A Few of Jungleman's Craziest Ups & Downs
So, I want to tell you about some of the craziest swings in my life—swings worth millions of dollars—that definitely kept me on edge.
First, you probably already know about Black Friday, when loads of poker players had their bankrolls locked up. I was one of them. In fact, I had the largest bankroll locked up of anyone I knew: about $4 million on Full Tilt Poker, which was seized by the federal government in 2011 because Full Tilt had been breaking regulations and engaging in money laundering. PokerStars, on the other hand, paid out immediately. To my surprise, even the $100,000 I had on Ultimate Bet Poker was paid out.
Full Tilt, however, was a different story. For years, it looked like we might get paid, but it never quite happened. Back in 2011, I thought I’d solved the problem by selling my Full Tilt bankroll to Tom Dwan for roughly 80 cents on the dollar. The very next day, news broke that Full Tilt was likely to be bought out and players would get their money back quickly. I called Tom to cancel the deal, and he agreed to unwind it with a small adjustment. He even gave me a guarantee—if Full Tilt collapsed and I ended up making no money, he would cover $2 million of my loss. That was generous of him, though I never actually collected on it.
Years passed without resolution, and then in 2014, out of nowhere, Full Tilt was sold and all player balances were paid. When I checked my account, I was over $4 million richer. That was a massive upswing.
The same year, another unexpected event happened. I had long suspected that I’d been hacked for a large amount, and I even messaged Lars-Magnus Rasmussen (known as “Lotten” on PokerStars) about it. I didn’t suspect him, but I did suspect his friend Peter Jepsen, who had a notorious reputation for being linked to multiple player hackings worth millions.
Then one day in Las Vegas, I got a text from a friend named Jacob. He told me he’d caught Peter trying to hack him. Peter had been staying at Jacob’s place while recovering from a hospital stay, and Jacob discovered that Peter had installed a Trojan on his device. Jacob told Peter he could either confess himself or be exposed. Peter ended up admitting to me—and to others—that he had hacked us. He promised to pay back the money, and to my surprise, he wired $250,000 directly into my bank account.
Another unexpected upswing.
On top of that, I was running hot at the tables, up over a million dollars in Las Vegas playing $2K/$4K mixed games. During this streak, a friend pitched me an investment opportunity projected to make $2 million in nine months. All I had to do was take out a hard money loan for about $4–5 million and put in $1 million of my own money. The deal involved a big-name real estate agent, Kurt Rappaport, and his protégé, developing a property in the Hollywood Hills. Supposedly, another investor named Charles was trying to buy back the contract, which made it seem like a great deal
Despite multiple people warning me against it, I had already invested around $100,000 and put down a deposit for the loan. Canceling cost me another $200,000. I convinced myself it was worth the risk because I wanted to do something beyond poker, something bigger.
That was the start of a costly story.
Around the same time, I was approached to help the Asian high-stakes group led by Paul Phua. Several members of the group had been arrested by the FBI for alleged sports betting violations. They needed people outside their group to post bail. After doing my own legal research and consulting with a lawyer, I agreed to post $1 million in bail for one of the defendants—not Paul. It seemed risky, but the legal advice suggested it was safe. I didn’t have access to that million for a while, but I did get it back eventually, along with a heartfelt note of thanks from the person I helped.
That was the environment I was operating in when the house situation began to unfold.
They needed people outside their group to post bail, and several others were already helping Paul and the rest of the group. I was one of the people approached to post $1 million in bail for someone—not Paul himself. The idea was that it would be a favor, and according to what I was told, the risk was minimal.
I did my own research and spoke with a lawyer to confirm that I wouldn’t be putting myself in legal jeopardy. On the surface, it looked risky, but in reality, it wasn’t. Still, posting $1 million meant I would be without that money for quite some time, and I had no guarantee I would get it back.
Fast forward a bit of time and the house deal completely fell apart. I had to eat the losses from my initial investment and the loan deposit I had put down. It stung even more because I had been warned by multiple people not to get involved in the first place, but I convinced myself it was a can’t-miss opportunity. Looking back, it was a painful but valuable lesson in trusting instincts and doing thorough due diligence before committing large sums outside my core expertise.
