Affiliate Marketing & Side Hustles on the Doug.Show

I share a few business ideas at the end. I talk about a trip to Dallas, Road Trip, Credit Card Points, and Hot Springs N.P. Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613 Join My Email list Song: Daisy by Stone Temple Pilots 00:00 Intro 01:14 Georgie Update 01:50 Recording Setup 02:30 Livestreaming Gigs 04:24 Dallas Trip Recap 05:46 Purple Stride Win 07:21 Credit Card Points 15:07 Food And Road Trip 17:42 Hot Springs Adventure 24:13 Business Ideas Wrap

Kyle Roof joins me to talk about the state of SEO and the impact of AI. In a twist, he tells me the Keyword Golden Ratio and affiliate marketing is still working well. KGR is even better that it was! Get the free course that Kyle mentions on POP. Check it out! I’m an affiliate, so thanks for the support. Previous Episode with Kyle: Truth About EEAT: An SEO Expert Shares Tips – Kyle Roof – DS473 00:00 Welcome 00:25 Kyle Updates and Business 01:10 Is SEO Dead Again 03:20 AI Search Adoption Reality 06:46 Echo Chambers and Marketers 09:44 Building AI Kyle in POP 12:12 Hallucinations and Counting 14:41 Why AI Content Fails SEO 22:26 Contextual Terms Explained 25:46 SEO Growth Opportunities Now 27:11 KGR and AI Search Insertion 29:39 Wrap Up and Where to Follow

I talk to Matt Giovanisci about suddenly quitting his podcast, email newsletter, and a few other things. It’s a long one! Buckle up! Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Welcome and Setup 00:58 Money Lab Origins 02:19 Rebrand to Business Casual 04:21 Podcast as Hobby 05:18 Trying to Improve 09:56 Quality vs Growth 15:10 Workload and Rewards 16:53 Chasing Views and Validation 24:53 Why Quit Abruptly 26:01 Focus 10 and Swim University 30:09 Mental Load and Identity 33:34 Culture Shift Hustle vs Lifestyle 34:29 FIRE After 2008 34:57 Finance Content Shift 35:45 Crypto and Day Trading 37:05 Insecure About Advice 39:29 Lifestyle Business Lane 42:04 Monetizing Without Selling 44:25 Refocus on Swim University 44:52 Garage Pacing and AI 46:29 Work Hours and Boredom 48:53 Learning Leisure Hobbies 49:39 External Goals Drive You 55:38 Three Pillars Problem 59:03 Boats Aren’t Leisure 01:01:22 Health as Productivity 01:06:15 One Thing and Freedom 01:07:54 Batching for Pure Time 01:08:43 YouTube Revenue Reality 01:10:37 Selling for Independence 01:12:55 Work Purpose and Volunteering 01:14:00 FIRE Scarcity Mindset 01:18:14 Leisure Without Guilt 01:21:50 Deleting the Podcast 01:23:08 Staying in the Pool Lane 01:26:32 Why Quit Business Content 01:28:32 Guitars and Amp Talk 01:33:02 Headphone Levels Wrap

I talk about how I lost motivation to work, my obvious advice that video is great, and a little update on my journaling. Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Intro 00:56 Work Optional Mindset 07:17 Audio Gear Tweaks 09:07 Why Video Wins 13:22 Ads and Sponsorships 19:43 Journals and Road Plans

I talk with Tony Herman about how he uses AI coding tools to build apps and business utilities, including a service-area coverage map generator that started as a client need and became a free public tool. He tells me about how he works with AI to create the tools, vibe coding, and Lovable. Connect with Tony Herman: https://tonyherman.com/ https://onyourmark.app/ https://tapclick.to/ Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Meet Tony Herman 01:50 AI Built Service Area Maps 03:30 From Client Fix to Public Tool 05:25 Origin Story Web and Affiliate Days 13:10 AI Kids Book and New Game App 20:59 Prompting Style and Iteration 22:18 Tweaking Code in VS Code 23:20 Do You Need to Code 26:43 Improving the Game UX 30:15 Micro Apps TapClickTo 35:13 SEO Rank Tracking Tool 36:40 Hosting and Tech Stack 38:30 Advice to Start Building 39:44 Tool Picks for Beginners 40:52 Future Ideas and Wrap Up

