Entrepreneurship Money and Life with Jason Coleman Cofounder of Paid Memberships Pro

LMScast with Chris Badgett

In this LMScast episode, Jason Coleman discusses insights into entrepreneurship, starting a consulting business. Also shares about important ideas from his company’s journey route map. In 2006, he and his wife Kim started their own consulting business.

Jason Coleman, CTO of LifterLMS and co-founder of Paid Memberships Pro. At first, they focused on e-commerce solutions, but later they switched their focus to Linux. Because of this, they made Paid Memberships Pro, a membership tool that became open source in 2012. By 2016, they were handling a virtual team of 15 people thanks to the help of this plugin, which helped them become a plugin-centric organization.

Jason looks at the value of open source projects, their involvement in the PHP community, and the inspiration behind PHP e-commerce development. Apart from the difficulties working with a partner, he looks at the need of reaching harmony and using effective communication. Their commitment to innovative ideas and community involvement has been crucial even if keeping competitiveness in an industry that is always changing and controlling their development presents difficulties. Jason counsels budding business owners to start small, experience real-world challenges, maintain a tenacious and strong attitude while open to honest criticism.

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Episode Transcript

Chris Badgett: Hello and welcome back to another episode of LMS cast. I’m joined by a very special guest. He’s a friend. He is co owner of Lifter LMS with his wife, Kim. He’s the founder, co founder of Paid Memberships Pro. We’re going to have an awesome conversation today. I know Jason really well. I think the world of the guy and I’m excited for you to listen in to our conversation.

Welcome to the show, Jason.

Jason Coleman: Thank you, Chris. I I’m happy to be here. I don’t know why it’s taken so long to get on this podcast, but hopefully this breaks the seal and I can be like your most frequent guest.

Chris Badgett: That would be fun. Jason and I have played around about starting a separate podcast by the way.

And so we want to hear what you think about this episode. But getting into it for those that don’t know you, at the beginning of 2023 you and your wife, Kim Coleman joined LFTR LMS as owners. You’ve been helping in the business. If you out there listening or watching is a user of LFTR LMS, and you’ve seen a lot of the great innovation and stuff that’s been happening over the past couple of years, Jason and Kim have been a huge part of that.

But I know Jason from back in the day when I first started using WordPress and I needed a membership plugin and I installed paid memberships pro, which they created. So give us the high level story of paid memberships pro where that started and what year it was and how that began.

Jason Coleman: Yeah, totally. So you’ve mentioned Kim a couple of times and.

It’s really Kim and I are married, but also business partners and been in business together since 2006 or so we started out as consultants building anything, lots of prototypes in the web 2. 0 era. And then we solely focused on WordPress and then focused on e commerce and then focused on membership sites.

And we. Back in 2010 or 11, we had four customers that needed membership functionality, excuse me. And we, didn’t like the plugin options that were there. We also saw how, building open source tools and making your code available and inviting other people to contribute and share and hosting your plugin on the wordpress.

org repository, that was a way to you don’t get more exposure for the software and more people involved. So we build a membership plugin for our four customers and open sourced it around 2012. Sometime in 2016, we were able to switch from being like a consultant company with a plugin to like a plugin company that only sold support and updates and, stuff around the plugin.

So since 2016, so now we’ve been growing just slow and steady every year. And at this point we’re about 15 people on the paid memberships pro side. And we all work remote updating the plugin, maintaining it, taking care of our customers.

Chris Badgett: One of the things I love about Jason is he’s a very humble dude.

And so I always find out things like, Oh, wow, this guy’s really good at investing, which we’re going to talk about later. But back in the day, you had an investing blog and you had a wine blog Gary Vaynerchuk, tell us about that, like your blogging era there.

Jason Coleman: Yeah that, and it’s turning out that like that’s like a magic moment of the internet where, like when blogging was taking off, that people were interested in things could write about it.

And that, that was useful. It wasn’t like right nowadays, there’s so much Content is automatically generated and generated for business. And now AI is generating content and social media is so fast. We there’s some blogs around that still work, but we, really don’t have the attention for the, I don’t know the golden era of blogging.

So we had a investing blog with a three friends. I think I met Gary. I. We had a site wine log, which was like a kind of social network for wine drinkers to keep track of their notes and things. And Gary advertised on the site. And I remember giving him a hard time. Like he, I forget what it was. He was like going to pay me 600 bucks and I forced him to pay me like whatever the industry standard CPM was.

And he’s like, all right, man, you’re driving a hard bargain. He’s you might regret this. Cause it’s more important, the biz dev than the 600 bucks. But but. He pay for the ad. That’s funny. And so at different conferences, I used to run into him back in the day when he was doing the wine library TV thing.

Chris Badgett: And then the

Jason Coleman: investing blog, like what happened there? Yeah, that was interesting. Like I thought we did, a good job. So it was just me and two friends. Like we newly out of college, we had like 401ks, but we didn’t know what they were. So writing about something forces you to learn it. I was really interested in it.

And so it was as we invested and thought about investment, we just wrote about what we learned. And part of me regrets because we, it got pretty popular was like one of the top whatever, what was the site that used to like rank. Blogs, but we were always fighting for the top five investing blogs.

And I think the three of us had different separate ways. I tapped my table. Sorry about that. And and so we never really got to lean into it, but it’s always, so it’s been a hobby of mine, but that really is like the first time I used WordPress was for that investing blog. And it’s still around that one.

Investorgeeks. com has the old content and it’s like a lot of it holds up. As the economy goes through a cycle again, like the last time, like the yield curve inverted, I was like, Hey, what does this mean? What’s the yield curve? It’s Oh, this old Jason kind of is pretty smart. He did some research.

So it’s funny.

Chris Badgett: One of the other stories I love that I don’t think gets enough attention is you created possibly the first e commerce transaction on WordPress. What was that about?

