On Cards, Crypto, and Christ

I used to think Christians were stupid.

I grew up in Colorado Springs, a deeply conservative area in Colorado home to Pikes Peak, the Air Force Academy, and megachurches. My classmates would come in on Mondays talking about their experiences at church while I’d spent the weekends studying for the Spelling Bee and Geography Bee. They wasted their time while I zoomed ahead, victories and accolades piling up in the real world.

My parents were Hindu and I followed their faith out of filial piety until college where philosophical and scientific books convinced me that there was no justification for any religion, let alone Hinduism. These were myths that had been passed down for generations and that people believed solely based on what their parents taught them and where they’d grown up. There was no scientific evidence behind them. All religions were largely the same and full of hypocrites who proclaimed themselves morally superior while committing immoral acts.

After college, I began to read Eliezer Yudkowsky and other writers from the rationality movement. Yudkowsky proposed that morals could be derived from reason. Like Sam Harris and Richard Dawkins, he mocked the backwards beliefs of religious people. 

These were simply people who were not rational. They had something broken in their brains that caused them to believe in a God, despite all evidence to the contrary. Christianity was a mental error, akin to a cognitive bias or logical fallacy. Through reason, you could arrive at better moral principles than the Bible. As the religion most familiar to us in the West, Christianity is the easiest and safest one to dismiss.¹

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One of the rational things I wanted to do was make as much money as possible and retire at a young age. I assuaged any personal doubts I had about whether this was a selfish goal by telling myself I would donate to charity after I made enough money. The more money I made, the more I could direct money towards noble causes. This is a comforting story that people chasing self-glory often tell themselves.

In 2015, I was ranked #2 in the world on the Global Poker Index and privately boasted to friends I was the best player in the world. The dedication and singular focus had cost me a relationship, but the goal of accumulating a retirement nest egg before 30 and never working again seemed within my grasp. 

However, after being so close to the mountaintop, I suddenly encountered a string of bad luck that compounded into bad play that led to a massive downswing. I began drinking heavily, eating heavily, and partying like a maniac. I put on fifty pounds and gambled more and more in tournaments in a chase to get back the money I’d lost.

Turns out a diet of KFC Zingers and red wine isn’t conducive to a healthy body

By December, I found myself at a crossroads: depressed, overweight, nearly broke, and alone. I went to the Bellagio WPT Five Diamond Tournament in Las Vegas having torched 90% of my wealth from peak net worth in less than a year. During the tournament, I got dinner with Kory Kilpatrick and he told me that he’d been in a similarly dark place recently.

The pursuit of money, and money alone, has many fellow travelers.

He suggested I begin listening to the Tim Ferriss podcast focusing on Stoicism and Buddhism, especially one from a guy called “Naval Ravikant.”² I began to get healthy, start working out, and listened to podcasts non-stop. 

The WSOP 2016-WSOP 2017 season was possibly my best ever and included an EPT Highroller trophy. However, the disappointment of a close result in the SuperHighRoller Bowl and the lack of excitement for gearing up for another full year of poker study, travel, and play led to my unofficial retirement in July 2017.³

I’d first heard of crypto in 2015 through the Wired Silk Road article although I didn’t really start allocating significant capital towards it until early 2017. I eventually settled on a quasi-Bitcoin maximalist strategy. In retrospect, this was more of an aesthetic Libertarian view based in government distrust than a well-researched investment strategy. After my retirement, I decided to put roughly 10% of my net worth into Bitcoin as an asymmetric upside bet and decided I would keep the rest in “safe” assets like a Vanguard account and cash.

In the meantime, I was free to pursue my intellectual interests. I began watching a Jordan Peterson Bible series and was blown away by the depth and analysis he provided in retelling the Judeo-Christian stories. It was tied up in comparisons to the ancient myths and somewhat implausible claims, but the key understanding was the power of these stories. They may not have been factual, but they had deep psychological significance and implications. There was truth bound up in these stories that was hard to explain or comprehend, yet they were incontrovertibly representative of reality. One of the most interesting things about the Bible is that the “heroes” are often incredibly weak, have few redeeming qualities, and make mistakes repeatedly, sometimes even getting rewarded when they fail. These weaknesses are part of what lets the rationalist mind look at the stories and say “Hey, I could write a better story of morals!” but what they fail to comprehend is the truth of human behavior and a pathway to freedom is more bound up in Biblical stories than fictional stories with idealized characters.

