

Affiliate Marketing & Side Hustles on the Doug.Show
Doug Cunnington, PMP
The Doug Show is where I’ll talk to other marketers, side hustlers, & experts, share success stories, talk about making the leap from corporate worker bee to entrepreneur. We'll go deep on affiliate marketing, side hustles, SEO, entrepreneurship, management, and working online.
Episodes
Mentioned books

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

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

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

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

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

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

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)

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

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

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


