Many online poker pros have taken on big challenges in the name of prop bets. But nobody has accepted more crazy challenges than Joey “ChicagoJoey” Ingram.
The longtime internet poker pro has done everything from setting hand-volume records to attaining elite VIP status quicker than anybody.
Ingram is by far one of the world’s most-interesting poker players due to all the crazy challenges that he’s undertook. And what’s interesting is that he continues to accept near-impossible prop bets today.
I’m going to cover the challenges that Ingram has conquered from the past to present. But first, I’ll discuss more on ChicagoJoey’s poker career.
Who Is Joe “ChicagoJoey” Ingram?
Joe Ingram is a mid-stakes poker pro who specializes in pot-limit Omaha. He’s won a fortune by multi-tabling mid-stakes PLO and picking up loyalty rewards.
But the Chicago native was far from successful when he first started playing in the mid-2000s. Ingram was nothing more than a recreational grinder during his first few years.
He made deposits worth up to $1,000, only to bust his bankroll again and again. Ingram worked as a waiter on the side to pay bills and replenish his bankroll.
He continued in this fashion for three years before a more-successful poker friend helped him out. Ingram’s buddy taught him bankroll management lessons and encouraged him to start at $0.05/$0.10 no-limit hold’em.
Joey quickly found that he was more successful at these stakes. But this didn’t stop him from taking undisciplined shots at higher limits and multi-tabling before he was ready.
Ingram finally honed his skills to the point where he was consistently winning at low stakes. He then set out to play more volume than anybody else and earn profits through both his low-stakes winnings and rewards.
ChicagoJoey, which is his TwoPlusTwo handle, eventually switched his focus to PLO and began moving up the limits. He was successful enough to grind out a living by multi-tabling mid-stakes PLO.
Unfortunately, Black Friday struck and forced Ingram to make a decision: stay in America and play on low-traffic sites, or move to a different country and continue playing at PokerStars.
He chose the latter and moved to Vancouver, Canada with some poker friends. Ingram began dedicating more time to online high stakes PLO while staying in Canada.
He competed against some of the world’s best PL Omaha players, including Ben “Ben86” Tollerene, Ben “Sauce123” Sulsky, and Jens “Jeans89” Kyllonen.
Ingram was initially successful at these higher limits. However, he hit a downswing and lost $280k before switching back to mid stakes. He now stays within the $5/$10 to $10/$20 range while focusing on volume.
ChicagoJoey eventually moved back to his hometown, where he currently lives. Although this prevents him from playing on PokerStars, he does grind on US-facing sites like AmericasCardroom.
Ingram has become well known for his “Poker Life Podcast” in recent years. He interviews famous players about poker and other aspects of their lives.
Some of his guests have included Kyllonen, Sulsky, Tollerene, Doug Polk, Dan “jungleman12” Cates, Luke Schwartz, Prahlad Friedman, Fedor Holz, and Daniel Negreanu.
Ingram’s podcast appeals to die-hard poker fans who want to hear in-depth chats with their favorite players. His show is well received too, because he’s been nominated for “Media Person of the Year” and “Podcast of the Year” at the American Poker Awards.
Of course, Ingram is also well known for accepting extremely tough challenges. Below you can see some of the craziest tasks that he’s completed or at least attempted.
Playing 600,000 Hands in One Month
Despite becoming a successful online poker player in the late 2000s, ChicagoJoey was still an unknown player. This changed, though, when he took on his first publicized challenge in May 2009.
Ingram set out to play 600,000 internet poker hands within a month. This amounted to playing an average of 20,000 hands per day.
Putting this further into perspective, one would have to log 1,000 hands over 20 hours just to keep pace. Many high-volume grinders feel exhausted after 20,000 hands within a few days – let alone every day for an entire month.
Ingram cemented his ironman status by logging 600,400 hands within 30 days and beating the challenge. Not only did he win a prop bet, but he also put himself on the map by setting the record for hands played within a month.
Playing 50,000 Hands in 24 Hours
Ingram didn’t wait long to accept his next near-impossible challenge. He bet that he could break another record by playing 50,000 hands within 24 hours.
This forced him to average 2,083 hands per hour over the course of an entire day. He also had to show a profit while grinding exclusively in $0.10/$0.25 NL hold’em stakes.