I could no longer call Christians stupid. I certainly didn’t believe in their God in the sky, but I didn’t think they were stupid. Maybe there was some value they got out of their religion that made it worth it for them. Reading Girard and other writers also helped me understand some of the deep differentiation between Christianity and other ancient myths, dissuading me of the notion these were all the same just with slightly different twists. 

Meanwhile, Bitcoin was rocketing up towards $20k in late 2017 and I could’ve easily felt like a genius. However, I heard about friends making millions flipping ICOs and trading altcoins. The old siren song of greed began to be irresistible. I once again reassured myself that if I made my millions, I would donate to good causes and that would justify my pursuit of wealth. 

I messaged those poker friends who’d gone all-in on crypto and quickly got involved in several ICOs. I moved my Vanguard money into crypto. Everyone knew it was a bubble, but we all thought we could sell to some other sucker before the music stopped. We saw tons of “blockchain for X” startup concepts and invested in any of them that seemed borderline credible.⁴

Poker had desensitized me enough to money that even the daily 20-30% swings in net worth that I was taking in the height of the mania in late 2017-2018 felt like nothing. I just had to bet more to win more. If I played the next 6 months right, I could make life-changing amounts of money and be done working for life. I hit my peak net worth sometime in January 2018 and glory seemed right around the corner.

The market crashed a month later. 

I kept trading, but watched my net worth slowly get decimated over the course of 2018. I initially kept up many of the practices I’d learned from podcasts: the weird stew of Buddhism, Stoicism, and rationality that attracts many high-performing males who realize that wealth and success has not granted them the happiness they thought they’d find. However, as things continued to worsen for me in life, I couldn’t help but notice that these practices offered me little solace.

I thought about more extreme ideas: maybe I should do a 10 day silent retreat? Psychedelics? 72 hour fasts? Wim Hof breathing? I even tried a few sessions of hypnotherapy. I was a prototypical hamster on a spinning wheel, searching for solutions in things that can be great coping band-aids, but fail to create sustainable and finalized change. We always need the next, more extreme solution. If you trace the path of many who go on this ‘enlightenment journey’ over the years, you’ll see that they’re still on the same wheel, in search of something new that will give them the next answer after the previous high wears off. There’s always a new practice, a new drug experience, or something that they’re super excited about, sure that it will unlock a new level of enlightenment.

In January 2019, I flew to Singapore to meet the guys from Three Arrows Capital. They were still largely an FX fund at the time, but both Kyle Davies and Su Zhu were deeply interested in crypto and had been investing personally for years. They had an idea for an application they wanted to build on Ethereum: a Keynesian Beauty Contest betting game similar to Hot or Not, but for crypto. We would use the success of the first game to build all sorts of unique games, culminating in a decentralized on-chain casino. The moral and ethical quandaries of building Hot or Not or a gambling project were far from my mind. Despite my original interest in crypto stemming from an ideological lens, I could hardly care about that given how much of my net worth had been torched in the past year. This was a lifeline I could hardly throw away. 

We hired a couple developers and built towards the launch of the MVP. In retrospect, I had no idea what I was doing, and we made tons of mistakes that I would advise startups against. We should’ve launched quicker, tested the game loop, iterated more etc. We very much had a “if we build it, they will come” attitude.

I was under immense pressure. If this game didn’t succeed, I’d be on a plane back to the US, with no money and no prospects. I knew I didn’t want to crawl back into poker despite the backing I could likely get. I also had zero work experience and was 30 years old, what felt like a late time to start over in a career.

I began drinking heavily again. A bottle of wine was the minimum every night and most nights were two. I used to have a health spreadsheet where I tracked various metrics like sleep, diet, etc. I ended up adding a column called “CS” which would be tracked by 1 (yes) or 0 (no). CS stood for “Contemplated Suicide.”

That column had a lot of 1’s in the spring of 2019.

