Affiliate Marketing & Side Hustles on the Doug.Show

Doug Cunnington, PMP
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Mar 30, 2026 • 46min

Teacher to Tech Builder: How I Replaced My Income in 5 Months | DS610

I talk to Elliot about not being a tech guy, but now he’s building tools using AI. He used to be a teacher and didn’t even have a computer. It’s a great, inspiring story! Connect with Elliott Zelinskas YouTube Instagram X Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Intro 01:10 From Teacher to Online Income 02:24 Entrepreneur Roots and Early Hustles 05:07 Teachers Boost Tool Overview 11:18 Validation, MVP, and Growth Lessons 22:31 Teachers Boost Vision 22:58 Partnership With TPT 23:36 Rebuilding The Tool 25:04 AI Features Upgrade 26:57 Payments Email Automation 30:20 Agentic AI Shift 31:33 Defensibility And Moats 35:02 YouTube Community Strategy 39:11 Automated Publishing Workflow 44:18 Wrap Up And Where To Find
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Mar 23, 2026 • 47min

SEO Dead for Affiliates? How to Pivot | wecantrack | DS609

I chat with Jorge Barbosa from wecantrack about how affiliates can improve earnings, get higher ROI, and pivot by using data to make better decisions. Learn more about wecantrack Grow your affiliate revenue through seamless integration of your performance data with the best marketing tools. No developer needed. Get a free 15-day trial Explore the wecantrack Affiliate Dashboard Connect with Jorge Barbosa Jorge on Linkedin This episode is brought to you by wecantrack. Thanks for the support! Join My Email list Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 00:00 Intro 01:38 George’s Affiliate Origin Story 03:54 SEO Updates and AI Shockwaves 09:01 Revenue Recovery With Better Tracking 12:54 What We Can Track Actually Does 22:41 CTR to Conversion Analysis 24:48 Why Benchmarks Fail 30:24 Tracking Enables Pivoting 33:39 Who It’s For and Setup 39:38 Advanced Link Automation Tools
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Mar 16, 2026 • 1h 17min

Touring Musician to YouTube Success: "Kyle Orla" Strategy | DS608

I talk to Kyle Orla of K.O. String works in Duluth, MN. We geek out on YouTube and being a touring musician. Then, at the end, we geek out for 20 minutes about 90 – 100+ year old guitars. Kyle is a folk musician and educator, specializing in dexterous fingerstyle and hard driving American folk music. Connect with Kyle k.o. stringworks Kyle Orla on YouTube More with Doug: Mile High Fi Also, check out: MileHighFi Etsy Join My Email list Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 00:00 Turning a Guitar Obsession into a YouTube Business 06:06 Scaling a Music School: Why “Saying No” is Essential 16:27 The Secret to Video Storytelling: Tension & Release 24:33 Monetizing a Niche: How Patreon Changed Everything 39:52 Beating Creator Burnout: Analytics vs. Community 56:26 Vintage Guitar Deep Dive: Guitar Geek Out! 01:03:59 Telecasters, Kalamazoos, & When to Sell Your Gear
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Mar 9, 2026 • 29min

3 Case Studies of AI Coding w/ChatGPT, Claude Code, & Gemini | DS607

I heard from a few audience members about their experinces with AI Coding using ChatGPT, Claude Code, and Gemini. Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 00:00 Intro 01:20 Voicemail and YouTube slump 03:45 Case study Annie invoicing app 07:50 Dog interruption and lessons 09:17 Voicemail from William 11:57 Simple problems and stock builds 14:29 Case study Corey AI workflows 16:21 Planning vs rigid process 21:43 Personal projects and next steps 22:41 YouTube ads and algorithm impact 27:25 Wrap up email list and outro
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Mar 2, 2026 • 32min

