The New Way Of Building a World Class Money Making Online Education Business With Emily Middleton

Emily Middleton explains her different approach to creating online course websites and learning platforms, which involves working live with clients over Zoom instead of relying on the conventional freelancer model of email exchanges.

In addition to the technical work, she highlights that successful entrepreneurs often benefit from robust emotional support systems, including mentors, coaches, and therapists that help them maintain resilience and motivation throughout their journey.

Emily stressed that minor discussions in these sessions can result in significant enhancements, like modifying pricing models for scalability or revising headlines to resonate more with customers. She and Chris Badgett talked about the emotional aspects of collaboration as well: fostering a culture in which individuals feel tied to the work, motivated, and eager to exchange ideas candidly.

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Episode Transcript

Chris Badgett: You’ve come to the right place if you’re looking to create, launch, and scale a high value online training program. I’m your guide, Chris Badget. I’m the co-founder of lifter LMS, the most powerful learning management system for WordPress. State of the end, I’ve got something special for you. Enjoy the show.

Hello, and welcome back to another episode of LMS Cast. I’m joined by a special guest. We’ve got Emily Middleton coming back on the show. We’re gonna talk about some exciting stuff around the future of collaboration around building a brand and a company culture. How to immerse yourself in your project in a way that’s gonna lead to a lot higher odds of success.

But first, welcome to the show, Emily. 

Emily Middleton: Thank you. I’m happy to be here. I’m making another appearance close to episode 500. Y’all have been going for a long time and it’s been a cool journey. 

Chris Badgett: Yeah, it has been fun. I can’t believe we’ve been podcasting for over 10 years. That’s that’s wild. So yeah, getting up there to half a thousand episodes.

I wanted to get you on today to really dive into some counterintuitive or more just deeper insights into the learning management system projects, the online courses, the coaching programs, the membership sites. We see out there that are working you have clients in the space. You can find [email protected].

Check that out. She’s also over at Progress on Fire, on Twitter. But you work with your clients a little bit differently than a lot of web developers, WordPress developers, website builders. Tell us about. Your collaborative style of working with clients and how it’s different from the typical, I’m gonna hire a freelancer to help me build my site.

Emily Middleton: Yeah. Yeah, so I do a lot of client work, and I’ve done a lot of client work for about eight years now, and it’s all been in WordPress from. Content entry into a website, copying and pasting content from one platform to the other, to now doing like full custom coding and full website builds and all that kind of stuff.

There’s a lot of different types of service that you can get when it comes to working with freelancers. When it comes to working with consultants, for me, I have a DHD. And I like need to be live on Zoom with people. So for me it evolved out of necessity that I’m like, I, it’s hard for me to pay attention to what’s going on if I’m not like working with somebody or doing like body doubling and it turned into a value add to say I.

To clients. The primary way I work is with you live on Zoom. It feels maybe like it would be easier if you were to just send me an email and I were to do the work in the background. But what that ends up with a lot of back and forth and a lot of expectations not being hit. And I can’t ask you the small questions when we’re actually working.

So if we’re live on Zoom together, if we’re live in a format where we can directly talk, I can share my screen, you can see me do the work live. It just creates so much more of a, an atmosphere of collaboration. And that’s really big for my. Consulting and client work business that I don’t see in a lot of in a lot of other businesses where that consulting and working together really comes first and foremost.

Chris Badgett: This is really a special aspect. It’s a known stereotype that I. A lot of website builders, try to minimize the amount of client contact time to as little as possible and just get in, get out, send me the stuff, and then here you go. But what ends up inevitably happening, like you mentioned, is there’s actually an iteration cycle.

Like where, okay, now I see the finished product, but I have feedback or I have new ideas as we get into this. What about this? What about that? Yeah, so this collaborative style, it makes a lot of sense to me. When do you see the light bulb really turn on for your clients when they’re getting into it?

They’re on the zoom call with you. You’re building the site. What kind of thing happens where they it clicks and they get it where they’re like, oh yeah, I’m glad we’re doing it this way. I thought maybe I could just tell ’em, build me a site. I’m selling beekeeping courses to beekeepers.

But the fact that you’re collaborating something kind of magical happens. What kind of thing is that? 

