. My wife was patient, but my absence both being busy with work, traveling and also having too much on my mind when I was with them took a toll on my family. Despite trying to internalize the pythy Twitter threads of other founders talking about how they ruthlessly manage their time, execute at work and somehow don’t drop dead from lack of sleep and stress, I felt inadequate not only as a leader at my company, but also as a husband and a father. Even though I wasn’t personally financially at risk due to selling assets for a cash buffer, my health and relationships were absolutely at risk and seeing the chances of finding success with my business dwindle as each day passed my mental, physical and emotional state became worse and worse.

I think back with gratitude for my family and friends who tried to be there for me throughout this - my wife and son especially. I can’t even count the number of times I’d be out doing something nice with family or friends and just couldn’t bring myself to be present as I was worried about work constantly, or worse complaining about it. I wouldn’t have wanted to be around myself if I was someone else and I often can’t imagine why others tolerated me during this time. Time was moving faster and faster and I felt unable to slow down and really feel my own and others emotions clearly and presently.

In the middle of 2023 the writing was on the wall that my business could not succeed - we had run out of money and I had to lay off my entire team. We did manage to deploy an open source version of the software I had dreamed of building, which I am still proud of today, but we lacked the capital and manpower to bring it to market successfully. I had anticipated and mourned that decision being made for some time, dreading when I’d actually have to say it out loud to teammates, investors and the public. But I had to make the decision with finality sooner or later.

Coming to the end of a journey I had to sit with the uncomfortable position of seeing an end in sight but not knowing, and having to be okay with not knowing what would be on the other side. My entire adult life I had always jumped from one job to the next after getting laid off or making lateral jumps for better pay or opportunity, often deferring the process of healing from what I’d experienced. Like interest compounding, I felt in my heart and in my gut that I needed to slow things down and be okay with not knowing.

I worked diligently with my attorney who stuck with me through thick and thin to shut things down in an orderly way that offered whatever justice I could to my investors while trying not to distract myself too much from the deep discomfort that was rising to the surface from within. As the workload shifted to more operational tasks of the shutdown, I resolved myself to slowly focus more on my physical, emotional and mental health. I started writing again, not for the purpose of personal branding or getting myself another job, but just to work out some of the feelings I had inside and rekindle the creativity I once felt had gotten me to the point in my career that felt right to me. I also began more regularly attending BJJ classes, lifting weights, sleeping more (and better) and reading books - things I had neglected most of the time I was running my company. I also had to begin doing the more important work of evaluating and healing the relationships in my life that’d be glazing over for too long. Obviously I had been a mess for so long that some people in my life rightfully were skeptical of my intention to change and be better - I had to show them through actions, not words or deferred promises - which is where I am still working to get better today.

In the thick of the process, especially at the end I had a deep resentment towards my company and what I felt I had sacrificed despite not finding success. When I shared this with people close to me it made them deeply uncomfortable, like why hadn’t I gleaned some sort of wisdom from this whole experience that would make me strong and confident to move forward? This, I came to realize, was part of the process of healing and growth that I could not speed run and fake my way through. As days, weeks and months pass I absolutely feel more grounded in understanding the reasons I made the decisions I made along the way, what I had hoped, however foolishly, would result from sacrifices made. To this day, I could be reading a book, watching a movie or writing a blog post like this and get choked up to the point of tears realizing most of what I did was with good intentions but poor perspective or limited information. The hardest lesson to date is that I need to believe in myself that despite being a highly flawed individual, I deserve kindness, especially from myself, as much as anyone else in life and I need to be patient.

The question I often hear from others and ask myself is, would I do this all over again knowing what I know now? I am not sure if it’s helpful to dwell on that framework too much - however I do know with great certainty that I have experienced enough to make wiser choices in my career and personal life, regardless if I ever do my own startup again. The ability to prioritize what is most important to me, things I came close to losing and the dreams I almost gave up on is what I’m most grateful to have right now.

The shock of how fast time seemed to slip through my fingertips is the reminder I cherish, as it allows me to look more soberly at what seems like an opportunity and weigh it against the costs. I don’t view this as a hindrance to taking chances, but rather a better way to move through life with a more holistic mind frame and attitude. While I am now older, coming up on 40, having less energy, needing more sleep and less alcohol and late nights, I cherish the opportunities to more clearly view my world and how I interact with it.

Being able to sit down and white knuckle my way through writing this post was incredibly healing and if nothing else besides getting it off my chest, I hope sharing my path can at least help anyone else going through a massive life challenge to know that hard times don’t have to last and even through failure, there’s still opportunity and hope on the other side.

As of today I am getting to the tail end of taking things slow - I’m starting to entertain new job ideas, new startup ideas and just generally exploring possibilities through my own thinking process. I’ve had other founders reach out to me with condolences and even share their own struggles in confidence, which I feel is a true honor to be able to listen to others and help them realize their own path isn’t as alone and isolated as they feel.

I am deeply grateful and excited for the opportunities I have and will have and cannot wait to continue to have an impact on the world, however big or small, through my own perspective, effort and heartfelt intention to make the most of this limited and precious time on earth. Thank you for being part of this.