Affiliate Marketing & Side Hustles on the Doug.Show

Affiliate Marketing & Side Hustles on the Doug.Show

https://doug.show/feed/podcast/
40 Followers 500 Episodes Claim Ownership
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.

Episode List

Project Management Skills for Life – DS284

Sep 29th, 2025 12:00 PM

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

Niche Sites, Vibe Coding, Real talk – Jason Paul Hendricks – DS583

Sep 22nd, 2025 3:46 PM

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 the marketing thing for the companies I work with. I usually work with small companies, but, uh. I think in earnest, I started building out sites in 1516, we’ll say. Okay, 20 15, 20 16. And so there’s a bunch of sites that I continue to, to work on or help maintain. So there’s a couple of folks that, uh, uh, have subject matter expertise in certain areas of, uh, travel traveler food, uh, and I help them with the upkeep of the site. But, um. None of these were ever heavily, uh, focused on traffic and ad revenue or affiliate. They were, they were more brand for, for sort of brand maintenance and, um, you know, for other business activities. And this was sort of the brochure of the business. Mm-hmm. Uh, and even my consulting business, I’ve got websites related to that, but I’m not looking to organic, uh, or SEO to, to bring in customers. I, I, I do that through other meat. Doug: Got it. Okay, cool. And you, I was gonna say, um, not to name Drop, but Matt Esei is around here and you followed him for a little while also. Yes. And and the cool thing is I was like, Matt, you should maybe come. It’s like awesome in Portland. Like he loves Portland. He’s a big beer guy. And the thing is like Matt came to these events for years, so he. Um, is like one of the original people and he knows some of the, I mean, there’s a handful of people that have been to all of the Fincons, or they’ve been fixtures for many years. Yep. And he knows them from like eight or 10 years ago, stuff like that. So anyway, he’s around here. We’ll gonna be able to hang out. Funny you guys haven’t crossed paths yet, but we’ll be able to Well, I know Jason: him, but he doesn’t know me as well. But although I, I did, uh, when you first moved down to Colorado, I don’t know if you remember, I sent an intro email and you guys knew of. B each other before, I think. But I, I had said, I was like, Hey Matt, this guy Doug is, is moving down. You gotta, Doug: and I think, yeah. ’cause we, we knew, I remember listening the first time that I remember like, oh yeah, this guy, Matt. It was, um, on Nick Loppers podcast Side Hustle Nation. And the funny thing, it’s ’cause I, I’m a podcast listener, um, all, many different, uh, topic areas. But I was listening to that and I remember, ’cause I was living in Bozeman and I was walking, um, my dog on a specific trail and I could just picture, ’cause Matt was talking about, um, brew Cabin and he was like, and I’m a home brewer. So we had, we had all these different interests. The funny thing is like Matt and I actually finally met. Um, at, it was like a, a brew day at the coworking space where we know, um, like Mr. Money mustache, that’s a name drop. Right, right, right. Our other friend Pete aid me. Um, and yeah, yeah, so it was, it was there and we were just brewing beer hanging out and then Nice. Like, we didn’t even talk about business, but I was like. Hey, we basically do the same thing, like let’s talk about it. And then we started hanging out after that and now he lives like a, a mile and a half away or something. Nice. So, okay, well it’s cool that we’re gonna be able to cover a lot of things. Uh, do you, and we recorded it FinCon a couple years ago. Yeah. You Orleans. And do you remember what we talked about? What were you working on then? Jason: I don’t remember. So I was working on another SaaS product at the time, Chrome extension. I still have that. Um, a, a little something has changed in the SERPs, you know, the Google SERPs. So, so I don’t focus on that Chrome extension quite as much. Um, we also, uh, debated a little bit about, about, uh, you know, opinions on fire and whatnot. ’cause we’re at FinCon. Oh, right, right. No need to, uh, to re-litigate. Of course. Who won? Yeah. It’s like Doug: we Jason: both lost. I remember. Doug: Yeah. I think, did we talk? I don’t even remember that. Okay. Obviously very memorable Jason: ever. So briefly. Doug: Alright, so one of the topics that you mentioned is just essentially like online business. And we passed, um, Ricky Kessler from in Income School. We was sitting right over there and I haven’t had a chance to chat with him too much, but I think his talk is, uh, related to blogging in general. And yeah, we were kind of talking like, is Blo like. For years, people were like, oh, is blogging dead? And I, I mean, I kind of think, yeah, like a website can serve a different purpose, but it’s not like, it was like the, the people creating that content. Like most of the talks here, people are interested. It’s video. Like currently everyone’s just like video pick whatever platform, but it’s video. People aren’t writing like in the same way. So yeah. What’s your take? What do you think? Uh, blogging and SEO and the whole thing. Yeah. Yeah. I think, Jason: I think. The term blogging, uh, when it was used more commonly was about, you know, uh, consistently in, in a recurring fashion, creating content. And if you did that and, you know, the, the algorithm gods sort of, uh, smiled on you, then you would get traffic, uh, from Google, usually. Right. Uh, people say vlogging, now they don’t, they don’t hesitate to use that term. Mm-hmm. But of course you have to publish on YouTube if you’re gonna do that. And will the algorithm Gods shine on you if you do that? Sometimes yes, sometimes no. But I think to the degree to which a website is still a thing you own, it’s still your property, you know, your stake in the ground. Um, I, I think it’s silly to suggest that websites are dead. Right. So is the word blogging sort of antiquated? Probably. You know, I, I think if you just, you know, build, you know, write content and they will come. I don’t think that’s a thing anymore. Right. Um, and so, but, but is it important if you’re running your, you know, doing this as a business, is it important to have a place that is your home base where you can bring leads? This is where you’re gonna collect an email from a visitor and, and through email interactions, you’re going to grow a relationship with them when you podcast, right? Mm-hmm. You have the distribution platforms for podcasting. Uh, but there again. It’s nice if you can bring them back to a place and, and, you know, interact with them there. If you, if you’re selling a course or mm-hmm. You know, uh, selling a ebook or something, then, uh, another antiquated term, but still, but still a thing. Right, right. A digital product. Then, uh, you know, for that reason, I think, uh, you know, websites are still important. Doug: Do you still have, ’cause you built a handful of niche sites like. So what do you have around, you kind of mentioned earlier, some things are around how many sites do you have left or like, are you earning money in a traditional way with them or what’s going on? Jason: Yeah. No, my, the websites that generate income for me are there to advertise and promote my skills and expertise. I give visitors an opportunity to make an appointment with me. Uh, the, the, the sort of consulting. Business I do, it’s, it’s much more one-on-one. Mm-hmm. So it, and it’s, to that degree, it’s kind of high ticket relative to what, uh, some people may be in the traditional affiliate space would consider. Uh, it also doesn’t scale like consulting the way I’m doing it isn’t, isn’t something you can replicate. I, I would like to in time, uh, when I feel confident to do so, you know, create digital products that, that can, you know, serve many people without. Me having to get involved. But, uh, at the moment, my focus with those sites are to, you know, get visitors, uh, tell them what I do, who I do it for, and, and get them to engage with me. And from there I’ll sign a consulting agreement with them and, uh, okay. And take it from there. Doug: Similar, you know, uh, essentially you mentioned, uh, like an online course model where, you know, you create the asset Jason: Yep. Doug: And then you’re able to, whatever it may be, it could be text-based or could be probably video, but it could be something else. It could be whatever you want it to be. Um, I, I have heard some people say, and I have not researched it, so I’m curious if you have any, um, if you’ve heard anything on the streets out there, you know where people are talking about. Online courses on the streets. Yep. Of Portland Street. Yeah. It’s um, it’s crazy out here in Portland some, ’cause I was, uh, you know, I was walking around this morning and Yeah, someone’s like passed out on the stairs and like other, there’s, it’s just a little, it’s wild or it’s like that dive doesn’t happen in your Jason: hometown, but, Doug: um, yeah, I was, I was watching this documentary, um, Portlandia. Did you see that? Did you see that one? Documentary. I think that it was, as far as I could tell, it was a documentary. So I was gonna ask a question, drew, but it was all that for a joke about course, Jason: course courses on the street. Yep, yep. I gotcha. Doug: Alright. The great thing is like since um, I. Don’t edit these, so I’m leaving all that in that whole mess in there. That’s good. So, okay, so online courses, I heard