Jason Coleman: Yeah. It’s like hard to claim that. When I’ve, I was talking with you about that. Made me think, is there a way I could validate this and I’m certain I wasn’t like the very 1st, but definitely 1 of the 1st.

Kim actually was still in college and she went to a business school and had to like, start a business in a quarter and they started a laundry service. And so it was a website. Built on WordPress do something maybe, or like 2000 four ish, and we embedded PayPal into it. And then after that we, got other customers and we embedded like OS commerce was a open source.

It’s still around, I think PHP based we embedded OS commerce into WordPress. And then sometime around 2006, we were like, we should build like the e commerce directly into WordPress instead of taking another tool and swapping it in. So we built like an early e commerce plugin, but we only managed it for like our four customers that were doing e commerce and they integrated with PayPal at the time was like the only gateway really in town.

And so we saw it was awesome. It had like integration with FedEx shipping. And I always thought the way that we did options was pretty clever. But it, yeah, it was, so that was back in like 2006, we were building e commerce in the WordPress. And we saw how the open source version of that WP e commerce was like the first big one.

There was one called shop with two P’s. And then later Jiggo shop. We’re like, it’s like, Oh, like you could build this in an open source way and share it with everyone. And other people would use your tools and that helps build a better tool. But also I, feel good that we can enable people to make money on the internet without having to be like they’re single developer on a single site.

Chris Badgett: Yeah that’s, awesome. Piece of history there. And I’ve heard you interviewed before, so we don’t have to park on it for long, but people always ask you and Kim, what’s not, what’s it like to work so closely with your spouse, but you guys do a really good job and I’m sure you have family stuff and whatever, but if somebody is like thinking about working with their spouse or trying to make it better, what.

What’s the big lesson that you’ve learned there, one or two things that like make it,

Jason Coleman: man, I, don’t know if it’s something you can learn. So it’s you have to try it. I suspect definitely not every couple can do this, but if it does work, it’s awesome. Cause you get to spend Kim and I get to spend tons of quality time together.

And actually now that the business has grown, we have different. Areas that we have to manage. We don’t work together as much. And it’s man, can we just like work on a little project together? That’s really fun. First like just managing different teams and, bring in each other, like the headaches that come up in like normal course of business.

But I guess like some tips, we were both the type of people that work through problems and don’t take things personal. And so we’re able to get heated, about work things and then separate it as good as possible. It doesn’t always sometimes it bleeds over into the personal life.

But we’re good in general. Outside of business, when there’s conflict between Kim and I or things coming up We talk and communicate well and solve it. So that, like the, fact, if you can manage that part of your relationship well together, that’s like an indicator that you can manage those same kinds of issues in business.

And then like it is, it’s good to, set time for each other and the typical things of Hey, we’re not working now, but it’s harder, especially like you work from home in the home business. And you were so when we hang out, we go out to dinner, we’re talking about work.

It’s interesting. Yeah. And we, try to make time for other things, but we also don’t get too hard on ourselves. I think Alex or Mazzi had, or Layla they’re another like couple that work together and they, say we just we’d doing the work, like I don’t feel guilty about it.

So that’s good too. I don’t feel guilty. Like we got to dinner and we talk about work. It’s fun. Like we’re enjoying building stuff together. So we, don’t feel guilty about it, but we do try to make safe spaces where it’s like, Hey, we’re with the family, with the

Chris Badgett: kids, we’re doing all this stuff.

Speaking of building stuff together we’re part of the creator economy. We create software, we’ve done blogs, we make content. What’s your view on how the creator economy is, what it used to be and where it’s going, it seems like it’s having a moment right now where like creator, it’s like, there’s a lot of desire and drive.

For people to build creator businesses, but it’s always been around change. What’s your perspective there?

Jason Coleman: We are riding a wave of people selling themselves online in some way, creating courses, content. And so that’s been interesting aspect of the business. And it, feels like that kind of thing is.

Going to continue that, we’re building all these tools for people to start these online businesses. They’re going to use them. What, one of the most important things about this is just I even don’t really understand it as the scale of the internet. So there’s so many people out there. And, so when you sell a course or some content online or a membership site.

Your total addressable market is huge. Even it’s just it’s not just like the little town you’re in. It’s like all of America, but also all of the world. And I think so some stat is like for every 22, 000 people in the United States, there’s a McDonald’s. So if you like, that’s like a unit of a metric.

And so if there’s a McDonald’s, there’s probably like a law office, like a garage to fix your car like all these services that a dentist for every 22, 000 people. So if you imagine like the 22, 000 people around the McDonald’s is closest to you could you sell your course to 1 of them?

Okay, cool. Now, There’s not 22, 000 people in the world. There’s 3 billion people on the internet. I did the math earlier. It’s 150, 000 times more people on the internet than like around your local McDonald’s. And so it’s 150, 000 is like a huge number. So if you could sell one person at the McDonald’s, like over the course of a week, there’s 150, 000 people like that person in the rest of the world I don’t know if the math works out.

And it’s that’s just why, and that’s, I think that’s like the, one of the secret sauces of why. This career path is so successful is that if you really can build something that people need in one. There’s, you can find the audience online and that’s not easy. That’s work sometimes.

But if you do there’s tons of money to be made and also you’re making a bigger impact. If you are in the education space and you’re teaching people. Like it’s very admirable to be a teacher at a school and you get like a classroom every year, 30 or so kids per year.

But if you’re teaching online and you can hit 150, 000 people every year, it’s just like a bigger impact. So I think that’s why people are drawn to the space.

Chris Badgett: One of the core missions of paid memberships pro is helping people get paid. Where does that where did that mission come from? I can see it in the thread of your story, like, all right, I’m deleting commerce.

On WordPress and figuring that out and helping facilitate the money to go through you’re trying, you’re, you built your own creator career, but where does, what’s the genesis of helping people get paid?

