The Side Hustle Show

714: My 2025 Progress Report: What Worked, What Didn’t, and What’s Next?

December 25, 2025

Key Takeaways Copied to clipboard!

  • The podcast experienced significant growth in downloads (220k-230k monthly) and maintained a high publishing frequency, with ad sales through Yap Media being a crucial revenue bright spot amidst declining website income. 
  • AI tools, specifically custom Claude projects, are being integrated to streamline podcast editing suggestions and significantly speed up show notes summarization, though challenges remain in achieving the host's specific voice. 
  • YouTube audience behavior is shifting, with listeners increasingly preferring to find the podcast content on YouTube over dedicated podcast apps, prompting a strategy shift toward video sponsorship sales in 2026. 

Segments

Podcast Performance and Monetization
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(00:00:15)
  • Key Takeaway: The Side Hustle Show maintained six episodes per month and relied heavily on the Yap Media ad sales network due to significant declines in website affiliate and display ad revenue.
  • Summary: The podcast surpassed 700 episodes and successfully maintained a high publishing schedule. Ad sales through the network were strong, compensating for a significant drop in income from the website’s affiliate partnerships and display ads. Audience size is estimated at 220,000 to 230,000 downloads per month.
Podcast Production Updates
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(00:01:24)
  • Key Takeaway: Production efficiency is being improved by using a new Shure SM7DB microphone and leveraging a custom Claude AI project for editing suggestions and show notes summarization.
  • Summary: The host switched to a Shure SM7DB microphone for better noise reduction and less desk clutter. A custom Claude AI tool assists in flagging repetitive or off-topic sections for editing, and it is a major time-saver for the show notes writer by generating initial summaries.
YouTube Strategy and Growth
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(00:03:20)
  • Key Takeaway: The strategy for YouTube is evolving to include platform-specific video intros and plans to sell combined audio/video sponsorships, recognizing that many listeners now default to YouTube for discovery.
  • Summary: The host is creating separate, ‘hookier’ intros for the video version of the podcast, inspired by successful peers. Future plans include selling sponsorships for both audio and video placements, anticipating YouTube’s dynamic ad insertion feature. A surprising observation was that four out of five new listeners immediately searched for the show on YouTube instead of a podcast app.
Non-Podcast YouTube Experiments
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(00:06:24)
  • Key Takeaway: Non-podcast YouTube content consistency was low, relying on repurposed website content and ‘competing channel’ analysis, with scripting identified as the primary production bottleneck.
  • Summary: The host published only seven or eight non-podcast videos, typically product reviews, repurposed website content targeting keywords, or attempts to recreate viral competitor topics. Scripting remains the biggest bottleneck, as AI-generated scripts often fail to capture the host’s authentic voice.
AI Tool Development
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(00:10:01)
  • Key Takeaway: The host successfully built a functional, vibe-coded YouTube script generator using Claude Code by inputting plain language functionality, combining competitor analysis with original site content.
  • Summary: The host created a working MVP script generator using Claude Code, which analyzes top-performing video URLs and combines that data with existing Side Hustle Nation content. This exercise demonstrated the potential for non-technical users to build internal tools or sell software products.
Website Traffic and Paid Ads Failure
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(00:14:33)
  • Key Takeaway: The Side Hustle Nation website traffic and revenue have suffered a slow erosion due to search algorithm changes, and a major paid search arbitrage experiment using AnyTrack for attribution proved to be an expensive, unprofitable failure.
  • Summary: The website income, historically the most passive revenue stream, has declined due to search engine changes, AI answers, and Reddit visibility burying organic content. The host spent significant time updating archives to slow the decline but abandoned paid traffic arbitrage after attribution software confirmed years of spending were likely unprofitable.
Email List Growth Tactics
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(00:18:47)
  • Key Takeaway: Email list growth slowed, prompting experiments with the Kit creator network, a paid partnership with a large Facebook group owner (which ended when the group was shut down), and the Refind newsletter discovery service.
  • Summary: The creator network within Kit drove over a thousand signups, while a paid partnership with a delivery driver Facebook group provided hundreds of signups monthly until the group was terminated. The host prioritizes podcast listeners for the list, as they represent a much stronger relationship than traffic from Google or other creators.
Digital Product and Workshop Sales
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(00:24:19)
  • Key Takeaway: A new digital product, the SMASH Masterclass, was launched successfully via the BC Stack bundle sale, generating $9,000 in sales and adding 500 subscribers, while four educational workshops were hosted for the audience.
  • Summary: The ‘Scale My Awesome Side Hustle’ (SMASH) Masterclass was launched during the June BC Stack bundle, yielding significant sales and list growth. The host also conducted four deep-dive workshops with guest experts like Anthony Keloje and Johnny Robinson, aiming to continue this value-add format.
Local Promotion and Book Authority
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(00:25:35)
  • Key Takeaway: A local vendor fair booth, where the host’s son sold 3D printed toys, unexpectedly highlighted the perceived authority of the host’s self-published book over his 700-episode podcast.
  • Summary: The host promoted the podcast locally, but neighbors who knew him expressed more surprise and interest in his self-published book than his long-running show. This suggested that a physical book still carries a higher level of perceived authority than extensive audio content.
Facebook Monetization Experiment
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(00:27:56)
  • Key Takeaway: The host began experimenting with the invite-only Facebook Content Monetization Program, inspired by peers earning significant daily revenue by reposting viral, niche-related content with polarizing captions.
  • Summary: This new income stream involves reposting viral material from other platforms with new captions to maximize engagement and ad revenue share. The host’s best day reached $40, and the main downside is the increased screen time and checking behavior, motivating a search for a social media manager.
Conference Travel and Industry Shifts
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(00:30:55)
  • Key Takeaway: Attendance at Podcast Movement showed a shift away from solo creators toward software companies and agencies, while FinCon highlighted the disappearance of the ‘creator middle class’ reliant on Google traffic.
  • Summary: The host attended Podcast Movement for the first time since 2017, noting fewer independent creators and more industry vendors. At FinCon, friends noted that many website-based entrepreneurs who relied on search traffic have pivoted or disappeared due to algorithm changes.
Health, Fitness, and Reading
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(00:36:10)
  • Key Takeaway: Inspired by Peter Attia’s ‘Outlive,’ the host focused on resistance training, including a challenging daily pull-up goal, and used ChatGPT to analyze DEXA scan results for personalized health insights.
  • Summary: The pull-up challenge ended after reaching the low 80s due to injury, but resulted in significantly more back and grip strength than previous years. Reading shifted heavily toward narrative nonfiction focusing on survival stories, which provided perspective when feeling frustrated with minor daily discomforts.