Around the same period, the bail situation with Paul Phua’s group eventually resolved without incident. The person I posted the million for showed up to court, the legal process played out, and I got the full bail amount returned. Along with it came a heartfelt note of thanks and a promise to return the favor in the future if I ever needed help. It was a massive relief, but also one of those moments where you realize just how much stress hangs over your head when that amount of money is in limbo.
All these events — the Full Tilt payout, the hacker repayment, the poker upswing, the failed house investment, and the bail posting — happened within a relatively short window. Each one could swing my net worth by hundreds of thousands or millions in either direction. It was like riding a financial roller coaster at top speed, with every loop and drop amplified by the sheer size of the numbers involved. Even though I came out ahead overall in that stretch, the volatility was exhausting, and it shaped the way I approached both poker and investments going forward.
It turned out there was a delay, and no one really knew why. Eventually, we discovered it was legally impossible to build another story on the house. The neighbor had made it clear from the beginning that they wouldn’t allow it, and they were adamant about blocking any attempts. That left us with a major problem — we couldn’t expand the house, but I still had to pay $40,000 a month on the hard money loan. It was a one-year term, and in 2014 I had figured that as long as I avoided a downswing, I could comfortably fund it. Unfortunately, in 2015, the downswing hit.
I started playing Deuce to Seven and other mixed games, and while I might have made some mistakes, the runouts were brutal. The losses piled up quickly. Meanwhile, the house wouldn’t sell, its value dropped, and I realized I was going to take a bigger hit than I had thought possible. On top of that, I had artwork that was supposed to be liquidated by this time, but it wasn’t moving. A lot of my private investments just weren’t panning out. The hacker who had returned some stolen money still hadn’t repaid the full amount, and I had to accept that part of that loss was permanent. Eventually, everyone took him to court.
As 2015 went on, things worsened. I went to Commerce Casino, but nothing went my way — I lost in every game.
In Chinese Poker, I was up $500,000 on Aussie Matt and thought I couldn’t lose. Then, he won it all back and kept going, completely crushing me. I checked out a poker opportunity in Panama that also turned out to be a bust. At least Panama City was beautiful, and I spent some time there and on the islands with my ex-girlfriend. She stuck with me through all of this, which was one of the few bright spots.
Later, I went to Monaco for big PLO games with Ben Lamb, Rafi Amit, Aussie Matt, and others. There, I lent £200,000 to Fred Sines, thinking he was trustworthy. I quickly learned otherwise — he never paid it back, no matter how I asked, and multiple people boycotted the game because of it. That loss stung badly, and I was already burning through cash on the house every month.
The only real relief was that I got my $1 million bail money back from posting for the Asian group. While WSOP was going on, I flew to Montenegro for a no-limit hold’em game — my best game — with a $4 million HKD buy-in (over $400,000 USD). I didn’t have the full roll, so I arranged a backing deal. I thought this was my shot to turn things around. Instead, I lost in the first session. I also played some props, which upset both the game runners and my backers. Then I kept losing, eventually dropping over 20 million HKD, and at one point hitting 30 million in losses. Then “Chairman” arrived, and the game doubled in size.
But I started running hot and thought, “Okay, this is my way out of this.” Things were going very well, only for me to lose a lot of it back toward the end of the night and eventually slip into the hole again. At some point, the game switched to PLO and my phone had died. I lost a bit more money, and some of the backers canceled their share because they didn’t think much of my PLO game, which cost me another $100,000. At this point, I was in deep trouble and feeling very despondent. Phil Ivey even sent me a text to make sure I was okay, because it was clear I was in distress. I still remember that moment.
The one bright side was that Montenegro had beautiful areas, like Kotor, where you could take a boat out and enjoy the scenery. But with my backers losing confidence and my bankroll spiraling, things were not looking good. After all this, I was down about 40 million Hong Kong dollars. Then I played a session and won 30 million back, leaving me only 10 million down, which was small given the 4 million HKD buy-ins. But then, more bad news: a partner in the game named Ye, who had been critical of my play early on, told me he had lost heavily. My share of his loss came to minus 800,000. While it was not catastrophic, it still added to the pile.