Sometimes I felt like the “universe” was against me. I’d gotten into poker right as the post-Moneymaker poker crash was about to begin after Black Friday. I’d continually come up short or gotten ridiculously unlucky in some of the biggest moments in my poker career. Similarly, I’d seemingly gotten into crypto right as the era of massive gains had ended. Yes, it was my fault for FOMOing into ICOs and other trades, but it’s hard to take responsibility for your own decisions when your life is in shambles. I felt like some invisible force was working against me even though my rational brain knew that was ridiculous.

I started going on a lot of dates, searching for salvation in a pretty girl. Like a lot of people on the dating treadmill, I was looking for affirmation and a feeling that at least in one part of my life, I wasn’t a complete loser.

In early June, I went on a date with a new girl called Gwen. I was massively hungover as I’d been out til 2 am drinking the night before. I walked through a museum with her, stifling yawns with zero chemistry or sparks flying between us. We later went to a fancy restaurant in Singapore, overlooking the river. What proceeded was the strangest first date I’ve ever been on. Rather than talking about our jobs or travel while subtly flirting, she asked me about my friends and what gave my life meaning. It was such a non-romantic conversation that I remember leaving the date thinking there was a good chance we’d never talk again and if we did, it would just be as friends.

Later that night, she texted me saying she had a good time and asked me if I’d like to go to church with her. Honestly, if it hadn’t been for my dabbling with Peterson and Girard a couple years earlier, I would’ve laughed and politely declined. After all, I used to think Christians were stupid. But since I didn’t think that anymore, I was curious to check it out.

She told me to meet at a mall in Singapore the following Sunday and we could go into the auditorium from there. I was confused (I thought churches were in cathedrals?) but went in with her anyway. The inside was what looked like a concert stage and when the clock hit 2:30 pm, five singers came out to the microphones with two full sections of a choir behind them.

“People, come together

Strange as neighbors, our blood is one.”

As the opening chords of “Good Grace” rang out through the room, I felt tears in my eyes. I was struck with pure, raw emotion. An overwhelming sense of truth and warmth, an inexplicable feeling of “Child, you’re home,” came over me. Sometimes a feeling can sound like a voice without being heard. I was momentarily awestruck and didn’t know how to explain what had just happened to me.

However, my hyper-rationalist brain hadn’t stopped working. As I got ice cream with Gwen after church, I discussed with her what had come over me, curious rather than convinced. She told me that was the voice of God speaking to me. He wanted to know me.

That wasn’t enough for me and I went home that night determined to learn more. I remembered that an investor I followed called Brent Beshore always posted on Twitter on Easter and Christmas about Jesus Christ. There were usually book recommendations buried in the replies. It had always struck me as curious. Brent was an oddity in the investing world, a Christian who was bold about his faith no matter how others may perceive him. That night, I started reading “Cold-Case Christianity” and a devotional Gwen had given me.

June bled into July. I was still going to church with Gwen and working on the gambling project. I went to Taiwan for the Asia Blockchain Summit to fundraise. This was the site of the famous “Tangle in Taipei” between Arthur Hayes and Nouriel Roubini. That trip likely broke whatever optimism I had remaining in crypto at the time. The industry was crawling with opportunists, scammers, and most of all, people whose only goal was to siphon personal wealth out of the game.

Most damningly, I was one of them.

I returned to Singapore and asked Gwen to be my girlfriend the following Sunday. I still wasn’t a Christian, but Gwen felt like a lifeline to a different future. It was like jumping on a boat with no idea where it was heading. All I knew was that I couldn’t stay where I was anymore.

I kept going to church with Gwen and it became increasingly awkward as her friends would ask me about my faith journey and I’d have to confess I wasn’t a Christian. I’d read a few books on Christianity by now, but despite how interesting and valuable the ideas of Christianity seemed to be, nothing had given me the conviction that there was a God. My rationalist brain could not comprehend the possibility of the supernatural. I would need God to appear in front of me and prove His reality before I would be able to acknowledge it.  

One day, she invited me to go to a worship concert with her as an American singer was in town. During the first half of the concert, I watched as those around me lifted their hands up to God and sang at the top of their lungs. I felt incredibly out of place and realized I was never going to be a believer. I needed evidence. I decided I would break up with Gwen when the night was over. She didn’t deserve to be strung along by me anymore when it was clear that I was simply too much of a rationalist to ever believe in God.

