In Case You Missed It…

Legendary tech guru and podcasting pioneer Leo Laporte graces our show, bringing his wealth of experience from a storied career that kicked off in the radio waves of 1976. In an engaging conversation, Leo recounts his transition from a beloved radio tech expert to a trailblazer in the podcasting world with the creation of the TWiT network. With trademark humor and insights, Leo shares tales from the early days of podcasting, underscoring the essential role that community and human connection play in creating compelling media. He also sheds light on the challenges he faced and the innovative paths he forged in an era when podcasting was still finding its feet.

Beyond Leo's journey, we explore the rapidly changing landscape of media consumption shaped by platforms like TikTok, Instagram, and YouTube. As younger audiences gravitate more towards these platforms, we're left to ponder the future of traditional media and Google's place within it. Through our dialogue, we stress the timeless appeal of authentic and passionate content that resonates with audiences on a deeper level. The conversation circles back to the enduring power of genuine connections, as those hosts who can cultivate a sense of friendship with their listeners, often discover lasting success in this ever-evolving media universe.

This Week in Tech (TWiT) Podcast

Salt Hank: A Five Napkin Situation (A Cookbook) by Henry Laporte

theanycast.com/s2e14

Matt Levine chats with Leo Laporte, a podcasting legend and founder of TWiT.tv, an Internet podcast network focusing on technology. They discuss the early days of podcasting, how tech media has shifted, and what it takes to stay relevant when trends change overnight. Learn how to grow a podcast that lasts, why niche matters more than ever, and what most creators get wrong about discovery and audience loyalty.

• Leo starts by explaining how he became tech radio’s go-to guy. He loved being on-air, but didn’t love the topics people expected from talk radio. So he carved out a space that let him dive into something he genuinely cared about—technology.
• Why Leo started a podcast network in 2005—before most people even knew what a podcast was. 
• Leo explains what it was like being one of the first 10 podcasters in the world. 
• Leo on the most important aspect of podcasting: “You need to know your audience. The more general a show is, the more difficult it is to promote it.”
• Leo explains just how easy it is to start a podcast today. All you need is a laptop and a mic. Unfortunately, this simplicity is both a blessing and a curse. 
• Leo says the barrier to entry has never been lower. But that also means the space is noisy, crowded, and competitive. Starting is easy; being found is the real challenge.
• Leo highlights why discoverability—not content—is what kills most podcasts today. Even the best ideas can get buried if no one knows you exist.
• Matt asks if discoverability can be fixed—and Leo says yes. However, it’s not about better SEO or thumbnails. It’s about being on platforms that are built to make things go viral like TikTok, Instagram, YouTube. 
• Leo shares how they post twice daily on all platforms and why short clips are key to long-term growth. You can’t always track what’s working, but you can see when momentum starts to build.
• Why the top 20 podcasts dominate half the ad revenue, and what that imbalance means for everyone else. If you’re not already at the top, you’re fighting over scraps. That’s why niche, loyalty, and consistency matter for the smaller podcasters. 
• Leo shares what COVID taught him about brand courage. The companies that kept showing up grew. Meanwhile, brands that pulled back lost their visibility and trust.
• Understand how podcast advertising has shifted away from consumer brands to niche B2B partners.
• Matt and Leo unpack why going niche is the smartest move a creator can make right now. Broad topics make it harder to build connection and loyalty. When you know exactly who you're talking to, they know exactly why they should listen. Specificity is your superpower.
• Leo explains why remote work weakens small teams in ways people often underestimate. 
• Matt shares how remote teams can work—but it takes unnatural amounts of structure and intention. You can’t just hope the culture will carry itself. You have to manufacture connections on purpose. Otherwise, people drift—even when they’re online every day.
• Leo shares why AI isn’t a threat to content creators, it’s a tool to be used with intention. He’s not worried about being replaced. He’s more focused on how to integrate AI in ways that save time and amplify creativity. 
• Leo’s take on AI in podcasting, especially when it comes to editing and marketing. There are tools now that can help you clip, caption, and distribute without a huge team. The trick is knowing what job you're trying to solve. Not every tool fits every creator.
• Leo breaks down how the YouTube algorithm is shifting—and why short-form content is the next big opportunity. With TikTok facing pressure, YouTube is positioning Shorts as its successor. That means if you're a podcaster, creating short clips is a must. 
• Why Leo believes chasing trends is a waste of energy—and what to do instead. If you stay true to what excites you, the trends eventually circle back. People can feel when something’s authentic, and when that happens, attention follows.
• Leo on the future of podcasting—it won’t be just audio anymore. Video, community, and personality are what people crave. For example, YouTube is where people are going right now. If you’re not on it, you’re missing where the next generation already is.