someone mention that like, maybe online courses have peaked and they’re kind of dropping down. Mm-hmm. But I, I wonder if it’s just the industry because I’ve seen, you know, other people say, oh yeah, I’m doing awesome. What, what do you think? Jason: Okay. So I, I strongly believe there’s going forward, increasingly there will be something I like to call a human premium. With all the AI content, uh, and, and even AI video getting better and better. It’s gonna, it’s gonna be used in different ways. It’s gonna be used in advertisements, so on and so forth, and people are gonna just accept it, right? And they’re still gonna buy the product. I mean, I think, I think there’s gonna be a period of time where you see o you know, obviously AI video used in an ad. Some people will say, well, I’m never gonna buy from that company. If they’re gonna do that. But over time, I think people are just gonna get anesthetized. However, I think when it comes to learning, especially, uh, things that are, you know, as a higher value, uh, or more important interaction, um, more important part of one’s life, money or, you know, whatever you could say, you know, money or health, these sort sorts of things, I think it’s become ever more important to. Identify and connect with real humans that you trust, that, you know, have provable, uh, expertise in, in an area. And I think, um, I think for, for that reason, I think that real human beings producing quality content. You know, where, where it’s important to do so if you’re, if you’re an affiliate niche site and you’re, you’re just writing about, uh, rice cookers, okay. That’s, those days are gone. Right? Right. Uh, it’s not, uh, it’s not an important enough purchase mm-hmm. To justify that. Okay. But, but I think, I think in a lot of areas, uh, I think, yeah. Online, so-called online courses is gonna continue to be an a, a thing. Um, but you know, you just have to be authentic and you have to be real. You have to bring real expertise and provide real quality. I mean, which is the things that, that Google always talked about. But I think, uh, yeah, so I, I don’t think courses are dead or whatever. Yeah, Doug: I see a lot of them. I watch a lot of, uh, guitar, YouTube, and the soundcheck, which we’ll play after the interview here. The, uh. Uh, yeah, we talk about guitars and stuff, so I watch a lot of guitar stuff on YouTube and a lot of those, I mean, I think the guys that are doing the best, they’re, they have courses. Hmm. And like, you know, they’re priced kind of all over the place. Some are fairly cheap, some are like 30 bucks a month. Some are like $75 for like one course where you’ll learn a specific thing. And just like probably any. Online course where people are creating the stuff on their own. There’s different quality. So like I think some I’ve, I bought a course, I love the creator, but, and the material was fine, but there were no exercises. So it’s just like spitting out information at me and then I. What am I supposed to be able to do after I know this? How do I know when I’ve like accomplished it? Mm. How do I know that I’ve mastered and, and I know the things that we went through. Again, I understand it when we’re talking through it, but that, does that mean I could play it afterwards? So, and ob obviously like that sort of thing. You could learn almost anything on YouTube and probably the same thing that’s within the courses. So it’s like, again, there’s varying levels of quality. ’cause most of the course was good, but I’m like, did I? I mean, I feel like I didn’t learn anything at the end of it. ’cause I didn’t know what he, anyway, I, I’m not sure. But there’s better ways to do courses in Jason: general. Doug: Yep. So, Jason: yep. But, but I assume that like, ’cause I think you said it, it starts with you sort of knowing and trusting at first. Yep. Totally. Yep. Had a relationship with him, albeit a virtual one from his content. Then you got the confidence level and then you. Yep. Bought the course Doug: and his videos are entertaining. So I was just like, oh, you know what? I wanna support him. So, because as I’m going through, you know, iterations of the Doug show and like how, um. I’m currently not earning money on Mile High five, but I used to earn just a little bit to cover the cost. Jason: Mm. Doug: And now I’m, I’m looking at it and I’m like, oh, I understand. Like if I like this guy’s videos and I want him to keep doing it, mm, I need to buy something. Otherwise there’s no reason for him to do it. ’cause like at the end of the day, I mean, that guy, you know, he’s younger, he is not in the FI space. He needs to work and earns some fucking money. But if I’m looking at like what I’m doing and I see. Friends of mine that retired years ago and they like kind of just stopped logging ’cause they reached their goal and they’re like, well, I’m not getting anything out of this and I’m not earning money from it anymore. So that’s where I’m like, okay, I need to make sure I understand why I’m doing it and for who and like, are we both getting value from this? And occasionally, I don’t know, we’ll do a telethon. I I, I have an idea to do a telephone. Interesting. Just like, uh, Jerry Lewis back in the day, and I’m like, support. I’ll send you this $800 fucking tote bag. The kids in the audience aren’t gonna know the reference, but I get it. I’ll send you a t-shirt with Georgie or I’ll send you this $85 sticker with Georgie’s face on it. Jason: I’m telling you, you should do. Some people have, uh, Instagram accounts for their dogs. You should just do a whole separate YouTube channel for I Doug: I could, yeah. Yeah. Georgie camp. The GE camp I thought about because I have like another webcam and I thought about just like setting it where she sits and then I’m just like, there’s a picture. Picture. Little picture. Yeah. And then she like looks up or licks herself or some kind of inter, I’ll just put, I have to put a blur thing right over her. Alright. So anything else on sites before we move on to some of the other stuff? Jason: Um, websites are not dead. Doug: Okay. Yeah, it’s um. Well, in all sorts of other areas outside of affiliate and Jason: content, you know, ad revenue and stuff. There’s, there’s all sorts of reasons why they’re not dead. Doug: Okay. So there have been a lot of, uh, talks, I think at least I don’t go to as many talks, but there’s AI talk, there’s talk, talk about, I saw one this morning. Okay. Yep. And there’s, um, as soon as I heard. People talk about vibe coding. I stopped listening ’cause I was like, I think I’m just gonna be a little annoyed with it. ’cause I kind of saw some of the, I saw symptoms of issues that might arise from it very quickly. So, um, actually can you define vibe coding? Um, just in a general sense, so I don’t mangle Jason: it. Sure. Well, this is my take. Uh, it’s, you know, if you use one of the AI tools. Okay. And you simply ask for an output, and you could do that for, give me a script for a YouTube, uh, video. Here’s the topic. It will give you a bunch of output. You can do the same with code. Mm-hmm. Give me the whatever JavaScript code necessary for this purpose. Right. For this application. I’m going to use it here. It should do the following. Uh, the person who’s doing that might be a coder or mm-hmm. Some, somebody who knows programming or maybe not. Mm-hmm. But, you know, they’re just sort of feeling their way through the process. Uh, we don’t, we don’t call it something special when we ask the AI to give us written content, because we all use language every day. So everyone presumably can speak English, you know? At least in this country. And, uh, and, you know, we’re just amazed by the output. The, the, the coder or the programmer who does the same thing with these same tools, uh, also gets output. Uh, the reason I think the, the concept of vibe coding came up is because non-programmers started asking AI to produce this software, produce an application. I wanted to do this, that, or the other thing, but that. Mm-hmm. As you just alluded to, can lead to problems. Doug: And I think the big, I have many, uh, biases around this, so I’ll call ’em out so it’s a little bit easier. I have a software background, so I think I’m better than other people. Right. I mean, that’s just, that’s the fastest way to say it. Jason: And with regard to software design, you probably are better than most other people, statistically speaking. So then, go ahead. Doug: Yeah. And, and, and then the, the project management, which I mean like when you peel that back, the project management stuff does help you in the software development life cycle. It helps you understand all that shit and like testing and regression testing. And basically when someone, uh, a vibe coder, for example, maybe they find a bug and then they’re gonna go fix it, and then they fix the bug that they were trying to fix, but they accidentally broke something before you have to test things. To make sure that you didn’t break something that was working before. Yeah, and testing is most of like the software process. It’s just like fucking testing it over and over again. Very well said. And I think it’s, it’s really cool that maybe a someone without a coding background, a designer perhaps. Um, yeah, maybe they just have like a more art artistic background. Yeah. And they don’t know the, the coding process and they get something going. It’s really awesome to be able to get it going without having to consult with like a technical person. Right. And it’s much cheaper to prototype to get it kind of in the right