Emily Middleton: Yeah I think it’s when we realized that there was a problem that would’ve gone completely unnoticed when it’s why do you want this feature? We want to have a course about. Clients will ask me questions about pricing when we’re building a site live.

They’re like what’s your pricing? And they’re like we just came up with this one. This is what other people in the industry are doing. Or, we asked chat, GPT, and this is what it said whatever the strategy was that they came up with their pricing. Having the insight about how they came up with that decision allows me to ask specific questions about like, where they’re at in the process.

It’s not just send me an email, tell me what the price of your course is. It’s we’re entering the price and I realize that you’re a little uncertain about how you came up with your price, and so maybe we need to dive in to be like, what pricing options do you have? Do you know that recurring membership pricing is one of the most scalable things you can do because it’s easier to retain customers than it is to sell new customers all the time and stuff like that.

And so I’m able to make those suggestions while we’re working that I wouldn’t really otherwise be able to ask without building this like insanely complex gravity form. And it’s so much easier to. Snuff all these questions out when it comes to working live with somebody. And so they’ll, when we’re asking the questions that they didn’t know they had, that’s really when it clicks.

Chris Badgett: There’s a counterintuitive product development strategy where you can actually build a whole product or business around the price is actually the very first thing, and pricing is a lot more complicated than people think. Whereas a lot the, what people usually do is they do what you said, which is they just kinda hold up a finger and guess, or do some studying or just kinda shoot from the hip.

But there’s a big difference between selling a course for 50 bucks or 5,000 or 500 a month. So whichever one of those options we pick. Your advice as the professional is gonna be completely different. So if you do want passive income, don’t want to talk to anybody, sit on the beach, we’re looking at the $50 course ’cause to get higher pricing, how are you gonna support them?

Are they gonna get coaching? Is there community? Is there other support mechanisms and so on. And that’s a conversation you can’t get a client to like just. Tell you all that without, and get all your insight into that without actually talking to 

Emily Middleton: totally. Like I was working with a client recently putting together their first online course.

It’s like an, a new kind of course for their industry. And It’s an industry that they’re putting together like a leadership course, but there’s so many courses on leadership. It’s like a generic practice, but they’re doing like specifically leadership within an industry to solve a certain problem.

And so their headline was like. Fix your productivity. It’s that’s not, I was like, or we fix your productivity or something. I was like, what if we could reframe this headline to talk about how it helps the customer? And what we came up with was something like clients tell us that they’re constantly.

Everything is on fire all of the time. We put the fires out, click below to get started. Something like that and just noticing that kind of thing from someone who’s been exposed to the industry in so many core sites for so long. If you can take the value that you innately have as a freelancer or even as a course creator and position to the customer directly, that’s such a useful tip.

You have so much insight and you wanna lean into the insight you have as a freelancer or as a course grader. 

Chris Badgett: I’m probably gonna miss some in this list, but the thing is, when you work, collaborate collaboratively, you realize that a talented web developer like Emily is not just a web developer. Emily is a graphic designer, a web developer, a web designer.

A copywriter, a business strategist, a writer, a video maker. The list goes on and on and you like, people just put somebody in a box like, oh, I need a developer to build my site. But you’re actually getting like this whole team of people and one person, but you gotta learn how to leverage their strengths, right?

And that copywriting thing. Pro tip for you out there listening an exercise. I like to do when helping somebody write a good headline or a value proposition is you think about your ideal client at two o’clock in the morning sitting up in bed at night. And this is a trick I learned from somebody named Aaron Fletcher.

So I like to give credit where it’s due, but they sit up at two o’clock in the night or they’re they go into the bathroom and they’re staring at themselves in the mirror and they say. If I could just, and then fill in the blank, so nobody says at two o’clock in the morning, if I could just increase my productivity here at two o’clock in the morning and they say, man, if I could just put out all these fires in my business or whatever, and.

Love my life and work again. These are like real living language words that people use and that’s a great copywriter will intuitively write like that and provide outside perspective. To help sharpen the message. The message is huge. 

Emily Middleton: Yeah. Yeah. And I think not pigeonholing other people who are working with you on your business, like consultants into having a certain role, like you are a developer, you are a marketer.

It’s just get everyone you trust into the same room and have them collaborate on a plan that’s I feel like such a big gain. There’s like a lot of. You know how like with remote work, there’s a lot of like anxiety and depression that comes from people being alone in their cubicles in their houses, isolated from other people, only interacting.

