YouTube’s Most Sought-After Tennis Coach Is Here in Milwaukee

Ian Westermann has leveraged YouTube, video analysis and the telling of painful truths to run what might be the world’s most expensive tennis lessons in, of all places, Milwaukee.

The best part of Ian Westermann’s new book, Essential Tennis, is when he suggests that the reader return it for a refund.

Page 29: “If you have twenty-five dollars to spend on tennis and not a penny more, here’s what I suggest you do: Read this chapter. Return this book and get your money back. Spend the money on a tripod for your phone.”

It’s classic Westermann: Honest, humble, unconventional, dryly mischievous. Hundreds of thousands of tennis players follow the Milwaukee tennis instructor online and hang on every morsel of his philosophy, making him the most popular tennis guru on YouTube. He helped pioneer online tennis coaching and has parlayed his success into what might be the most expensive private lesson on the planet: $6,000 for two days. And it happens in Milwaukee, nowhere near tennis’s nerve center. With – despite Westermann’s Internet fame – a rather undistinguished player.

As John McEnroe famously said, You cannot be serious.

Westermann, 41, is nothing if not serious – at least about helping recreational tennis players improve and find happiness on the court. The local native left a cushy job as a teaching pro at a prestigious club in Maryland to spread his gospel to beginning and intermediate club players. Westermann’s Word has three verses:

  1. Habit. You can’t escape it. You’re either training habits or you’re breaking them. 
  2. Truth. Tennis players need to hear it.
  3. Video. Actually, they need to see it. 

“Most players are completely out of touch with reality,” Westermann says. “There’s much more beneath the surface of their awareness than they realize, and those hidden things mostly make up who they are as a player.” He believes you can’t make meaningful, lasting improvement in tennis – or any part of life – without excavating into the behavioral core of habit.

Ian Westermann; Photo by Kat Schleicher


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Applied on the tennis court, it’s a sharp departure from the typical lesson or clinic. Usually, a tennis pro stands in one place with a cart full of balls and feeds them to players, pausing to give occasional instruction and demonstration. Westermann, instead, walks around the court with an iPad and films the student hitting, edits clips on the fly, and breaks down the form frame by frame. He scribbles notes on a 72-inch TV screen on the court, then has the player start from square one with the proper technique. For much of the time, there might not be a ball in play as student and teacher practice slow-motion swings or talk about mental and emotional demons. The mood is friendly and supportive, but it’s work, not play. Past the reality check of seeing oneself on video – it’s never as pretty as a player imagines – it’s uncomfortable and not exactly fun to practice Westermann’s way. You get a lot worse before you get better.

Westermann with Essential Tennis coach Matt Lemery (left) and a student at Elite Sports Club in Brookfield; Photo by Kat Schleicher

Using screens for analysis might not sound revolutionary, but in a sport resistant to technology, it is. So revolutionary that Westermann can now charge more for a tennis lesson than the Mouratoglou Tennis Academy on the French Riviera, where Serena Williams trained for a decade.

Westermann’s students don’t want just a lesson, and they don’t want a vacation in tennis paradise. They want therapy. “They have been to a bunch of clubs, worked with a bunch of coaches, and spent thousands and thousands of dollars,” he says. “After years of chasing their tails and assuming they are building skill upon skill only to look over at their win-loss column and see the same results for 10 years, they get so frustrated.”

He cracks his warm, knowing, good-natured grin, known so well by hundreds of thousands of tennis players online.

“Then they come to Milwaukee.”

Photo courtesy of Westermann


WESTERMANN IS THE FIRST to admit that it doesn’t make sense to travel to Milwaukee for lessons in this warm-weather sport. “Tennis is a fringe activity here, and then the way I do my teaching is kind of fringe,” he says. “When someone makes the effort to come to Wisconsin to work with me, I know they really value my time.”

On paper, it’s just as bizarre that this player with a relatively undistinguished resume became a highly paid, in-demand coach. Westermann grew up on the South Side of Milwaukee with three younger siblings, before his family moved to Waterford and then West Allis. No one in the family played tennis. His mother, a photographer, and dad, a graphic designer, homeschooled their brood, reared them in church and encouraged their hobbies. Westermann’s was ham radio – he got his license when he was 12 or 13, his first foray into media. Around the same time, his mom asked if he’d like to take golf or tennis through a school rec program. He chose tennis and took the city bus to Nathan Hale High School to learn the basics.