spot. The issue is like if someone tries to sell that prototype version to, uh, I know as a finished product. Yep. And they’re trying to fail fast. They’re trying to iterate all these. Like one sentence, things that we learned from Silicon Valley Great show. So if like, if you’re trying to do that, then you’ll end up in a spot where like, okay. And I basically like if I see a product that that was done in that way and I buy it and I’m like, oh cool, I’m getting a lifetime. I’m getting a lifetime access to this thing. And I’m thinking that the person is gonna stand behind it and they’re gonna iterate on it. And you know, version five’s gonna be amazing, but. Uh, they kind of lose steam on it. And then I paid a hundred bucks for something that never gets past the prototype. And then I’m like, oh, this whole thing was a waste. So, and we, I saw it before when coders were doing it. Yeah. In fucking, um, what’s Noah Kagan’s cheap? Ab Sumo. Ab Sumo. So it’s like, oh yeah. Lifetime. You get the lifetime access. It’s not sustainable. The company goes outta business and then you have software that doesn’t work. So like, that’s stupid. Right. Well, you, you. Jason: We started very general and you’ve gotten very specific, but yeah, so fuck all. No, I’m just kidding. So, okay, so, so, so a little bit to unpack there. So first of all, I think, I think it’s clear that, uh, in companies, large and small, the actual programmers, the, the development departments are using these tools. There’s no question. Just, just like. Marketers or writers or whoever, what we’ve been doing with what you’ve done in the past with, uh, ai, uh, tools for, for content, for whatever prose, fiction, nonfiction, whatever. Uh, you can use these things as efficiency tools. The right way to do it is to get outlines, idea starters, right? And of course you need a human to come back. And humanize it, not, not for purposes of avoiding AI detection, but to actually make it good, right? Mm-hmm. To, to move it from passable to good. And, uh, and when folks, for instance, that maybe for, for which English is not a first language, uh, couple years ago started, got their hands on these tools and would just whatever, auto crap out these articles and push ’em live without any kind of interaction. It was obvious. It was, it was shit. Right. Um, in the same way, a non programmer, a non coder, and so, so the, the coders, the, the programs, the developers are using these tools to speed up their process. Okay. For, for the non-developers, the so-called vibe coders, to bring it back to the, the fun part of what you said it, when, when they do it, they don’t have the coding background to actually look at the code. It would be as if they had. Produced this English language article, but they didn’t speak English. So they have no way of discerning whether this is good or excellent, right? Mm-hmm. And, and they have no way of looking at the code. And, and so this is, this is a problem now, I think, as you said, the, the selling lifetime deals and, and pushing these sort of half-baked products out there, that’s been happening for a long time. Right? Uh, I, I dunno if it was you or somebody like I, I also. Associate that with like ClickBank. Mm-hmm. And like these kinds of offers, like maybe there’s some useful thing there, but like you just put a wrapper or package around it, sell it for a ridiculous amount of money and then whatever you’re done. And, uh, having said that. The lifetime deal thing, right. So I, I say this because one of the companies that I’m is, they’re, they’ve got a marketing related sa, it’s a link link related SaaS tool. Um, they’re, they’re sort of second in their space. They’re, they’re, you know, uh, doing well. They’ve got, uh, good growth in their MRR and all of that stuff. You know, they, they got their start with lifetime deals. They didn’t do it through AppSumo. They did like direct lifetime deals, but for them, it was like a way to get early funding. To, to, to do more development and also to get, uh, early feedback from customers. They have, you know, made a very hard decision to move to actual subscriptions. They say hard because they could easily keep selling lifetime deals. They keep putting investment into their code and developing the product, but they have to like wean themselves from lifetime deals because it’s so easy for them to do that if they wanted to. They made the right choice and they moved away. So I, I would say that lifetime deals aren’t always bad, but, but yeah, if you’re, if you’re the scammy type and you’re just crapping out a product, uh, whether you use AI to do it or not. Mm-hmm. Uh, and then you have no intention of supporting the product or your customers, that’s always a bad thing. Doug: Yeah. And I, I do agree, like lifetime deals aren’t always bad. They can be done in a bad way. Absolutely. They’re Jason: abused by Doug: a lot, but, but it’s not always, and I guess this is the perfect time to let you know I have a new product out and you can actually get a lifetime deal, but only on this episode. Jason: Well, I thought it was, yeah, that’s the, that’s the $0 Subscribe to the Doug Show Doug: deal, right? Yeah, yeah, yeah. Lifetime. Jason: Well, you’ll have access to all the episodes for a lifetime. It’s not a commitment on Doug’s part that he’s gonna keep producing it for his life, some life. Doug: Okay. So cool. Alright, anything else with the vibe coding area? No, but, Jason: oh, okay. Well, I will say one extra thing. This is a little bit of a pitch. So, uh, I, my, my tech partner for, for my s product, he’s got a tool of his own, which came out of some of our. Sort of efforts of playing around with Vibe. So I’ve, I’ve tried some of these tools. Um, I mean, some of ’em are just, so you’re programmer guy, you know, an IDE. It’s just, it’s a, it’s a enhanced sort of coating window that developers use. Um, so there’s a bunch of those like cursor and windsurf and stuff that are AI enabled, right? But then there’s like lovable, you heard of Lovable, I think I have. And uh, repli is another one. So these, these ones are really going after this sort of non-program or. Uh, uh, vibe coder type, and they, they let you sort of see the, the tool working in the window. They also make it so you can publish your project, but it really is not that at all. Like you can’t deploy the product. It’s, it’s still just an MVP, like you said. Mm-hmm. And, uh, but what, what we identified when we tried to play around with these things and then quickly went back to our human programmers, uh, was. This, this code auditing problem. And so he came up with a tool that makes it easy for folks that have done this sort of programming to run their, uh, their GitHub repo through this auditing tool. And it’ll tell you if you’ve got security vulnerabilities. ’cause the thing people forget is that these AI tools, they scraped the internet for everything. Right? Right. They, they scraped the text, but they scraped all the code. And as a result, they scraped security vulnerabilities as well. And so those things will creep into the code that the AI writes. So anyway, there are, there are ways to sort of make it more secure, but you still need human beings. That’s the punchline. Gotcha. Doug: So that’s, that’s a thing that you, that is a product. Yeah. That’s a, well, Jason: that’s a, that’s, let me check AI if I can name drop it, but yeah, that’s my, my. Tech partners product. Right. Okay. Gotcha. So people can just go check it out. But you know, if you don’t have a GitHub repo and already have code, you’re not gonna be able to do much with it. Okay. That’s what it’s for. Doug: What do you think, well it sounds like maybe tools like that might be where Vibe coding is going so that people can like effectively use the AI tools to code, have products, and then have, um, other AI check it. To make sure it’s, uh, high quality. Is that, that’s where you see it going. Jason: So there’s, so the a Yeah. I mean, so the AI involved in this product is, uh, suggestions for how to fix it. The, actually, the auditing part is, is not AI related. It’s uses other methods, but, but yeah, I think, I think the point is the, the tools like this have been used by programmers all this time. Mm-hmm. This, this tool makes it easy for non-programmers to just plug their. They repo in and, and use it. I, I think where it’s going is human programmers are still gonna have jobs. That’s where I think it’s going. Okay. Just like write copywriters and authors and the human premium that I, I mentioned earlier, I, I still think, you know, humans need to be in the loop for all this stuff. Doug: One, uh, you know, social media is horrible as, as we know, but I saw that. Creators they’re taking real content, so they’re taking like our conversation. Mm-hmm. They’re like stripping the, uh, transcript. Yep. And then they’re putting AI, and it’s essentially like a little avatar, like it looks like a human. ’cause AI is very good. And then it’s like a reaction video and they put something else in the background. And the thing is like. If you go on shorts or reels, or, I’m sure TikTok, which I’m not on, I’m sure I know. I see all the time just copy written stuff. Uh, people take it even like, they take it from TikTok and then they put it on Instagram and they’re like, let me know if you have any issues with this. And they like credit it by putting the, you know, the handle on there. But yeah, there’s all the, all this theft going on. Yep. And yeah. Any thoughts on that? Jason: Well. So, I mean, some of these platforms really encourage