Jason Coleman: I remember I was on a, like a radio show in the Philly area. And the interviewer kept pressing me like, what did your parents teach you about business?

And at first I was like, nothing, man. I’m my own, I’m self made. Like they had nothing to do with it. I did this all myself. And I I was like, I don’t remember that as childhood. Like I this is my adult life. Why are you keep pushing me back to my childhood? He’s there’s something in your childhood that did it.

So it forced me to reflect. And I was like, they’re absolutely right that when I was a child, like my family had money problems, I came from like a middle class maybe like lower middle class. And when my parents got slightly better jobs, moved up a little bit family and like money was tight.

I saw money problems. And my dad would talk to me very openly about it. And he was optimistic about he’s you don’t want to work in a factory like I do. You should be a doctor or a lawyer, or you could do more. Like he was, he opened my mind to like entrepreneurship, even though he didn’t do it himself, he knew it was an opportunity.

And so as a child, he’d have these conversations with me and he always encouraged it when we did it as kids, like we were selling newspapers on the side at school, we got in trouble. Cause it was like a underground newspaper verse, like the official school newspaper. And like selling candy to your friends and stuff.

Like I was always doing these entrepreneurial things and my dad He saw that like I was a path and so instilled in me that if you have money problems, you actually can address them. You can take control of them. And, I took that in my childhood and whenever it’s you got to get to college and you need, how do you get scholarships for this?

It’s figure it out. You want to get a car. So I, and, and so I saw the flip side of that, both like the people who don’t have money, and then people also who feel like. They don’t have the power to do anything about it. Like they feel victimized by it. So I was like, Oh, like it’s, it feels good to build these tools to help people get paid and then also teach them how to use them so that they can.

Take care of themselves and also like associations and charities that use our tools collectively use the money to like, to do good in the world that that they want to do

Chris Badgett: speaking of building tools, why open source, like, why is that important to you as a engineer and entrepreneur?

Jason Coleman: Yeah, so part of that was that story of when we had basically a closed source solution for our four customers, they were the only ones who could use it. So I see it as a way of putting making it public and available for others to use. And then I also feel like it makes the best software. The more people who use it, the more people who get involved, the more kind of incentive and motivation it is for a random consultant implementing it for one customer, finds the bug and helps you patch it.

So I was It seems like the way to make the best software. And then I think I there’s also like this kind of like business model, like the business model aspect of it, of giving it away for free and just charging for the services that for some reason that bothers me, like when a business model feels like a tall.

I think I, I developed this like watching the MP3s Napster music industry phenomenon. And there’s a version of that going on with AI content too, where like the technology Is moving in a direction and it’s get on board or there’s like a physics of it of information is free.

And like the cost to clone an MP3 and give it away is free. So it has to happen. Like people want it for free and they don’t want to pay for it. And you set up a toll. It just, it doesn’t feel right. So I kind of business models like that where like software is you like charge for it and you only give it to people if they charge.

Like it, it just feels. I’m fighting against the physics of the information of the internet. And so I was more inclined to like, hey, give it away for free and then find ways to build businesses on top of that get people using it. And then if I’m helping people make money and saving time and stuff I’ll find ways to make money business.

On top of that,

Chris Badgett: you’re probably one of the biggest champions of open source. I know. And in some ways you take it the challenge to be even more open source than WordPress itself. What does that look like to you? How do you think about that? Like, how can we be even more open source?

Jason Coleman: Yeah. Like one kind of specific way is that the code that we write all, we make all of it publicly available on GitHub.

There’s some internal tools that aren’t. And sometimes when we’re starting a new project, we keep it private for a little bit until it’s ready to go. But otherwise all there’s 198 repositories or so stranger studios, every line of code is on GitHub. So people can. Interact with it, but also use it like it’s easy to like, you download a zip file, you install it and run it like there’s no kind of complication.

There’s no service required to get it running. The same exact plug in that you would get off wordpress. org. Or if you come to our site and give us money or go to get hub, it’s like the same exact plug in. And as a developer myself, that just enables so many things like weekly, I’m working on something.

Just today it was or I was building something and I know that this other company has a similar thing. And I’m like, I wish I could just look at that code and see how they do it. And I know I can get it. I can go to find someone who has it or buy it from them or GPL vault.

It’s like weird that I have to go through these hoops to gain access to the code. Because what we’re going to end up doing is is building a better thing. So I don’t want. That friction on our, software. They’re still like putting the code away for free. And I feel like when automatic bought WooCommerce a few years ago, I know WooCommerce had closed repositories for their plugins and be at that time, most of the WordPress plugin type stuff automatic did was on.

org and open. And so I was like, what’s going to happen here? We’ll like the automatic influence over WooCommerce and their plugins will get open or will. The WooCommerce kind of business aspect, charging for software. Influence automatic. And I think the latter happened, like you still, the extensions.

And as I’m talking about this, I’m not judging. I’m just saying what I see out there. Cause there’s very valid reasons for doing things the way that they do they, and they have business relationships with all the developers who made those extensions and they feel that keeping the code hidden will drive more revenue.

What I’d like to do a naturally lifter could be an example of this. Also has Extensions that aren’t fully open on GitHub is we can test that because I saw it with our own plugins that it doesn’t seem to have an impact on revenue with some of the sand hill stuff that they did before the awesome mode of acquisition.

I think they’ve had repositories that went from private to public, I believe, or either the other direction. They didn’t see any change in sales. And so I think we can make money off, other things than just keeping people from using the tool. And I, also, it’s we’re motivated to get people to use the tool.

Like I, if someone uses our plugin and makes money off it and I’m not involved I’m like, that’s great. That’s actually the goal is Like I’m doing well, we’ll do well enough. We’ll make enough money to maintain the plugin. Like my real goal is to get as many people using the software as possible.