I talk to Baltimore musician, Mark Hopkins, about working on YouTube. We cover how he got started and how he doesn’t really care about analytics. We geek out on guitars and gear at the end. Follow Mark on YouTube Mark on Instagram   Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Meet Mark Hopkins 01:11 Why Authentic Content Wins 03:06 Interview Kickoff and Channel Stats 05:09 Pandemic Pivot to YouTube 07:02 Launching At Home With Mark 08:42 Seasons and Publishing Rhythm 09:53 No Analytics Just Passion 12:17 Music Career and Big Goals 15:05 Monetization and Honest Demos 17:17 Gear Review Workflow and Filming Setup 21:19 Booking Bigger Guests 30:46 Research and Interview Prep 32:52 Guest Booking Mindset 33:30 Passion Versus Profit 34:42 Pretty War Origin Story 37:49 First Gigs And Momentum 40:17 Writing Duo Workflow 42:35 Jam Versus Record 44:44 Where To Find Mark 45:25 Go To Guitars 50:56 Grandfathers Harmony Restore 57:49 Amp Rigs And Tone Lessons

I talk about interviews on the podcast again, in person events, and vertical integration. Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Welcome 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: [email protected] 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: [email protected] 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: [email protected] 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: Acumen Wire (Corey’s newsletter) MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] 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: [email protected] 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: [email protected] 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’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: [email protected] 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: [email protected] Leave a voicemail: (406) 813-0613 00:00 Intro 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: [email protected] 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: [email protected] 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. 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: [email protected] Leave a voicemail: (406) 813-0613 00:00 Introduction 00:31 Using AI for Content Creation 02:07 Starting the Online Journey 03:25 The Reality of Working Online 05:55 Financial Potential and Challenges 10:50 Flexibility and Workload 17:20 Managing Multiple Projects 19:32 Income Variability and Financial Planning 22:51 Isolation and Human Interaction 24:51 Mastermind Groups: A Hack for Isolation 25:24 Sales and Self-Marketing Essentials 26:46 Managing Your Tools and Expenses 31:27 The Importance of Continuous Learning 32:29 Dealing with Burnout 36:12 Focusing on Long-Term Goals 37:44 The Reality of Success and Change 41:10 Planning Your Exit Strategy 42:45 Separating Identity from Work

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. So, show notes and summary… Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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. Find Jesse: GeniusLink LinkedIn X Email Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 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. Yes, I sound like an old man yelling at kids to get off my yard. BUT hear me out! Get the FREE eBook (First $1k from Cody Berman) 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: [email protected] 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: [email protected] Leave a voicemail: (406) 813-0613 00:00 Intro 02:07 Alex’s Current Projects 03:27 The Evolution of WordPress and Niche Websites 07:37 Networking and Conferences 13:44 Creating WordPress Content 17:42 Local Influence and Short Form Content 23:25 Monetization and Future Plans 25:59 Generous Affiliate Programs 26:49 Enjoying Content Creation 27:41 Exploring AI Tools 29:15 AI in Content Creation 30:16 AI’s Impact on Professions 32:22 The Future of AI and Society 38:12 Personal Projects and AI 49:28 Upcoming Content and Projects

Cody tells me how he earned $1000 per month in about 115 days in 2024. This business model still works today! Get the FREE eBook here *Use Code DOUG E-Printables Course* *I’m an affiliate for Cody’s so I get a commission if you buy something. Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 00:00 Intro 01:20 Travel Adventures and Digital Product Success 02:39 The Shift from Amazon Affiliates to Digital Products 03:43 Fitness and Travel Routine 05:33 Starting the $1,000 Per Month Challenge 05:51 Understanding Digital Products on Etsy 07:16 Creating and Listing Digital Products 09:10 The Journey to $1,000 Per Month 11:46 Scaling Up and Student Success Stories 14:46 Niche and Keyword Research Strategies 18:40 Product Variations and Seasonal Trends 27:13 Challenges and Mistakes 27:53 Sticking to What Works 28:42 Finding the Right Competition 31:36 Niche Down for Success 35:26 Time Investment and Effort 36:46 Tools and Resources 40:52 Realistic Expectations 48:07 Who Should Avoid This Side Hustle 50:33 Wrapping Up and Final Thoughts

