BWLT was super excited to have the pleasure to interview Ian Westermann of Essential Tennis.
Ian is a lifelong tennis lover turned content creator, entrepreneur and business builder. He began his digital career in 2008 publishing the Essential Tennis Podcast and then building an online business full time since 2011. He now hosts the #1 rated tennis podcast on iTunes and the most subscribed channel on YouTube for tennis improvement.
Click here or the photo below to listen to his fascinating business journey.
Interview Highlights
Ian's Passion for Tennis
I started tennis as a pastime as a 10 year old 11 year old just playing at local public park courts. I’m not exactly sure why I gravitated so strongly towards it, but before too long, by the time I was 12 or 13, I really just had to play. I had to figure out how I could be on the court as much as possible. It just resonated with me and my personality so strongly. By the time I got into high school, I was thinking down the road, okay, how can I make this work? What can I do, how can I figure out how to get paid to be on a tennis court?
How Ian Got Into Podcasting
I had like an hour commute each way. And I hated the radio. Just the commercials and all the ads drove me crazy. So I found podcasts, which was incredible. Like I get to hear somebody talk about a topic I was interested in for, for my whole commute and just connect with that person and learn something and grow and have more knowledge in an area that I was interested in. And when I saw that nobody was doing it in tennis. It just seemed like a really odd to me, it seemed like a very obvious thing. Like I talked about tennis all day
Becoming a Content Creator
For my first couple years, podcasting was my primary focus. I started my YouTube channel in 2009.
In 2010/ 2011, I started putting a lot of effort and energy into that platform. It became obvious to me, that for a skill like tennis, that’s so technical, that people wanted to see, patterns and strategies and positions and techniques. They wanted to see me hit a ball. They wanted to see a student hit a ball and see a before and after, side by side image. So I started putting much, much more energy in the video side of things. And that’s been the main focus for the last 10 years or so. As of right now, I don’t know what the total number is, but it’s definitely north of 10,000 pieces of content. There’s over 2000 videos on our YouTube channel. There’s over 2000 probably over 3000 videos now in our paid courses when you sign up for one of our paid courses online. And then blog posts, emails, podcast, social media posts, easily another another 5000 pieces of content.
How Tennis, Business and Life Intertwine
I think a big reason why I resonated with it (tennis) so strongly, so early was, it really is an allegory for the rest of life in so many ways. For example, being able to come face to face with an opponent or an adversary, even when that adversary might be yourself and not necessarily the other person across the net from you; figuring out how to problem solve that obstacle, and find the best path forwards in real time while you’re being challenged by that force, whether it’s visible or invisible; then figuring out how to reflect on that failure or a success and learning from it to become smarter and wiser and more adaptable and successful down the road for the next time; celebrating the victory, and reflecting on what worked well and what was successful or in in a lot of cases being okay with mourning, a loss. All of those things and many, many more are analogous (to everyday life).
We could make a bullet list of 1000 different things that are important on the tennis court and all great tennis players have in common. And then when you take those elements and apply them to everyday life, whether it’s career or relationships, or self care or self love and self development, dealing with with family members, driving in traffic, there’s unlimited connections, and that’s always been fascinating to me.
Managing It All
I don’t have days that I finished what I wanted to finish. And that’s just become the norm for me and, and I enjoy that. I enjoy the challenge. There’s a part of me now that enjoys going home, leaving things undone because I know that I packed in as much as I possibly could that day. But I would say on average, during an average week, I probably spend about 75% of my time either planning or in production or in publishing of content, whether audio written or, or video. Thankfully, I have two production people on staff that all they do is edit and publish, and prepare for whatever the next piece of content is. There’s no way I could with the volume of stuff we’re doing now —-there’s a zero chance I could do it by myself. So that’s probably three quarters of my time. And then the other quarter on average, and an average week is actually working with with students whether it’s one on one or in a, in a group setting, obviously, these days it’s, it’s, it’s all one on one, I haven’t done a group in quite a while but I’m grateful I still have the ability to be out here on the court and and work with people in person.
Collaboration and Building a Team
There was a big turning point for me six years ago —- up until that point I had worn all the hats in my my business of marketer, production, publishing, customer service, coaching, content creator. I did everything myself and I enjoyed it that way for several years. But then I got to a point where the metrics were very clear that things had leveled out. And I knew that there was no way there was going to be any kind of significant growth unless there was a change in the amount of man hours, just in terms of practical hours spent in a day.
I knew that I had basically maxed myself out. It came to a point where I had to make a decision —- is this going to continue to be the Ian show (it was great supporting my family and basically I had reached all the initial goals that I set for myself ) or can I take a leap of faith and try to make it something bigger than what I can do by myself?
I’m really grateful that I made an effort to do that, because now through that collaborative process, I’m able to hand off individual hats to different people who specialize and have a personality and have skills and passions for those individual hats that I don’t necessarily have. Over the years, I’ve realized that there’s a whole lot of humans out there that have a passion and a talent for things that I don’t necessarily want to spend my time on.
