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Jonathan Little Builds On Lucrative Poker Career With Successful Coaching Business

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by Steve Schult |  Published: Mar 10, 2021

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During the height of the poker boom, Jonathan Little was one of the most successful poker pros traveling the live poker circuit. The Pensacola, Florida native crisscrossed the globe playing high-stakes tournaments, going on to rack up more than $7 million in live cashes, including a pair of World Poker Tour titles in 2007 and 2008.

But for Little, life is different now. He has a family, a home in New York City, and a thriving business to run.

Like most successful businessmen, Little stuck with what he knew. And what he knew was how to win at no-limit hold’em. Now, the 36-year-old travels much less, plays more online, and spends his days constantly churning out cutting edge content on his training site PokerCoaching.com.

The seeds for what eventually blossomed into his coaching empire began at the beginning of his poker career, which started shortly after Chris Moneymaker won the World Series of Poker main event in 2003, moving poker into the mainstream.

Like most products of said boom, Little got his start online and built up a six-figure bankroll playing single table sit-n-go’s before he eventually transitioned to tournaments. But as it turned out, the skills he learned from mastering the sit-n-go format did not necessarily translate to large field, live tournaments.

“Sit-n-go’s didn’t actually help much at all,” said Little. “Because they’re very different than multi-table tournaments. In sit-n-go’s, the goal is to get into the top 30-ish percent of the field, whereas in multi-table tournaments, the goal is to get in the top one percent of the field. And that requires a very different strategy.”

What he learned was that he was simply playing too tight to win money in large field tournaments. In sit-n-go’s, it was right to play tight, get in the money, and then try to accumulate chips. That doesn’t work when you have to maneuver your way through a field of several thousand players, as opposed to just eight other opponents.

“When I first started playing live tournaments, I lost a large chunk of my bankroll, about $200,000,” Little admitted. “I realized that I was clearly bad at them and needed to study.”

After bouncing ideas off some of his colleagues, Little learned where his leaks were and how to plug them.

“I recognized that you have to get in there and you have to gamble a little bit harder,” he said. “If you are not willing to gamble in the early and middle stages, you’re never going to build a big chip stack. If you never build a big chip stack, then all it takes is one hand to bust you. You don’t want that to happen. You want to be able to lose lots of hands and still be in the tournament.”

Aside from switching his aggression levels, he also needed to learn how to play deep-stacked poker. The late stages of sit-n-go’s are where the money is made, but it’s also where the stacks are the shallowest. Little had to adjust from playing with fewer than 10 big blinds to play as deep as 100 big blinds.

This was the adjustment that gave him his first taste of what poker training was becoming in the age of the internet. At 21 years old, after losing a large amount of his bankroll, Little joined the now-defunct CardRunners and PokerXFactor, the two leading training sites available at the time.

Before these sites were created, the only training resources that were widely available were the handful of strategy books that were quickly becoming outdated. Armed with a new arsenal of poker strategies, Little went on a tear that most couldn’t even dream of.

He started 2007 with a fifth-place finish at the PokerStars Caribbean Adventure main event for $317,873, which gave him his first TV appearance as he battled it out with the likes of Isaac Haxton and eventual winner Ryan Daut on the windy, outdoor, final table set. He then earned a runner-up finish to JC Tran in a $3,000 buy-in side event just a couple months later for $146,760 at the Five-Star World Poker Classic.

Then he really started to cash in.

In May of that year, Little topped a 309-entry field in the $10,000 WPT Mirage Poker Showdown for $1.06 million, topping a final table that featured poker legend Phil Ivey. In October, he finished runner-up to Scott Clements at the CAD$10,000 WPT North American Poker Championship in Niagara Falls for another $714,905, which basically put a bow on a year that saw Little earn more than $2.5 million. He followed that up with a 2008 campaign that included another seven-figure score when he took down the WPT Foxwoods World Poker Finals for $1.12 million.

But despite becoming one of the most successful players in the tournament world, those days are a bit of a blur for him.

“I don’t actually remember those times all that well. I don’t even remember yesterday all that well,” he said with a laugh. “I think that’s actually a skill that makes me a decent poker player, because I can have a bad day at the table, or a bad month, and wake up perfectly fine the next day.”

Those monster years shored up any bankroll liabilities he may have had in the early portion of his career and turned him into a mainstay at high-stakes live tournaments. Throughout his career as a player and now as an instructor, he has seen countless students and pros alike go broke because of poor management of their funds.

“All you really have to do to win at poker is find a game you can beat, play it a lot, and play properly bankrolled for that game,” said Little. “And if you do those three things, you will win at poker. But most people do not do those three things. Most people will play games they cannot beat. Most people do not want to play a lot, they just want to play on the weekend for a few hours with their friends. And most people do not play with a proper bankroll.”

Little says that what is considered a proper bankroll is different for each player. In order to come up with a number that works for you, you need to think about what games you are playing, what kind of return you’ll have in those games, and how much variance comes along with it.