I’ve been talking poorly of the Amazon Affiliate model lately. But I haven’t been looking for stories in this area. So, I invited my friend, Jesse Lakes, to talk about it and provide some perspective. Find Jesse: GeniusLink LinkedIn X Email *I’m an affiliate for the links below, so I get a commission if you sign up! Thank you!! MDD Hosting – smaller company Cloudways Hosting – bigger company Eprintables with Cody Berman Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 00:00 Intro 00:13 Catching Up with Jesse Lakes 00:36 Mastering Amazon Associates 01:48 Genius Link Overview 06:35 Success Stories and Platforms 14:10 Challenges with AI and Content Accuracy 19:59 Navigating Trust in Online Information 20:43 Amazon’s Major Updates: Email Affiliate Links 22:33 Amazon’s Attribution API and Seller Networks 28:21 Deep Linking and Conversion Optimization 32:52 Getting Started with Amazon Associates 36:14 Common Mistakes and Final Tips

AI is bananas. In accurate. It’s shitty. It thinks niche sites can work in 2025. Alex Cooper’s Video (I Thought I Cracked Instagram Reels… Until This ) Mastering Amazon Associates: A Creators Guide To The Amazon Affiliate Program * By Jesse Lakes *I’m an affiliate for the links below, so I get a commission if you sign up! Thank you!! MDD Hosting – smaller company Cloudways Hosting – bigger company Eprintables with Cody Berman Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course.   Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 00:00 Intro 00:13 Exploring Niche Sites and Amazon Affiliate Marketing 01:46 Challenges with Social Media Traffic 03:17 Insights from Jesse at Genius Link 04:52 AI’s Role in Affiliate Marketing 06:17 Personal Experiences with AI Inaccuracies 19:51 Community Feedback and Responses 33:31 Concluding Thoughts and Future Directions

Someone asked about starting a new niche site with Amazon Associates as the monetization. Don’t do it! *I’m an affiliate for the links below, so I get a commission if you sign up! Thank you!! MDD Hosting – smaller company Cloudways Hosting – bigger company Eprintables with Cody Berman Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course.   Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi   00:00 Introduction and Episode Overview 00:03 Addressing Audience Questions 02:13 Housekeeping and Feedback 06:03 Diving into the Main Question 09:06 Answering Specific Questions 33:42 Concluding Thoughts and Call to Action

I chat about the unpredictability of recording outdoors, project management skills, and using them for personal projects…like breaking down big tasks into manageable pieces. I ramble about my experience with guitar learning platform, Pickup Music. I also cover how to avoid burnout by creating content you love and not relying on analytics for satisfaction. Georgie also makes a guest appearance. The guitar SOLD! But if you want to see the playing demo, it’s here on youtube. 00:00 Introduction and Outdoor Recording Challenges 02:11 Project Management Skills for Personal Projects 03:23 Exploring Online Guitar Lessons 08:14 Structuring Big Projects Effectively 15:22 Avoiding Burnout and Audience Capture 22:16 Guitar for Sale and Closing Remarks

I talk about Fincon 2025 in Portland and my critique on the keynotes. They weren’t helpful for most people, and the advice can lead to an audience capture approach. Then, I roast Pat Flynn, probably unfairly. I’m selling My Epiphone Les Paul on craigslist. Playing Demo on YouTube. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 00:00 Introduction and Backyard Setup 01:47 Reflections on FinCon Experience 02:45 Keynote Sessions and Critiques 05:08 Advice for New Creators 09:15 Audience Capture and Analytics 14:58 Challenges of Recording Outside 15:56 Disappointment with Pat Flynn 20:07 Guitar Sale Announcement

I talk about some how project manangement skills can be useful outside of the corporate world. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 00:00 Introduction to the Doug Show 00:25 HOA Drama and Prairie Dog Relocation 03:13 Project Management Skills Overview 06:45 Practical Applications of Project Management 12:42 Portland Trip Recap 17:31 Challenges in Estimating Work 23:26 Negotiation and Diplomacy in HOA 35:09 Risk Management and Final Thoughts

