Betting the Impossible: 

The Wall Street Dropout:

 Wall Street was supposed to be the dream. I followed the blueprint—go to a good college, cold-email a thousand people, land the internship, and work as hard as possible to secure the offer. But dreams never play out the way you expect. I thought loving the markets and wanting to work nonstop would shield me from the usual pitfalls of hating your job. What I didn’t account for was how much of my experience would depend on having the right boss.

I was used to dealing with difficult personalities, but I never expected to face it in a professional setting. My boss cursed constantly, snapped over small mistakes, and refused to admit when he was wrong. At times, it felt less like working under a mentor and more like dealing with a high school bully. Every day felt like a battle, and I started to feel trapped.

Looking back, I should have gone straight to HR, but I stayed silent, afraid of backlash and the possibility of being blacklisted from future roles on Wall Street. It wasn’t as if people on the trading floor didn’t see how I was being treated—I assumed it was just a rite of passage. But my mental health quickly deteriorated. When I started having nightmares about work, I knew it was time to leave. I had never questioned my own abilities, and I was confident I could succeed elsewhere. So why force myself to keep suffering?

I made up my mind and never looked back. I quit and took time off to recharge, but I couldn’t sit on the beach forever. As I started considering my next steps, I struggled to find another trading role.

I thought about getting my master’s degree and started studying for the GRE. I was never enthusiastic about school, but I wasn’t sure I had a choice. I had begun the application process when an otherwise ordinary night playing Fortnite with Miles changed everything.

Miles told me he had found a flaw in the sports books and had won three different bets at nearly +100000 odds. I wasn’t surprised he had discovered an edge—I was surprised at just how badly the sportsbooks had miscalculated.

During COVID, our friend group spent hours looking for ways to beat the sportsbooks. I focused on live betting, recognizing its similarities to day trading in the stock market. Like the markets, sports events are momentum-driven, and I believed I could apply the same skill set.

I noticed patterns at key points in the game where sportsbooks consistently mispriced live spreads. A spread, simply put, is the expected margin of victory for one team. By ‘day-trading’ the lines, I structured my bets so that I would win regardless of the outcome—I would simply profit more in certain scenarios.

The strategy was highly profitable. I turned a few hundred dollars into nearly $10,000 in just a few weeks. But like all winning bettors, I hit the inevitable roadblock—my wagers were restricted to just a few cents. I kept finding profitable strategies, but the outcome never changed. No matter what I did, I was banned before I could truly capitalize on them.

This is what made Miles’s discovery so fascinating. He had won nearly $150,000, yet instead of restricting him, the sportsbooks were sending him champagne! To them, he was just another lucky bettor—someone who would eventually give it all back.

And why would they think any differently? No parlay bettor in history had consistently beaten the books. Long-shot parlays were nothing more than lottery tickets, heavily stacked in the house’s favor. Why would sportsbooks suddenly question the very foundation of their odds making because of a few ‘lucky’ wins?

The answer was simple: statistics. It was mathematically impossible for Miles to have won three bets at such long odds while placing fewer than 200 wagers. And his strategy was still being refined, meaning the win rate would likely improve over time. I was convinced. I asked if I could tail his bets and offered one piece of advice—he needed to increase his bet size.

If Miles kept wagering $100 per bet, he could win another $100,000, but the risk was obvious. After four wins, the sportsbook would likely catch on and shut him down.

I faced the same dilemma. I was convinced Miles’s strategy worked and that he would win again, but I didn’t know how long the opportunity would last. There was just one problem—I had no money. Asking for a loan to fund sports bets wasn’t exactly an option, so I did the only thing that made sense to me. I liquidated my 401k, paid the early withdrawal tax (which I do not recommend to anyone), and committed to a $50 unit size. Miles scaled to $250.

I was under tremendous pressure. My friends and family were still in shock that I had left my job, and now they found out I had also dropped out of the grad school application process. When they heard I did it to sports bet, they lost it.

I knew their concerns came from the right place, but I also knew they would never understand. After all, who actually believes the guy who says he can beat the casino?

I won’t lie; the beginning was rough. Miles had already won, but all I saw were losses. I was betting hundreds of dollars a day, and each bet felt more unlikely than the last. Injuries were taking a toll on teams, and they made games increasingly difficult to bet. I started to believe we wouldn’t win until next season. I worried I had burned through all my money, only for the sportsbooks to adjust their odds before I had a real chance.

As my doubts grew, the universe threw me one more curveball. I’m not a religious person, but there are moments in life that make you question if something greater is at play. For me, that moment came on the day my grandfather passed away.

I was heartbroken and angry at myself for not making more time to visit him. I had no excuse—why had I wasted so much time gambling? The regret was crushing. Frustrated and needing to clear my head, I went to the only place that ever made sense. I grabbed a basketball and started shooting.

For hours, I told myself I had to get my life together. Maybe I was just unlucky. Maybe this whole thing was a mistake. I felt overwhelmed, ready to walk away and go back to the conventional path.

But life is strange. That same night, I won my first bet—on what was probably the worst bet Miles and I have ever placed. It had no right to win. The way it hit was so improbable, it felt like divine intervention. It was as if my grandfather was telling me: Don’t give up. You’re on the right path.

By some final stroke of luck, neither Miles nor I got limited. Honestly, if I were the sportsbook and saw that bet hit, I wouldn’t have known what to think either. At this point, however, we were wary of placing the same bet on both accounts, worried it might trigger a deeper review of Miles’s activity. To stay under the radar, we decided to bet separately but continued collaborating, constantly sharing our slips and refining our approach.

As I gained confidence, I started incorporating my own ideas into the strategy and gradually developed a distinct style. While the core approach remained the same, my bet slips began to reflect my own preferences. But just as I was settling into a rhythm, I learned my most important lesson.

Two months after my first win, I was offered an incredible opportunity to be an instructor for Wall Street Prep, a role I accepted immediately. It wasn’t a few days before the seminar, however, that I realized the event was in Toronto. That presented a massive problem—I wouldn’t be able to place bets while I was there. But I had already given my word, and I wouldn’t back out last minute.

I figured the odds of a bet hitting during the three days I was gone were slim. But, of course, the world had other plans. I had placed 81 bets, none of which came close—until the 82^nd, which would have hit. While I was away, Miles won his fifth bet, this time for over $900,000. I remember standing there, being congratulated by the other instructors, while the realization sank in. I had just cost myself $250,000 because I had chosen to work.

It was a brutal, costly lesson. From that day forward, I have skipped holidays, birthdays, work opportunities, and vacations, knowing I have no control over when the next win might come.

The day after Miles’s big win, FanDuel rolled out a nationwide update, forcing every user to update their app. They removed certain betting options and adjusted how odds were calculated. It was the first—but not the last—time we forced a major sportsbook to change its system.

It took us around 10 minutes to crack their new odds, and that’s when we realized their flaw wasn’t so easy to fix. They allowed Miles to keep betting but capped his wager limit at $250. I can only assume they wanted to analyze his betting patterns, but why his limit was so high is a mystery. 

Four days later, I won $60,000 on a bet where multiple legs were voided due to last-minute player scratches. Two weeks later the book lost another $250,000 because they had let Miles keep betting at such high limits.

Within a few months, I had cleared over $100,000 in profit and Miles had made more than $1.3 million. The only question now was if the sportsbook would spend the summer fixing their odds, or if our edge would still be there when the season returned. Miles had made his million. Would I be able to do the same?

 

Don't miss Part 4 - The Greatest Bet Ever Won!