Ian Westermann at Ferris State University, 2002; Photo courtesy of Westermann

After a couple of years, he was able to take occasional lessons at a local club, but the family couldn’t afford many. By the time he was a high school junior, he was good enough to lead the team when he enrolled at Martin Luther High School in Greendale. In two years, the lefty won enough matches to reach No. 3 on the small school’s all-time leaderboard. But he wasn’t college-scholarship material. He attended Ferris State University in Michigan to study business and tried to walk on to the tennis team his freshman year. He didn’t make it. But he worked hard enough to earn a spot as a sophomore and peaked at No. 19 in the country in doubles.

A serve-and-volleyer like his favorite player, Pete Sampras, Westermann was in love with tennis, a sport that can enchant a perfectionist like him with its endless complexities. But it can also torture the same person with its miniscule margins. In tennis, winning looks a lot like losing – even the best players in the world lose nearly half the points they play. Westermann took it too seriously. Chasing perfection made him deeply unhappy by his senior year, and he walked away midseason.

Off the court, he still loved the game and graduated in 2004 with a minor in tennis coaching. Westermann took a job back home at Western Racquet & Fitness Club in Elm Grove, but soon lit out for Maryland for a job (facilitated by Ferris State’s former program director) at Congressional Country Club near Washington, D.C. 

The club’s prestige – the initiation fee alone is $120,000 – was part of the appeal for Westermann after a decade as a court rat. The likes of Bill Clinton and Tiger Woods hit the club’s golf course regularly. Political journalists including Wolf Blitzer played tennis there. Martina Navratilova came by for a practice session once, and Westermann was among three staffers tapped to play doubles with her. He and his partner won. 

It was a glitzy gig with plenty of members to keep the white-clad tennis coaches busy, and he was in his element among smart, passionate teachers. “He knows the fundamentals inside and out, which is rare. He’s a gifted teacher,” says fellow Congressional teaching pro David Parker. “He was very popular, and people gravitated toward him.”

But Westermann hated it.

He fit in just fine. The problem was that he was teaching at a tennis club. Any tennis club. 

“It’s a sales commission job,” Westermann says. “You have to keep the buyer happy. I went into it naively thinking that people were signing up for lessons because they wanted to get better, and that wasn’t the case. About 50-60% of the people I spent time with on court just wanted exercise or something to do. For me to shelve my passion for teaching in order to be a cruise director” – Westermann’s term for a more casual, less critical type of instructor – “and keep the action moving, that was slowly killing me.”

He needed to find his circle. More than 21 million Americans play tennis – participation jumped 20% percent during COVID – and it’s one of the few sports with a robust, organized amateur competition structure for adults. Thousands of teams play in USTA-sanctioned leagues year-round, separated by age and ability level, and dozens advance to annual national championships in Florida, California and other sunny tennis destinations. Four teams from Milwaukee went to national championships last year. There’s no money at stake, just a commemorative towel and a banner to hang at your home club. But a heck of a lot of weekend warriors take it seriously, spending most of their free time and energy on it, plus thousands of dollars on equipment, clinics, lessons, travel, and hip and knee surgeries.

Ian Westermann; Photo by Kat Schleicher

Westermann estimates that about 90% of those players aren’t truly interested in real improvement, which he believes requires unlearning a bunch of bad habits and spending months, maybe years, painstakingly practicing new ones. “The whole culture of a normal tennis lesson is a feedback loop of surface-level focus. Most students are looking for a quick fix, and most coaches are used to providing that kind of guidance,” he says.

Westermann wasn’t interested in this at all.

What he was interested in, other than tennis, was online media – recording, filming, editing, producing. He started a tennis podcast in 2008, and one fall day in 2009, sitting in his car outside of a D.C. sandwich shop on lunch break, he posted a YouTube video analyzing a rec player’s serve against Sampras’ in slow-motion, side-by-side clips. 

For three years, Westermann geeked out on creating analysis content like this on his own and posted it for free online. He quit his job in 2011 to focus on Essential Tennis full-time, taking the plunge with the support of his wife, Alison, who was staying home with their 1-year-old daughter. A few other players and coaches were doing the same thing as Westermann, and many more would come and go over the next decade, but the unheralded walk-on from a tennis hinterland outworked them all. 

To date, he estimates his 10,000 videos, blogs and podcasts have reached 11 million players. 