Many players were skeptical of Ingram completing the challenge, given that he was just coming a 25,000-hand session where he lost 20 buy-ins. People saw this on PokerTableRatings and lined up to bet against Joey.
He accepted over $30,000 in prop bets at 3:1 odds. This added extra pressure to the challenge, because he was on the hook for over $10,000 if he couldn’t finish with a profit.
Despite the pressure involved, Ingram was able to play 50,000 hands within 24 hours. He also booked a profit during the marathon session and collected over $30k in prop bet winnings.
An online player by the handle of “Chiren” was later able to log 58,000 hands within 24 hours. However, nobody counts this as the record since he lost money.
Reaching Supernova Elite with Time Running Out
Approximately one year after the two records discussed above, Ingram took on another insane challenge. This time, he needed to reach PokerStars’ Supernova Elite VIP status by the end of 2010.
Achieving the now-defunct Supernova Elite (SNE) level was hard enough with a year’s planning. Reaching PokerStars’ former highest loyalty level required earning 1 million VIP Player Points (VPPs) within a single year.
Making Ingram’s task even tougher is that he made the prop bet in mid-October. He only had 347k VPPs at the time, which meant that he needed to earn 653k VPPs within two and a half months.
Nearly every SNE member needed the entire year to reach this level. Most players who set out for SNE status fell off pace within a few months and never made it.
Ingram was trying to squeeze almost eight months’ worth of Supernova Elite VPPs into 2.5 months. Nevertheless, he was confident in the matter and made a 3:1 prop bet with his roommate “BallCup.”
“Just ended my life for the rest of the year and booked a SNE prop bet with my roommate BallCup,” Ingram wrote at the time.
“I got 3-1 odds and it’s my $15,000 to his $45,000. And the amount in bonuses I will accumulate along the way is around $90,000.”
Ingram noted how he’d have to play 12-16 hours per day for the rest of the year to reach his goal. This essentially amounted to 400k-600k hands per month.
ChicagoJoey 24-tabled PLO cash games in order to earn the necessary VPPs. He also reworked his strategy to play “a super tight game,” then find a new table as soon as it filled with regs and nits.
Ingram somehow managed to earn the remaining 653k VPPs in record time. He won $45,000 from BallCap along with the aforementioned $90,000 in loyalty rewards after reaching SNE.
Win 20 Million Play Money Chips
Nearly all poker-based prop bets revolve around real money games. But Ingram made a very interesting prop wager that involved play money tables.
This challenge required him to turn a starting bankroll of 3,000 play money chips into 20 million. The challenge started off well enough, and he was nearly on pace to reach the necessary chips.
However, Ingram eventually realized that he would be just short on time. He began playing riskier hands in hopes of making up the ground, only to fall short after losing a few large pots towards the end.
One Mile Swimming Prop Bet
Hedge fund manager and billionaire Bill Perkins is quite a prop bettor himself. He infamously bet $600,000 that Dan Bilzerian couldn’t ride a bike from Las Vegas to L.A., which he lost.
Appearing on the Poker Life Podcast, Perkins found out that Ingram didn’t know how to swim. So he bet ChicagoJoey that he couldn’t swim a mile by the end of September 2017 – two months from the time of their wager.
Ingram, who’d never swam in his life, put up $5,000 against Perkins’ $15,000 (3:1 odds) that he could swim the mile in St. Thomas (Caribbean Sea). He wasn’t allowed to use any assistance, such as flotation devices or fins.
Perkins was very confident that Ingram couldn’t travel the 5,280 feet in the open ocean.
“You’ve never swam,” Perkins said on the podcast. “You don’t know how your lungs are going to feel.”
Unfortunately, the poker world never got to see this bet play out. Inclement weather forced them to table the wager. Perkins and Ingram had never come back around to this prop bet.
Write a 40,000-Word Book in 11 Days
ChicagoJoey has recently moved away from poker prop bets and into a variety of new wagers. Case in point, he made a book-based prop bet in 2017.
Ingram needed to write and publish a 40,000-word poker ebook in 11 days. Writing was another new area to Ingram, because he’d never written anything close to the size of a book.
He was still willing to take the bet, though, wagering $1,000 against daily fantasy sports pros Saahil Sud and Jonathan Bales.
