Lessons From a Year of Podcasting, YouTube, and Experiments (My 2025 Progress Report)

What’s working, what’s not, and where Side Hustle Nation is headed next?

I’m pulling back the curtain on my 2025 annual progress report, sharing insights from a year of podcasting, YouTube experiments, business challenges, and personal growth.

Tune in to Episode 714 of the Side Hustle Show to learn:

what’s working (and what’s not) in podcast and YouTube monetization
how AI is streamlining content production
lessons from a year of health experiments and personal reading

Table of Contents show

The Podcast: 700 Episodes and Growing

The Side Hustle Show crossed 700 episodes this year and maintained a consistent schedule of 6 episodes per month.

Download stats: The show is reaching around 225,000 downloads per month, or an estimated 100,000 unique devices, which serves as an approximation of audience size.

In a year where website income from affiliate partnerships and display ad revenue was down significantly, ad sales through YAP Media (Young and Profiting) helped offset those losses by selling out all available inventory.

Production Updates and AI Integration

I continue using Riverside to record remote interviews, then mark up transcripts with sections to trim for the editor.

Equipment upgrade: A few months ago, I switched from the Heil PR40 (which had powered the show for the previous 400 episodes) to a Shure SM7DB microphone, advertised as being better at cutting out background noise and room reverb.

AI workflow: I built a custom Claude project to help with editing suggestions. I fed in multiple before-and-after transcripts to teach the AI how Side Hustle Show episodes are edited.

The prompt looks for sections that are long-winded, repetitive, off-topic, or take too long to get to the answer.

The bigger time saver came for my show notes writer, who can now use Claude to get a solid summary of each conversation, then just edit and format, add images and links, instead of starting from scratch.

YouTube: The Future of Podcasting?

Following tips from Whitney Bonds and Chad Carson (who both do better on YouTube than I do for interview content), I started recording separate intros for the video version of the podcast, creating a more sizzle-reel, YouTube-hook-style intro specific to that platform.

The plan for 2026 is to begin selling sponsorships as both audio and video placements. YouTube is introducing a dynamic ad insertion feature, similar to what’s available on Megaphone for the audio side.

An interesting observation: Over the summer, when I told people about the show, 4 out of 5 people opened up YouTube to find it instead of a podcast app. That was surprising and maybe telling about the future of podcasting.

I continue to invest in listener growth, primarily through AudienceLift and PodRoll. After testing about a dozen different podcast promotion channels and spending around $30,000, those two have proven most cost-effective.

Paid Traffic Experiment: A Costly Reality Check

With organic traffic continuing to slide, I wanted to see if paid traffic could help fill the gap. Specifically, I tested paid search traffic arbitrage — sending Google Ads traffic to content pages with affiliate offers and hoping to earn more than I spent.

This was actually how my very first online business worked years ago, so it wasn’t a totally foreign idea. But the ecosystem has gotten a lot more complex. While I’d been running small Google Ads tests for years, I never had revenue attribution I fully trusted. It felt profitable, but I couldn’t say for sure.

This year, I decided to fix that.

I signed up for AnyTrack to get clearer attribution — and what it showed was… uncomfortable. According to the data, the Google Ads I’d been running for years were likely not profitable, and maybe not even close.

I refined landing pages, tested bidding strategies, and worked with paid traffic specialists, but I never got it to a place where the numbers consistently worked.

So I’ll chalk this one up as a big, expensive L.

Email List Growth (and the First Time It Went Backwards)

Another ripple effect of declining website traffic was slower email list growth — and eventually something I’d never seen before: the list actually started shrinking.

Unsubscribes have always been normal, but historically new sign-ups easily outpaced them. In the second half of the year, that wasn’t happening anymore.

That sent me into experiment mode.

Here are a few things I tested:

Creator Network (Kit):

This is the “you might also like” recommendation during newsletter sign-ups. Just by being part of it, I’ve picked up 1,000+ subscribers, which feels like a nice bonus for something relatively passive.

Facebook Group Partnerships:

Earlier this year, I partnered with the owner of a large delivery-driver Facebook group. We tested paying per email sign-up using GroupLeads. It worked (hundreds of sign-ups per month) until the group got shut down and the faucet turned off. Still, I’d be open to similar partnerships again.

Refind:

After hearing Lewis Waldron mention it, I tested Refind at about $1.50 per engaged subscriber. Their filtering is aggressive, so you’re paying only for people who actually open emails.

Podcast-First Lead Magnets:

And honestly, this continues to work best. Podcast listeners already know me, trust me, and stick around longer than SEO or co-reg traffic. I created a few new resources this year — including a local directory research file, an AI-assisted brainstorming worksheet, and a weighted decision matrix — which together added around 500 new subscribers.

If I could only grow the list one way going forward, it would be through the podcast.

Non-Podcast YouTube Content

I didn’t publish with much consistency this year (maybe 7 or 8 videos total). These videos typically fall into three categories:

Product review videos, which have done well for the channel in the past and tend to have a long shelf life
Repurposed website content videos, which usually target a specific keyword and can perform well for months or years
Videos that target topics that have done well for other channels, but with my own spin. For example, I found a video called “Top 5 Online Business Ideas You Can Start TODAY With $0” with 400,000 views and made my own version.