And that’s not the goal of every business out there. There is like a weight of a user who’s not paying you and you have to support them and stuff like that, and it’s fair that businesses make business decisions to not support people that aren’t giving them money. But it’s weird. I I was watching a Sam Altman interview.

It’s like weird to compare myself to him. He’s like the most popular person in the planet right now, but, but something that rung true with me that he was talking about how, when, they did some kind of reformation of open AI, he didn’t take any equity in the business. And people were like, why not?

He’s I’m already a billionaire. I don’t need any more money. And they’re like, so why are you doing this? He’s I want to build AGI and give it to humanity. And everyone’s yeah, but what do you really want to do? What’s your real goal? Like people don’t trust that’s his incentive. And everyone.

He said on an interview, something like, if I just took a bunch of money and said, I’m trying to make as much money as possible, they’d be like, oh, okay. And then he can make the money and give it away or something. It like society and the business partners and everyone would accept it. More readily than him saying I’m just trying to make cool software.

So I feel like I’m in the same boat. It’s a different kind of thing. Like we’re making a membership plugin and he’s making like AGI, but I’m like, I’m really just trying to like, that, that is the goal. And I struggle with it. Cause it feels like you’re fighting, like going uphill. It’s, like, it’s similar to that, like the physics of the information.

I’m trying to like, go with that wave, but there’s this like capitalism saying nah, man, like people understand when you’re asking for money. People understand when business relationships are incentivized by the money involved. It is like the common currency of like how deals get done. And I don’t I know it’s a strain that I got to work out in the business.

Chris Badgett: And that’s not a magic trick. There is value for paying for the software and accessing the support team and having automatic updates. Like it’s not like a win lose scenario. My big takeaway from listening to you is there’s the physics of innovation. And if you really care about that and care about an open source and decentralization and empowering people, that can work with greater velocity if you are truly open source and you can still build a business around at the same time, it’s not mutually exclusive.

Jason Coleman: Yeah. Yeah. It’s you don’t want to fight those factors. I think maybe like a tip that helps like the course creators and content creators out there too, or if you believe in this thing I’m talking about, it’s similar to that MP3 analogy where Spotify is the way people get their music now or similar tools.

And it’s all about the easing the delivery like they they, I’m grasping at the words here, but it’s not the actual music that they deliver. It’s the, the ease of use, they make it easier. They package it better. They, bring it to all the devices where you want it, They make it as fast as possible, all that stuff.

And I think there’s a similar thing in the content space where I’ve often told people, and I’d like to like, hands on feel this experiment. Cause, To know that it really works, but a lot of people are scared to put their content out there, or they have free content and they want to make paid content.

And now they feel like their paid content has to be better. And it’s no you already have the awesome video that teaches someone how to stop, quit drinking or how to build something or how to connect this tool. You don’t have to make a better version of that. You just have to, ease the delivery package it up in the right way that the people want, find the customers where they are and put it in the format and everywhere they want it, like just value in that. So that’s very similar in terms of like music. It’s all about delivering it to them in the way that they want our plugins with delivering it to them in the way that they want.

We make it easier for them. They’re happy to give us some money to do it. So they don’t have to download it off, get hub and figure it out on their own. And the course content that we give them, they can find the same stuff in YouTube or ask chat GPT, but. If we deliver it exactly where they want it in the format that best works for them.

And, also maybe like we segue to the AI conversation, like with the human touch people, you can ask chat GPT about things and it’s getting more and more knowledgeable and smarter and able to browse the web and figure things out and reason, but people still like learning certain things in particular from human, other humans.

And they, like chatting, I think like communities becoming more popular. It’s that’s like a, that’s a thing that you. Putting these people of like interest in the same chat room to talk with each other and facilitating that is that’s something that, you that’s valuable that people are willing to pay for it.

And it can’t be automated yet. Maybe that’s an opportunity to automate it. But,

Chris Badgett: Yeah, you have a lot of experimentation with AI and have studied it and language models and all this. And you’re definitely on the front end of all that stuff. What, how can course creators, people building coaching programs, membership sites, just building websites in general, what are some of, what are some of your principles around AI and where it’s going for the creator?

Jason Coleman: Yeah, it, for myself, I’m, trying to have an AI first mentality when I’m solving problems or doing work where. I might like struggle through a first draft on my own and I’m like, man, the AI is really good at taking my notes and turn it into a first draft take my notes turn into a first draft.

And so that’s 1, 2 is if you really embrace the tools and use them, it can speed up a lot of things and it can get you over these like creative humps that you have. And it’s It’s very similar. It’s like writing in particular, but there’s analogies to video production and other things is it’s easier to make a bad first draft and then go into edit mode and edit it.

And so using the AI, it’s like good at both those things in different ways. It’s it can help you get that bad first draft more quickly and it can also help you with the editing. So, like embracing the tools is good. I do think like in terms of the type of content the creators are making, AI is going to have an influence.

So in the short term, there’s going to be this phase where humans plus AI will make better content than AI alone or humans alone, even, and that’s similar to what happens in chess and poker and other places where computers got really good at playing those games. If you think of course, creation as a game the computer is getting good at it.

I don’t know how long that phase is going to be, but say it’s 5 years, you got to so embrace the tools and try to use them. You’ll be able to make better stuff than without it. But again back on that, like the type of content, I think, there was a kind of content that was mostly informational, It was like how to pass a test and, the language models have a lot of this even built in, or they can figure it out, they find it.

And I think they’re only going to get better. Like the, it’s just like the MP3 world, like the data’s out there. Even if the LLM in some way is going to consume someone else’s old course, regurgitate it, you can’t stop that from happening. Like the information, so courses that were informational I would fade those.

