A Funny Thing Happened On The Way To Becoming A Billionaire
Musing 📝 (8m read)
In 2018, I packed up and moved to the Bay Area to pursue an MFE at UC Berkeley. After eight years as a macro quant trader, building proprietary models and strategies that delivered three consecutive years of 20% annual returns, I decided it was time to formally solidify my technical expertise. The plan was simple: finish my degree and head straight for the bright lights of New York, London or Chicago to manifest my dream of becoming a hedge fund legend. Northern California was meant to be a brief stopover, nothing more.
But a funny thing happened on the way to becoming a billionaire…
I still vividly remember standing in the hallway at Haas holding two offers. One was a high-profile role in London to spearhead algorithmic trading at a commodities hedge fund. The other was a two man team developing a special project at the fintech Opendoor in San Francisco. For most of my classmates, the choice was obvious: London promised limitless earnings, while SF looked like a financial dead end.
So I did what I typically have done throughout my entire life: I followed my heart, more than my head. My decision shocked everyone, especially Linda, the MFE Director, who frequently reminded me that a recent alum, working at the same fund, had raked in a $10 million trading bonus the year before.
I had already achieved and acclimated to a financial foundation that few get to experience that the marginal utility of additional wealth was losing its luster.
Founder Detour
I wasn’t running on pure ambition anymore, but I stepped into a new role that still carried prestige: founder. This time, the goal was different—helping people and building something that could touch millions, maybe even billions, of lives. It took me a few years to come to terms with the fact that fintech and crypto projects never quite aligned with the mission of helping people. But that’s a story for another post.
Self-Sabotage or Self-Discovery
Every now and then, I let myself imagine what my life in London or New York could have been. Naturally, in my dreams, I see myself as an enigmatic figure—an eccentric billionaire whose insights command reverence, gracing CNBC with rare, masterful appearances. But I’ve learned there’s little use in chasing fantasies of an alternate reality, no matter how gilded they appear.
Is my story a cautionary tale or one of transcendence?
Perhaps it is both, or neither—an ever-shifting tale that changes with time and the place I find myself in. Truth, I’ve discovered, isn’t universal; it is personal, dynamic and lived moment by moment. In embracing my truth, I’ve found freedom—the freedom to be present, to savor life with abandon, sucking the joy-sickle from every moment.
Ego Death
Since the end of the lockdowns, I have been navigating what feels like a slow ego death, a gradual unraveling of the self I once clung to. There’s a quiet mourning in this process—a grieving of the identity tied to financial ambition and status. Yet, as I shed that self-centered drive, I’ve discovered joy in exploring new ways of being. It’s liberating, though not without moments of deep suffering that leave me questioning who I am becoming.
Earlier this year, in 2024, while working in New York City I met with old friends from my days in finance. Many of them, still entrenched in trading, talked about their money, their jobs, the parties, the women and their glittering lives. I felt like an outsider. Their world, once familiar and aspirational, now felt distant and hollow to me. Some came to the table, I think, hoping for crypto or AI investment tips. A kind friend even extended an open invitation if I ever decided to come back to trading. All I wanted to talk about was how they were doing, the relationships they had forged and the love in their lives.
Soldier of Fortune
The erosion of my ego didn’t wipe away all my self-centered dreams. I’d be lying if I said there wasn’t still a part of me that fantasizes about striking it big—those lottery ticket moments—or craves the thrill of being widely recognized as a master of the universe or a captain of industry. But the difference now is that those thoughts don’t hit the same. I imagine the cheers, the compliments, the strangers singing my praises, and it just feels… hollow. It’s strange. I’ve spent so much of my life chasing validation, but the truth is, I’ve always shied away from it the moment it arrived. It’s not that I think I’m unworthy; it’s just that so much of success feels like luck, and that makes the applause feel shallow.
The success I chase now feels almost like coming home—a bittersweet echo of the dreams I held as a child, born from pura vida.
Growing up in Southern California, I was surrounded by people who followed their bliss and built something real—surfers, innovators, musicians. From Kelly Slater carving waves to Edward Thorpe’s breakthroughs in math and finance, from garage bands like No Doubt to local legends, I’ve always seen true success as something that grows organically from presence and passion. Every now and then, I find myself daydreaming about playing bass guitar in a garage band, just hanging out and jamming for the sheer fun of it.
I’d rather be lucky than good any day
Sometimes, the universe sprinkles serendipity dust in the most unexpected ways. Recently, my lifeless crypto portfolio—mostly amassed by chance while working in the web3/crypto space—have turned into a mini lottery ticket.
Dharma Bum
As I delve deeper into the intersection of human connection and spirituality, I’ve been revisiting Jack Kerouac’s The Dharma Bums, a work that feels more rich with meaning each time I return to it.
The term 'Dharma Bum' was popularized as a wandering seeker of truth and enlightenment.
Given that loose definition, I suppose I’d describe myself as a Dharma Bum these days. But let’s be clear—I’m not planning to adopt the silk robes or return to the long-haired, bearded mystic look anytime soon. That doesn’t feel like my authentic vibe. What captivates me instead is spirituality’s potential to help us reconnect with our humanity and recalibrate the delicate balance in our relationships, particularly as we navigate the growing influence of technology.
The Birth of Buddha
I find myself drawn to the tale of Siddhartha Gautama, The Buddha. A prince who cast aside his crown to walk the path of pain and compassion, discovering truths that would ripple through history. Even now, his teachings offer a beacon of hope and clarity, shining across the centuries.
I’m not about to trade the modern world for a monk’s robes, but I crave a passionate life infused with spirituality—a way to feel more rooted, more alive in every breath.
From time to time, when the weight of fear and solitude in this new direction feels heaviest, I turn back to a poignant parable from Dr. Strange for comfort.
The Ancient One: Do you wonder what I see in your future?
Dr. Stephen Strange: No. Yes.
The Ancient One: I never saw your future, only its possibilities. You have such a capacity for goodness. You always excelled, but not because you crave success, but because of your fear of failure.
Dr. Stephen Strange: It's what made me a great doctor.
The Ancient One: It's precisely what kept you from greatness. Arrogance and fear still keep you from learning the simplest and most significant lesson of all.
Dr. Stephen Strange: Which is?
The Ancient One: It's not about you.
The past few years have broken me in ways I never imagined, with 2024 being the heaviest burden yet. Though a few may glimpse the shadows of my sorrow, I’ve become skilled at concealing it—sometimes even from myself. But this story isn’t about hiding. It’s a reminder of who I am at my core: someone who cherishes connection and love above all, someone ready to face today with an open heart, someone whose story is both ending and beginning, dying and being reborn.