During the intermission, the pastor announced that some people would be giving testimonies. The first was a kid in a wheelchair who had cerebral palsy. I’d briefly worked with kids who had cerebral palsy in high school and had a soft spot for them. What proceeded was one of the best five-minute speeches I’d ever heard. He shared that his parents had been told that he would never be able to read, write, or speak well, but after becoming a believer and through prayer, he’d gone further than his family had ever expected. He was studying economics at a Singaporean university and going on mission trips. God had been so good to him in his life and all he wanted to do was share the good news.

I was floored. Here was someone who could have easily blamed God for his condition and yet chose instead to glorify Him and see the goodness in his life. 

I whispered to myself: If he could give God a chance, why couldn’t I? God, if you’re real, show yourself to me tonight.

I’m not even sure what song it was. It may have been “Good, Good Father” or “Build My Life.” All I can remember was singing a song and suddenly feeling an internal resonance within me, a oneness with something far greater and more powerful than anything I had ever experienced. It took me out of where I was in that small church in Singapore and connected me with the divine.

The second before I didn’t believe in God.

After that moment that felt like a lifetime, I knew He was real.

I wish I had a better story like the audible voice of God telling me something or seeing a miracle. I know many of you who are skeptical reading this would love to hear what “evidence” convinced me to change my mind. Unfortunately, this is all I have. In a way, that might be God’s way: that’s why it’s called faith.

I gave my life to Christ that night. My relationship continued blossoming with Gwen. I stopped drinking heavily, never contemplated suicide anymore, and started eating healthy again. I was finally free in a way that I could hardly believe possible. Even to this day, there is a peace that surpasses understanding: this is the peace of Christ.

I had an even more powerful moment a month after my conversion when I realized not only God was real, but that He loved me. I broke down in tears while watching a sermon that ends with Jesus cleanses the leper. For most of my adult life, I’d felt somewhat like a modern leper, a degenerate gambler on the outskirts of society, unable to form real or meaningful relationships. The tears were a purifying cleansing, a personal release of my broken messy past and stepping anew into the things God had for me.

We were a couple weeks away from launching the MVP and I felt like I owed it to Kyle, Su, and the others to see it through despite some reservations. After launch, it failed to gain any meaningful adoption or traction and we decided to sunset the project with the option to potentially revive it.⁵ In retrospect, we had been thinking about a lot of the same ideas that would prove immensely popular two years later like NFTs and play-to-earn gaming, but were stuck with a bad core game loop and poor market timing.

I was nearly flat broke and soon to be engaged, but instead of feeling anxiety or fear, I felt comfortable, knowing that Christ had told us not to worry about what we would eat or drink. To the world, I was in a humble and lowly place, but perhaps that’s where God’s blessings can overflow the most.

As I thought about what was next for me, I knew that my Christian faith would have to be at the center of it. I also knew that the things that used to matter to me like money, status, and power no longer drove me.

“No one can serve two masters. Either you will hate the one and love the other, or you will be devoted to the one and despise the other. You cannot serve both God and money.”-Matthew 6:24

The world tells you to worship and chase after these things. For all my life, my scoreboard had been determined externally by either winning competitions or wealth accumulation. It was an extremely zero-sum mindset: my gain was someone else’s loss and this became even more explicit in my poker career. Whatever was next for me needed to be something where I could participate in a culture of abundance.

Why can venture be a suitable career for a Christian? There’s a parable in Luke 19 where servants are given money by their master. The faithful servants take what has been given to them and invest it, doubling the initial capital. The Bible says no one knows what time and hour He will return, but our commission in the meantime is diligent and faithful stewards of the gifts He has given, always prepared for His return. Despite initially thinking that the only way to serve God was by becoming a pastor, I eventually realized that all of us can serve Him and help bring the Kingdom of Heaven to Earth, either inside or outside the church. As I prayed about it, I became increasingly certain that the world of technology was the one I was called to be in.