They seem less useful because people are going to have these answers, like really good versions of the answers at their fingertips, but there’s other kinds of courses, like I said, like community type stuff, bringing humans together, stuff that’s like IRL in the real world, almost what are the best places to eat in Paris is like a better course maybe in the future than how to pass X, Y, Z test because people want a human to answer obviously the LLMs can’t eat yet.

But like people, they can aggregate reviews but like people, even if you could get like the aggregated reviews and you get like the human aspect, like people want that content from a human. So I think actually ask that question, what kinds of content, what kinds of interactions do people.

Yeah. Want to do with a human, I think like art is big. So even though the generative models are good at writing, they’re good at painting and making images and stuff. There’s something like human about art that like, it, like it devalues the art when you can just ask the computer to generate a painting and you’re like I’ve seen this in my, I felt it.

Other people probably interact with these tools. They’re like, yeah, so what big deal. And you’re like, so you’re not amazed by the awesome painting of a dragon in space and like neon colors, but like art, like the story of the art, the connection to humanity, the connection to your own story, like all that stuff is real and you can’t, you can’t make, it’s not artificial.

You can’t make it. So that kind of stuff will have value. So I think like communities, stuff that’s in real life, stuff related to art, people are going to value, like learning about that stuff from humans.

Chris Badgett: What’s your take as an engineer and a developer with AI? If you’re, let’s say customizing, you want to write a custom plugin for paid memberships pro or lift your LMS and you’re not a developer.

Can AI do that? Maybe not now, maybe in the future. Like how do you use AI as a developer and where do you see it going?

Jason Coleman: Yeah, it feels like the tools now. are really good for experts and also good for training, but like a little dangerous in the tools in the hands of a beginner. And I get in certain contexts that’s okay.

But if you’ve never programmed before you like 90 percent of the time, it’ll be like 95 percent of the time, maybe 99 percent of the time you get code that works. And that’s exactly what you want. But that 1 percent of the time, like if you don’t understand. And it’s more than 1 percent now, but this stuff will get better.

But it’s often making like little mistakes, adding S’s to the end of something that totally breaks. And so people using the tools, it’s good. I tell my teams, it’s you have to check every single line that of code that the AI writes. And you, have to understand every line of code. So it speeds up the process, especially for some like tedious things that when you’re programming, there’s like tedious things that you do.

And the AI is just here’s a pattern and then you, similar to like writing content, it helps you get over that hump it gives you bad code and then you fix it up. It’s really good at if you know how to, so if you know how to program one language, it’s really good to help you learn another language.

And so that’s good. Like when the world is changing and it’s like, Hey old, timer. Now learn, react it’s shoot. And it doesn’t feel like starting at square one. It feels like you get a couple of steps ahead. Cause the, the co pilots and things like that, help you pull it up.

But if you have enough programming knowledge to know, like when something is wrong, It helps a lot. It saves time. I it’s, almost, it’s almost, it’s like calculators in school. There’s a reason to learn it’s hard. I think education is tough with LMS. Like you, you have to not have that tool.

So you learn how to do it with your human brain and appreciate it. And then okay, here’s a tool. And you’re like, oh my God, now I can do so much more. But these language models and AI now, they’re also good tutors. Like they can watch you, what you’re doing and help you learn. So there’s such a temptation, like it can just do it for you, but there’s still value in learning how to program, I think.

And you want to try to use the tool to help you learn rather than just like leaning on it to just give you the answer. It’s tough. I don’t know.

Chris Badgett: Crossing back over to the human side, if or one of the things I love about working with you and Kim is. You’re positive people, right? And you treat people well and, but you navigate complex and situations, sometimes conflict.

What I’ve learned is I know you have as well when you’re reaching, this, those so many people, the one out of 22 at every McDonald’s around the world. You’re like interacting with humanity at scale through the internet. Sometimes you get treated, a little nasty, let’s say, like in a support ticket or, just some kind of communication or a review of your software.

Even just more broadly, like working remotely when you’re not like in an office together or whatever, like sometimes people behave differently than when they’re in person, pressing the flesh, how, and it can hurt people especially if you’re sensitive and empathetic. And somebody treats you nasty when you’re trying to provide this tool and you’re genuinely care about helping them.

And how do you, how have you, it’s not just like building thick skin or whatever, like how do you navigate negativity when you’re operating at scale on the internet?

Jason Coleman: Yeah, this is, important to me. Cause I like, two reasons. One is, like you said, it’s not just developing a thick skin and getting over it I don’t know, you can’t get your skin thick enough for those negative interactions to not ruin your day.

Like the first time I I yelled at my kid cause I was like, In a mood, because I was talking with a bad customer in the morning, it was like, wow, this is wrong. I have to get a handle on this so that the negative stress of work doesn’t bleed into my, the rest of my life. And then I also, I talked to other creators, people building products, you want to sell things and they’re like, oh I would, do that.

I’d rather sell to a small number of people. Cause I don’t want to deal with the backlash or I don’t want to go on Instagram. Like people are gonna make fun of me or talk this, or I don’t want to do this. Cause these people get upset. So people are making business decisions based on like their perceived inability to handle the negative feedback in certain cases.

So I, there’s a, I’ll talk about this. I have a blog post called dealing with haters on the paid memberships pro blogs. So if you search for that, you might find it. It lays out a lot of this stuff, but, there’s some things like you can do some things to prevent it. If you have a all money guarantee give them their money back and get them away from you as soon as possible that can diffuse it.

So you don’t even have to deal with it. You can, process your refunds quickly every time someone gets upset about something like we often end up adding a line to our terms of service or tweaking on this line here. Like famously someone said you said this would be easy.

And I was like, who said business would be easy. I was like, so I was like, told the team. Scrub the word easy from our website, which is it’s like inverse marketing. Like everyone’s like the easiest plugin. And I was like, this stuff ain’t easy. And I was like, we got to find like other messaging.

