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Published by 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.
On the charts
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From the feed
The latest episodes published to this podcast’s own RSS feed. Titles and descriptions are the publisher’s.
I talk to Paul about how he covers AI and teaches on his youtube channel. Follow Paul: https://www.youtube.com/@PaulJLipsky https://pauljlipsky.com/ 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 AI Focus 01:18 Skepticism and AI Hype 02:56 Data Poisoning Amp Story 07:35 AI YouTube Saturation Myth 11:41 Tracking News with X Agents 17:25 Titles Formats and Viewing Habits 24:02 Bubble Talk Vibe Coding Wrap
I talk to Paul Lipsky about pivoting his channel on YouTube and growing like crazy! It’s part one of two. Next time we talk about AI specifically. Follow Paul: https://www.youtube.com/@PaulJLipsky https://pauljlipsky.com/ Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Meet Paul and the Pivot 03:23 From Ecommerce to AI 10:10 AI Aha and Tool Choices 14:15 Monetization and Topic Strategy 20:53 Avoiding AI Hype 24:22 ChatGPT Voice Workflow 26:48 Publishing Rhythm 32:43 Monetization Choices
I talk about the pitfalls of over optimizing and why “good enough” is good enough. I prefer good enough most of the time. 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 Topic 02:12 Semi Retired Creator Life 03:11 Camp FI and Monetization 04:55 Productivity Obsession Origins 07:11 Metrics and Fun Balance 09:18 Eight Over Optimizing Traps 11:05 AI Outline Fail and Gear 15:53 Trade Offs Not Perfection 18:52 Tool Switching Overhead 23:23 Keep It Simple 24:00 Analysis Paralysis 24:38 Good Enough and Choice 30:16 Hobbies and Product Research 37:11 Maintenance and Opportunity Cost 42:24 Manual First Then Automate 46:16 Wrap Up and Whats Next
I talk about tokenmaxxing, backlash against AI, how I actually use AI, and echo chambers. Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 Join My Email list 00:00 AI Backlash Update 01:26 New Mic Gear Test 03:31 Walmart Pulls Back 05:35 How Doug Uses AI 07:59 Copywriter Pushback 10:52 Poisoning Search Results 14:54 Echo Chambers and Hype 17:58 Sandbox Escape Scare 20:26 Creativity and Copyright 23:58 Avoiding Negativity Trap 29:23 Wrap Up and Next Steps
I got to chat with a Guitar YouTuber that I really enjoy, AJ De Vera. He’s a talented guitarist and song writer, plus he’s a fellow Filipino. We chat about starting on YouTube, planning videos, and of course, guitars! We have a similar taste in music and influences. We talked for another 30 minutes after we finished up with the recording and identified a few other commonalities. Connect with AJ YouTube Spotify: Villain Heart The Dark Horses Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 Join My Email list
I talk with Justin Peters about how his hobby podcast led to co-founding SimplePod Studios with his brother, including their team setup, early clients, pricing and package evolution, and why they focus on high-ROI finance-adjacent creators. We also get into his sabbatical and FI journey, what it takes to produce an episode consistently, keeping the agency as a lifestyle business, and how he sees platforms and video trending. Connect with Justin Peters SimplePod Studios Podcast Playbook FI Minded – Financial Independence Without the Extremes Doug’s appearance on FI Minded Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Meet Justin Peters 00:57 SimplePod Origin Story 05:49 Sabbatical to Podcasting 17:56 Agency Growth and Niching 31:40 Anatomy of One Episode 34:30 Consistency Over Perfection 39:46 Co-Founder Communication Rules 49:13 Industry Trends
I talk about pizza, beer, and FB Marketplace tales and tips. 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 Topics 00:48 Marketplace Camera Sale 02:32 Georgie Health Update 03:46 Pizza Obsession Returns 07:29 Gear and Grill Experiments 10:04 Pizza Boom Meets Business 24:21 Marketplace Pricing Tactics 43:47 Listings Tips and Wrap Up
I chat with my friend, Cody Berman, about retiring as soon as possible. It’s basically talking through the ideas in his book, Retire By 30 . Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Meet Cody and the Book 02:33 Quitting Corporate for FI 10:35 Side Hustle Framework and Lessons 19:19 Nest Egg vs Cash Flow FI 23:27 Finding Deals Today 25:10 Designing Your Ideal Life 28:37 Spending Tests and Buying Time 42:44 Side Hustles and Final Wrap
I got a new studio camera (Canon R8). I’m planning getting rid of some of the old gear so I’m hopeful I can move it on facebook marketplace. Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Studio Gear Upgrade Dilemma 01:23 New Canon R8 Camera 04:30 Lenses Over Bodies Mindset 09:27 4K Workflow Hits Mac Mini 21:04 Selling Gear on Marketplace 31:00 Wrap Up and Next Interviews
I talk to the founders of Oakwell Beer Spa about starting a business from scratch! I visited the Beer Spa with a friend and it was an epic experience. Highly recommended. We talk about the origin story of the business and the early struggles, then growth and expansion. Website: https://oakwell.com/ Franchise: https://oakwellfranchise.com/ LinkedIn: https://www.linkedin.com/company/oakwell-beer-spa Facebook: https://www.facebook.com/OakwellBeerSpa Instagram: https://www.instagram.com/oakwellbeerspa/ YouTube: https://www.youtube.com/@OakwellBeerSpa TikTok: https://www.tiktok.com/@oakwellbeerspa Contact me. Ask Questions! Send me an email here: feedback@doug.show Leave a voicemail: (406) 813-0613 Join My Email list 00:00 Meet Oakwell Founders 01:07 Beer Spa Idea Abroad 06:47 Building the US Concept 33:25 Taproom Vibes and Membership Perks 37:23 Funding the Beer Spa Build 53:41 Scaling Up and Franchising Nationwide
I talk about selling some stuff on Facebook Marketplace and trying to declutter around the house. 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 02:51 Decluttering books for sale 06:34 AI powered Marketplace listings 11:33 Guitars gear and computer upgrades 17:14 Marketplace rules pricing and time 25:24 White label SEO and cash flow wrap
I talk to my brother-in-law, Sam, about travel budgets, pizza, and coffee. 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 03:27 Meet Sam And Trip Plans 07:31 Budgeting With Points 17:01 Iceland Eclipse Trip 34:20 Longmont Pizza Crawl 38:36 Chasing the Perfect Char 39:23 Pizza Steel vs Stone Debate 47:27 Grill Pizza on a Kamado 58:02 Coffee Gear and Espresso Mods 01:14:01 Wrapping Up
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: feedback@doug.show 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. 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: feedback@doug.show 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: feedback@doug.show 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: feedback@doug.show 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: feedback@doug.show 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: 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
Ranking source
Apple Podcasts rankings via the Mato Topic Intelligence Platform.
Observed September 19, 2026. Cached outside the daily freshness window; the positions keep the date they were taken on.
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