Most exits in the media business are, frankly, pretty messy. They happen abruptly on a random Tuesday, or they unfold quietly during a corporate budget cycle. Worse, talent sometimes stays five years too long and burns out the engine.
But every once in a while, someone gives us the blueprint for the perfect exit.
A Legacy Built in San Diego
Enter Kimo Jensen. In July, after over 30 years anchoring the afternoons at KSON in San Diego, Kimo is hanging up the headphones. He isn’t just retiring. He and his wife, Shannon, are jumping in with both feet, packing their bags, and moving across the globe to the Italian countryside. Arrivederci, San Diego!
Staying at one major-market heritage brand for three decades isn’t just an elite professional accomplishment — it’s a statistical anomaly. It means you survived multiple ownership flips, structural turnarounds, and a total evolution of the media landscape. More than that, it requires you to be a genuinely world-class human being.
Back when I was the Regional VP of Programming for Audacy and Program Director for KSON, rooms could get predictably tense — as radio rooms often do. Kimo was always the antidote to that friction. He brought an unflappable chill into the building every single day.
My absolute favorite memory of our time together was our morning routine. I’d text him early with promo adjustments or station imaging needs. Every so often, I’d get a quick reply: “I’ll circle back with you in a bit, KC. I’m in a board meeting.”
For any other employee, that meant a mind-numbing deck or a status update. For Kimo, it meant he was out on the water, sitting on a surfboard, catching waves — keeping his head exactly where it needed to be.
I caught up with the “Smilin’ Hawaiian” to download his 30-year masterclass in longevity, managing corporate weather, and how to successfully steer your life into the ultimate Dolce Vita.
*Editor’s Note: Answers have been edited for clarity and length.*
The Masterclass in Longevity
Kevin Callahan: Kimo, staying at one station for nearly three decades in modern media is like finding a unicorn in the air-studio. What is the secret to staying fresh, relevant, and hungry when you’ve been looking at the same market and the same dashboard since the ’90s?
Kimo Jensen: “Being open to always learning. As radio has evolved over the past thirty-plus years, so has the market, and so has technology. Staying on the pulse of that — and the latest technology and social media — helps to keep things fresh and relevant.”
KC: You’ve survived multiple ownership changes, corporate turnarounds, and programming shifts. What did you understand about managing the “corporate weather” that you can share with other talent?
Kimo: “Be a good communicator, BUT also be a good listener. With the shifts in programming, ownership, and corporate turnarounds come plenty of fresh ideas. Always be receptive to new ideas and direction. The minute you stop is the minute you stop growing.”
KC: KSON is one of the most storied, heritage brands in the Country format. When you look back at day one versus your final sign-off, how much of the station’s soul remained exactly the same, despite how much the platform changed?
Kimo: “The one thing that never changed was the passion the listeners have — not only for the radio station itself, but the voices they hear daily. They really consider us part of the family.”
Curation, Egos, and the 20-Something Blueprint
KC: Beyond being an elite afternoon personality, you’ve been a massive weapon for Audacy’s national imaging team. How did your approach to production and ‘theater of the mind’ change over the years?
Kimo: “When I started at KSON, imaging was all about making everything bigger than life. It seems to have evolved more into word economy. In other words: get the message out, keep it short, and whatever you do, don’t get in the way of the music. So, in today’s imaging, be the spice.”
KC: What is one piece of advice you’d give to a 20-something talent entering a multi-station cluster today who wants to build the kind of legacy and brand longevity you accomplished?
Kimo: “Always have an open mind, and be ready to try anything. I mean, I never thought I’d end up playing country music following ten years of Top 40 and hip-hop! But once I jumped in, it ended up being a blast.”
KC: The industry knows you as a world-class creative, but your peers constantly point out that you are simply a good guy. In a business that can easily breed cynicism, how did you protect your optimism and manage to stay entirely grounded while carrying the weight of being a major-market cornerstone?
Kimo: “Simple! When I saw how much the egos were hated by fellow coworkers, air staff, and management, I always tried to go above and beyond to NOT be that guy. That sales guy you just pissed off is not coming back around with a client who wants you to endorse his product. You’re obviously too tough to work with.”
Destination Italy
KC: You are trading Southern California beaches for the Italian countryside next month. What was the exact moment you and Shannon looked at each other and said, “We aren’t just retiring; we are moving across the globe”?
Kimo: “With dual citizenship (American & Italian), my wife has always wanted to try it, but both of us were working. The best we could do was visit for about ten days. Now we can jump in with both feet and be totally immersed. Not only in Italy, but anywhere in Europe. Surf in France, snowboard the Swiss Alps, cappuccinos in Rome.”
KC: Radio people are notoriously addicted to timelines. How long do you think it’s going to take your internal clock to adapt to the Italian lifestyle where time is basically a suggestion?
Kimo: “I love that line, ‘Time is basically a suggestion.’ Not sure how long it will take, but anyway you slice it, that just sounds like a great retirement.”
KC: If you had to pick one Country song that serves as the official theme song for this upcoming Italian chapter of your life, what is it?
Kimo: “Haha, like you said, time is basically a suggestion… Maybe ‘It’s 5:00 Somewhere.'”
The Executive Summary
Look at Kimo’s career path and you’ll find the ultimate antidote to the anxiety gripping our industry right now. So often, we spend too much time overthinking it. Ultimately, Kimo survived it all by relying on three simple, unshakeable pillars: stay open to learning, treat the support staff with respect, and never stop being the “spice” on the air.
He didn’t let the grind consume his life. Instead, he protected his peace, put in his time, and built a legendary family relationship with San Diego. Perhaps most importantly, he knew exactly when it was time to step away and go live.
To my friend Kimo: thank you for decades of elite radio, and thank you for always bringing the chill when the building needed it most. Enjoy the lifelong board meeting in Italy. You earned every single wave. The next time I text, I hope you’re in a board meeting.
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As the Executive Director of Programming & Operations for Pamal Broadcasting, Kevin Callahan oversees 25 stations across five markets, including the company’s four Country brands. An award-winning brand specialist, Kevin is a passionate advocate for talent development, dedicated to mentoring personalities and restoring our medium to its most vibrant, high-impact form. His career is highlighted by 12 years as Audacy’s West Coast Regional VP of Programming for the Country format, where he managed premier brands across major markets including San Diego, Seattle, Phoenix, Riverside and more. Today, Kevin balances his corporate leadership with his role as President of Sonic Maple Media, serving as a fractional executive advisor to broadcast leadership and fractional programmer and talent coach to broadcasters nationwide. He can be reached at kevin@pamal.com