“If you’re playing a 45-person tournament with a decent return on investment, then a 100-buy-in bankroll is perfectly fine,” said Little. “But if you’re playing gigantic tournaments with 1,000 people or more with a small return on investment, then you need a huge amount of buy-ins. Like 300. Many players have not sat down and done the work to realize how big of a bankroll they actually need.”

Over the course of his career, Little has seen the entire evolution of the modern game, from both a strategic standpoint and a logistical one. He’s watched the buy-ins drop while re-entries increase, all while the game got tougher to succeed at.

“There aren’t nearly as many $10,000 buy-in tournaments that have very soft fields anymore,” said Little. “Also, back then, the tournaments were all freezeouts, which is a different game. As people can re-enter over and over again, everyone’s return on investment gets lower because the good players are usually willing to re-enter more often than the weaker players, which results in the fields proportionally having more good players in them.”

He has also seen the online version of the game become insanely tough, even at what would be considered mid-stakes live.

“The $1,000 buy-in tournaments online are tougher than any major live tournament you will find,” said Little.

But this is a natural progression. In any sport, any game, any competition, the ability to succeed at the highest level will naturally shrink. It will always take more to excel as more people study it.

“Look at athletes. They run faster today than they did 50 years ago,” said Little. “Why? Because they have better tools, and better training techniques, and better studying materials. That results in them performing better, and poker is no different. People are going to continue to get better and better over time.”

Despite how good the rest of the field has gotten, Little doesn’t feel that the steeper learning curve should scare people away from the game. Nor does he feel that the action has dried up. There is still plenty of money to be made, and he has witnessed it first-hand.

“The small- and medium-stakes games are still wildly profitable,” said Little. “I have plenty of students who are crushing them, and I still succeed at the highest stakes.”

After several years of globetrotting as a live poker player, Little met his wife Amie. They ended up tying the knot in 2015 and Little moved to New York to be with her and start a family.

“She’s from New York… and she was not moving from New York,” said Little about why he chose to continue his career from a place that’s lacking a lot of live poker action. “Her parents live here, she works here and she loves it. If I would like to be with her, I have to live here.”

With plans to start a family, Little’s old lifestyle of being on the road for three or four weeks out of the month just wasn’t going to work out long term.

“I knew about five or six years ago that I wanted to be able to stay at home a little more often,” said Little. “I wanted to start a family and do my best to be a good dad. I knew that would require me to stay at home some portion of the time. I needed to figure out a way to make reasonable money from home.”

So, he founded PokerCoaching.com in 2016, and quickly began helping others beat the game that gave him so much.

“I don’t know if anything ever made me want to become a poker coach other than people asking for my advice,” said Little. “I used to participate on various poker forums back in the day, when they were full of good poker players who were actively trying to improve their skills and help others. And eventually, people came to me for private coaching, and I was happy to do that.”

Little’s advice became a highly sought-after commodity. And before he knew it, he was spending all of his time either playing poker or coaching it.

Little was one of the first poker coaches to move beyond in-game videos. During the first wave of poker training sites, most of the content was comprised of a professional giving the play-by-play of their session, opening up their thought process for paying members.

After spending a lot of time learning how people learn, Little developed a model of training that moved past this approach and offered other avenues for players to understand these new concepts. Since everyone retains information differently, Little decided to give his students options. It wasn’t enough to stay on top of his YouTube channel, or his numerous podcasts, or even the now 15 poker books he has authored!

“At PokerCoaching.com, we teach students using many different methods. There are interactive live webinars where you can ask the coach your questions in real-time, similar to a one-on-one coaching session. We also have interactive quizzes, and private live streams where you can ask us questions as we play in real time,” said Little. “The result is the students get substantially better at a fast rate, which is my goal.”

Little can’t give up playing altogether, however. As an instructor, playing, and playing well for that matter, is the only way to stay on top of the strategy trends that are always changing in the poker world. He is just forced to be more scheduled with his time.

“It’s really important that I stay up to date on what is happening in the poker strategy space because consolidating and sharing that information with my students is my job,” said Little.

But just in case he misses anything, Little isn’t leaving anything to chance. He employs a team of coaches for his site, many of which have had success at the game’s highest levels. WPT Champions Jonathan Jaffe and James Romero, former WPT Player of the Year Faraz Jaka, WSOP bracelet winner Tristan Wade, tournament grinder Matt Affleck, and online legend Bert ‘girafganger7’ Stevens all actively produce high level training content at PokerCoaching.com.

“I look for people who have a long, successful track record,” said Little about how he chooses other coaches for his site. “I essentially hire coaches who I wish I had to teach me when I first started playing, or coaches who I want to learn from today. That’s why I hired James Romero and Bert Stevens, who are among the absolute best tournament players in the world.”

If you want to learn from the best and take your game to the next level, check out PokerCoaching.com/CP25 and get started today. ♠