When it comes to talking about work. Creating that feeling where everyone in your company is collaborating with each other to make a vision happen is just such a, it feels obvious. But it doesn’t feel intuitive to do. It doesn’t feel like it’s a good use of time to take your developer from Upwork. And have them talk to the consultant that you hired a few months ago. Then also sit in the room with you and figure out what action items everyone’s gonna do and what they’re really stressed about.

It’s that doesn’t feel like an intuitive, good use of time. But the things that come up in those conversations are so huge. So I recommend really just creating space for the people you choose to work with. 

Chris Badgett: Another mindset tip I’ll throw in there is coming from a place of abundance and without anxiety and just having an open mind.

And what I mean by that is you can, if you’re scared and you wanna be the boss that hired the freelancer, and you just wanna maintain the frame of control and all this, but if you actually let your guard down a little bit. I know when I work with a client that I’m subconsciously like reading them.

I’m like, all right, this person already has pretty good technical skills and WordPress, so we’re not, we’re pretty strong there. We’re gonna figure out the site. It’s fine. Oh, this person is, has a low level of design chops, or they have a high level of design chops, and whatever the answer is there. We may need to spend more time and where the gaps are so you can blend with each other and fill in the gaps and you as the, 

Emily Middleton: yeah.

Chris Badgett: The website creator you will not understand their industry expertise likely, unless it’s something you’re also very into as much as them. So they, the more they tell you, oh let me help you understand what. Beekeepers wanna learn and stuff like [00:12:00] that. It helps you better be like, oh, they really care about this thing.

Like maybe we should feature whatever. Like you’ve, it really, that’s a collaboration and you can’t do that over email. 

Emily Middleton: You can’t watch the expressions on people’s face when they’re reading your email and. I don’t know. Getting people excited about what you’re doing is so underrated and getting yourself excited about what you’re doing is so underrated.

Like I think when I got started on my entrepreneurial journey, I was really interested in creating financial freedom and it was motivating for me to get out of a tough situation where I didn’t wanna work a nine to five. Forever that was such a big motivator. But like nowadays, now that I’m like established enough to be able to make an income working remotely from home, I’m very fortunate to have that.

I’m asking questions and I think a lot of people listening are probably also asking questions like, how do I get passionate about what I’m doing? How do I like ignite my spark? And as Dan Martel says, shine your light in through what you’re doing. And I think that’s. That’s a big piece of the puzzle towards motivation for you and other people around you.

’cause you gotta light up the people around you. Like I know you do that a lot, Chris, where you’re a founder of Lifter. You’re still in the company 10 years later. You started the podcast before starting the product. You were talking to people before then and you’re like. Always trying to connect with the people that you’re working with on a personal level. So that like they can, like you. What they’re doing and you can just get them engaged in what they’re doing in their own lives and for the work that they do with the company.

I think that’s huge. 

Chris Badgett: Yeah. I think a great coach related to that will and you mentioned Dan Martel. He was like this, he would. He sees more potential in his clients than they see in themselves, 

Emily Middleton: right? 

Chris Badgett: When you do that as a web developer and the client will feel that if you believe that, and it’s true, like they will feel that and it will create an energy around the project that is just 10 times more productive and valuable than just some transaction between two people.

Emily Middleton: Yeah.

Chris Badgett: Let’s, you mentioned like. Being in an industry for 10 years or just really time in the trenches, how, what patterns do you see in successful clients in terms of immersion and their subject matter versus the opposite where maybe this project isn’t gonna work out in terms of really being deep on a topic.

Emily Middleton: Yeah, I would say something like have a therapist have someone you can talk to, like a mentor or a life coach or a therapist, someone who’s involved with hearing direct feedback from your business. If you are like internalizing a lot of the stress that comes from your business and you don’t have someone like a mentor, a therapist, a psychiatrist, a life coach, somebody to talk to and help walk you through this process wherever you’re at in the process.

It’s just really isolating. I’ve noticed like times. In my life and in my business where I felt the most alone, where I felt the most demotivated is when I was talking to the least amount of people about what I’m going through. When I have a support network, I have a [00:15:00] mentor like Chris, when I have a life coach I have a life coach named Michael who’s in the lift MS community.