That’s not easy. Cause of course we’re trying to make the software as easy to use as possible, but dude you’re, building a business. Like it’s not, going to be easy. So yeah, like up to Managing expectations helps, but you can’t avoid it because as if you go from 30, we went from consulting the products.

So we had 30 customers a year, maybe. And you could deal with it. And then actually like the way to deal with it, it’s different. Like when, you’re in consulting, you go above and beyond and someone’s getting out of line. You would just find the time poured on them over deliver.

Clear your conscience and then stop working with them, but you really could pour on the love and give them some good stuff to smooth it over but you have 30, 000 users, like you just can’t do that. And there’s so many more people who are just having a bad day.

There are raids, they’re having to fall in through the cracks. They’re upset. And they lash out at you. So so it’s like finding, so some tips too, is look for that criticism. So like I said, update the terms of service and your expectations and your copy is there positive feedback in there?

Can you like pull your most, not get defensive and be like they have a point we messed up here so you got to look for those, you can like a trick I do is like you write a draft. So to get the energy out someone calls you an asshole, try delete the email address or whatever it is.

So you don’t actually accidentally send or maybe copy it into a notepad and then type up like what you really want to say to this guy. A couple of those leaked out and got out when I’ve done that in the past. Usually I get it out of my system and then you okay, I got it off my chest. And I can try to respond to them in a What’s best for the business and them and everyone else spectating sometimes in public forums on this stuff.

I also like, yeah, just always. Reply professionally you don’t want to get involved. You don’t want to lead them on. There’s the isolate. Isolation that’s important in a number of ways. 1 is, like I said, make sure that you’re not answering customer support from your phone at the dinner table, where your kids are around do it at a time when you have time before and after.

To transition, so try to like, if you’re doing that activity, don’t just do it whenever it comes up, schedule it so that you’re doing a certain time. Also we get the higher folks to handle the support and I always try to monitor this. I feel like I’m like, putting them on the front lines of a war to like, deal with this negative energy.

Some people are just better at doing it. So they’re okay. They’re also like, they don’t take it as personal. I assume they don’t take it as personal because they’re not invested in it. Like we are. Or sometimes you’re literally saying like Jason I’d want to punch Jason in the face. So if you’re not Jason and you read that it, it, hits different.

But so we gotta take care of those people cause they but you can hire people to insulate you from it. And then so you’ll get the stress from these things. I think also like, I think I’m gonna say is you I said, you can’t avoid it. It’s going to happen.

And there’s different people who said versions of this, but like anything that’s useful and beneficial to the world is going to have people who hate it and fight it. And you don’t want to like, you want to listen to it as much as possible, but you’re like, like you can’t avoid it.

So you have to deal with that stress. And I started meditating. As a practice really helped a lot to separate and slow things down. So I’m not as responsive. Another tip then in isolation, buddy system, having people help you. Another one is like engaging with happy customers.

So we’ve done this almost as a cleansing, you get a bunch of 1 star reviews and you can, if you have access to your community through a newsletter or slack space, You can just be like, Hey do you all mind writing a positive review over at this place and just send them the link and you’ll get a few, or ask for feedback from your happy customers that like you, and you’ll get some of that.

So that’ll help warm your heart and counterbalance the negativity bias that we have in dealing with these things,

Chris Badgett: so many good tips. If we shift back to helping people get paid or just thinking about money in general, one of the things just watching you operate over almost two decades, is that’s two decades.

You’re in the long game. There’s this thing with creator economy, get rich quick, or if you’re building software, build it up and scale it and sell it as fast as possible. But you tend to, you’ve shown like. Long game chops, like playing the long game. What are your thoughts? Or, and I’m not saying that get rich quick is even a bad thing or scaling and starting software, scaling it fast and selling it as a bad thing.

But what’s, your take on the long game versus the short game when it comes to making money on the internet?

Jason Coleman: Yeah, I think there’s many paths. And so there are those other paths, but. They’re very shiny. So people are aware of them. And maybe it’s not as shiny to just have a business that grows 2025 percent per year for 20 years.

But like compounding interest, you’re like, oh, that goes from making 150, 000 a year to making 2 million a year over a few years. And so My personality is like conservative with money in a sense. Like I didn’t like taking loans or pushing for like huge wins in a sense, I we, really just always, we have an old spreadsheet when we did consulting that was how many customers, what’s the average price how much money can we expect to make?

And then the fun thing is we’ll try to grow 25 percent per year and you drag the Excel sheet down. And then you’re like, I don’t know the money we make. But the hard part of that, so that’s easy. You’re like, cool, the number moves. And I like that target. The hard part then is it forces you to figure out okay, how do we actually do that?

How can we actually make 25 percent more money? We’re either raising our prices, getting more customers or selling more stuff to the same people. And, that’s how we operated. And I guess we started there at the business. We were just Let’s try to grow. How are we going to do it?

And at some point it made sense to flop from like consulting the products. And maybe at this point in our life, we’re we still set those growth targets, but we struggle with do we really need to grow? Cause we’re, but, yeah, so maybe it’s just my personality. I think, yeah, like it’s good to know it’s an option and there, there are returns in this.

I think I’m benefiting in ways and I’ll continue to benefit that. Becoming an expert in the same thing and kind of driving home the point and working on the same thing over so long. You become an asset to the world as long as that thing is useful still. And all the people who are in it for the get quick, rich kind of bounce in and out.

And I think probably our plugins are in a phase where. There’s a lot of consolidation in the WordPress space. And this happens like in other spaces too. But we, if we’re well run profitable businesses that don’t have these issues, cause we didn’t like swing for the fences and waste a bunch of money. And so we can just sit around and as the competitors fall, we can hopefully we can pick them up, but we compete with these giant public companies.