Mentioned in This Episode:

This Week in Tech (TWiT) Podcast

Salt Hank: A Five Napkin Situation (A Cookbook) by Henry Laporte

theanycast.com/s2e14

Full episode launches on July 17

In Case You Missed It…

Gordon Firemark, the esteemed podcast lawyer, joins us for an enlightening discussion on the ever-evolving podcasting industry. Gordon's journey from a mere podcast enthusiast to hosting his own show, "Entertainment Law Update," offers a fascinating backdrop to our exploration of legal intricacies in the digital age. We unravel the complexities of AI-generated content, addressing the thorny issues of copyright and ownership when AI tools repurpose existing materials. Gordon offers invaluable guidance on safeguarding intellectual property, underlining the importance of robust contracts, work-for-hire clauses, and guest releases. Also, if you're in need of a legal edge, Gordon generously provides a free guest release template.

In a world where we're often unprepared for today's challenges, we share insights from Gordon's latest book that promises to guide content creators through the podcasting maze. Our conversation emphasizes the necessity of securing podcast releases and explores how to navigate the industry with confidence. Don't miss this opportunity to connect with us on social media and catch my show, "My Legit Podcast Pro," on YouTube. Gordon is reachable for any legal guidance, and we extend our gratitude for this illuminating exchange. Stay tuned for future episodes, where we promise to bring you more compelling topics and expert insights.

Mentioned in This Episode:

Get the Podcast Blog & New Media Producer's Legal Survival Guide

Podcastrelease.com

GordonFiremark.com

Follow Gordon on YouTube

theanycast.com/s2e13

Matt Levine chats with Gordon Firemark, the CEO of Firemark Enterprises and a leading voice in entertainment law. They discuss the legal side of podcasting, what creators get wrong about copyright, why “fair use” isn’t a free pass, and how to avoid costly mistakes with content and licensing. Learn how to protect your podcast, navigate grey areas, and stay one step ahead as the industry evolves.

• Gordon shares how a podcast guest spot back in 2006 changed the course of his legal and podcasting career. Learn why saying yes to small opportunities can start something way bigger than you expect.
• Gordon explains the one mindset shift that helps him stand out in a sea of 4 million shows. 
• Gordon explains the difference between podcasting in 2009 and today.
• Gordon reveals what most podcasters still get wrong about copyright, and why good intentions won’t save you in court.
• Gordon shares how he built trust with a niche audience, and explains why his audience tunes in every week. 
• Learn the legal blind spot Gordon says most beginner podcasters have. He also reveals how “freedom of speech” can land you in trouble.
• How to tell if your podcast idea is a smart niche or not. Gordon explains the two filters he uses to tell if a niche is worth pursuing.
• Gordon explains why thinking of yourself as a small creator is a mistake, even if you only have 10 listeners. What you say still carries weight and counts legally.
• Mark asks what makes YouTube outperform Spotify in podcast growth. Gordon shares the subtle tech shift that makes all the difference, as it's not just about video.
• Gordon breaks down the myth of ”fair use” with a simple example that will make you rethink how you clip content. 
• Learn how Gordon sees the future of podcast monetization, and why ad money isn’t the only route. What he suggests for smaller creators might be the fastest route to profitability.
• Matt and Gordon agree that AI won’t replace podcasters, but could still create a different kind of legal headache that goes beyond copyright. 
• Gordon shares the line between inspiration and infringement when using AI-generated content. Knowing where that line is might save you more than just legal fees.
• Matt challenges Gordon on whether podcasters are influencers. Gordon believes every content creator with an audience is an influencer. 
• As an influencer, every word you share carries weight, because even the best intentions can be misunderstood by parts of your audience.
• Learn why Gordon believes podcasters need legal representation just like Hollywood creatives, and why he feels creators should get representation in Congress.
• Gordon explains why entertainment law is more complicated than most lawyers admit, and how small misunderstandings could land you in trouble. 
• How to avoid the most common mistake podcasters make when quoting or sharing other people's content. Gordon reveals the legal principle most creators overlook when it comes to copyright laws. 
• Gordon shares what he thinks will happen in podcasting over the next five years, and why it’s not too late to launch your own podcast. 
• Discover how Gordon uses AI in his own podcast production, and why he’s not afraid of it, but is intentionally careful with it. His approach could save you time and keep you protected.