This challenge took every bit of Ingram’s grinding skills, as he spent grueling days writing the 40k words within the allotted time. He really picked it up over the last three days in order to complete the ebook.
Ingram was successful, finishing Chasing the Dream: The Qualities of a Successful Poker Player within the given time frame. The work is currently available on Amazon for $9.99.
Bales may have lost $1k to Ingram. But he got the last laugh after tweeting about Ingram’s obvious title misspelling of the word “chasing”:
“Just lost a 40k-word book prop bet to a kid who published with a typo in the title. Congrats @Joeingram1. Way to keep chasting your dreams.”
Speak Mandarin Chinese Fluently in One Year
2017 was a busy year for Joe Ingram’s prop betting exploits, because he accepted yet another interesting wager. He put up $7,500 against two friends’ $45,000 that he could learn to speak Mandarin Chinese fluently in a year’s time.
Mandarin Chinese is considered by some to be the most-difficult language to learn. It’s full of weird idioms, aphorisms, and homophones, making it extremely hard to master over the course of several years — let alone one.
Ingram, who made the bet in October 2017, was required to take a 30-podcast test to prove his Mandarin-speaking skills.
His training for the task included spending several hours a day learning Mandarin apps, watching movies in this language, and listening to music.
In all, he planned on dedicating over 2,000 hours to the matter. This is a significant amount of time when considering that there are 8,760 hours in a year.
It’s now towards the end of 2018, and I’ve yet to hear an update on the challenge. I’m assuming that he bought out of this prop bet after realizing the extreme difficulty level.
What Is Joe Ingram Doing Today?
Joe Ingram used to solely be an online poker pro. However, he’s been dedicating more time to his business pursuits in recent years. This has required ChicagoJoey to maintain a balancing act between his PLO sessions and entrepreneurship.
“It’s tough to excel at both.” he said, “I don’t really know how to balance it.
“Playing poker, staying really sharp, always thinking about it and studying your game; while at the same time, doing all this other stuff.”
Regardless of the tough balancing act, Ingram has found a way to remain a good poker player while also doing well in business. His Poker Life Podcast has nearly 70,000 YouTube followers and is growing steadily every month.
Joey isn’t interested in leaving poker behind at the moment. But he believes it’s tough to remain a competitive poker player and also keep up with his side projects.
“It is interesting because you feel your understanding of certain situations is just not as quick as it used to be,” he said of poker.
“But that [poker knowledge] has come back as I’ve been playing more hands and trying to think about it too. But with that, everything else has suffered.
“I guess there is probably a happy medium I can get to but I don’t know if there is a point to keep competing online.”
Ingram has also found it difficult to remain motivated enough to continue grinding the same volume that he used to. This is especially the case when considering that he can’t play at PokerStars from Chicago.
On the other hand, he still wants to remain good enough at PLO to where he can maintain respect when discussing the game.
“At the same time, I do a lot of poker content, I talk about PLO, so I still want to be good at the game.” Ingram said. “That was the reason I started, I could merge those two things together.”
Ingram certainly won’t be trying to earn the same kind of poker profits and rewards that he once did. But it looks like he’s found his niche in combining sensible PLO sessions with his poker podcasts.
ChicagoJoey has completed some of the most awe-inspiring poker challenges ever. He’s played 600k hands in a month, logged 50k hands in a day, and reached Supernova Elite in a near-impossible situation.
These challenges speak to Ingram’s incredible poker endurance, which has allowed him to play the type of volume most players only dream about.
But he’s no longer interested in making prop bets on ridiculous feats. ChicagoJoey is instead more focused on his podcast and making non-poker prop wagers.
The latter has included writing a poker book in 11 days, learning/training to swim one mile, and learning Mandarin Chinese in a year’s time.
Ingram is also heavily focused on growing viewership for the Poker Life Podcast. He already has a sizeable audience at 70k followers, but he’s constantly trying to grow this.
Given ChicagoJoey’s current goals, he probably won’t ever play online poker at a high rate again. He instead seems to be playing just enough to make fair profits and maintain his PLO knowledge.
But even if he never returns to his insane grinding ways, Ingram will always be known for some of the most-impressive internet poker accomplishments ever.