It’s easier for them to pick up the pieces. So that’s something I have to figure out, but yeah. Yeah. So it’s like sticking with it. It, yeah. Compounding. Like it makes sense in investing the compounding interest is hard. I used to, but it also happens in terms of like your skillset and your ability to influence the world that compounds to, if you stick with it.

When around investing, one of the things I did on the investor geek site was like a spreadsheet where it was like, if you you could buy a brand new car now, or buy like a used car. And I forget it was at the time, if you save like 10, 000, all right, now invest that 10, 000 in the average stock market returns.

And then in 25 years, you’ll have a hundred grand or something like that. But I remember like enough money to buy a sports car when you’re going through your midlife crisis. So it’s like you’re fresh out of school by the use car. Now put some money away in, in an account, let it grow. And when you have your midlife crisis, you can buy a Porsche.

And so like that, like spreadsheets can show that compound growth when we don’t really feel it. It’s hard to delay gratification that way. And I, for some reason, it’s easy for me with money and things like that. It’s harder with eating the best food in the restaurant. It’s hard for me to eat a little less to delay gratification into my old age.

Chris Badgett: But yeah. Speaking of compounding, I think it was Warren Buffett who said the eighth wonder of the world is compounding. It’s one of those things like. The scale of the internet is really hard to comprehend. The power of compounding is really hard to comprehend. One of the things I look up to you with is your experience and skills and advice and investing.

And we could do a whole episode about investing. So just to frame it in for the creators out there, or if you build websites for clients, or you’re getting you’re getting paid and you’re able to like you’ve got your cost of living down and you’re thinking about what should I do with this money?

How do you think people that are new to investing should think about getting in the game and you know You can invest in your business. You can invest in yourself and your own education There’s stocks, real estate, crypto collectibles. There’s like all this stuff. And like how would you advise like an, a newer person to investing to start making some smart moves?

Jason Coleman: And yeah, maybe so a fun, maybe a fun, humble brag story to set the tone. I guess people understand investing is important. But we’ve always, we’ve worked, Kim and I have kept our expenses lean. And, always have been like set targets to invest. So it was there was a time when it was like all the money went away, we run through that and then we were lucky enough to have this skillset that we could sell.

And we we became, Hey, we can live and eat and do things. But then we operated lean so we could always save money. And so we’ve always been saving like 10 or 20 percent of our income over time which is a lot. Not everyone can get there, but we, kept that as like a, as a goal and I made some good moves in Bitcoin and Netflix and Tesla and whatever.

But the power of that is that like recent, like a few years ago, there’s this consolidation and WordPress space and people are trying to buy the plugin. And I was like, we should talk to them like this March, let’s talk to everyone and hear their best offer. And they’re making offers and they’re like, dude, this could be life changing money for you.

This could be life changing money for you. And I remember talking to Kim, I was like, what’s your number, like what’s your number that like you would need to sell the business and get out. And she gave me a number and I was like, We already have that much money. Like we’ve invested well and sure.

It feels good to have a lot of money, but it was like, I have the freedom. I didn’t have to sell my business to someone to make that money. Cause I want to send my kids through college or cause I don’t want to work. I, have the free, like Kim and I have the freedom to choose to show up and do this instead of being forced to, and that’s partially due to saving.

Being disciplined about money, saving money and letting it compound over 15 years, but so that’s it. It’s you want to, save, you want to get to that spot. If you have to spend all your money cause you’re you’re. You’re only making enough to really sustain yourself where you’re living.

You have to get there first. And then it’s you want a skill that the world values, you can parlay that into making money. So you want to set aside a big chunk. It helps to like, do it first, have a separate savings account. Like when the money comes to your check ins account, always put some into the savings account, that’s that’s the money to save.

And there’s a number of ways to do it. Like you should invest in your 401k or IRA. Most people should just invest in like total market funds, like the VTI, the NASDAQ funds, like technology. That’s like maybe one tip if you want to be like a little risky is put half your money in the QQQ, the NASDAQ has most of the tech companies.

And if you’re optimistic about technology, like I am, like they should outperform, like they continue to outperform like they have in the past. But, If you start picking stocks and things, I do that because it’s fun. I realized, it’s in my wheelhouse and especially the technology stuff that I have an understanding of how it all interplays in the players and the companies and what they’re doing.

So when I hear Microsoft say, we’re going to make AI that will change the world. And Facebook says, we’re going to make AI that will change the world. I can judge who’s really going to benefit from that. In other areas where I don’t have domain expertise, like, the energy sector or in pharmaceuticals, I, they all say the same thing.

And I was like, I can’t pick which pharmaceutical company is going to outperform. But, you want to keep it simple. And there’s different ways, the, what’s that little book of invest in John. Bogle is like invest 60, 40 portfolio, something simple. There’s timeframe ETFs.

You can just you can buy like a I’m going to retire in 30 years and they just generally invest in the stock market. So specifically what to do, like you should do that. So it Hey, make enough money to get by as soon as you do set up an account. That’s separate from your main checking account.

So you can hide the money away and you don’t feel it. And whenever you get a raise or you make more money, set aside a certain percentage of that goes into the investment account and then regularly move that money into a very generalized, Investing scheme. And that’s probably like the number one thing you can do is then as your income grows, as you’re going, like you’re continually setting aside certain amount into investing.

Chris Badgett: How do you think about time horizon for a beginner? Yeah.

Jason Coleman: For, of investing time horizons.

Chris Badgett: Yeah, I heard this advice once, think of it as being a collector, not an investor. Long time horizon. Yeah. You can day trade and have short term stuff that you do, but if you’re investing for your future, just start as young as possible and forget about it, put it,

Jason Coleman: but what would you say?

There was like Robert Kawasaki, rich dad, poor dad, that, that book is decent, especially if you. Come from a poor dad. That character Kawasaki is a problematic these days, but, but I remember he had a game that like you would play, it was like Monopoly, but it was a little more real world and it was all about building assets versus expenses.

