Ask the Podcast Coach

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On this episode, I was joined as always by Jim Collison, and we had the pleasure of welcoming Ralph Estep from AskRalph.com—the Content Creators' Accountant—to dive into recent changes in how the IRS handles tips for content creators. Ralph walked us through the new law allowing up to $25,000 in tip income (like Super Chats, Buy Me a Coffee, etc.) to be excluded from income taxes in 2025, provided you track it properly. We talked about the importance of keeping tip income separate from memberships or other payments where the cust...

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Welcome to this holiday edition of Ask the Podcast Coach! I’m Dave Jackson, flying solo with special guest Chris Stone from Castahead.net. In this lively episode, we kick things off debating the most overplayed Christmas songs (sorry, Mariah Carey!), slide into podcast mic setups—covering everything from phantom power to Cloudlifters and USB/XLR combos—and share our biggest podcast merch mistakes. 

Sponsors:
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Basedonastruestorypodcast.com - Comparing Hollywood with History...

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Welcome to this week’s episode of Ask the Podcast Coach! I’m Dave Jackson, and I’m excited to be joined by my good friend Jim Collison as we kick back after Thanksgiving and dig into everything from surviving power outages as a podcaster to getting serious about connecting with your audience. We’ll swap stories from behind the mic, share practical tips for managing your listeners, debate the best batteries for your gear, and tackle questions about websites, live show feedback, and the ever-changing world of podcast tech. Let’s get into...

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In this episode of Ask the Podcast Coach, Dave Jackson and Jim Collison dive into the evolving world of podcasting where authenticity wrestles against the growing pressures of monetization and consolidation. Are podcasts losing their unique spirit and turning into just another version of radio? Dave and Jim reflect on the rise of dynamic ads, syndication, and free hosting, dissect the pitfalls of “following the money,” and urge podcasters to stay true to their voices.

They also share hard-earned insights on:

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First up, I share some behind-the-scenes updates, including my recent move from a lifetime video hosting deal that went south to Voomly, and how AI tools like ChatGPT are helping me generate show notes and summaries more efficiently. We also discuss the mysterious rise of EM dashes in AI-generated writing—did anyone use them before AI took over our grammar?

We talk about what’s happening at Libsyn, including some big changes in leadership and strategy, and my insider thoughts about their direction and features (or lack thereof). If you’...

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Ever wonder if daily podcasting helps or hurts? We break down how to use November-style challenges to build reps without burning yourself out, and why the best consistency is consistently delivering value. From there, we get real about “reality” podcasts: celebrity banter can skate by on fame, but most shows need a promise listeners can feel—make them laugh, teach them something, or save them time. If your friends love hanging out, great. If strangers stick around, you’ve got a show.

We also dive deep into AI as a workfl...

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What happens when your listener’s device can generate a personalized podcast on command—your voice, their preferences, zero friction? We dig into a bold forecast from Joe Pulizzi and use it as a springboard to map what creators must do now to stay essential. The headline: you have time, but not to waste. The next three years will reward human connection, not just output.

We break down why live shows build a moat AI can’t cross: people show up to participate, not just consume. That interaction turns casual...

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The feed isn’t “social” anymore—it’s an endless parade of AI-recommended video. So why are we still hoping a 30-second short will magically convert strangers into hour-long listeners? We pull back the curtain on what the platforms actually reward, why shorts are best used for brand awareness, and the specific moves that help listeners cross the bridge to your long-form show.

We talk about the algorithm reality—how little time people spend with actual friends on major platforms—and what that means for podcasters betting on reels to drive growt...

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What happens when AI gets good enough to sit in the co-host chair—but not good enough to replace a heartbeat? We dig into the real trade-offs behind AI in podcasting, from research assistants and auto-summaries to voice cloning, live translation, and whether anyone actually wants a synthetic sidekick. The conversation is honest and a little contrarian: yes, the tools are powerful and getting better by the week; no, they can’t carry the weight of human curiosity, risk-taking, and the messy surprises that make a show worth hearing.

We a...

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Ever feel like your show is stuck at 30 downloads and your guests won’t share your episode? We’ve been there, and we’re putting it all on the table—how language choices affect your brand and reach, why “big name” guests almost never translate to listener growth, and how to structure improv so it lands without a live audience. We get honest about impostor syndrome, burnout, and the moment you realize your strategy isn’t working. Then we walk through practical fixes: crafting episode promises that stop the scroll, building segments that...

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Dave Jackson flies solo this week (with special guest appearances from Randy Black and Ralph Estep Jr.) to tackle this challenging question and more. Randy shares a heart-wrenching story about losing his podcast co-host and friend, reminding us of the human connections that make this medium so powerful. His emotional recounting serves as a poignant reminder that beyond analytics and strategies, podcasting creates meaningful relationships that transcend the microphone.

The conversation takes a practical turn when Ralph joins to break down the differences between LLC and sole proprietorship structures...

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How do you find guests when your podcast covers extremely niche topics? It's a challenge many creators face, especially when starting out. Dave Jackson and Jim Cullison tackle this question head-on, providing practical strategies that go beyond the standard advice. Rather than endless online searching, they suggest going directly to where your potential guests gather, leveraging existing connections, and most importantly, asking current guests for recommendations.

The episode takes a heartfelt turn as the hosts pay tribute to podcasting pioneer Todd Cochran, founder of Blubrry, who recently passed away...

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The boundaries between legal protection and audience engagement blur when we confront one of podcasting's persistent questions: do you need release forms from your guests? This episode dives deep into this conundrum, revealing why adding friction to your listener experience might actually sabotage your growth efforts.

Sponsors:
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Basedonastruestorypodcast.com - Comparing Hollywood with History?

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