Mentioned in This Episode:

Get the Podcast Blog & New Media Producer's Legal Survival Guide

Podcastrelease.com

GordonFiremark.com

Follow Gordon on YouTube

theanycast.com/s2e13

Full episode launches on June 26

In Case You Missed It…

Meet Dave Hamilton, an iconic figure in the podcasting world, known for his blend of geeky charm and musical prowess. In this episode, we chat with Dave about his remarkable journey from the dawn of the digital age with the Mac Observer in 1998 to his current role as a leader in the podcast space with shows like Mac Geek Gab, Business Brain, and Gig Gab. Dave shares his thoughts on the evolution of podcasting, highlighting the significance of audio quality and the power of fostering a tight-knit community through platforms like Discord. Whether he's discussing the art of maintaining listener loyalty or the intricacies of managing sponsorships through Backbeat Media, Dave brings a wealth of knowledge and experience to the table.

We also delve into the world of listener support systems, with Dave candidly reflecting on his own creations and the potential benefits of using services like Patreon today. With a touch of humor, he recounts how his innovative, yet sometimes insular, approach led to unique challenges and victories. We explore the current state of podcasting's lifecycle, and what it takes to keep a show not just alive, but thriving. If you're a podcaster aiming to build a lasting connection with your audience, or simply a listener curious about what goes on behind the scenes, this conversation with Dave Hamilton is packed with insights and inspiration.

Dave Hamilton on LinkedIn

The inaugural episode of The Mac Geek Gab Podcast

theanycast.com/s2e12

Matt Levine chats with Dave Hamilton, Founder of BackBeat Media. They discuss what it really takes to build a podcast—from building community and attracting sponsors to maintaining top-tier audio quality and treating your show like a business. Dave shares hard-earned insights from nearly 20 years behind the mic, including how to get your first 25,000 listeners, why most podcasters quit too early, and what separates the pros from the rest. Learn how to grow your audience, build a sustainable podcasting brand, and create a show listeners genuinely care about.