I talked to Jason Hendricks while we were in Portland for Fincon 2025. We talk about the old days of niche sites. Then, I have harsh words about vibe coding. And More! Connect with Jason – https://www.jphendricks.com/ AI App On Site – Add AI-Powered Apps To Any Site In Minutes Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 00:00 Introduction and Setting the Scene 01:01 Meet Jason Hendricks: Background and Expertise 02:02 Journey into Online Business and Side Hustles 06:28 Discussing Blogging and SEO 11:53 The Future of Online Courses 18:13 AI and Vibe Coding: Opportunities and Challenges 28:10 Exploring AI-Enabled Tools for Non-Programmers 28:43 The Code Auditing Problem and Security Vulnerabilities 29:53 The Future of AI in Coding and Human Involvement 30:55 Content Theft and Reaction Videos on Social Media 33:52 The Value of Human Connection and Live Events 34:58 AI in Business and FinTech Innovations 37:04 Introducing AI App Onsite: A Smart Form Solution 40:10 Challenges and Successes in Developing AI App Onsite 46:38 Guitar Talk: Pre-War Acoustics and Restoration   Doug: Hey, what’s going on? Welcome to the Doug Show. I’m Doug Cunnington, and today I’m joined by my good friend Jason Paul Hendricks. How are you today? Doing good. And we’re at FinCon recording in a. The convention center here in Portland, we’re sitting like in a big corridor. It’s huge. The ceiling must be 30 feet high, and it’s quiet in here. So a lot of times I’m like recording live and there’s a noise from the crowd. There’s just people walking by, so it’s pretty chill and quiet. We knew we were gonna hang out and I’m like, we gotta record together. And Jason, you sent me a bunch of, uh, ideas that you had, which is great. That’s my homework and I didn’t have to do it. So we’re gonna go through a lot of stuff, but like for people that don’t know who you are, give a little intro and you’ve been on the show a couple times, but, um, we will link up. But who are you? Jason: Sure. it’s great to be back. Thanks for having me. Jason Hendricks, uh, I do a variety of things. , From a, from a. You know, earnings standpoint, I do, uh, , business development consulting, broadly for FinTech companies. I’ve always had one foot in the marketing space. And, you know, that’s, that’s, that’s the area that, originally got me connected to you in a long time. Listener and, uh, watcher of the channel. And, uh, so on that side of the thing of the, of the, of my brain, I’ve, uh. Built a couple of SaaS products and, uh, I live in Asia, so I currently live in Bangkok. Uh, long time, lived in Hong Kong before that. Again, this, this related to the finance industry work that I’ve done, but there’s a whole lot of SEO and marketing conferences in Asia as well. And so a big part of the community that I interact with is over there on the Asia side, even though the US is my home. Doug: And you were, I mean, you were into side hustle stuff. For several years. ’cause I, I mean, I’ve been doing my stuff since 2014 ish when I started publishing online. When did you get started, like working online? Um, in, in this sort of like, niche site area? Mm-hmm. Or SaaS products related. Jason: Yeah. So, so right throughout my career, uh, I sort of do, it did t

I talk about a typical week and how semi-retirement is treating me. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 00:00 Introduction and Outdoor Recording Challenges 00:52 When to Quit Blogging and Projects 01:50 Doug’s Current Work and Lifestyle 03:52 Daily Routine and Productivity 07:09 Interview Preferences and Podcasting 14:34 Fitness, Health, and Cooking 18:59 Hobbies and Personal Interests 22:51 Financial Independence and Early Retirement 31:55 Conclusion and Final Thoughts Transcript Doug: Hey, what’s going on? Welcome to the Doug Show. I’m Doug Cunnington, and today I’m trying to record outside. There’s, uh, dogs barking. There’s crickets making noise. The sun could give me a hard time. The audio might not even be recording, but we’re gonna do our best I was about to make notes and then I thought, uh, fuck it. We’ll just go for it, you know? So we’re gonna go for it today. The topic will be something that, uh, Lauren Hunter put a seed into my head, and we were talking a couple weeks ago about when to. Quit blogging or stop projects and that sort of thing, which is a hard thing to figure out. There’s sunk costs. There’s the fact that sometimes if you wanna work on something, it takes a long time before you get traction. There’s plenty of examples out there, but there’s other times where maybe you should quit and you are actually wasting your time and you should move on to something else. Really hard to tell. It’s extremely hard to tell. So one thing in the conversation, Lauren mentioned a, actually it was before we started recording, and she maybe was like, ah, you know, how much time do you spend working? And like, what do you do? And I’m like, I’m in a really weird spot. I don’t work that much right now. And the thing is with the Doug Show and the Niche Site project and all that kind of, uh, sort of content. Hm. You know, we were talking about side hustles. We’re talking about like how to earn money online and that sort of thing. And I’m not really testing that stuff out anymore. There’s some dog around here, uh, that. The people must have locked the dog outside and it just wants to be with his family or something like that. So I apologize for that. Georgie’s hanging out right behind me. She’s just chilling. She may come up closer in a few minutes. The people that are just listening, you won’t obviously see this, but Georgie’s in the, in the frame here and, uh, she likes to play, but she just. She’s taking a little rest right now. She has, she’s like, uh, laying down, but she has a Frisbee, like laying across her, uh, arms or legs, I guess their legs, but it’s her front leg, so I consider them arms. All right, so Lauren was like, Hey, how much time do you spend working? And I was like, I don’t spend that much time working. Um, I’ve whittled things down and my other podcast is Mile Hi-Fi, and it’s about early retirement. My wife retired about 18 months ago, and I have been working for myself for. About a decade. I didn’t even celebrate my, like, layoff day. I kind of forgot about it. I, it’s so far from, it’s removed from my, like, daily thinking. I don’t even think about the corporate job anymore. I don’t do that much work, and it’s r