it, right? Maybe even YouTube does now, right? If you want to clip it and repurpose it and whatnot. Mm-hmm. So, and it’ll strip out your, if there’s copyright music in there, I guess it’ll strip it. I mean, so the platforms encourage it. I think it’s, uh, unfortunately, I think it’s a symptom of, uh, our nature as. Human consumers like, I think, I think your exact, your, your specific example is, uh, a form of criticism, right. The sort of reaction mm-hmm. That, that reaction video thing, whether it’s in shorts or not. Mm-hmm. That’s, that’s a whole genre of, of content. Right. And I don’t think that’s gonna, that’s two people talking over the fence in their backyard, I mean, about the neighbors. That’s, that’s not gonna go away. But, uh, well actually, but the fact that there’s theft, Doug: yeah. Jason: Even before the AI started doing it to us. Right? Doug: Yeah. Yeah. Well no, I’m talking So that’s one thing, the reaction video, ’cause you could claim that as fair use. That’s right, that’s true. So that, that is probably Okay. Um. If someone is actually adding something to the conversation, some value, but I’m saying people are literally taking like stuff that you and I say and then the direct transcript just giving Jason: an avatar to you. Yep. Doug: So it’s a different voice and then it gets views and it looks different. Human premium. Yeah. Man, Jason: I think in time that’s, but it looks like a human, Doug: and it’s our words. So because that’s the thing, like it ended up being like, oh man, I, I agree a hundred percent. That’s why I do these shows, but. At the same time, I’m like, I don’t even, I don’t know how you defend against that other than just like, Jason: don’t, don’t the platforms at least attempt to market as AI produced? Doug: I don’t know. I I would hope so, but at the end of the day, if it keeps you on the platform and they show more ads, I don’t know if they give a fuck. I would suspect not. Jason: I think you’re right. I don’t know. I, I, all I can say is I have faith and hope that originality. Yeah. And uh, human connection will persevere. Doug: Yeah. It’s interesting. It’s very interesting. I think, um, yeah, the human premium, especially like coming to, we’re at a live event, it’s really awesome. There’s no replacing, just hanging out. So you’ve been to how many Fincons now? Jason: This is my second. Doug: It is your second. Okay. I was in New Jason: Orleans. I skipped Atlanta. I apologize. I know Doug: it’s your hometown. That’s okay. That’s all right. It was pretty fun. Like one cool thing there was, um, there were way more parties and I was, I was like, this is what I heard. They were like before. Um, but we don’t have, there’s not as many parties this year. The other thing in Atlanta, it was also a Hyatt Regency, but they had like breakfast in the morning, like nice breakfast in the morning if you stayed at the hotel, and they don’t have it here. So it’s a little bit of a bummer for. Some of the amenity things. Mm-hmm. It’s, um, it’s really cool to hang out. So is there anything that you were looking to get out of coming to FinCon this year? Jason: Well, I’m, so we’re talking all this AI stuff and, and so that, that does play a role in some of my startup and business activities. I mean, it’s hard to avoid it. Uh, even my consulting clients ask how they can use it. So one of the things I was, you know, looking forward to is seeing how it’s seeping into. The broader content, uh, sorry, con Yeah. Content creator. Mm-hmm. Um, ecosystem. Uh, like we mentioned, I went to a, a panel this morning, a, a talk. It was pretty good. There was, it was, it was very automation focused. It was about how to, how to create efficiencies. And I, I think, and, and the only point where it brushed up against content creation was, you know, giving outlines and ideas and stuff and, and, and she never. Even alluded to the idea of using it to produce the actual content. And I think, I think there’s a, people are coming to the conclusion that, that, you know, it’s good for some things we still need to do, do the work. Mm-hmm. Uh, and I’m, I was glad to see that. I’m also here to check out the, the FinTech companies. ’cause you know, although my focus is more B2B fintechs. Um, I’ve already met a couple of founders or CEOs of some of these B2C FinTech companies that are here, and that’s been, that’s been super interesting. Doug: Very cool. Yeah, it’s, it’s a cool event if people are able to check it out. Um, I know like the Doug show audience, uh, actually it’s a broad range. So a handful of the folks would be literally interested in this type of thing, even if you’re adjacent to anything money or financially related. Like it works. And then there’s a lot of overlap, like as you walk around, like it’s like people that are super into YouTube or whatever platform. So it’s very fun. Alright, cool. Anything else you got on your mind that you’re working on or? Jason: Uh, yes. Well, my, uh. Enthusiastic support for websites. Uh, I, I do have a, a reason why that’s on my mind these days. Uh, so my other SaaS project that I’m working on is called AI App Onsite. Uh, it’s currently a WordPress plugin, but it will be CMS Agnostic soon. Uh, and it has an AI component, obviously you can tell from the name. Uh, it’s on the tin. So the idea here is, uh, just think AI power smart forms. And apps, um, if there was something that you built a GPT for on, on OpenAI, folks are not aware, right? OpenAI has this thing where you can build these little GPTs, it, it’ll be a, a canned prompt. Uh, maybe you upload some extra content to make it smarter and it becomes this sort of app. But it lives on open ai. And what folks a lot of folks here are even talking about is, you know, build this GPT and you’re, you know, you can send your audience over to it and it helps them in some way. Uh, my premise, uh, here is that you, you shouldn’t have to send people away from your website, like bring them to your website. And this tool allows you to effectively build the equivalent of A GBT on your website with no code. You don’t have to do any crazy, uh, you know, coding to make it happen. Uh, the other common use case would be, you know, if you have a contact form, uh, or a, a support form on your website. Right now, these are sort of dumb forms. Uh, most people don’t even use them unless they wanna complain to you about something, you know. But, uh, if you can instead offer a smart form that, that asks them for their email, but ask them a couple more questions and they’re going to get a real time answer, a real time analysis or report, whatever the business you happen to be in. This makes it easy to build this sort of, uh, AI powered real time, uh, uh, app on your site. And you still get the, the content sent to you. You can send it into your CMS, uh, you know, all of that sort of thing. But, uh, your client, uh, your prospect, your site visitor, gets a real time response instead of just clicking the button and hoping someone gets back to them someday. Doug: You Jason: know? Doug: Okay. And it sounds like it could. Be for almost any industry. It’s just like someone, someone would need to know what they wanted to do. Jason: Right. So you bring your own API key as well. So you may recall from, from when you were covering the AI stuff. Mm-hmm. You know, there’s a lot you can do. Just go into a chat GBT window. Uh, but you can also get an API key and you can put that in other tools. There’s other tools where you can use that. Uh, so you get your own API Key. Uh. Which means I’m not charging credits. Right. This is another thing, the free version of this, it’s, it’s completely free right now. Um, and you could do a lot with a free tier. You bring your own key, uh, and yeah, you, you can, uh, you also have full control over the prompt as well, so if you know how to write a prompt and talk to chat GPT, you can build one of these as well. Gotcha. Pretty cool. How long have you been working on that? Uh, since inception, about a year and a half. Okay. Which is way longer than it should have been. ’cause I, I, you vibe coded it, didn’t you? No. Admit it. I, come on. You did. I, I didn’t. I didn’t. I I, I can tell you of my, my vibe coding story, it’s just, but it ended in disaster, so I, it is not as fun a story. No, I didn’t, this is, uh, this is definitely human coders. In fact, I’m on my second development team. The first ones didn’t work out okay. So Doug: that’s probably why it took. Took a while, right? Oh, you’re being kind. Jason: Yeah. Doug: Alright, that’s pretty cool. So we’ll link up to that so people could check it out. And like what size business? Um, or like, who should check out that tool? Like, Jason: well, anybody who has a website and, and so we’re going after sort of, there’s two ICPs, right? So anybody with a website who gets visitors but needs to convert more of them. So one of the ideas is like we get. Far less traffic to our websites, any kinda websites than we used to. Thank you, Google. Right? So you need to do more with the visitors. You still get. And so the idea here is, is by offering this real time value, you can convert more visitors. So anybody who’s got a site with a form could potentially get value from this. Uh, the other folks that I would suggest take a look is agencies, because if you, if you’re a marketing agency or a web development agency, you’ve got existing clients. Uh, you may have a retainer with ’em, you’re doing regular monthly maintenance, but, uh, offering them to build, uh, an AI app on the site represents a new project. Uh, you can get an