I. Then also have a therapist. I’ve got a lot of support from people around me who I can take my problems to and get all these perspectives, and I think the people who really can ignite their spark and really engage in the way that you need to in order to build a business successfully. They have those support networks.

They have co-founders that they can talk to. And they have co-investors, co-owners they can talk to. They have mentors in the ecosystem and those relationships, those genuine connections. Fuel their motivation to build their product, build their brand, get out in the ecosystem, motivate others to get involved with the product, and then keep doing it better.

That’s how I look at it. And that’s very different from just opportunity chasing. Yeah. Okay. So ai, artificial intelligence is hot right now, so maybe I should make a course about that because it’s hot in a growing industry. You could. But if I’m not all in on AI and been doing it forever, and I use AI every day, but, and I will make, I am, I actually have made some courses that aren’t done yet about using AI for course creation and so on.

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But you really gotta be into your subject matter and not just chasing opportunity. It is fine to want to make money online. But if you’re gonna commit and you’re gonna get clients particularly recurring, coaching clients or ongoing relationship. It’s really important to love your topic and then surround yourself with help.

I like the [00:18:00] framework. I heard once of plus minus equal, which is that if you’re in an industry it’s really good to have a mastermind of peers trying to do same or similar things and then also get coaching help in different aspects of life and business, like with people with more expertise.

That’s the plus. And then the minus is, extending a hand and helping people who are coming up behind you. A couple years or a decade behind where you’re at. And that creates like a well-rounded kind of ecosystem of support asking for help contributing back to your industry. Networking with your peers who are having very common challenges at the same time.

Yeah that’s super powerful. 

Emily Middleton: Yeah. Yeah, a lot of businesses and clients that. I’ve gotten related with that we’ve worked on their projects, it to some degree feels like a family and. I think it’s a really powerful thing to be able to relate to the people around you. And for me it required a lot of like psychological unblocking and a lot of working through my past and the challenges I had.

Why am I in business? I had such a big revenge agenda. I. As a part of like my whole life of I dropped outta high school because the principal slighted me by putting vandalism on my permanent record. And so I’m going to leave high school. I’m gonna prove that I can make a bunch of money and that I will be successful.

And then I’m like, I’m gonna prove to these people that I can do it. Be successful, but that revenge agenda ended up imploding on me. When I never was happy with what I was having as an outcome. So being able to approach business from a perspective of what do I want to create for my life?

Like genuinely with nobody else needing to see. It’s just like what internal feelings within me am I trying to create and how am I trying to help other people with my brand? With the consulting I do, with the YouTube videos I create, with the work I do with my clients and companies. I’m trying to create a feeling of peace with a lot of things.

Like you’re confused. You’re on Google and you’re frustrated at 2:00 AM Googling curse words and like, how do I fix my WordPress? Install all this stuff. And then you’ll find the videos solve the problem and feel much better about it. Or someone’s frustrated in their job day to day, like making them feel like they’re welcomed into their own life.

That’s what I. Bring just personally, but everybody brings a very unique set of values themselves to their work, and I think that’s critical to bring to the people around you. 

Chris Badgett: I will say I’ve met a lot of people who have entrepreneurs, successful entrepreneurs, that were at some point motivated by revenge.

Yeah. So it’s not all bad. It’s like I’m gonna show that person or that ex relationship or whatever. But I would advise like 80 20, it’s okay, that’s real. That’s natural, but 20% that 80% like positive. Yeah, mission, vision, values. It sounds like corporate speak, but it is so real and everything gets, just like we talked about, counterintuitively, you should build the price, the pricing first. Yeah, what do you want? Because that’s gonna dictate like what you’re doing, courses, coaching, whatever, what’s in the offer and all that stuff. How valuable is the result that this thing offers? Does that match up with our price?

If not, maybe we should change, but also your mission, vision and values. Life is so much easier when it’s aligned and. What’s particularly awesome, and I feel really fortunate in this regard, is when your life mission and your company mission are the same or very similar, ’cause then everything’s easy.

’cause you’re on mission like it, otherwise you’re it’s not really living a lie. It’s just you’re off you’re having to perform in a way. But when you’re on vision or on mission. It’s like wind in your sails and it’s pushing you along and your vibe attracts your tribe. So when somebody’s on mission and vision, like the right people show up at the right time.