OF THOSE, ONLY 15,000 people have ever given Essential Tennis money. Following the Internet Marketing 2.0 playbook, free YouTube videos and podcasts funnel the most die-hard ET followers to buy a video course, like Doubles Mastery or Easy Yoga for Tennis. About 1,000 fans pay $10 per month to be “academy members” and access live coaching from Westermann each week, during which he will analyze a student’s video clip. His book, Essential Tennis, hit No. 1 in nine categories on Amazon when it launched in May. Once a year, six students treat themselves to ET’s intensive clinics in Costa Rica and Hawaii, and three times a year, groups as large as 12 join him for a clinic in California.

The end of the funnel points to court 5 at Elite Sports Club in Brookfield. Booking it starts at $22 per hour, a going rate in the Midwest. But when Westermann has it four days a month, it’s $500 per hour.

Ian Westermann; Photo by Kat Schleicher

Westermann spends most of his time creating content for the top of the funnel. But he loves to teach on court – as long as he can do it his way, deep down on the habit level, with equal parts video analysis and psychoanalysis. His shortest private lesson is three hours for $1,000. With the VIP lesson, the $6,000 fee pays for 12 hours on court, camera operators during the lesson, video editing, the hotel stay, dinners with Westermann and his chauffeur services doubling as dashboard therapy sessions. He offers a maximum of two each month, and they book up. During ET’s pre-COVID halcyon days, when Westermann employed a few coaches full time, the student-teacher ratio was 1:4 and the lesson cost $8,000. “People happily paid it,” Westermann says. “Is that expensive? Yes. Can you get what I provide anywhere in the world? The answer is no.”

Recreational players have come from Australia, the U.K., Canada and all parts of the US for the VIP lesson. It attracts high-performing professionals and independent types: a horse rancher, an anesthesiologist, a shipping company owner, a veterinarian, a lawyer, a retired CFO, a Christmas tree farmer. A man who offered $10,000 for a four-day lesson was turned down – Westermann didn’t think he was serious enough.

John Malanga, a lawyer from Fort Worth, might be the unofficial fan-club president. An early follower of Essential Tennis, he has been to clinics in Costa Rica and California and several VIP sessions in Milwaukee. He and Westermann dissected his forehand and backhand to isolate issues with Malanga’s kinetic-chain movement, the transfer of weight into the ball. “I was looking for improvement and a path to better tennis,” the 58-year-old says. “I came away with more knowledge about the issues with my strokes, and a specific pathway to correcting bad habits that developed over years.”

Amadou Diallo, a 53-year-old writer on the hit TV show “Billions,” wanted a slice backhand – and just as important, a plan he could trust after years of trying to follow other coaches’ online instruction to no avail. Like all students, Diallo left Milwaukee with a detailed set of progressions to follow back home. He started with slow swings without a ball, then worked up to hitting the ball against a wall, then drop-feeding the ball to himself on the court. He would film himself with his phone on a tripod, watch the video at quarter-speed when he got home, and send clips to Westermann for feedback. “Ian broke down the shot to just such a discrete level that if anybody had walked past while I was doing these wall drills, it would have looked like I had just learned how to play,” Diallo says. “Now it’s a solid, reliable slice.”

Westermann says he can usually diagnose a technical problem in about 30 minutes, then start working on a personalized action plan to break and retrain the bad habit. But sometimes the iPad can’t capture the problem. Sometimes it’s a ghost. One student who came to Milwaukee had an excellent game, but like many players, couldn’t play as well in a match as she did in practice. After hours of probing and playing, Westermann had a theory: Subconsciously, she was too concerned for the opponent’s mental and emotional state to beat them. “When we brought her to that conclusion, she broke down,” Westermann says. “I don’t know what the connection was to the rest of her life, but every once in a while, I get to help someone indirectly through revealing a truth about their tennis that connects with other stuff. I really value that a lot.”

He isn’t sadistic – he doesn’t want to make students cry. He wants to give them a safe space to confront their worst tennis fears, and gently break it to them that they have been going in the opposite direction of improvement for years. “That’s earth-shattering news,” he says. “But I have no interest in going back to the old way of doing things.”

Photo courtesy of Westermann


WESTERMANN ISN’T GETTING RICH off these $6,000 lessons – or at least isn’t enjoying the high life. He lives on a hobby farm halfway between Milwaukee and Madison with his wife and two kids, and drives a 2009 Toyota Yaris. Most of the fee goes to pay for the on-court video crew, post-production and the player’s hotel and dining expenses. There was a time before COVID when Essential Tennis was scaling up, and Westermann dreamed of his own facility and reaching more players with the exquisite pain of tennis truth. The pandemic wasn’t the only thing that killed the dream by halting in-person coaching. Though it might have presented an opportunity for Essential Tennis with more people picking up rackets during the shutdown, Westermann thinks he and his two full-time coaches were tapping out their potential online anyway. 

