Career Profile: Entrepreneur

Ian Westermann is the Founder and Head Pro at Essential Tennis LLC. In this Q&A, he discusses his career path and his role in the company.

Ian Westermann created one of the first online learning sites to specialize in tennis. He is the founder of Essential Tennis, a website that hosts courses, videos, and podcasts. These resources help tennis players of all ages excel at their game. Before founding the site, Ian worked as a tennis coach at one of the best private clubs in the United States. He attended Ferris State University, where he earned a bachelor’s degree in Professional Tennis Management and Business Marketing.

How did you choose this career path?

My career was born out of my love for the game. I started playing tennis when I was about 10 or 11 and fell in love with it. When I was 15 or 16, my coach showed me an article about a professional tennis management in Michigan. The idea of being around tennis and on a court daily, and making a living  from it, sounded like utopia. I didn’t even apply anywhere else—I knew that’s what I wanted to do. At school, I played tennis and got certified as a teacher. I started teaching full-time right out of college and while I enjoyed that, I became frustrated with traditional methods of teaching tennis. That motivated me to start publishing content online and to start building my own business, Essential Tennis.

I feel very fortunate to be alive in 2016. Having grown up with computers, technology, and creative media, I started seeing other people with knowledge in particular areas  creating and publishing content, building an audience around that expertise and making a business of it. It seemed like a perfect marriage of my love of technology and media, and of tennis and coaching.

What exactly does the Head Pro do?

Given what I am doing, it’s hard to define that! There aren’t any typical days, and I appreciate that very much. During about half of my days, I have specific tasks that I need to accomplish. That could be shooting the content for one of our courses, or our YouTube channel or it could be creating marketing or promotional material for a new offering. Most of what I do is either promotional-related or content-related. The other half of my days are very free-form. I can walk into the office and pick and choose the things that need the most attention. I focus on what things will bring the highest return for my time and attention. I designed my business so that every day is a little bit different—I value that very much. It keeps me interested and engaged. Routine is valuable, but I don’t like feeling like I have to do something. Instead, I spend most days in meetings with my team members collaborating.

What’s the best part of the job?

I like the freedom that it affords me. I can do what I am doing anywhere in the world, as long as I have a decent Internet connection! I love that I get to create for a living. I get to serve an audience of enthusiastic, passionate people who appreciate what I do, and how I do it. That freedom is a double-edged sword. On the one hand, very few days are the same. On the other, we’re trying to stay at the forefront of using technology for media production.

Keeping people’s attention online is increasingly difficult. Using the different tools we do brings people together in an effective way. Yet that’s changing from day to day, so it keeps things interesting and new. That is what I like about it but can also be one of the frustrations. What worked a year ago doesn’t necessarily work today. The landscape never stops shifting. The way that people interact with technology and media is always changing. You can’t ever be comfortable with any given delivery method, system or communication style. We have to improve every day. That means improving how we produce things, deliver things, sell things. If not, we’ll become obsolete.

Another frustration is that we’re serving an audience that is not known to be tech-savvy. The tennis industry can sometimes be behind the technology curve, but that gives us an opportunity to bring along with us the people that we serve to the forefront of technology and show them its value and effectiveness.

What are some of the recent innovations you’ve seen in your field?

We constantly need to be evaluating what works and doesn’t work and adjusting our methods accordingly. We’re always looking at how we communicate, which platforms we focus on, and what kind of media we create. When I started the website in 2008, the big thing was podcasts. I was the first to do a tennis podcast, I believe. Now since 2011, that’s shifted heavily toward video, and now video is 99 percent of our focus. So we have a big transition from text and audio to more of the video format.

Even the plain vanilla video analysis of tennis players is still not standard among tennis teachers, or players who are self-teaching. That’s something I have been doing for over a decade. It’s frustrating that it hadn’t caught on sooner, but it’s starting to become more standard now. At a bare minimum, players and coaches need to use regular video analysis. It’s a third person perspective. For most players, there’s a gulf between their first person experience—what they feel they’re doing—and what they imagine they look like. There’s a chasm between those two realities. But anyone who’s serious about making improvements needs to see video analysis as an opportunity.

For the future, I am paying attention to virtual reality. Every pundit, expert, and practitioner I follow believes that virtual reality is the next big platform. It’s a benefit to be in a market that tends to lag behind technology a bit so I can watch cutting-edge markets and see what works and doesn’t work before having to invest in a new technology or a new platform. I know I have a couple of years before it catches on in tennis. I am not making any moves in virtual reality currently, but I am watching to see if it does trend in that direction.

I’ve also seen the use of smart courts start to grow, which intrigues me a lot. The courts use multiple cameras and video screens to show you what shots went in or out and can show patterns of play. I’ve also seen applications of player modeling or rendering. A player puts sensors on and then swings. Software creates a wireframe of the player to give biomechanical feedback. Those kinds of technologies have been used in golf and baseball, and other swing sports for a long time. and its just beginning to be used more in tennis.

Can you share any advice for high school students?

Well, the internet has changed everything. Anyone who wants to have a voice now can have a voice. When I first started in 2008, just the fact that I was online gave me an audience. There weren’t many people to listen to in the online tennis niche. Despite my shortcomings as a presenter and a content creator I was able to grow an audience.

Now, it’s not good enough to just be publishing. More and more, you have to be exceptional to break through all the noise. Becoming an excellent presenter and content creator is non-negotiable. If you want to do what I am doing, you have to create excellent content. The most important piece advice I can give is to start publishing in any medium. Just pick what is going to be easiest for you to jump into right away and publish on a regular basis as often as possible. Creating good content is just like any other skill or discipline. Without repetition, it’s impossible to be exceptional at it. There’s a huge learning curve not only in the skills and the tools needed to be successful but also in learning to be okay enough with yourself to hit the publish button. It takes a long time for most people to develop the ability to do that. To do what I’m doing you have to be comfortable with failure. The sooner that someone can get past the stigma of something not working as well as they wanted and view it as feedback and not “failure,” the easier it will be for them to become successful.

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