The strategy: Look at competing channels for videos that popped and have way more than their normal number of views, then try to recreate that magic in your own style and voice.

The logic being, YouTube viewers really liked that topic, and if it went viral once, it could go viral again.

For video editing, I have a part-time editor who’s been with me for years (she does the podcast episodes and shorts), another editor from Fiverr for one-off videos, and I do some editing myself in ScreenPal and pull in clips with Pictory.ai for sourcing stock footage and turning scripts into videos.

The Kids Enter the Content Game

My kids started their own Dude Perfect-inspired trick shot YouTube channel this year. They’ve stuck with it and made 10 or 12 videos so far.

My oldest edits all the clips in iMovie on his iPad. The kids are learning about setting up shots to get the right angle and avoid getting street signs and license plates in the frame. The neighbors help set up shots, and kids in their class are asking to be in the next video.

They’re motivated to beat Side Hustle Nation in subscribers, though I’m still gaining ground faster than they are.

While I was at FinCon, I got a text from my oldest: “102 views!! We went viral!!”

SMASH: A New Digital Product

I launched one new product this year: Scale My Awesome Side Hustle, or the SMASH Masterclass.

It walks through the three levers of growth:

Traffic
Conversion
Economics

I launched it as part of the BC Stack bundle, using the familiar “early access, half off” approach. That promotion generated about $9,000 in combined sales and affiliate commissions and added roughly 500 new email subscribers.

Bundles like this continue to be a sneaky-effective way to both monetize and grow the list.

Health and Fitness Focus

I started the year with a pull-up challenge: add 1 pull-up per day, starting with 1 pull-up on January 1st and building up to 365 on December 31st.

The kids got a pull-up bar for Christmas last year, and my youngest was knocking out dozens every day. The challenge seemed easy enough at first, but the problem was never fully recovering.

The first month was fine, the second month was more challenging (especially while traveling), but by March, I started incorporating rest days. The streak came to an end somewhere in the early 80s when my right lat couldn’t take it anymore. But I still do some every day and did way more than the zero pull-ups I’d done for years prior.

The pull-ups were part of a broader focus on resistance training this year, in addition to existing cardio, yoga, and walking, inspired in part by Peter Attia’s book Outlive.

Outlive by Peter Attia — https://peterattiamd.com/outlive/

The first part of the book details the most likely ways to die: heart disease, cancer, dementia, and diabetes (the “4 horsemen”). The second part covers actions to prolong healthspan, including building muscle.

One eye-opening takeaway: The recommended daily intake of protein was about 50% higher than I’d been eating.

The book also inspired me to book a couple DEXA scans this year. In the 6 months between scans, I was able to gain a couple pounds of muscle, which was an indicator things weren’t going in the wrong direction.

I uploaded the scan results into ChatGPT along with some bloodwork results to get recommendations. I was really impressed with the analysis, saying it felt like a way more in-depth conversation than I’ve ever had at the doctor’s office.

Influential Reads

Beyond Outlive, I also read Die With Zero by Bill Perkins.

My take: “This is a book for rich people by a rich person.” The author reportedly has a net worth around $100 million, so it can come across as out of touch at certain points.

What was helpful: The book illustrates people who’ve already earned the last dollar they’ll ever need, yet continue working for years (sometimes decades) accumulating “useless” dollars. It requires taking stock of realistic life span and spending to see where you might end up and ask what kind of margin of safety makes sense.

The book helped solidify thinking around Coast FIRE: the idea that at a certain point you can stop saving as aggressively, spend more of what you earn, and let compound interest do its thing with what you’ve already accumulated.

These factors, plus a healthy voluntary separation offer, inspired my wife Bryn to retire a couple months ago after putting in 20 years.

Discovering Narrative Nonfiction

Instead of traditional business books, I’ve gotten really into narrative nonfiction: true stories that read like novels.

I started a few years ago with Undaunted Courage, a day-by-day account of the Lewis and Clark expedition.

Other favorites included American Kingpin (about the Silk Road website) and The Wager, an incredible shipwreck survival story.

I started punching these titles into ChatGPT for recommendations, which led to:

One common thread: common people in uncommon situations, usually under extreme hardship. They’re facing starvation, being stranded, freezing, or being sold into slavery, and yet they found a way to survive and tell the tale.

This perspective helps whenever I feel bent out of shape about something minor. “I’m warm, I’m fed, I can deal with a few hours of discomfort if these people were able to deal with far, far worse.”

Episode Links

Looking for More Side Hustle Help?

Start Your Free $500 Challenge. My free 5-day email course shows you how to add $500 to your bottom line.
Join the free Side Hustle Nation Community. The free Facebook group is the best place to connect with other side hustlers and get your questions answered.
Download The Side Hustle Show. My free podcast shares how to make extra money with actionable weekly episodes.