Then, around the time the pandemic hit, he lost the facility he was renting in New Berlin and, an even harder hit, two of his coaches. The married couple were ready to move on and return to their hometown of Tulsa. “Seeing it wind down and closing the office and going back to being just me again was really sad,” he says. “I kind of had an existential crisis for what I wanted to do. I was really processing it for up to a year.”

On the Westermann farm with wife Alison and children Lucy and Joel; Photo courtesy of Westermann

He decided he wanted to play tennis again. Really play and compete, like he had in college. He needed to get in shape and work on his game, particularly his one-handed backhand. That shift gave him a new direction for Essential Tennis: His own improvement would become part of the show, complete with his own deep, dark, hairy truths. 

This switch turned the ET lens onto Milwaukee, mostly a group of high-level players associated with Western Racquet Club. Westermann asked Erick Martinez, a teaching pro at Western, to train him with intense workouts on the court. Taking his own advice, Westermann did shadow swings and progressions with his backhand and filmed himself, sometimes just in his driveway. YouTube saw it all.

Thousands of fans tuned into livestreams to see Westermann play practice matches against Western teaching pros Scott Broady and Ira Meiling (Westermann’s old buddy and first coach he hired at Essential Tennis), including commentators and player confessionals to the camera. A YouTube-famous player named Ben from Atlanta made a star turn in Milwaukee and played four matches, leading up to a prime-time clash with Westermann. More than 60,000 people have watched. 

Westermann’s success owes a lot to his self-styling as a type of (egoless) guru, in the mold of productivity, habit and life coaches like Tim Ferriss and Gary Vaynerchuk, two of Westermann’s professional influences. None are bigger, though, than his first tennis coach in Milwaukee, Ted Sprinkmann; and Will Hamilton, aka Fuzzy Yellow Balls on YouTube, a fellow pioneer of online tennis instruction who has mentored Westermann from the beginning. 

While the market for a $6,000 tennis lesson is limited, many casual tennis players higher up in the funnel grapple with the overlap of tennis and life. As good as Westermann is at coaching and creating content, he’s at his best as a relationship counselor – the marriage being the student’s with the sport. Part underdog and part star, he has a gift for articulating the most maddening aspects of tennis with a Midwestern-nice touch and the gravitas of wisdom, as well as the healthy perspective most players need to be happy on the court. 

The big question: What does it take to get there?

“Managing expectations, perspective, emotional buy-in,” he says. “Approaching tennis with a lot of passion and dedication, those are the people the sport crushes.”

And also the souls that Westermann wants to save. As long as they will come to Milwaukee.

Greatest Hits

Ian Westermann guarantees that most tennis players make these common mistakes. Here’s his best advice to fix them.

1. Mishitting the ball 

The goal is to hit the ball in the middle of the strings, aka the sweet spot. Even the best players hit all around it. Learning to recognize when you didn’t hit it is the first step toward more sweet contacts.

Fix: Hit easy forehand volleys off-center on purpose so you can recognize the feeling of missing the sweet spot and the racket twisting. Then hit in the center and notice the difference in the feel. 

2. Not split-stepping 

Every player thinks they are religiously performing this fundamental movement – a spry bounce on the balls of their feet when the opponent hits their stroke. Chances are, they aren’t doing it nearly as much as they think. Split-stepping will create instant improvement.

Fix: Practice while watching a match on TV. Choose a player, and every time that person hits their shot, split step right as they make contact with the ball. (Do this with or without a racket.) That’s what you should do every time your on-court opponent swings the racket, too. 

3. A tense arm 

Getting nervous or tentative creates tension in your arm or your grip, which leads to various hitches in your stroke. You have to loosen up to swing fluidly through the ball.

Fix: You’ll need a racket without strings – maybe the busted one hanging in your garage or a demo at your club. Drop-feed a ball or have a friend feed balls, and swing as normal, so the ball passes through the racket frame. Try to notice the point at which your arm tenses up. Then try to relax and make smooth, full swings. Go back to your strung racket and try to swing the same way.

Tennis rat Megan Fernandez was a longtime editor for Indianapolis Monthly. This is her first story for Milwaukee Magazine.


This story is part of Milwaukee Magazine‘s August issue.

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