DiscoverAffiliate Marketing & Side Hustles on the Doug.Show
Affiliate Marketing & Side Hustles on the Doug.Show
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Affiliate Marketing & Side Hustles on the Doug.Show

Author: Doug Cunnington, PMP

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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.
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I talk about interviews on the podcast again, in person events, and vertical integration. Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Welcome and Agenda 01:07 Interviews Are Back 02:51 Audio Quality Realities 03:43 Listener Stories and Voicemail 04:37 Podcast Audio Fail 07:22 Travel Recording Scramble 10:43 Econome Conference Recap 14:31 Why In Person Events Matter 16:34 Vertical Integration Explained 30:24 Wrap Up and Reviews  
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
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
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
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
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
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
I got Lucky - DS604

I got Lucky - DS604

2026-02-1632:58

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)
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
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
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
I’ve been working online, self employed for over 10 years. Here are some things I’ve learned.
Set goals for the year and use project management to get it done! (Okay, think of it like a New Years Resolution…) 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. Get the download! It’s a checklist of some of the ideas in the episode. It is basically a one-pager of show notes. 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
I give a short update on upcoming episodes. Then, I talk to Emily Odio-Sutton to discuss running a successful print on demand business on Etsy. Emily shares her journey of transitioning to full-time self-employment and the adjustments she made to manage her time effectively. $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 Introduction 12:48 Adjusting to Full-Time Self-Employment 17:32 Business Performance and Strategies 19:29 The Giftable Concept on Etsy 35:23 Balancing Variety and Cohesion in Your Etsy Shop 39:54 Focusing on Niche Markets and Product Expertise 42:53 Exploring New Products and Creative Opportunities 53:18 Adapting to Market Changes and Future Plans
I tell you how to calculate your Net Worth, and why tracking this one number is a great idea. Check out my podcasting and youtube gear *I’m an affiliate so I get a commission if you buy something. 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 00:29 The Importance of Calculating Net Worth 05:04 Steps to Calculate Your Net Worth 09:19 Tracking Your Financial Progress 11:19 Working with a Financial Advisor 15:21 Guitar Talk: 1933 Kalamazoo KG 11
I failed, but was I really trying? Here’s what to do instead… Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. Check out my podcasting and youtube gear *I’m an affiliate so I get a commission if you buy something. 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 02:16 Reflecting on 2025 Goals 03:45 Apple Watch Story and Fitness Insights 06:23 Reading and Journaling Habits 16:50 Guitar Adventures and Musical Growth 23:39 Thoughts on AI and Conclusion
I catch up with Shawna Newman to discuss her latest adventures including agency work, YouTube growth, and KDP books for Q4, AI in SEO, the complexities of Reddit marketing, vibe coding and building her own tools. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. Check out my podcasting and youtube gear *I’m an affiliate so I get a commission if you buy something. 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 00:53 Shauna’s Busy Schedule and Agency Work 02:21 Pivoting to Active Selling 04:08 Challenges and Learning in SEO 06:33 AI SEO: The New Frontier 09:26 The Downsides of AI Overviews 20:16 Reddit Marketing Strategies 24:08 Managing Multiple Reddit Accounts 25:17 Reputation Management on Reddit 25:46 Effective Reddit Marketing Strategies 27:42 Challenges and Maintenance of Reddit Accounts 29:45 Introduction to Vibe Coding 30:08 Developing Custom Tools with AI 33:19 Challenges in AI Tool Development 34:25 Issues with Lifetime Deals and SaaS Products 41:07 KDP Book Strategies for Q4 45:17 Upcoming YouTube Content and Conclusion
I chat with Jesse Lakes about his deep dive into video content creation. We discuss his 100 video challenge inspired by his new book, the importance of process and feedback loops, and the unique characteristics of different social media platforms. 00:00 Introduction and Welcome 00:20 Discussing Jesse’s New Book 00:30 Diving into Video Production 02:06 Jesse’s Background in Media Arts 05:45 Challenges and Learnings in Video Creation 09:57 Platform-Specific Insights 18:57 Future Plans and Final Thoughts
I talk about why I’m using AI less. Ma Get the FREE eBook here *Use Code DOUG E-Printables Course* Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate so I get a commission if you buy something. Check out my podcasting and youtube gear 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
We discuss Alex’s recent projects, including his YouTube channel’s direction, his new local project in Spain, how he integrates AI tools into his work, the impacts of AI in various fields, the current state of affiliate marketing, and the benefits and challenges of creating both short and long-form content. 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
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Comments (1)

Marty McLeod

Good stuff, Doug!

May 9th
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