affiliate kickback for me if you buy the, the paid tier, but, but you know, more importantly, you can, you can ask your client for a, which I think is perfectly reasonable if it takes. Five to 10 hours of work to develop the prompt and ideate with your client to build their app, then that’s billable time. So, uh, yeah, so marketing or web development agencies that want to increase the value of their existing clients can, can take a look at this too. Doug: Are any people using it now? Jason: Uh, handful of folks are in our, you know, our, our sort of early adopter, uh, pool lifetime deal. No, I’m sorry. I’m just kidding. Even better boss. They, they got it for free, so. Okay. Gotcha. By the way, I’d love to come back and talk about it ’cause I’m probably going to do a lifetime deal. Okay. I, I haven’t decided yet, but, okay. Yeah. Yeah. So, we’ll, we’ll see how it goes. Yeah. Because I can give you the inside scoop on AppSumo these days too. So like I would do it through AppSumo if I did it. Oh yeah. Okay. So it’s just gonna be a whole interesting experiment. Gotcha. Alright. Doug: Yeah. Yeah, that sounds interesting. ’cause like there’s one, I don’t know if this will come out as a fully formed thought. I like to know a Kagan a lot, and I, I don’t know him personally or anything like that. He seems like a good guy. Overall, I was not. I would watch his content and then I would feel bad, so I, I stopped watch. I was like, don’t show me this channel ever again. And I, I do that. I highly recommend it. If there’s something, even if it’s, I’m like, oh, I’m learning something, or whatever, I was like, you know what, this guy kind of gets me down. So I, I turned it off and I don’t want it anymore. Um, but I listened to his interview and I, I really, I listened to all his stuff, um, back in the day and found him influential. Um, but, but anyway, I think I heard an interview with, uh, Tim Ferris and Noah mention like, yeah, someone is like, um, kind of not committing. He’s like, come on, open your calendar right now, kind of pressuring them. Into scheduling a meeting or a follow up call. He’s like, let’s do it right now. Like, we’re not gonna wait. And I was like, I don’t like that kind of high pressure. I agree. On the flip side, there’s a wonderful interview, I think on the Knowledge project, um, podcast, good Channel with Shane Parrish, I think that’s his name. Yep. Daniel Kahneman. And Daniel Kahneman said, um, he got a phone call during the interview and. Someone was trying to get him to commit to something and he was like, Nope, I don’t say yes to anything on the phone. Uh, right away I think about it and I was just imagining Noah Kagan talking to Daniel Kahneman and Daniel Kahneman would be like, no, I’m not playing your game. You can’t high pressure me. And I would rather be like a Daniel Kahneman than Noah Kagan. And I was like, it’s very clear to me like Noah’s trying to pressure people into stuff. And I’m like, I don’t. I, I, and I’ve. Listen to the deals that they do with App Sumo, and I heard they’re like super hard negotiators. Yes. And it’s like they, Jason: that’s what I’ve heard. Doug: Yep. So I’m like, uh, I don’t really give a shit anymore. So I blocked his channel and I’m, I think he’s doing awesome. Those right. It has like a million subscribers or something. Jason: You know, they, they released their own SaaS, tidy Cal. Doug: Okay. Jason: And that, that calendar, right. It’s a, it’s a competitor to Calendly. Okay. But, but it’s so interesting you mentioned, I didn’t know about what, what, what you’ve mentioned just now, but it’s, it, it fits that a guy with that sort of attitude or approach wants a calendar program that makes it easy. Send a link, you know, get on my calendar, let’s do this kind of thing. Doug: And I’m like, it’s my time. Fuck that. No. So I’m with you. I’m Jason: with you. Doug: Interesting. So that I need to. F fully form that thought, but I, I, that was pretty fully formed. Thank you. Thank you. Yeah, because I think if you listen to those two things back to back, it’s like, oh yeah, I, I don’t wanna pressure people into do, I’m not buying a fucking used car, so, okay. I took a weird, weird direction. So we’ll link to, uh, AI app on site. Yep. So people could check it out. Thank you. Appreciate it. Um, anywhere else people should find you? Jason: Uh, j Paul Hendricks on most of the social platforms, but I don’t, I. You know, publish much, but you can, if you wanna connect with me, you can. LinkedIn is a good place. Okay, Doug: cool. We’ll put it in the link, uh, in the, or we will put the link in the description so people can get to it if they want to. And you’ll just send me all that stuff later. So Jason, always fun to catch up. Excellent. Thanks for joining me here. And yeah, we’ll get an update from you and, uh, whenever, whenever the time’s right. Look forward to it. Thank you Duck. And you know what we should do a sound check is, and that’s usually what I do for my other show. So you mentioned that you do wanna talk about guitars. So one thing I could tell you, one guitar that I, I think it’s my ro most recent, um, one that I got. Acquisition. Yeah. Acquisition. Yep. So I really love the idea of the pre-war acoustic. So we’re talking, uh. Well, maybe it’s not obvious. So basically like before 1940 ish or so? Mm-hmm. Mm-hmm. And I don’t know, they’re super cool. I really like the Gibson acoustics and those tend to be quite expensive. If they’re in great condition, they may be, uh, probably seven to $10,000, something like that. And then one that’s beat up. It might still be like two to three. However, there was a, a lower end brand. It’s still made by Gibson, but it’s called Kalamazoo and Interesting. And I, I found one of those. And essentially it’s like the same wood, some of the bracings different, some of the appointments are a little bit different, but these were budget guitars. Mm-hmm. And you know, very cheap. So basically I found one that looked to be underpriced. And it was in great shape. Uh, I, I don’t think there were any cracks. Wow. And, you know, I’m not an expert, but generally I was just like, man, this is in great shape. Didn’t need a, a neck reset and that sort of thing. Um, but, but anyway, it did need a little work and I finally dropped it off at a really good luthier and, uh, in the Denver area. Oh, look at you. And it does. I was a little afraid. That it might need a refre. So there were a couple loose braces. That’s not a big deal. The bridge was a little beat up. Mm. Um, tuner, uh, screw holes were a little off, so they, you know, that’s pretty easy to fix. Mm-hmm. But it does need a refre, so that’s gonna be expensive, but it’s gonna play much, much better. You plan on keeping that? I think so, yeah. Because you flipped guitars previous. Yep. I flipped and I think I would, I’m gonna keep it for a long time. I could see if I’m just like, um, I don’t connect with it. But I think with the new frets, ’cause old frets of that timeframe, they’re more near, have you played some old low fret? I can’t say that I have. So the frets are a little bit smaller and like less wide and they’re not as tall. And after years, like they get worn down. They get worn down. Yeah, that’s right. So after. You know, they, anyway, so I did drop it off at the shop. It’s gonna take a couple months. They were pretty backed up. It’s a very good luthier and stuff. Um, and it’s actually, I got a good deal on the guitar, but this, this work kind of erases it and I probably could get like a cheaper fret job, but I mean, this guy like specializes in like, um, vintage acoustic restoration. I think he worked at like Gruss or Carter’s Nice. Somewhere in Nashville. Yeah. Yeah. Well, I have to say, yeah, good. I love the. New intros for the Doug show. Oh, thanks. You gotta keep doing that. And I like that you’re mixing it up. There’s, it’s always something new and Yeah. And I, I please keep doing that. Okay. Right. Because it, it makes me, uh, I always listen to your episodes, but it makes me wanna say, okay, what’s he gonna play this time? Okay. It keeps it fresh. Yeah. When a couple times, like I have, I’ve sat down and I’m like, all right, I’m gonna do one. And like, I’m just not feeling it and I’m like, you know what? I’m not gonna force something. So I’m like, I I, at this point, like I, I’ve, I have been putting it off enough where I’m like, I need to fucking do it. So actually when I get home from this conference, ’cause I wanna do music for Mile High five and I keep punting it off and I need to, I need to just do it. Well, if you get two or three good ones in, you record all of them and then you can get them whenever, right? Yep. And, and that’s, that’s my hope. I want to have a few, and then I could just give it to my producer, Chris, and I’m like. You could use any of these. Mm, it’s totally fine. Mix it up depending on like, the mood of the episode. ’cause I think some will be acoustic, some will be electric, some will be just, um, yeah, I don’t know. I Nice. But thank you for saying that. So have you been playing a little bit more or, I have not because I relocated. So I’ve been very much in, uh, mobile mode. Okay. Uh, I, I did play with, uh, the band. The guys that I used to play with in Hong Kong, I played, uh, I’ll say two months ago. So that was my last show. So I guess I could say I played as, recently as two months ago, we did a, we did a show in Hong Kong, but uh, it wasn’t our best. We hadn’t been, we hadn’t been, uh, uh, rehearsing enough and so, okay. But it was fun. Yeah. Yeah. So, very good. Alright.