So it’s like you go on vacation, all that money leaves. If buy a stock, you get a return every year on that. If you buy a treasury bond, you get a return, or if you buy a business, it probably has a return or, that’s like a way to I just like that book talks about that, like building assets.

There’s also a good one called like Phil town has one called rule number one and then one called payback. And that’s interesting. Cause rule number one is he’s introduced to day trading and swing trading. I think actually he’s swing trader, which so swing trading is like over. You hold a investment over the course of a week or a month instead of a day.

So he’s all in and he has really good advice on picking stocks and then learning technical analysis. And his second book, he’s I was all wrong. Like I was, Investing way too active. The people who are really, rich, they just own the stock and hold it forever. And so that’s like that idea of collecting these assets over time.

I definitely have that. I think most, like I said, most people should just buy the ETF and maybe you can try to get as many shares of the VTI. It’s hard to personify like an ETF, the same way you can like net, like if you’re investing like companies, you’re like, I’m on team Facebook, I’m on team Apple.

And you can, make room for making individual investments like that. I do, when you do that, . And I do recommend you want to think of it as like you’re owning a business. You can even just take apple and chop off whatever it is, like six zeros. It’s oh it’s a company that has about 300, 000 and makes about 500, 000 a year and has about. If you are trained it’s if you’re buying a laundry mat.

First buying Apple, you can make like an investment in the stock with that same mindset. And if you’re not thinking about price going up and down, you’re just it is a superpower. If you’re investing in individual stocks to have a five year timeframe. Cause no, no one does really like you, like managers have a yearly timeframe.

They have to deliver. The fund managers who buy most of the stocks they have to deliver every year. And so they’re making moves and you’re like, only Warren Buffett is the guy who’s buying and holding stocks forever. And so you have an advantage if you can sit out the swings, but it’s hard.

You have to be able to, met like when stock you buy goes down, see it as a positive, if you really feel invested in the company, like I know it’s temporary. It’s easy though. It’s easier to hold that stock and you want to buy you like it’s on sale by more. If you’re thinking 5 years out and you have some kind of model saying it’s going to be worth 2 times 5 years out, you don’t mind that it dips 10, 20, even 50 percent now.

I don’t know. So yeah, just rambling about the way that, yeah, having that five year timeframe on those kinds of investments, no one, because no one else is thinking on that timeframe, it’s a superpower. Like you’re, it gets a little technical, but there’s things like, I always lose like options trading, like when options expire, that’s like a gamble you can say I think they’re going to win.

They’re going to lose. There’s like literally super computers that are analyzing all the trades and then they just figure out how to suck up all the money. Like they’re just Oh, like they have enough money that they can like manipulate the market. It’s like tinfoil hat stuff, but it’s effectively happening.

They can manipulate the market to have a stock go down. Everyone, like the most amount of people lose money on their options, then the stock goes back up and they get in. And so it’s like, when you’re. It’s like playing online poker and you’re playing with bots that are superhuman. If you’re, but if you’re investing on a short timeframe you’re literally investing against computers that are superhuman on it, but the computers aren’t investing on the five year timeframe.

So it’s like a different game. You’re like, you get to go hang out with the old guys at the poker lodge and they’re playing Omaha and they never even read a book, so it’s I’d rather be in that poker game that then a poker game with a bunch of computers that are better than I am.

I’m

Chris Badgett: sure you’d agree with me that if you must be a gambler or a DGN do it with 5% or some smaller percent or after a certain threshold. Like you don’t Yeah. It’s not like you have to choose to you can split that focus and like still feed that need to pick stocks ’cause they’re fun or try something risky, but Yeah.

Yeah. Don’t bet the farm,

Jason Coleman: right? Yeah, I think so. That’s like common advice I don’t know where it’s 10% or 5% you want. It’s good. You, I always treat it like, like it’s educational. And even, like I said I, always lose that, that options trading thing. I still do it from time to time. Cause it forces me to interact in the market in a way I don’t usually.

And I learn a lot and I lose money, but it’s a relatively small amount. It’s less than 10 it’s like less than 1 percent of what I have invested. I’m making bets on stuff like that. So yeah, if you have that mindset of it’s a small amount of money, I can lose it, I’m going to do this investment.

I’m going to learn. In the process, like you can’t lose, even if you lose the money, you’re like, okay I’ve learned a new way to lose money and I’m glad it was only extra cent and not everything. And I think that’s good. Cause sometimes I think there are opportunities. If you really understand the business well.

And the stock is on sale, if you had bought individual stocks before, you’ll feel more confident to be able to do it now, so you won’t miss those opportunities if you, educate yourself on that. But I struggle with that because I’m like a nerd about this and I spend like hours every day interacting with it.

And I’m like, if I didn’t do that, I don’t know, like, how it. But if, yeah, if you are going to do it, it’s good to do it. Like with that mindset of I’m going to learn and it’s a small amount of money. Yeah.

Chris Badgett: That’s Jason Coleman from paid memberships pro and partner at lifter LMS with his wife, Kim Coleman.

Thanks for coming on the show, Jason. I really appreciate it. I’d encourage you to go check out paid memberships pro as a paid memberships pro. com. They also have a feature for using LMS together called streamline. So you can actually use both tools side by side if you want, and it’s great to be on the journey with you, Jason.

Any final words for the people as we say goodbye or other ways that people can track you or connect with you on the Internet?

Jason Coleman: That’s good. I am on X Twitter, Jason underscore Coleman. That’s a decent way to follow. My occasional posting and get in touch with me by DM or something there.

Chris Badgett: Awesome.

Thanks so much for coming on the show and I look forward to doing it again with you sometime.

Jason Coleman: All right. Thanks, Chris. Thanks, everyone.

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