Acing it in Business and on the Court
I like the word accountability a lot. If I were to break down everything that we do into a really simple formula, at any given point in time when we set out to accomplish something, whether it be publishing a YouTube video, creating a digital training program, or working with somebody who comes here to try to fix their backhand or their serve. whatever it is, in a very, general way we go through (1) an evaluation phase where we ask, what are we trying to accomplish here? What different pieces can each of the team members take to make it as successful as possible?
(2) The actual implementation phase where we get behind the camera, we get behind the microphone, we stand in front of the student, and deliver whatever it is that we’re trying to communicate. Whether it’s a concept or a strategy, or a technique or a, a explanation of here’s why you’re falling short of your goals right now and here’s the road we’re going to take , here’s the process we’re going to follow.
(3) The reflection side of things. What we do is very unique in that I, I don’t do anything without it being recorded in a way that I can watch it back and thousands of people also watch it back. For most people, I think that’s probably terrifying. I literally don’t do anything without it being recorded and then published, so the rest of the world can watch it. That brings a very special kind of accountability and there’s no hiding. When I make a decision, and move forwards with it —If it’s YouTube video, —–we know within two hours of clicking the publish button, if it’s going to be a huge success, or a total dud, and nobody cares. When we launch a new online training program we know after 24 hours of of making it available for people to register if it’s going to support the business. And that’s a real outcome. Everybody who’s involved in my team sees the numbers. They see the views, they see the comments, they see the likes, they see the sales numbers. That, to me is ultimate accountability. I don’t have to try to fool anybody. It’s pointless for me to try to fake anything because everybody watching is going to know the moment I start trying to do that. And so after years of being on record, and publishing everything, there’s actually a very peaceful place for me where I know I’m giving my best effort.
On Not Quitting (Even When It's Difficult) and Conquering the Imposter Syndrome
First of all, I think it’s very hard to do something meaningful and impactful that really makes a big difference in the lives of people when you follow a path that’s already been laid out. In other words, if you do what people are expecting in the way they expect it and in a way that’s safe and comfortable, you’re not ever going to do anything that’s very impactful. And so I think you have to embrace the unknown and the discomfort. I heard somebody on a podcast, I don’t remember who it was. I’m sure you’re familiar with, with the idea of imposter syndrome. Meaning like, Who am I like, Who am I to get behind this microphone or in front of this camera and say what I think. Do I really think I’m that big of a big shot that people actually give a crap about what I have to say?
I heard somebody say something that was really profound. I think it was Seth Godin’s podcast. He said that imposter syndrome is a fantastic indicator that you’re doing the right thing. If you don’t feel imposter syndrome, then either you’ve got a massive ego and not very much humility if you think that you’re in the role that you’re made for, then you’re either not doing anything very challenging or your ego is probably going to get in the way at some point.
I remember early on feeling incredibly nervous all the time. And I made a pivot in my mind, I made a very conscious decision. I remember the moment that I made the decision and I had an epiphany, that holy crap, every time I feel that feeling, and I go do the thing, to the best of my ability on the other end of that experience, or on the other end of that effort, whatever it was, I always realized that that was the next step forwards—–the next progression in what I need to do to to reach my goals or get to where I’m trying to get.
I started viewing it as something to be grateful for. And I started viewing it as something where I knew that this place is where I should be right now because if I went days or weeks or months without feeling that feeling, then I’m stuck. I’m stagnant. I’m not doing anything very important anymore. So that’s number one.
I think once you get over that initial fear of the anxiety and the what if and the imposter syndrome you realize that that’s how you know you’re doing important work. I think the next most important thing, a good friend of mine who’s in the fitness space, named Michael Morelli says it’s it’s not failure, it’s feedback. Meaning when you try something, and it doesn’t work that you gave it your best shot. For me, as soon as I made that pivot from it being a failure and I started viewing it through the lens of, you know, Thomas Edison who was quoted as saying, It’s not that I failed to invent the light bulb, I just found 2000 ways that didn’t work.
Mentality if you’re going to try to be an entrepreneur, or if you’re going to try to be good at tennis, there’s a billion ways to mess up. And if you view the mess ups as failures, you’re going to walk off the tennis court feeling like a failure every time you play the game. Right? I mean, literally, not figuratively, you’re going to walk off the court feeling like a failure. Every time you play tennis. If when you make a mistake, it means to you that that you’re a loser or you’re a failure, because you’re never going to play without making a mistake. Ever. Roger Federer never plays without making a mistake. Serena Williams never plays without making a mistake.
Viewing those errors as feedback and as learning opportunities, may be the most important thing because otherwise you just end up feeling more and more depressed about what it is that you’re doing instead of the flip side of pivoting a little bit each time and becoming more and more effective every time that you make a mistake.