Typical Work Week in Early (semi)Retirement – DS582

Sep 15th, 2025 1:00 PM

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 really refined down to the work that I want to do most of the time. Now, you can’t get away from admin all the time, but I have stopped replying to so many emails. If I don’t wanna write an email newsletter that week, I don’t do it. If I want to, then I’ll go for it. I’ll write a few that week. So I’ll describe. Kind of what I’m working on, kind of how like a week looks for me. And I’ll also talk about, um, the fact that some people were probably nervous, like, well, if I, if I wasn’t working on something, then what do I do with my time? And I’ve chatted with at least dozens of retired people that are young, say in their thirties or forties or early fifties. Very few people are bored, so I’ll give you a little info on that. But more importantly, I mean a lot of people wanna get to a spot where like work is optional, and that is where I have arrived. So the work that I’m doing is optional. I don’t have to do it, and it’s. You know, it’s good to work on things and to be productive and creative, and I get that part of it, but it’s far less than whatever I expected. And again, I talk to people and I’m like, ah, yeah, my wife retired. And they’re like, I just don’t know what, uh, that’s crazy. I would be so bored. Like, I like to be productive. And I think I would’ve thought that back in the day. But I don’t think it anymore. And I don’t, I don’t do that much work, and I can tell you it’s fucking awesome. I love it. It’s not for everybody, but it works for me. So the bigger piece that I’ll cover today is just like what I did while I was working on my side hustles when I had a full, full-time gig, and it enabled us to have a work optional. Um, lifestyle. Some people would want to travel. Some people wanna work on their pet projects and, um, maybe like start the business that they actually wanna work on that doesn’t have to earn as much money. That said, I’m just gonna tell you stories. This is not financial or legal advice in any capacity. I’m just gonna tell you what I did and I’m not prescribing this to anyone. And it’s not financial advice to be explicit. It’s not financial advice in any way. And a lot of it’s simple. I’m not gonna even mention anything super specific. But anyway, typical week, I’m probably working a, I don’t know, three or four days. And on those days I’m probably working 45 minutes to say four hours or so. And the biggest chunks are when I’m actually like doing an interview and I’ll pause here ’cause there’s a plane flying overhead. It’s often nice outside, but if it’s not windy, there’s like other, other noise, but it’s peaceful out here, at least with the headphones on and I can’t hear the dog yiping back there. the days where I work longer, it’s usually like an hour or an hour and a half of like an interview. So that’s like the biggest chunk, and that actually goes by very quickly because it uh, it’s fun. And that’s the thing, I enjoy doing the interviews. It’s a conversation I get to learn about someone. Half the time I’m talking to a friend of mine, and we’re able to go into like a, a deeper conversation that you wouldn’t normally have. Let’s say I’m hiking with a group of people or it’s at a happy hour and there’s a lot of people around, maybe I don’t ask. As many questions and we don’t have the same kind of conversation. It’s different of course, when it’s for a podcast, but essentially I’m chatting with people that I wanna chat with and there was a time, and I’ve uh, complained about this in the past, where I would actually like interview people that had books coming out or I was interviewing people where it looked like it could be an interesting opportunity for me to make the connection. I’ve since learned that. I don’t enjoy that and it’s not good for me to make the connection, and it’s better for me to not do those interviews. And a lot of times these will come in. And it, it doesn’t have to be someone promoting a book. They could be just trying to get out there on podcast. So they have a promotion company working for ’em and they send an email and they’re like, um, Joe Blow is a CEO. He pulled himself up by. Bootstraps and he’s been able to become a multimillionaire and he’s a CEO and it would be great for your audience to chat with him ’cause he has all these great fucking stories and he has a big email newsletter and social following and all this stuff. And he’s gonna promote it to his audience of. 193,000 people, and I did a few of those and then realized, oh, these motherfuckers don’t bring any of their audience. They just want to get either links or in front of my audience, and I don’t care about their story. And they’re a dime a fucking dozen. I, I don’t give a shit. I don’t wanna talk to ’em. I now mark those as spam and I probably have a bunch of, um. Domains and emails where I just don’t get emails from ’em anymore. ’cause they kept sending me all this shit. I’m like, remove me from your list. And if it’s someone really good, they’re probably going to come in through like a channel that I’ll accept, which is typically like a warm introduction or if I meet someone in person. So I recently did an interview. Uh, for my other podcast, but I met him at a live event. I talked to him, hung out with him for, uh, a couple hours or whatever, and they were passing through town and I was like, great, come to the studio. We’ll do an interview. You guys have a cool story, so we’ll talk about it. And that worked out great. But typically if I get an email, cold email, I’m not, uh, I’m not even replying back these days. I used to say, ah, it’s not a good fit, whatever. But now. I tell, I, I just mark it as spam and move on with my I do interviews. There’s a little overhead, and if you’ve been following this podcast for a while, you know that I have somewhat struggled with what I was gonna cover in the last, say, six months or so, because I’m not trying to start new side hustles. I’m not. Doing this stuff that people might be interested in, in the same way. I’m still interviewing some people here and there, but I’m mostly just, I’m just talking about stuff. Right? Turns out people want to hear about that. It, it sounds like it’s, uh, more interesting because, uh, number one, I’m not trying to sell anything, so that’s. That’s different. ’cause before I was at least trying to place everything in, uh, like the context of building websites and stuff like that. But I’m not selling anything now. So it pretty much frees me, uh, from anything. And again, I don’t have to talk to anyone. I don’t want to or have content that’s, um, different than exactly what I want to create. So you hear the crickets here. You hear the. Plane and the dog barking in the background here and it’s a little bit more interesting. It took more work, but I think once I get a couple of these under my belt, it won’t be too, too bad. Alright, so skipping forward, it’s just a few hours the rest of my day like. Today it’s, um, it, it doesn’t even matter what day, but today is, uh, happens to be a Saturday. I, uh, did normal, uh, like house cleaning stuff, so I like cleaned the bathrooms up a little bit, did a quick sweep, and a lot of times we just, we still do this on, on the weekends. We don’t have as many plans. Uh. Maybe on weekends, but the, our days run together, so we don’t even pay attention to weekends other than we don’t want to go to a place that’s crowded because it is a weekend. So we may hike more during the week because there’s less, less people out there hiking. So. That’s one thing where, you know, I go to the grocery store early in the morning on Monday through Wednesday, typically, because if you go to a Costco or Sam’s on the weekend, it’s packed. That’s when everybody else goes. So typically I’m trying to avoid crowds, but generally. A day consists of, you know, me walking Georgie for an hour or two. Uh, yeah, about an hour, give or take. And then I’ll do any sort of productive thing that I need to do in the morning. Usually before 2:00 PM is like my productive time of day and. Occasionally I’ll do an interview later if time zones don’t allow for it. But again, because I’ve distilled down, I’m like, I don’t wanna wake up early to meet somebody’s time zone and I’m not gonna work later than I want to. So I have a window and I’m somewhat uncompromising for that unless there’s some exceptional reason for me to do, um, something outside of the window that I want to do things. I usually go to the gym. Uh, I would say four to seven times a week depending on what’s going on. And I’ll work out for one to two and a half hours, depending on what’s going on and what I want to do. And it just varies and I kind of, I kind of, uh, just kind of figure out what I’m gonna work on that. Day, or sorry, the workout that day, depending on like what I did the previous days, how sore I am, how good my sleep was, a number of different factors. So I’m kind of like listening to my, my body and my mind on like how much, how much stuff I want to do. I think now we have a baby crying out here, so it’s sort of a cookie cutter, uh, suburban neighborhood. So while we have these privacy fences up, there’s probably, there’s like eight houses with an earshot. So if you bring a crying baby out, you know, it kind of carries, I don’t know if you could hear it, but I can’t. A little bit. It’s like me trying to record at an airport or something like that. Okay. I don’t work that much and it turns out it’s great because there’s always stuff coming up or one thing you could kind of spend, not an infinite amount of time on, but like fitness and health is something that you can spend a lot of time on. And occasionally here. Recently, in the last, I would say six weeks, I would do. Two workouts a day, which is not typical. ’cause I, I really don’t wanna wear