That whole saying about when the student is ready, the master appears and all that stuff, that all comes from being on a particular mission and vision. Otherwise, you’re just wandering around and, maybe chasing some gimmicks or fads or I. Some ad that had good advertising that you could end up in some funnel or something.

But mission and vision is really cool and I would recommend that for any course creator or coach or if you’re building a website for clients, the about page, it can be hard to write an about page for a client, particularly if they’re not a copywriter and they’re like, oh, here’s my cv. I went to school here and have this thing and that thing.

But just add like the vision, like what’s the change you wanna make in the world? The mission is how you’re gonna get there, and then what are your core values? You can only pick five or six. And just doing that exercise, that’s an example of collaborating with a client. You could be on a call like figuring out the about page and literally transform their life by helping them figure out their mission, vision, and values.

Emily Middleton: Totally. That’s that’s underrated work. That’s so underrated work like we’re thinking like we need a developer to build a site. We need a marketer to tell everybody about it, and we need a sales person to make sure those sales close. But underlying all that stuff is mission, vision, values.

Chris Badgett: Once we have that, it puts the entrepreneur on path. But then they wanna enlist other people, like a somebody to help build the site. Maybe they want to get a virtual assistant, maybe they want to get somebody to help with marketing and sales. Maybe they want to get somebody to teach on the platform.

How have you seen some of your clients with a strong. Kind of company culture, it comes from mission, vision, and values, but over time it gets bigger than the, like the personal brand of the founder, even though that’s strong. What what have you seen with like [00:24:00] strong culture brands that, build magnetic courses and coaching programs and tend to, I feel like one of the most common questions we get asked, even though we’re a software company at Lifter LMS, is how do I get clients.

Do you have mission, vision, values and the company culture and have you put your brand out there and are you attracting like team members and clients? What would you say to that? I. 

Emily Middleton: I it’s so complicated. It’s almost like a paradox of you need to be engaging and you need to have an audience, and you have a community and somehow get attention.

It’s where do you start with that? Like for people who have like no audience. I feel like for me it was answering the questions that were directly in front of me, like on a Facebook groups. And I was seeing with the people that were physically around me, they were asking questions I would create YouTube videos to answer those questions and send them the answers to those videos.

I think there’s a few different ways you can go about it. My strategy was to directly answer the questions, sitting in my email inbox directly, answer the questions I heard on Zoom meetings, and directly answer the questions. I saw in the comment section. Be really direct. I think that there, there’s not a perfect place to start really ever.

And I see so many people get caught up on finding that perfect place to start. And for some people. That’s what they feel like they’ve gotta do. But what I try to do through my work and what I think others that I’ve seen are successful do with their work is that they encourage people to start with what they have and where they’re at.

They have a messaging to their audience that says, you are valid in where you’re at in your journey. Your frustrations are totally real, and we’re here to help address those concerns. They’re not like, I’m ready to be a millionaire. Check out how cool my course is. They’re not like on that vibe.

They’re on the vibe of being legitimately helpful to the people around them. And for me it took a lot of, it’s like constant. Humility, I’ll produce YouTube videos and I’m like, I hate the way I sound. I hate the way I look and I hate the way that I edited this. I’m like, I’m not happy with what I did but it helps other people and even if like just a handful of people are helped by that content or it answers a question, it’s good enough for now.

So I’m producing what is good enough for now to help somebody, and I will iterate and improve over time and encouraging others to do the same whether you are billing sites for clients. And encouraging them to launch and feel comfortable with what they’re doing or whether you’re having a course or membership site and encouraging the people who are signing up for your course or membership site to feel like they are ready to start approaching whatever problem they’re looking to solve or what they’re looking to get out of life from your program.

Chris Badgett: I agree with that. Rand and culture is built one conversation at a time and the thing that people don’t get, ’cause the human mind can’t, you can’t really comprehend exponential curves is the compounding effect. So when you show up, like you said, and I call this the ground game, when you’re just helping one person, you’re like, all right, this one [00:27:00] person, I’m gonna be a, I’m gonna be the guide and I’m gonna give ’em the solution in a free video or whatever.

That’s just one person, one interaction. Video goes up. Other people search for it. They find it, they discover you and your brand, and then they find out you have paid programs or services or whatever. And then you do that daily, weekly, monthly for years, and then all of a sudden you’re like a known entity, like you have you are recognized.

