Winning the Away Games: Bob Skinstad chats to AI guru Jon Flynn

In this captivating episode of ‘Winning the Away Games’ in collaboration with Elixirr, host Bob Skinstad welcomes Jon Flynn, Microsoft’s sports visionary, on a journey exploring the intersection of technology and sports. From Jon’s Southern African roots to his role at Microsoft, discover the transformative power of data and AI in modernising the business of sports. Jon shares insights into the NBA app rollout, revolutionising how fans experience games. Uncover why sports, recession-proof and pandemic-resistant, is now a serious business, with AI giving rise to the professional fan. Don’t miss this dynamic conversation shaping the future of sports and technology.

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Edited transcript of the interview by Bob Skinstad with Jon Flynn

Bob Skinstad: Hi, I’m Bob Skinstad, and welcome again to Winning the Away Games. We’re on a fantastic journey, looking for displaced executives, not dissimilar to myself. The founder of Alexa, Steven Newton, and many others have connected with me recently, loving the journey and the intimate background stories on people worldwide. Some are from South Africa, reflecting our story, while others are from New Zealand or Scottish people sitting in Singapore.

Today, it’s a great privilege for me to welcome a person I know well due to a connection through a mutual friend. We’ve spent time watching sports around the world, right in his backyard, Jon Flynn. A big welcome to the show.

Jon Flynn: Thank you, Bob. It’s great to be here, and thank you for having me on, man.

Bob Skinstad: No, well, it’s our privilege to have you here. John, at the beginning of the show, I do a 30-second pitch. I promised not to take much more than 20 minutes of your time, but I know you have a great story. In 2020, you moved to Microsoft with the purpose of modernising the business of sport through data, a sentence that gets everybody excited. You also set up the Azure for Sports podcast, telling the story of sports leagues, clubs, and teams using technology to enhance the game and fan experience.

You’re a fellow Southern African by birth, now living in the United States. Let’s go to the beginning of the story. Where do we find you right now, and how did you get there?

Jon Flynn: I’ll give you a 7 out of 10 for that one, Bob. It was pretty spot on. I’m currently in New York, originally from the southern motherlands. I’ve been in the United States for over 20 years now. Every time I call the family back home, they say, “Man, you sound like such an American.”

I’m sort of in between the accents as it is right now. The most interesting part is that self-professed data and AI nerd. Everything I’ve done has revolved around taking technology and applying it to business, whether in financial services, consumer goods with Apple, or now in sports using data and AI.

Bob Skinstad: It so often is interconnected. Tell us how it fits together.

Jon Flynn: Exactly right. The journey started when I went to Europe for the first time, sparking my curiosity about how people around the world live and achieve the same goals. I finished school in South Africa, got my post-grad degree, went to Europe, worked for Bloomberg in New York, and the pace matched my fascination. New York was a different world, a different planet. The passion, drive, and pace here are unmatched.

Jon Flynn: My sister asked me, “Why New York?” I said, “They do everything like it’s possibly the last thing they’re ever going to get to do on earth.” That’s what I can get attached to. There are so many things you can do, and it couldn’t be any truer than that statement.

Bob Skinstad: Wow, I mean, what an amazing way to look at it. You’ve got to have a certain kind of mindset to sit in an airport and say, “I could go there.” Many people are twiddling their thumbs, hesitant about decisions. A friend of mine wrote a fantastic book about sports and psychology, highlighting the deliberation before action. I believe worrying too much before making a decision is like dying twice. Were you confident enough in yourself to say, “I can go anywhere and do anything”? Do you think people, post-COVID, might get closer to that mindset again?

Jon Flynn: Yes, I think it’s a combination, Bob. I was fortunate to have a well-traveled upbringing. My dad, being in the Navy, instilled in me the idea that there’s a big world out there. He encouraged me to go see it. Deliberation was something I experienced when choosing a university. I deliberated about going to Cape Town or Rhodes, choosing the latter took me out of my safety zone, and that’s when the itchy feet kicked in.

Bob Skinstad: It’s almost like a skill set. Some people can’t do that. I love taking leaps into the unknown. How has that helped in the work environment, especially at Microsoft, working with real-time data and analytics in sports, one of the most exciting areas? How did your ability to leap into anything contribute to getting you there?

Jon Flynn: Living my life by “why nots,” I joined Microsoft to play in the world of data and sports. Sports wasn’t a top-of-mind need for data, but I believed it was a perfect fit. I wanted to tell our story and take calculated risks. Understanding the audience was crucial. Transitioning sports into a business mindset involved showing that we could apply the same principles as in retail, consumer goods, and financial services. Treating sports like a business means optimising stadiums, much like ensuring a machine won’t break down in a factory.

Bob Skinstad: When did you feel sports as a business would be as big as internet, retail, or e-commerce?

Jon Flynn: I’ve always been an avid sports fan. While I gave up on becoming a professional athlete, I realised the global pervasiveness of sports. Wherever I went, there was a sport, and the passion transcended cultures. Whether it was rugby in South Africa or MMA in Southeast Asia, the tangible passion was always there.

And where it really hit home for me, and where I truly invested my career in sports, was during COVID when it was taken away. If people miss something, it’s pervasive. What we did at Microsoft and in the sports community through various cloud providers, startups, and established companies was find a way to present sports virtually. Whether it’s teams playing in the Disney bubble or playing to empty stadiums with crowd reactions piped in from home, sports proved recession-proof and pandemic-proof. It’s remarkable how we found a different way to consume sports, and that’s when I realised it’s something irreplaceable.

Sports, number one, is recession-proof. People still buy tickets, making it pandemic-proof. The numbers didn’t drop; we just found a different way to consume sports. The world of sports is now being taken seriously as a business. Look at it from a sheer salary perspective. Coaching staff salaries are substantial, indicating sports organisations are profitable. This ability to agitate further revenues and opportunities is incredible. People now follow not only teams and players but also coaches. It’s a business with multiple entry points that will be around for a long time.

I believe it’s changing with AI, giving rise to the professional fan. Casual fans have access to more data than ever before, becoming somewhat legitimate armchair quarterbacks on Monday morning.

Bob Skinstad: That’s true. Taking you to a working example, Microsoft’s close involvement with the NBA and the successful rollout of an app for fans. Tell us about that journey and what it’s been like for you and your team.

Jon Flynn: Magic! The NBA, a forward-thinking organisation, wanted to enhance the fan experience. We helped create and launch an app where fans can watch games the way they want, choosing different audio feeds or watching multiple games simultaneously. The app also brings fans deeper into the game, with features like NBA Fitness, allowing them to train like their favourite stars.

Bob Skinstad: And do you think other sports will follow suit, engaging fans better and utilising technology to compete for attention and revenue?

Jon Flynn: Absolutely. Both scenarios will play out. Sports with revenue goals will invest in technology, while others may fall away. Technology is the tide that lifts all ships. Big tech and sports will join hands to create premium sporting experiences, allowing sports companies to focus on what they do best.

Bob Skinstad: Yeah, exactly. You’ll see more leadership from tech companies, saying, “We pick for sport.” John, we’re out of time. I appreciate your time. Happy with people following you on LinkedIn?

Jon Flynn: Absolutely. Feel free to reach out on LinkedIn and tune into the podcast. Deeply appreciative of the conversation. Thank you, Bob.

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