• Dave shares how the Mac Geek Gab podcast went from 1,000 to 25,000 listeners, three weeks after Apple added podcasts to iTunes.
• Dave highlights the two rules that became the foundation of his podcast: always release on time, and never compromise on audio quality. 
• To him, consistency wasn’t just about discipline, it was a promise to the listener that they could count on the show to show up and sound good every single time.
• Dave believes poor audio wears people out because bad audio makes it hard to focus, and that makes it harder for your audience to care about you.
• Dave emphasizes that building a loyal audience is less about numbers and more about ownership. When people feel like the show belongs to them and they’re part of the community, they stick around longer, engage more, and tell their friends.
• Dave explains the benefits of getting a listener to financially support your show. The moment someone gives you even a dollar, they become twice as invested in following your podcast. 
• Dave questions the logic of removing ads for paying supporters. He argues that if someone values your show enough to pay for it, they’re also likely to value your sponsors, especially if those sponsors are a good fit. 
• Mark and Dave explain why your audience shouldn’t feel like they’re being sold to—they should feel like they’re being shown something useful by someone they trust. That’s how sponsorship becomes service, not interruption. 
• Dave insists on vetting every potential sponsor by asking: Will this resonate with my audience? Can I genuinely get behind this? 
• If you can’t speak about a product with conviction, your audience will hear it, and the trust you’ve built could evaporate.
• Dave describes what it means to be a fiercely independent podcaster. 
• Dave shares a powerful truth about discoverability: most podcast listeners are looking for their next favorite show. The easiest way to get in front of them is to partner with other podcasters, promote each other’s work, and give your audience new voices to trust.
• Dave reminds us that podcasting is one of the most intentional media formats in the world. 
• No one stumbles into a podcast; every listener has already opted in, and that level of buy-in makes the connection between host and audience deeply valuable.
• Dave leans into the concept of 1,000 true fans. He believes that when you build an audience that shows up for you, not just your content, you’re already halfway to financial sustainability. 
• Dave believes the best podcasters sit in front of the mic because they have something to say, and they say it with conviction. If others listen, great. But the drive comes from within.
• Dave shares a powerful insight: if one person reaches out, whether to thank you or argue with you, you’ve won. That kind of emotional reaction means they’re invested, and that kind of listener will come back. 
• Matt and Dave break down the critical early drop-off point for podcasters. 
• Most people quit before episode 10. But if you can stay consistent for six months, you massively increase your odds of long-term success.
• Dave draws a line between podcasting and music. A good podcaster, like a good musician, doesn’t just deliver sound—they create a feeling.
• Dave outlines the traits that define great podcasters: discipline, sincerity, curiosity, and a genuine desire to serve. You don’t need to be a performer—you need to be someone worth listening to.
• According to Dave, we’re still in the early innings of podcasting. Despite how crowded it feels, the majority of people still don’t listen regularly. That means the biggest opportunities haven’t even hit yet.
• Dave sees podcasting as the most effective form of modern word-of-mouth. When a trusted voice says, “go check this out,” people act on it. And that’s what makes podcast advertising, done right, so powerful.
• Dave ends with a message of hope: there are infinite corners of the market still unclaimed—and if you’re willing to show up with consistency and care, one of them can be yours.

Mentioned in This Episode:

Dave Hamilton on LinkedIn

The inaugural episode of The Mac Geek Gab Podcast

theanycast.com/s2e12

Full episode launches on June 5

In Case You Missed It…

Podcasting legend Dave Jackson joins us for a captivating conversation that traces his awe-inspiring journey from the early days of podcasting in 2005 to his celebrated status in the industry today. With anecdotes that highlight the global reach of podcasting, including a memorable connection with a listener in Germany, Dave shares the evolution of his career. From launching the School of Podcasting to his impactful roles at Libsyn and PodPage, his story is filled with insights into his professional milestones. We also explore the honor of his Podcasting Hall of Fame induction and its influence on his approach to self-promotion. Dave brings to light his strategies for monetizing podcasts, referencing his insightful book, "Profit from Your Podcast."

In the second half, we shift gears with an intriguing podcast recommendation that offers a unique take on U.S. news, blending sound effects with storytelling that invites both laughter and reflection. The show captivates a global audience and strives for neutrality, despite occasional leanings, with new episodes eagerly awaited on Thursdays and Sundays. As we conclude, we express our heartfelt thanks to Dave Jackson for his engaging storytelling and encourage our listeners to passionately pursue their own podcasting dreams. Get ready for a session that promises both inspiration and entertainment!

Podpage.com

Access Dave’s School of Podcasting

Profit from Your Podcast: Proven Strategies to Turn Listeners into a Livelihood by Dave Jackson

The Audience Is Listening: A Little Guide to Building a Big Podcast by Tom Webster

theanycast.com/s2e11