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Grow Your Network: Kevin Leahy Is A Bridge Builder Between The Analog And Digital Audio World

Here's HOW and WHY to connect with Kevin Leahy

For years, I've been connecting with interesting people and documenting insights that might help my clients and myself. What was once private is now (mostly) public.

People often ask: "How do you know all these people?" and "How do you connect these (re: random) ideas?" The answer is simple: consistent relationship cultivation and thoughtful note taking. My north star is trusting my instincts, my maps are the constellations in these reflections.

This approach to multidisciplinary networking has helped dozens of clients, colleagues, and friends strengthen their networks and unlock new opportunities. Feel free to steal these ideas directly - that's what they're for! I can't promise you'll learn FROM me, but I guarantee you can learn something WITH me. Let's go. Count it off: 1-2-3-4!

Introducing... Kevin Leahy!

Do you know Kevin Leahy? He's the founder of Podcast Pointman, the guy who started as a courtroom reporter hunting jury letters, joined NPR as a potential producer obsessed with Howard Stern (in his cover letter - great story), and somehow along the way, became one of the key people I now call whenever I have questions about audio brand building.

If not, allow me to introduce you. Kevin has spent the last decade building bridges between traditional media and the podcast revolution. He's worked with NPR on little shows like, "How I Built This" and now advises podcasters and media organizations on strategy, production, and sustainability.

I wanted to connect with him because he embodies something I value deeply: the willingness to leave the machine once you understand it well enough to rebuild it differently.

Our conversation is LIVE now on the Just Press Record YouTube channel. Listen and you'll hear us dig into why courtroom reporting taught him more about journalism than any credential ever could, why local podcasts might be the most underrated media opportunity right now, and what it means to work on one thing for a long time in a world obsessed with jumping around.

THREE: That's The Magic Number of Lessons

In the meantime, I wanted to pull THREE KEY LESSONS from my time with Kevin to share with you (and drop into my Personal Archive).

Read on and you'll find a quote with a lesson and a reflection you can Take to work with you, Bring home with you, and Leave behind with your legacy.

WORK: Doing the Job Beats Having the Title

"I had always heard of college as a proxy for, you know, ‘how to finish something.’ That was the line my parents always gave to me. And - everyone just accepted it. But people like my brother, who dropped out of college, or plenty other people I know, were they finishing other things in their life? They were finishing albums. My brother finished a novel when he was like 21 years old."

-Kevin Leahy, Just Press Record on Cultish Creative YouTube

Key Concept: Kevin's breakthrough insight is that pedigree and credentials have become proxies for competence when what we should actually be measuring is demonstrated work. When he covered court cases as a young reporter - not because anyone assigned him to but because he had the curiosity to show up - he was doing real journalism while sitting alongside professionals with far more impressive resumes. Portfolio beats pedigree. The actual work you've finished matters infinitely more than the box you checked or the institution whose name is on your degree. This applies whether you're hiring, building, or evaluating yourself.

Personal Archive Note-To-Self: I remember meeting a college buddy at a diner for breakfast. He wanted to ask if I’d help with a senior project. As he gave me the key dates, most of which were several months out, I took out my planner (it was the early 2000s, OK?) and started checking. He looked at me and said, “I think you’re the busiest person I know.”

Always stuck with me. Such a weird thing to hear when you’re 22. But I knew he wasn’t wrong, too. Because while a bunch of my peers in college were studying hard or partying hard or both, I was working a crappy job (line cook), some other jobs (guitar lessons, lots of gigging around for music), managing a recording studio while its owner was on tour, and, oh yeah, college itself.

I didn’t just know what I had in my life several months out, I had a vague idea for my capacity to put more of myself into anything extra that was just for a one-off, that felt like a ton to my friend, which I appreciated. Of course I said yes. We did a badass version of a bari sax and guitar song that I wish I could remember the name to (or how to play, ha).

But the point is, you don’t have to wait around to do anything. You can always just start. And, while the grades and the certifications are all nice to have, they never capture the real tests of merit - the results of getting up and making something happen, especially with other people onboard.

Work question for you: When was the last time you evaluated someone (including yourself) based on what they actually made rather than where they came from?

LIFE: Leave Your House to Find Your Life

"I feel like I need to summon that at times now. I guess I've done it. My brother who's a standup comedian always calls it getting outside your house. Like you have to go and leave your house to be a comedian, you gotta go in the club and put in the reps and get, you know, go through the eat some s***."