I remember getting recognized in an airport, coming back from a business event, and I thought the person that recognized me was at the business event where I’m well known. But it was actually just a regular user who had no idea about the business event. And I, they saw my lifter LMS hat and we took a picture together and stuff.

I’m like, how did this happen? But when I think about it, it’s I’ve been helping people doing the ground games for over a decade, almost two decades, and the stuff compounds and I think of it like this. It’s, [00:28:00] it’s okay to want to make money and all that stuff, but if you’re in service to your community, they can feel it.

And over time you get known, ideally as the most helpful person in whatever niche or specialty. And then, if there’s a lot of people in that niche, that’s fine. There’s only one, you and your personality, your way of delivery, how you communicate. The way you help, like through video, audio, text, all of it, whatever it’s gonna attract certain people, but it really compounds.

And I think that’s the the it’s the counterintuitive because in our industry there’s a lot of, I wanna automate everything. I don’t want to talk to people. I. And I just want my online business to cash flow while I do something else. The reality is the people that really make it are super engaged.

I was looking at a LifterLMS user site the other day who I heard about that was doing really well. Many five figures a week. I’m looking at the site and I’m like, this site from a design perspective is not great. I went to the course catalog and there were like a couple things there. Not much, excuse me.

But I went to the about page and learned about how this person had been doing it for 20 years and there you go. And they’ve just been helping people for two decades. 

Emily Middleton: And it’s I asked my girlfriend like a couple weeks ago. I don’t understand why clients pay me the money they do.

I like, don’t know all the answers. I’m like fumbling around and like I’m, I come up with a solution. We get something that works and we work our way to a solution that works for them. Something that something that clicks and, but I don’t get it. I don’t get it, I don’t feel like a professional. And I feel like I’m just like.

I don’t know, stumbling around in the woods with them. And she was like what I think people see is that you genuinely care about solving their problem. That you’re just as present with solving their problem as they are. And if that can be communicated, I feel like quality doesn’t matter.

Like as long as people are with you and you’re with them on solving their problem. And that genuineness and shining your light in whatever way that you have to bring to the world through your course membership or freelance practice. If that can be shown and we’re learning how to show that more, that’s what I would lean into.

Chris Badgett: Yeah. And just to throw out another Dan Martel it’s not about your resources, it’s about your resourcefulness. We all have imposter syndrome and all that. But if you can become known as the type of person who can figure it out. And maybe you don’t have the answer right on the tip of your tongue. But you know where to go to find it or who to collaborate with to figure it out.

That’s what makes nobody’s perfect. Nobody has all the stuff, but how resourceful is this person? How unstoppable are they? It’s not how. Intelligent. They are. They have 180 IQ and have every answer. Otherwise, just go to Chad, GBT. Why don’t people do that? Because they, they want people that can, be creative figure it out, get into nuances, read between the lines.

This is this is the way, 

Emily Middleton: this is the way. 

Chris Badgett: Awesome. Emily, this has been a great discussion. Hat’s off to you on your collaborative work style. I think it’s super unique in the space and also super valuable to people who want that. And I think the magic of it is when somebody gets into that, they’re like, oh, I didn’t know you could do all this.

And like you had these other set of skills and you’re synthesizing across these different industries. It’s like going to a doctor, right? Where you’re not a doctor and all the doctor is seeing a lot more than the patient. They’re just like, oh, this thing hurts. Or whatever. But you’re like, broadly looking at systems all over the place. And able to help with that and it’s so cool and it’s very rare in our space.

If people want to connect with you, what’s the best way for them to track you down? 

Emily Middleton: My website is wp course guide.com. That’s where all my WordPress course stuff is. You can also Google Magic, Emily Middleton, and you’ll find my YouTube content. Awesome, Emily. Thanks for coming on back on the show.

Chris Badgett: Really appreciate it and keep up the amazing work. 

Emily Middleton: Thank you.

Chris Badgett: And that’s a wrap for this episode of LMS Cast. Did you enjoy that episode? Tell your friends and be sure to subscribe so you don’t miss the next episode. And I’ve got a gift for you [email protected] slash gift. Go to lifter lms.com/gift. Keep learning.  Keep taking action, and I’ll see you. In the next episode.