I talk about some rules for saying no, a listener email, and retiring early. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 00:00 Introduction and Podcast Feedback 01:35 Saying No: The Art of Rejection 06:36 The Podcast Consultation Dilemma 17:01 Listener Feedback and Email Responses 23:18 Trip to Yellowstone National Park 25:53 Unplugging and Social Media Detox 28:43 Financial Independence and Minimal Work 35:21 SEO and Podcast Sponsorship Opportunities 38:24 Conclusion and Future Plans

I talked to Dave Fox about his recent projects after selling his sites for about $50,000 a few years ago. Successes, failures, funny stories, and guitars — we talk about it all! Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi 00:00 Introduction & Guest Background 01:18 Dave’s Music Journey 02:51 Selling Niche Sites in 2021 05:29 Exploring AI and SEO 16:10 Computer Repair Business Venture 30:43 Redbubble Adventures and Copyright Issues 43:41 The Viral Jesus Meme on Redbubble 44:58 Exploring Niche Markets on Etsy 45:50 Challenges of Defensible Products 46:43 Experimenting with Political Merchandise 47:59 The Realities of Landscaping Work 51:04 Pricing Strategies for Landscaping Jobs 54:08 Dealing with Difficult Clients 01:02:15 Seasonal Work and Diversifying Income 01:05:50 Cold Calling and Client Management 01:09:58 Passion Projects and Music 01:18:58 Final Thoughts

I talk to Lauren about when to quit on projects and move on… Lauren Hunter is a faith-focused entrepreneur passionate about helping creative visionaries bring their ideas to life. She offers author services, book and life coaching, freelance writing, and musician services. Links: https://laurenhunter.net (author/music blog) https://hspjourney.com https://earnitsaveit.com (might sell it) Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi   00:00 Introduction and Welcome 00:18 Lauren Hunter’s Background and Initial Discussion 02:08 When to Quit a Project 05:00 Lauren’s PR Journey and Blog Creation 10:04 Selling the Blog and Transition 14:14 Starting a New Niche Blog 19:13 Challenges and Strategies in Niche Blogging 21:11 Advice for Aspiring Bloggers and Podcasters 25:43 Social Media and Time Management 31:54 Evaluating Efforts and Reducing Stress 33:02 Signs of Burnout and Seeking Encouragement 33:34 Quick Wins and the Plateau Effect 36:11 Streamlining and Simplifying Workflows 37:07 Deciding to Quit, Pivot, or Maintain 39:20 The Value of Simplification and Streamlining 43:36 The Emotional Attachment to Projects 48:06 Financial Considerations and Simplifying Strategies 53:15 Concluding Thoughts and Future Plans

A listener asked for help on his sites and what he should do to earn $500/month. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi

I jammed with my friend Tyler for new intro music, dealt with a Shutterstock copyright claim, and reviewed Wonderful Things beer from Four Noses Brewery. I also discussed feedback on calling out scammers and shared updates on my upcoming national parks trip. Stay tuned for thoughts on future podcast directions. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] 00:00 Welcome to the DougShow 00:19 Doug’s Jam Session and New Intro Music 01:48 Beer Review: Wonderful Things by Four Noses 04:24 Copyright Claim on Intro Music 07:41 Calling Out Scammers and Influencers 14:58 Upcoming Trip to National Parks 21:55 Future of the Doug Show and Listener Feedback 30:25 Conclusion and Outro

I got a huge response from people about calling out the shady people in the make money online space. But I’m not sure if I’ll do it… And I don’t recommend shutterstock dot com…they filed a Content ID claim on YouTube for a song I paid for 6 years ago. Silly!   Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected]

I discuss affiliate links, side hustles, provides updates on my podcasts, livestreams, and shares insights into affiliate marketing challenges. Plus, I rant on the AI-generated content and its pitfalls for those starting niche sites. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] 00:00 Introduction and Podcast Updates 02:35 Mile HiFi Podcast Insights 03:48 Affiliate Marketing Challenges 09:01 Side Hustles Discussion 15:29 SEO and Online Marketing Realities 20:22 YouTube Strategy and Live Streams 28:42 Final Thoughts and Community Engagement