-Kevin Leahy, Just Press Record on Cultish Creative YouTube

Key Concept: There's a physical and emotional truth to "leaving your house." It's not just about getting out of your home office or your comfort zone - it's about the willingness to show up unprepared, to fail in public, to feel slightly out of place. Kevin learned this from his brother, a comedian who understands that reps in front of a real audience create an entirely different learning curve than practice alone. The podcast he wants to launch locally, the neighborhood stories he wants to tell, the people he wants to meet - none of that happens in the theorizing phase. It happens when you walk out the door.

Personal Archive Note-To-Self: I played a lot of guitar and music alone in my room. I had the boombox and the little amp. I had the headphones for when I had to turn it down (or off). It was great practice. But it was not performance. Even if I looked at myself in a mirror on rare occasion. Pure daydream belief building.

There was nothing like hanging out with some friends at a bowling alley and finding out a few of them had started a band. Jon knew I played and suggested I come over to join them. That was my first time officially out of the house in Kevin’s terms. I was probably 14? Totally different experience plugging in and turning up with a bunch of friends.

Now what happens next isn’t anything glamourous. We just played the same music we'd all been practicing alone in our rooms, but doing it together changed everything. Because in a short amount of time, friends would stop by and check it out. Not terribly long after, we got up the nerve to ask a guy at a local coffee shop who had all-ages punk shows how we could get on a bill.

I remember how out of place I felt at each stage, and at the same time, how completely at home and comfortable I was taking the risk. I just could never imagine not taking the risk. How would that feel - to know you could take the next step but never take it? Eek.

When Kevin talks about his brothers learning how to get outside and try things across non-traditional paths, you know they were drinking the same tap water.

Life Question For You: What would you do more often if you simply gave yourself permission to leave your house without a perfect plan?

LEGACY: Build the Thing Even If You Can't Measure It

"There's a faith-based component of you just gotta trust that you're doing something good and that the ripple effects will be good, and that it's just worth it. No matter any little number you try to ascribe."

-Kevin Leahy, Just Press Record on Cultish Creative YouTube

Key Concept: Kevin's local podcast project isn't about vanity metrics or building a personal brand engine. It's driven by intuition, community connection, and something that feels urgent but unmeasurable. He knows people in Takoma Park, MD have stories worth telling. He knows there's value in building a media bridge in his neighborhood. He also knows he can't A/B test that intuition or show you the ROI dashboard. What he can do is show up consistently and trust that the ripples - the business connections, the neighborhood resilience, the relationships that form - matter even if they never appear in your analytics. That's legacy thinking. That's the "professional fairy godmother" mentality that transforms communities.

Personal Archive Note-To-Self: What is it about people who understand something on a grand level, like Kevin being a part of some of the biggest podcasts and radio shows in modern media, who have the deepest appreciation for the smallest, most compelling communities?

I would have expected Kevin to tell me about making a run at Joe Rogan. I never would have guessed he wanted to create an audio zine for a neighborhood he loves. But it makes total sense. I completely relate to this. It’s punk rock economics at its core - where you just want to find the people who care and give them a space to gather. Growth is an after-effect, at most.

When you start to realize that joy is joy, no matter how you scale it or how many people recognize it as joy together, it starts to shift your thinking. This is very much something I can increasingly say at 40 that would've felt defensive at 22, let alone 14.

The joy you feel on the biggest stage of the world is pretty much the same as the joy you can feel on a tiny stage. Now, you can appreciate the joy you’re bringing others, and you can wrestle with the feedback on the experience others are having (i.e. you can read the comments if you dare), but your internal joy barometer just recognizes joy, period.

When you stop worrying about scale and just focus on making something that matters to the people in front of you, you offer a genuine transformation. That's what Kevin's about to do in Takoma Park. And that's special.

Legacy question for you: What would you build if you didn't need to measure its success?

BEFORE YOU GO: Be sure to…

You have a Personal Network and a Personal Archive just waiting for you to build them up stronger. Look at your work, look at your life, and look at your legacy - and then, start small in each category. Today it's one person and one reflection. Tomorrow? Who knows what connections you'll create.

Don't forget to click reply/click here and tell me who you're adding to your network and why! Plus, if you already have your own Personal Archive too, let me know, I'm creating a database.

Want more? Find my Personal Archive on CultishCreative.com, watch me build a better Personal Network on the Cultish Creative YouTube channel, and listen to Just Press Record on Spotify or Apple Podcasts, and follow me on social media (LinkedIn and X) - now distributed by Epsilon Theory.

You can also check out my work as Managing Director at Sunpointe, as a host on top investment YouTube channel Excess Returns, and as Senior Editor at Perscient.