While I didn’t get a VC job in early 2020, I joined a great startup in Volley and had a tremendous year of learning. More recently, I got the chance to join the Susa Ventures investing team. The past few months have been a journey of learning the craft of venture, but I’ve lately started to think about the types of founders I want to work with and where I want to invest.

Gwen and I married in July 2021 (Sydney Jai Photography)

The most expedient thing is to look for deals or sectors that are hot. It’s a great way to make your venture career early by having logos in your portfolio that give you an aura of inevitability. The long cycle of feedback loops for decision-making means that even if those companies eventually cool off or fail to reach the valuations needed, your venture trajectory may already be secured.

“Show me the incentive and I’ll show you the outcome.”-Charlie Munger

As crypto has gotten hot again over the past year, we’ve seen a huge influx of interest in the space I formerly called home. It has powerful new memes and access to culture, with returns that are almost too good to ignore.

I’ve been grappling with whether I wanted to spend time in the space again. My own recklessness had decimated a good chunk of personal capital in it. I’ve viscerally felt the pain that crypto volatility can give. I’ve met many of the short-term mindset folks that are drawn to an industry like this: one that’s promising and nascent with low friction and recourse for reputation destruction. A lot of this can be glossed over in a raging bull market, but if there’s ever another sustained downswing, the transactional nature of financialized relationships and the naked desperate opportunism that was rampant in 2018-2019 could certainly come roaring back. The most optimistic people in crypto are the people who call themselves web3 investors and have mostly lived through 2020-2021. Nearly everyone I talk to who has survived one or two bear cycles is similarly excited about the long-term prospects, but balances it with significantly more caution and risk management.

What sealed my decision to dive back in were recent conversations with friends like AureliusBTC, hedgedhog7, and Fjvdb7. All could have been said to have “made” it in some way during the past few years. However, instead of being focused on continued wealth accumulation, all were focused on building and investing in real technology and use cases. They started introducing me to other people who were similarly inclined. Crypto may be one of the hardest industries to separate signal from noise, but there is still signal out there.

More importantly, instead of hunting for status and wealth or identity in what I’m investing in, I am secure in my identity in Christ. He knows me, sees me, and loves me. That makes me free to work with the people I want to work with, invest in the people and technology I believe in, and avoid the pitfalls that have tripped me up before.

Venture, when done well, is a service industry. Peter Fenton says the best VCs are stagehands, while the entrepreneurs are the stars of the show. You'll notice most of the truly outstanding ones are quiet and always defer to and shine a spotlight on the founder. The ones who try to grab power or be the star of the show fail at their most important function and often lose their way.

Some of the most impactful Christians in the Bible are those who are advisors, quietly helping a king rule wisely: Joseph, Daniel, or Esther. The Gospels are full of references to having a servant heart or mindset, whether it’s washing others’ feet or a reminder that Jesus came to serve first, not rule. Similarly, I want firstly to serve others, shunning glory and holding the admiration and status games of the world at bay. Those can come and go, but what remains is stewardship and our dutifulness to what God has put in our hands.

What’s next for me is to find the true optimists and builders, wherever they are, whether that’s in crypto, education, charter cities, or even enterprise SaaS. What matters is not the industry, but the relationship we can build, the goals we can set together, and the purpose that unites and drives us: technology creation that instantiates greatest prosperity and abundance for all.

I’m pumped for the next few decades. We’ve got a lot of work to do so let’s go out and do it.

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Thanks to Blake Eastman and my wife, Gwendolyn Buddiga, for reading early drafts of this piece.

1. This does not necessarily apply to Harris, Yudkowsky, or the New Atheist movement. They duly mock all religions, which can often lead to controversy. Conversely, most secular elites are comfortable ridiculing Christianity, but squeamish about doing the same for other religions lest they come off as Western chauvinists. 

2. My origin story as a startup thinkboi is devastatingly cliché.

3. The story and lessons of the SuperHighRoller Bowl is chronicled here.

4. It’s not lost on me that many of these concepts have been recycled as “web3 for X” in the current run-up. Sometimes experience is the best teacher for helping you keep an even-keeled mind.

5. Following the wind-down of the project, Kyle and Su did one of the kindest things anyone’s ever done for me. I’m still incredibly grateful for that and appreciated the experience working with them, despite the outcome.