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20 Years at the Edge of Tech and Audio with Leo Laporte

The Anycast with Matt Levine

Release Date: 07/17/2025

ICYMI - 20 Years at the Edge of Tech and Audio with Leo Laporte show art ICYMI - 20 Years at the Edge of Tech and Audio with Leo Laporte

The Anycast with Matt Levine

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...

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20 Years at the Edge of Tech and Audio with Leo Laporte show art 20 Years at the Edge of Tech and Audio with Leo Laporte

The Anycast with Matt Levine

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...

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The Anycast with Matt Levine

Full episode launches on July 17

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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...

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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...

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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...

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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...

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More Episodes

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