I dive into innovation in online business, inspired by a video about REI and product innovation. Then, I discuss the future of my podcast and share some of the analytics. Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613 00:00 Intro 01:35 Innovation in Retail and Business 04:57 The Blue Chip Guitar Pick Story 08:44 Applying Innovation to Online Business 10:56 Podcast Analytics and Reflections 15:07 Challenges and Future of the Podcast 19:06 Conclusion and Listener Engagement

I ramble about Sonora Guitar Intensive sales funnel and my experience with high-ticket music mentorship programs. And highlights on adjusting my podcast setup. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613 00:00 Introduction 00:15 Doug’s Sales Funnel Experience 02:12 Microphone Setup and Audio Quality 08:00 Guitar Passion and YouTube Influence 12:43 Sonora Guitar Intensive Sales Funnel 19:37 Reddit Reviews and Pricing Concerns 28:12 Morbid Curiosity: The Sales Call Experience 28:17 Understanding My Musical Goals 30:24 The Sonora Music School Pitch 31:16 Comparing Sonora to Elite Music Schools 32:47 The Cost Breakdown and My Budget 33:27 Evaluating the Sonora Program 35:46 The Mentor and Lesson Structure 38:12 Group Classes and Office Hours 45:15 Custom Curriculum and Software 52:46 Final Thoughts and Decision

I complain about Descript, gush over my new pre-amp (JHS Colourbox v2), and eventually talk about my podcasting dilemma. I have a couple other mini updates too. Sponsored by Cloudways Hosting! Please check out Cloudways for your hosting solutions. Giftlab (by Emily Odio-Sutton) The Print-On-Demand Etsy Course. *I’m an affiliate for both, so I get a commission if you sign up! Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613

I talk about Print on Demand, Etsy, and things I’m obsessed with. Giftlab (by Emily Odio-Sutton) Check out MDD Hosting *I’m an affiliate, so I get a commission if you sign up!

I discuss the current struggles and declining revenue of my business. I share how I’m cutting costs, including letting go of his long-time VA, Callie, and eliminating unnecessary expenses. Guitar Accessories Hiking & Outdoor Gear Sleep Essentials Supplements & More Also, check out: MileHighFi Etsy Join My Email list More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613 00:00 Introduction and Current Business Challenges 01:40 Evaluating Expenses and Making Tough Decisions 02:52 Content Strategy and Audience Engagement 04:36 Revenue Decline and Simplifying Operations 05:00 Shutting Down Projects and Future Plans 05:45 Reflecting on Past Successes and Setting New Goals 08:02 Conference Costs and Financial Planning 09:45 Domain Management and Cost Cutting 16:23 Course Shutdown and Revenue Impact 22:38 Sponsorship Challenges and Revenue Struggles 24:21 Cutting Costs and Shifting Focus 27:39 Exploring New Ventures: Etsy Print on Demand 30:12 Donation Model and Affiliate Marketing 34:41 Amazon Influencer Program and Product Recommendations 41:31 Concluding Thoughts and Future Plans

Doug discusses the often-overlooked difficulties that come with being an entrepreneur. He outlines five major challenges, including the continuous pressure, financial instability, the burden of doing everything yourself, high expectations, and the perpetual learning curve. Also, check out: MileHighFi Etsy Join My Email list DS568 Transcript More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613

Doug interviews Steve Stewart, a renowned podcast editor in the personal finance space. Steve discusses his journey from financial coaching and blogging to becoming a full-time podcast editor. He shares insights about his work, his experience with podcast editing tools, and tips on managing a business using the Profit First method. Connect with Steve Website Podcast Editor Academy Also, check out: MileHighFi Etsy Join My Email list DS567 Transcript More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613

Doug is joined by Emily Odio-Sutton to discuss the dynamics of 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. They dive into the benefits of focusing on giftable products, the importance of niche targeting, and using tools like Printify and AI for designing. $500K in 2 Years Esty Print on Demand DS550 Mind Lab Pro They have performance lab Multi Vitamin Giftlab I’m an affiliate for all of the above, so if you buy something, I may get a commission. Thanks! MileHighFi Etsy Join My Email list DS566 Transcript More with Doug: Mile High Fi Contact me. Ask Questions! Send me an email here: [email protected] Leave a voicemail: (406) 813-0613