The Evolution of Podcasting with Hall of Famer Dave Jackson

The Anycast with Matt Levine

Matt Levine chats with Dave Jackson, Head of Podpage and founder of The School of Podcasting.

Dave shares how he got started in podcasting, the lessons he’s learned across nearly two decades, and why staying true to your audience matters more than ever. They discuss the early struggles of launching a show, the right way to grow without losing your voice, how AI is reshaping content creation, and the real keys to standing out in a crowded podcasting world.

• Dave shares how he got into podcasting back in 2006, launched The School of Podcasting, worked for Libsyn for eight years, and got inducted into the Podcast Hall of Fame.
• Dave gets honest about the painful early days of launching a podcast in 2006 — when the tech was clunky, the process was ugly, and few people knew what a podcast was.
• Dave explains why the first few minutes of a podcast should set the tone and direction for the entire episode.
• Dave shares the easiest way to get more clicks on your podcast: write amazing titles and then make sure you deliver on the promise that’s on your titles.
• Dave explains his view on AI in podcasting: he’s not anti-AI, but warns that podcasters can’t afford to get lazy. Personality matters, and if you strip that out, you risk losing what makes your show special.
• How podcasting is different from radio and why podcasters should resist cramming shows with ads the way radio did.
• Dave and Matt share their thoughts on what really defines a podcast. For them, if it’s wrapped in an RSS feed, it counts — which makes them a little skeptical about stats that claim YouTube is now the top way to find podcasts.
• Matt brings up a powerful point: whenever you put an algorithm between you and your audience, you risk shifting your focus from serving your people to pleasing the algorithm.
• According to Dave, YouTube monetization can quietly pulls creators away from focusing on their listeners. The more you chase impressions and ad dollars, the easier it is to forget about the people you're actually creating for.
• Matt and Dave discuss how podcasters can balance creating for their audience while still navigating the algorithm.
• Dave uses a "three-legged stool" analogy to explain sustainable podcasting: you need your health, your attitude, and strong support around you. Lose one, and the whole thing can fall apart.
• Matt and Dave break down two of the biggest challenges in podcasting today: discovery and audience building.
• Dave’s advice for new podcasters: get feedback early. Make your first episode as good as possible, share it with people and ask them what they think.
• Dave points out the mistake most new podcasters make: they obsess over tech, microphones, and platforms, when in reality, listeners only care about good content.
• Dave talks about self-promotion and why it shouldn’t feel salesy if you genuinely believe in your product and your mission to help people.
• The two must-haves for podcasting success:you need to know exactly who your audience is, and your 'why.'
• Matt and Dave explore the fine line between AI and podcasting. For Matt, technology will always keep moving forward. Rather than resist it, creators need to accept, adjust, and evolve with it.
• Matt makes a sharp distinction: AI and language models are good at facts but they can't capture meaning. Turning facts into something truly meaningful still takes a human touch.
• Matt and Dave agree that what separates a good show from a bad show is not tech tricks or having celebrities as guests, it’s whether your content genuinely gives people what they came for.
• Dave shares his definition of a great podcast: it needs to make you laugh, cry, think, groan, educate, or entertain.
• Dave explains why great podcasts aren’t just about great content, they’re about how that content is delivered. You can have the best material, but if the delivery is bad, it won’t connect.
• Dave gets real about the early days of starting a podcast: when you start, you’ll often be talking to nobody, for no money, and for a long time. You have to love your subject so much that you’d do it anyway.
• Dave looks back on how different podcasting was in 2006 compared to today — and shares his honest thoughts about where he believes the space is heading by 2030.

Mentioned in This Episode:

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