myself out. I don’t want to injure myself and that is a great way to overtrain. But I would go to the gym in the morning for only about half an hour. And the thing is, I could walk to the gym. So if I walk over there, I get a handful of steps. I could do a couple or, uh, say two to five sets of some exercise. Let’s say I’m focusing on. My shoulders or something. So I could work on that specific thing and then I can come back to the gym later in the day, uh, maybe when it’s not as crowded and I could do a little bit of a different kind of workout, uh, maybe more cardio or maybe I do, uh, more compound lifts or whatever. I’m just making up an example, but I’ve been working out a couple times a day, just a couple or few times a week. I’m not getting a huge number of steps, but like over the course of six weeks, it does make a difference. If you look at like the total step count per day kind of thing or like, uh, just how many workouts I’m getting, how many sets I’m getting on the shoulders, or something like that. Again, just an example. No one look at my shoulders and judge if they’re larger or smaller than they were the last time you saw me. Okay. The other part is I spent a huge amount of time cooking and on food. So yesterday was a kind of a. An odd day, but I end, end up doing this maybe once every two weeks. I’ll buy a huge amount of meat and then I’ll grill most of it all in one day. I use a charcoal grill typically, which you might be able to see in the background of this video. It’s just your standard like Keter Kettle, it’s your standard Weber Kettle. I think it’s a 22 and. When you fire up the charcoal, it stays hot for a while. So I thought, oh, if I have the grill hot already, I may as well go ahead and grill a bunch of other food. So I probably grilled, I don’t know, eight to 10 pounds of meat yesterday. I’ll freeze a, a good portion of it. We label and date it and we eat through it over the next week or so, and then we have frozen stuff that we can thaw whenever we’re like, oh, you know what, I’ll just uh, thaw that, those, those chicken breast out or whatever. They’re already cooked and um, you know, we have a vacuum sealer, so it’s a great way to, to save the food there. Alright, so. I spend a ton of time on food. It’s what I’m into. I like to shop for it. I like to cook it. I like to prepare it Super fun. I probably spent six hours doing that yesterday. It’s like a flow state. I didn’t even real, I’m like, oh, shit. Like whole afternoon’s gone. I’ve been cooking. This is awesome. The grill’s going pretty fun. I’ll have a beer and it’s great. I’ll listen to a podcast or put some music on or whatever. Georgie hangs out, Elizabeth. My wife will come out and play with Georgie and we’ll just kind of be out here grilling. So that is fun and I spend a lot of time on that. And then I put, you know, food in with the health aspect because I. I mean, I’m not saying everybody needs to spend time on food. I spend a abnormal amount of time on food, but I enjoy it and it’s a hobby. And I’ve always cooked since I was a little kid. Big in my family. And some families, you know, they spend their time doing something else and that’s totally fine. But for me. Super fun and it, you know, cooking is, uh, it’s a good way to spend my time and it ends up being healthier than if we eat out. Typically. It’s also cheaper too, even though I’m getting like premium meat and like great steaks and like prime filets or whatever. It’s, uh, much cheaper than eating out, which is surprising, but that’s just the way it works out. And I have no issue spending money on food. The other thing that I have been spending more time on in the last couple years is music and guitar and I, I don’t practice enough. Again, it’s sort of like fitness and health. There’s kind of an unlimited amount of time that you could put into like music and practicing, and if I put in eight hours a day. You know, assuming I didn’t have like hand fatigue or anything like that, I put in eight hours a day, I would probably make a lot more progress. And it’s super fun. I have been playing with a couple friends. I have a friend that lives, um, sort of south of. Denver, so he’s about an hour away, but he plays drums and we’ve been going to this spot where he could play drums really loud and then I could bring my loud tube amp and turn it up all the way. And it’s a lot of fun. Again, totally in a flow state. Lose track of time. It’s a blast. And we will, we’ll mostly just improvise and jam. We work together pretty well on that. Some people are a little more formalized and they wanna learn songs and stuff, and we will, we’ll both say, ah, yeah, you know what? We’ll, we will check out this song. And then even if it’s a song that I propose and practice a little bit, I usually don’t quite have it under my fingers. There’s very few songs that I do. But anyway, he’ll improvise, play, uh, some great drums, nice groove going on, and I’ll try to jump in and we’ll go back and forth and that sort of thing. It’s really fun. I don’t think we have any ambition to like start a band or perform in any way. However strong chance like, we’ll, we will work on something to have like intro music for this show and for my other podcast as well. So that’s how I spend my time, which was a bit rambly. So I appreciate you going along for the ride. Again, I did create notes today. The other thing I’m gonna cover is something that. I alluded to, if you’re a long time viewer and listener, number one, I appreciate that, that you do check out the content I’m putting out. However, the point here is you may have read in between the lines or if you’ve met me in person and you’ve asked me a few questions, um. Maybe at FinCon or other places like that, I probably told you. Oh yeah. Like I am not reinvesting everything back into my niche side. So we wind say to 2017 to 2020 or so, kind of the heyday of like niche sites and affiliate marketing in the way that we were building content websites. In those days and very effective, you could add a bunch of content. It was before AI writers and before chats, GPT. And if you were using an AI writer, you could tell the content was just pretty bad. And even a lay person could read the intro and think that this didn’t quite sound right. But if you rewind and you know what, I’ll broaden it, say 2015 to 2020. ’cause those years I, I think I worked pretty hard. I put on a lot of hours trying to figure out how to work for myself and basically. I was reinvesting some money back into the sites, sometimes a significant amount. So back in those days, I was probably only reinvesting 10 to 15% back into the sites, and some people probably would have said I was crazy. And I, I don’t think I like publicized it widely. And again, I didn’t keep track exactly, but if I look back. Probably something like that. Alright. And with the rest of the money, I, you know, paid for some living expenses, but largely like we just saved that money. And this is, uh, the part that is not financial advice. This is just what I did and I’m not, I’m not advising anyone on anything. We basically invested in low cost index funds and. Vanguard is the company that we primarily used. They are one of many that have these low cost index funds, and we generally went for the total stock market index fund. So there’s like s and p 500, there’s the total stock market, and they’re pretty darn close. The total stock market has like, I don’t know, 3,500 or 4,000 companies. S and p 500 has 500 of course, but they pretty much track, um, pretty closely and. Uh, that is pretty much what we did. So we just invested that money and I did, my wife did as well. And then, uh, there were good returns for several years and at some point, compound interest kicks in and. You are earning money, uh, via the interest. So people, you could look up the 4% rule, which gets you pretty close. But the shorthand of that is if you look at your annual expenses each year and then you multiply that by 25, that is the inverse. That’s a reciprocal of 4% is multiplying by 25, and that tells you like what nest egg you need. Now, that said, these days, um, some of the. Original folks that did those studies and the way the market has been in many other details. Some people will say, oh, maybe it’s 5%, or Maybe five and a half percent is what you could say. If we withdraw each year and never run out of money, that’s debatable. Some people say it’s 3% or three and a half, so you have to figure out what works for you, what you’re most comfortable with, and. You have some leeway, but essentially if you aim for 4%, that’s a lot of money. You know, uh, the other, I’ll give you an example just to make the math easy. If your annual expenses are $40,000 a year, then you would need to save $1 million, or you could double that, right? It’s, it’s linear. So if your expenses are 80 K, then you need to save. $2 million. So not anything to sneeze at, but if you’re in your mid forties like I am, and you’ve been saving since you were in your twenties, compound interest does kick in and everybody’s in a different situation. Like we don’t have kids, like some people have a family or you have to support, um, your parents or sibling or whatever, you know, aunt, uncle, fill in the blank, right? Like everyone’s in a different situation, but at some point. You end up with compound interest working for you. And I have, um, a couple friends where they, they actually like working. They actually like the, the corporate structure, which I, you know, I don’t, I don’t understand why, but there’s some reason they enjoy the corporate structure. Doug (2): Basically like I have some friends and let’s say they have, they have $4 million and the guy was like, ah, I thought about working again. And he’s been retired for about four years. He was like, ah, I thought about working, but like we’ve saved up so much money