In 2024, I parted ways with the startup I’d worked at for three years. At a high level I’d ultimately chalk it up to philosophical differences around product and team culture. In this post, I’ll briefly cover those two aspects and then go onto discuss some lessons learned working in crypto.
Philosophical Divergences in Product Strategy
In the Fall of 2022, we conceived of a product with three possible use cases. FTX had recently gone under, and people distrusted centralized exchanges. We believed our product could help empower crypto users to control their assets while still using them throughout the DeFi and CeFi ecosystem. I wanted to get that out as fast as possible to see which of the three use cases would gain the most traction with potential partners and users and iterate from there. I might have been slightly biased toward a rapid launch since my role was in business development, and thus, I wanted to have something I could sell, but in any event, that was my perspective.
The alternative approach that we followed was to build out a more complete version of a product behind closed doors with hope that when we launched, we correctly assessed the product and positioning. I think there were good arguments for both approaches, particularly in DeFi where real money is at risk from the start. Still, as someone whose role was business development, I was itching to have something I could sell, and after a year and a half of trying to help out in other ways, I was getting a bit antsy.
The Challenges of Team Culture
The culture had some great aspects: good teammates who were intelligent and aligned to the project's mission and lots of freedom to work in whatever way suited you. I don’t want to say too much about the negatives because, overall, I enjoyed this chapter in my professional life and learned a lot. That said, some persistent team culture dynamics started to grind me down, as these things do, and that was ultimately a big part of why I felt it was time to move on.
What I Learned Working in Crypto
Forging Partnerships in a Nascent Industry
Working at the intersection of crypto, payments, and DeFi was incredibly interesting, as was forging partnerships in a nascent industry with no unified business norms. People come to crypto from every country and every imaginable background. Working in crypto felt like navigating an international airport where norms clashed, and assumptions varied wildly depending on the traveler.
Add to the mix the palpable impact that the market cycle has on the prevailing sentiment, and it was a fascinating place to build partnerships. During the bull market, certain teams that were the flavor of the moment would make the most insane demands or comments, their army of freshly hired new college grads blissfully unaware that the bear market comes for us all. Once the industry was deep in the wintery depths of the bear market, only the most dedicated teams kept building. This meant that partnerships were much easier to forge as everyone’s egos were much lower - the tradeoff was that everyone had far less money and resources for partnerships.
The Perils of Building a Startup Under Public Scrutiny
It was also eye-opening to work on a startup where the public was so involved from an early stage due to the token being publicly available for purchase. It gave me a small window into the challenges that CEOs of public companies face. Every comment and decision was scrutinized and discussed on Reddit forums or Discord groups. An army of online sleuths dug up every little detail of every new hire, who they might know, what anyone on your team was doing, who they connected to on Linkedin, what they tweeted, and how everything might connect. It’s as if the fandom of Lost directed their attention toward your startup. I also dealt with a couple of creepy online stalkers because of this, which made me consider just how public I wanted to be (yes - I am aware of the irony given how long this post is).
Navigating the Political and Media Landscape
Working in crypto during a time when the government (unfortunately, specifically Democrats) was hellbent on destroying crypto rather than providing a regulatory framework made me even more skeptical of politics and media. Watching the best-intentioned companies get harassed by the regulators while criminals and blatant scammers operated with impunity was incredibly frustrating. Equally frustrating was how even when regulators got something wrong and would acknowledge that privately, they would never publicly correct it. Most companies don’t want to risk correcting it publicly out of concern that such actions would further draw the attention of regulators. Additionally, seeing how much the media got wrong regularly made me extremely aware of Gell-Mann Amnesia.
"Briefly stated, the Gell-Mann Amnesia effect is as follows. You open the newspaper to an article on some subject you know well. In Murray's case, physics. In mine, show business. You read the article and see the journalist has absolutely no understanding of either the facts or the issues. Often, the article is so wrong it actually presents the story backward—reversing cause and effect. I call these the "wet streets cause rain" stories. Paper's full of them.
In any case, you read with exasperation or amusement the multiple errors in a story, and then turn the page to national or international affairs, and read as if the rest of the newspaper was somehow more accurate about Palestine than the baloney you just read. You turn the page, and forget what you know."
-Michael Crichton
The Stress of Token-Based Compensation
One of the peculiar quirks of working in crypto is the potential to get paid partially or fully in tokens. In some ways, it’s not so different than many tech jobs where you get options, shadow equity or regular equity. Yet, there is one key difference: liquidity. In most startups, liquidity events are rare and companies are only valued during funding rounds.
With crypto tokens, as long as they’re trading somewhere, there’s always a price, making the volatility of startup valuations impossible to ignore. During my tenure, the Amp token experienced dramatic swings, with gains of over 400% and losses of around 95%. Although my tokens were subject to cliffs and vesting schedules, the sheer volatility was distracting whenever they unlocked.
Because tokens are subject to income tax, you’re forced to make tough decisions. You can sell some tokens to cover your tax burden or double down—pay taxes with cash and hold onto your tokens. The latter feels reckless, given the inherent risk of working in a high-risk startup in a high-risk industry. But even the responsible choice has its pitfalls. Say you sell your tokens to pay taxes, only to see their price surge 400% a month later, making you wish you’d held onto them. Conversely, if you hold and the tokens plummet 95%, you’re left owing taxes on their original value, with losses that only offset your taxable income by $3,000 a year. In either scenario, the tax implications can be a nightmare.
Adding to this complexity is the emotional weight. You feel a sense of responsibility to your project’s community and team to avoid selling, but also to your spouse or family to sell and secure some income. It’s an ongoing stress. Layer on the timing factor, and the outcomes can vary wildly. In my case, the token rose 400% in my first quarter, which felt great. But had I started six months earlier, my tokens would have been worth 3,300% more to me. Had I joined a quarter later, I’d only have seen two years of declining prices.
This timing-dependent variability also happens with public companies, as seen recently with NVIDIA. However, before crypto, most startup employees didn’t have to worry about this level of liquidity and volatility—after all, most startups fail before a liquidity event ever occurs.
Charting My Next Course
Reflecting on my time in the crypto and startup world, I’m struck by how much it sharpened my understanding of risk, decision-making, and the interplay of external forces when building something meaningful. These lessons continue to shape how I approach challenges and opportunities today.
Since leaving the startup, I’ve embraced the freedom and intellectual stimulation that comes with trading for a living. It’s a path filled with its own complexities, but I’m enjoying the autonomy and focus it demands.
For now, I’m content navigating this unpredictable world on my own terms. That said, I remain open to opportunities that truly excite and challenge me. Life has a way of surprising us, and I’ve learned not to predict what’s next. My goal is simply to meet whatever comes with acceptance and curiosity.