I went back to Las Vegas. The good news was I won there, but the bad news was I was still stuck in an overall downswing. Online, I was losing as well. I even played a couple of $100,000+ sit and goes with Leon Tsoukernik, thinking it was a good shot to recover, but Leon beat me a few times. He ran hot but also played better than expected with strong intuitive reads. That pushed me further into the hole.
Later that year, someone stepped in to back me again, which was crucial. I traveled to Monaco, Manila, and other places to play the $4 million HKD buy-in game with the Asian group. I had to hustle to keep my spot because people were losing confidence in me. Many strong players, including Isaac Haxton, Igor Kurganov, and Philipp Gruissem, had played in this game, lost, and quit. The game was tougher than expected, but still beatable.
One downswing came when I played a hand passively with two pair against someone I suspected had me beat. I just check-called and ended up losing to a better two pair. Out of frustration, I banged the table with a chip, which flew past Chairman’s ear. Since Chairman was the big boss, that could have ended badly, but he and his friend Shanghai Wong found it amusing rather than offensive.
I kept losing and had to fight to keep my share in the game. Eventually, I turned to studying solvers, and that completely changed my approach. I realized how much conventional wisdom was wrong, how many missed possibilities there were, and how many sizing strategies people were getting wrong. This work improved my no-limit and mixed games significantly.
While still on a downswing, I went on a huge upswing later in the year, winning hundreds of thousands, even around a million, thanks in part to solver study. Around that time, I faced another major problem: the government put a lien on my account for nearly $2 million in back taxes from 2014. I needed to refinance my house to pay it off, but I didn’t have the cash on hand.
I was able to sell a piece of art I had invested in, but the deal wouldn’t close for another week. Erik Seidel loaned me money against that sale so I could pay off the lien in time.
Soon after, a massive $1 million USD buy-in game ran in Manila. Chairman declared no one could leave until they lost $1 million (10 million HKD). The game lasted 72 hours, and I only slept one hour. In the middle of it, I had to take a call to finalize the refinance on my house, which brought my interest rate down to a manageable 3% and saved me from financial collapse.
Even though I lost in that session, it worked out in the long run. Over the next couple of years, I became the biggest winner in that Manila game. That opened doors to even larger games and new opportunities. Despite my earlier slow play and reactive behavior, the other players tolerated me until I adjusted my table demeanor. Meanwhile, selling the property turned out to be more complicated than expected. I even turned down an offer in the 6-million range from one potential buyer.
He said that was his final offer, but for whatever reason I didn’t believe him or thought the property would go up in value. I really wish I had taken that offer, but I couldn’t go back. There were other offers in the 5.8 million range, but when I tried to accept them later, it was too late. I attempted to rent the property, but it turned out you couldn’t list it for sale and rent it at the same time. There were also issues with maintaining it, and no one told me I needed to keep it in good condition for showings or rentals. The floor panels became damaged, and other problems piled up.
One memorable moment from that period was a house party toward the end of 2014 that Justin Smith organized. It brought in several well-known guests, including Pamela Anderson, Rick Salomon, Andy Milonakis, and other Hollywood personalities. It was surreal to have celebrities in my home, and while that didn’t have monetary value, it was a unique experience in the middle of everything else.
Despite the stress, there were still enjoyable moments—fancy places, great food, and relaxing times. In the end, I sold the house for a much worse price than the earlier offers I had received. Looking back, I should have sold immediately instead of waiting. I learned an important lesson about not being greedy with valuations and letting go of a bad investment.
I ended up losing at least 1.5 million, possibly more than 2 million, on the property. The good news was I remained wealthy overall, still holding a large portion of my net worth, and I came away with valuable lessons. The biggest were to be more cautious when trusting people—not only their intentions, but also making sure their actions matched their words—and to ensure business deals are properly structured.
Ultimately, I hope these lessons can be applied on a larger scale. I expect to operate at even higher stakes in the future, and I know that things rarely turn out exactly as expected, whether good or bad. There is always potential for both positive and negative surprises, so the best approach is to play your best game as each situation develops.