Requirements for AI Assisted Coding - DS606

I talk about how to prepare requirements for coding with AI, based on my project management experience. Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 00:00 Welcome 00:24 Podcast Inspiration Story 02:37 What Requirements Mean 05:21 Field Research and Workflows 07:05 Build in Small Units 10:51 Viral AI Claims Skepticism 15:00 Simple Requirements Framework 17:42 Testing and Debugging Basics 21:51 Regression Testing Matters 24:03 Wrap Up and Next Steps 25:35 Notebook Tangent Field Notes 30:46 Final Call for Feedback
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Feb 23, 2026 • 32min

If I Started Over in 2026 - DS605

I talk about a few business models I’d consider if I was starting over in 2026. $500K in 2 Years Esty Print on Demand DS550 Giftlab I’m an affiliate for all of the above, so if you buy something, I may get a commission. Thanks! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 00:00 intro 03:43 Idea #1: Print-on-Demand Digital Products 07:59 Idea #2: SEO Skills → AI Search 12:49 Don’t Oversell 17:27 Ideas #3–4: Content Creation + Newsletters 24:13 Last Idea: Building Software with AI Tools 28:24 Reality Check: 31:14 Wrap-Up
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Feb 16, 2026 • 33min

I got Lucky - DS604

I’m not that good and just got lucky. Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 00:00 Luck, Survivorship Bias & Why Success Stories Mislead 02:39 Georgie the Needy Dog (Quick Detour) 03:28 Starting in 2013: Early SEO Wins and “Simpler Times” 05:40 AI Changes Everything: Fake Podcasts, Better Content, More Competition 08:39 Others Don’t See Their Luck Either: Interviews & Coaching Wake-Up Call 09:20 When the Game Changed: Google Updates, AI, and Sites Going to Zero 11:49 Types of Luck: Timing, Platforms, and Getting in Early 14:15 You Only Need a Few Wins: Small Shop, Consistency, and Pivoting 18:28 What I’m Actually Good At: Finishing Projects (and Quitting When Needed) 22:43 Ranking Revolution Case Study: When Timing Is Off 24:38 Actionable Takeaway: Create More Chances to Get Lucky 29:57 Final Thoughts: Show Up, Take Action, and a Missed AI Opportunity 32:31 Wrap-Up & Thanks (Georgie Finally Sleeps)
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Feb 9, 2026 • 40min

10 Things I Learned From 900+ Episodes - DS603

I published over 900 podcast episodes. I learned a few things along the way. Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 00:00 Introduction and Episode Overview 01:47 The Importance of Quantity Over Quality 08:05 Value of Personal Perspective 10:14 Audio Quality Matters 13:55 Guest Appearances and Inflection Points 16:54 The Power of Editing 18:42 Batching Content for Efficiency 22:11 Handling Audience Feedback 27:25 The Role of Intro and Outro Music 29:35 Niche Down but Stay Flexible 32:29 One-Take Approach and Final Thoughts
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Feb 2, 2026 • 27min

Dry January, Coffee, Caffeine, YouTube - DS602

This is an old fashioned catch up. I talk about cutting back on alcohol, caffeine, and some YouTube advertising updates. Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 00:00 Intro 02:33 Doug’s Coffee Journey 06:46 Moist January 11:10 Podcast Sponsorship & Listener Support 19:05 YouTube Ads & Subscriber Growth 26:06 Conclusion & Teaser for Next Episode
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Jan 19, 2026 • 41min

Sustainable Solopreneur 7 Rules for Online Success - DS600

I give you 7 ideas for being successful online. Brought to you by Semrush Affiliate Program Promote the Semrush Affiliate Program, which offers high commissions (up to $300 per sale) and a long 120-day cookie window, by highlighting their new AI Visibility Toolkit that solves the current business pain point of tracking brand presence on AI platforms like ChatGPT and Google AI Mode. Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 00:00 Introduction and Overview 02:29 Think Long Term 08:32 Incremental Stair Step Approach 15:23 SEMrush Affiliate Program 17:56 Avoid Burnout 24:12 Focus on Revenue Drivers 28:56 Take Action Over Research 34:08 Learn from Others’ Mistakes 36:28 Don’t Copy End Stage Giants 39:33 Conclusion and Call to Action

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