Doug Cunnington, PMP
Affiliate Marketing & Side Hustles on the Doug.Show
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.
Where to listen?
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Episodes
Building a Lifestyle Podcast Agency: SimplePod Studios & Financial Independence - DS624 06.07.2026 1:03:41
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 p...
Over Expanding & More FB Marketplace Tales | DS623 29.06.2026 50:07
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:...
How To Retire FASTER | Cody Berman | DS622 22.06.2026 50:47
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...
Upgrading my YouTube Studio | DS621 15.06.2026 34:17
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 Sellin...
Turning A European Idea Into U.S. Success | Oakwell Beer Spa | DS620 08.06.2026 1:09:03
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...
Decluttering & Facebook Marketplace | DS619 01.06.2026 34:57
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 la...
Finance & Food: Iceland Adventures + Pizza Passion | DS618 25.05.2026 1:16:51
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 Pi...
Recent Travel, Tech, Business Ideas | DS617 18.05.2026 42:20
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 St...
Kyle Roof on the Future of SEO & AI - DS616 11.05.2026 31:56
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 Adoptio...
The Real Reason Matt Giovanisci QUIT Almost Everything | DS615 04.05.2026 1:35:07
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...
Video Content & Balancing Creativity & Consistency | DS614 27.04.2026 25:42
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
Building Real Apps with AI: Micro Tools, SEO Utilities | DS613 20.04.2026 45:31
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. As...
Unfiltered: Passion, Music, and YouTube | Mark Hopkins Music | DS612 13.04.2026 1:02:25
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 C...
Vertical Integration | DS611 06.04.2026 32:22
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...
Teacher to Tech Builder: How I Replaced My Income in 5 Months | DS610 30.03.2026 46:12
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 En...
SEO Dead for Affiliates? How to Pivot | wecantrack | DS609 23.03.2026 46:38
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 B...
Touring Musician to YouTube Success: "Kyle Orla" Strategy | DS608 16.03.2026 1:17:10
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 o...
3 Case Studies of AI Coding w/ChatGPT, Claude Code, & Gemini | DS607 09.03.2026 28:30
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 interrupt...
Requirements for AI Assisted Coding - DS606 02.03.2026 32:17
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...
If I Started Over in 2026 - DS605 23.02.2026 32:17
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: (40...
I got Lucky - DS604 16.02.2026 32:58
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 Cha...
10 Things I Learned From 900+ Episodes - DS603 09.02.2026 40:01
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 Quali...
Dry January, Coffee, Caffeine, YouTube - DS602 02.02.2026 26:41
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 & Lis...
Sustainable Solopreneur 7 Rules for Online Success - DS600 19.01.2026 40:55
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...
17 things I wish I knew before working online | DS599 12.01.2026 48:45
I’ve been working online, self employed for over 10 years. Here are some things I’ve learned.
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