that. Whatever job he gets, it’ll be, he’ll be earning less than the interest that he is making on their nest egg. So again, if they’ve saved $4 million, if you take that, uh, you know, 40,000 number, multiply it by four, you know. 40,000, 1 million. So 160 K. So he is like, ah, you know, if I got a job I would make less than 160 K. And we’re making that by not doing anything. So he’s like, ah, I’m having a great time, you know, spending time with family. He spends time on cooking. And I just made up the amount that I’m not even mentioning the person, but he’s like, even if I got a job, I would not make as much as we’re making by not doing anything. So overall. That is like the idea of the, the fire movement. The financial independence retire early and. I’ve basically ended up talking to people who are roughly my age that, you know, they discovered it, um, in their mid thirties and they were doing most things okay, nothing perfect. Maybe they weren’t saving enough, maybe they had some credit card debt. Maybe they have, uh, car payments and a couple other things like that. But within. A couple years, they get everything on track, no more credit card debt. They’re watching their expenses a little more closely so they’re not, you know, mindlessly buying things that they don’t need and they get rid of the car payment. And within another few years, because they were doing most things right, not everything, they’re able to retire in their early forties. So many people I’ve talked to are in that situation where as long as they didn’t completely, um, disregard like any financial responsibility, usually they’re able to get things in place pretty quickly. There’s some other folks where like, maybe they, they. They didn’t pay attention, um, to any of this retire early stuff, but they were doing very well. Maybe they don’t have car payments. Maybe they, they, um, they’re pretty frugal. Anyway. They’ve been socking away 15, 20% in their 4 0 1 ks for, uh, 20, 25 years. And I’m thinking of a, a specific couple, some friends of mine, and basically they. Were getting tired of work and one of them was gonna get laid off and then they, they checked their numbers, they did some research, and then they realized, oh, we can quit working. So one of ’em quit within, uh, months, I think, and the other one kept working for about a year. Um, she just wasn’t sure yet about. Stopping work and she needed to wind things down a little bit and it allowed them to sort of like gradually get into it. One big advantage I had is I was able to slowly do less work as I was self-employed, essentially. I say I quite quit on myself. ’cause I was just like, you know what? I don’t like doing this stuff. And I, I mean, it’s the job that I created. I worked for myself, right? So I slowly like backed away from certain things to the point where. The work that I was, or the work I am doing now is distilled down to the creative stuff that I wanna work on. And I imagine at some point I will get a little bit more bored and think, oh, I want to actually do a little bit more work. One of those things, which has been on the back burner, is a book on laziness and anti productivity. So it actually fits in really well with some of the stuff that I talked about. Where I just wanted to work on the stuff that I wanna work on or nothing. And there’s some strategies and ideas that I’ve slowly, um, come around to. ’cause I would’ve been pretty resistant probably in my say. Early twenties to mid thirties, fairly resistant. But then, uh, the corporate structure kind of wore me down a little bit. That said, I think I have some innate like, um, self-motivation and I don’t get a lot of validation from like external sources so much, you know, whether that’s performance reviews or like getting promoted. Although if they fucking paid me more, then prob, I would’ve been like a lot more interested. It’s, it’s funny, it’s like the noisiest day. I think someone is, uh, throwing rocks around now. I, I, uh, it’s a real ambiance out here, but, um, basically like that book, it’s something that I worked on for a little while. I was working on with my old podcast partner, Carl Jensen, and we worked on it for a while and I think, uh. Carl was very busy, so he got part of the way done. But I think it’s something that I may take and spend more time on it. And there’s actually a lot of interest I get, uh, unfortunately now there’s people asking me about once a month. They’re like, oh, how’s the book coming along? And I’m like, ah, I haven’t touched it in a while. So nothing’s happening. So in an average week, I’m probably working about 10 hours per week. I also realized that there’s probably one week per month that I don’t do any work, and I either am traveling a little bit or. I just decided I’m gonna play guitar mostly this week. I’m gonna work out and then I just look at my email and make sure that I don’t need to, actually, I don’t even look at my email every day now, which is, uh, pretty freeing. ’cause you think, ah, I really have to, turns out you don’t, you don’t have to look at it every day and it’s totally fine. So the other part is, while a lot of, uh, people in the niche site industry, I think a lot of people did. Reinvest a great deal of the money that they were earning back into the sites. I did not. I only reinvested. Uh, 10 or 15% and then invest. I de-risk. ’cause I viewed the niche sites and that side of the business to be extremely volatile. And I learned that right away with some of my first sites where they would, they would get a lot of traffic, they would earn money and then they would, uh, tank and earn nothing. So I was like, this is way too volatile to like reinvest everything. I can’t go that route. So I de-risk and put it into another investment. And then over time, compound interest kicked in. And then it’s great. I really enjoy not working. I can’t imagine like working a full-time job. It would’ve to be something very specific and I can’t, can’t even imagine it. So the other part is, you know. You could spend your time on your hobbies and things that you enjoy. And most of the people that I talk to that have several hobbies, they end up having a really great time not working. I’ll mention there was a handful of people, I’ll make up an example too, but there’s a handful of people who are like, I’m gonna retire early, and then they try it. And then they do the thing that they thought that they were gonna enjoy, and it doesn’t quite work out how they think. And then they go back to work. And I feel so bad for ’em, and I think they’re making a huge mistake. 99.9% of the time. The example that I’ll give is someone’s like, oh, I want to retire and then I’m gonna travel. ’cause that’s the thing, everybody’s like, oh, I wanna travel. Most people would wanna travel more, but some people, they don’t wanna be away from home too much. And I real like, we don’t wanna be away from home too much. Everyone’s different. And some people wanna be on the road, whatever, constantly, uh, every day of the year, they just want to move into a van, fucking travel around. And that works for some people. But the big issue is like, if you think. You’re gonna love Van Life. And then you quit your job, you saved up a huge pile of money, and then you hop into a van, you start driving around, you realize, oh, this sucks. I don’t like being in a van. I want to have a more permanent place. But you think that it’s, um, the van and you’re like, oh, you know what? This didn’t work out. It looks like I better go back to work and then just automatically go back to work. There’s a decent number of people that do that, and part of it is like their identity and ego is tied up with their old work, and part of it is just like they’re not willing to test and and admit, I thought I was gonna enjoy traveling, but it turns out I don’t enjoy traveling and I should probably try something else. And they don’t test anything out, they just. They get their old company, they call ’em back and they’re like, Hey, uh, so and so quit. Do you wanna work here again? And they fucking go back to work and then they’re right back into the grind. And maybe that frees them ’cause it’s an option now, like they’re choosing to do it. They don’t have to do it. But at the same time, I believe the opportunity costs are too great to go back to do something that you. I apparently didn’t like before. ’cause there’s so much stuff you could do. You have infinite choices. So it’s when people think that they’re gonna enjoy something, they try it and then it doesn’t work. That’s when they freak out and they get a job again. And I think it’s a huge waste of time. Depends on the company. Like if you’re a social worker and you’re like, I wanna continue helping people, that’s great. Corporate structure, I mean, I’ve been meeting a lot of lawyers recently, corporate, uh, high level lawyers, high stress. They typically hate it and they, they quit and they’re like, I don’t wanna look back. I’m having a great time. I had like a consulting and engineering job. You know, a lot of consultants and engineers, they don’t like it. Once they get out, they’re like, this is great. I have a ton of hobbies and I, they work on that stuff. Georgie. You’re a good dog. ? All right. I guess I’ll try to play us outta here. Okay, Georgie, you’re a good dog. All right, Georgie.

Saying NO, Feedback, and F.I.R.E – DS581

Sep 8th, 2025 1:00 PM

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

Pivoting After Selling Niche Sites for $50k – Dave Fox – DS580

Sep 1st, 2025 1:00 PM

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

Get this podcast on your phone, Free

Create Your Podcast In Minutes

  • Full-featured podcast site
  • Unlimited storage and bandwidth
  • Comprehensive podcast stats
  • Distribute to Apple Podcasts, Spotify, and more
  • Make money with your podcast
Get Started
It is Free