Episode 155: How To Create A Subscription Website Your Users Will Love with Ryan Jordan
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Episode 155

How To Create A Subscription Website Your Users Will Love with Ryan Jordan

Podcast Guest

Ryan Jordan

Founder of Backpacking Light

Backpacking Light

Ryan Jordan is a MemberMouse Customer

"We've been a membership site since 2003. It's our core. And so, we can return to those roots and invest heavily into user experience and know that it's going to be okay."

Quick question:

When someone visits your website for the first time, is it easy for them to find what they need?

Does it deliver a clear and intuitive user experience?

Since you've probably seen your own website a zillion times, it can be easy to develop a sort of “blindness” to it.

Because of that, you can assume that you know how new visitors will interact with it.

While you may know where to find everything on your site, someone who is brand-new to your world might find it unclear, confusing, or downright overwhelming.

And here's the thing:

The experience someone has on your website plays a huge role in whether or not they'll come back a second, third, or fourth time.

It will either encourage a visitor to dive deeper into your content and further explore your world…

…or make them instinctively punch their browser's back button and continue their search elsewhere.

This means that the user experience on your website is of the utmost importance.

It can make or break whether someone even discovers your paid membership (and trusts you enough to sign up for it) or not.

That's why we're excited to share this in-depth episode of our podcast with you today.

Our guest is Ryan Jordan – an accomplished online entrepreneur with over 20 years of experience staring at his own website and making meaningful improvements 😉.

Ryan started his online business — Backpacking Light — way back in 2001.

This was before WordPress was even a thing and online memberships were essentially non-existent.

In fact, back in the early 2000's, people thought it was “suicidal” for Ryan to rely on the membership model — rather than ad and affiliate revenue.

Oh, how things have changed!

Since then, he's poured his heart and soul into the business, growing it into a thriving community website with over a million posts and 150,000 forum topics.

Today, Ryan comes on the show to share how he's preparing for a major website redesign with the goal of improving user experience and ensuring the long-term success of the business.

We have a fascinating conversation and we have a feeling you'll learn a lot from the lessons he shares from his own entrepreneurial journey.


1:43 Meet Ryan Jordan of Backpacking Light!
6:03 How Ryan plans to improve his membership site
10:23 Ryan gets real about affiliate marketing
13:04 How Backpacking Lights converts visitors into paying members
17:15 When is it time to redesign your site?
22:17 The nitty gritty details about server architecture & databases
30:37 The UI/UX Improvements Ryan will make to his new site
40:36 Reflections on entrepreneurship & team Building
48:48 Closing thoughts from Ryan

Full Transcript

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Eric: Welcome to the show, Ryan.

Ryan: Thanks for having me. I really appreciate it.

Eric: Yes, my pleasure. Just before we get started here, have you recently, or are you going to be recently going on a backpacking trip?

Ryan: Yeah. My son is actually heading off to graduate school in Hartford, Connecticut, and I’m flying out there to help him move in, in mid-August. So, we’re trying to squeeze in one last hurrah before we go.

Eric: Nice. That’s awesome. And for those people who don’t know, the reason I asked you that is because the thing that you do is you have had a website, since what? Early 2000s now, was maybe beyond that, right? When did you start Backpacking Light?

Ryan: The site itself came online in 2000, and then the concept was incubated the years preceding that.

Eric: Yeah. So, tell us a little bit about what the site is about and what the journey has been like for you for the last 20 years.

Ryan: Sure. So, Backpacking Light is at its core, a community of people who are interested in wilderness travel, backpacking, multi-day hiking. So, the glue that brings us all together is we’re really interested in doing this with gear and techniques that allow us to reduce our pack weights. So, that’s an end in and of itself for some people, but for others, it’s a way to maybe stay out in a wild place for a longer duration, more days at a time, or to travel longer miles or to do longer expeditions.

Eric: So, what are some of the iterations that your website has taken over the years? Because I think it’s gone through a number of iterations and I know you’re working on a new one as we speak.

Ryan: When we launched in November of 2000, it was a one-page website. And the front page was an editorial that I had written about the use of quilts for backpacking and instead of sleeping bags. And then we added another page as we wrote another article, and we added another page as we wrote another article. And we didn’t really get into a content management system until probably 2003. So, it became this behemoth that was starting to get difficult to manage. And then we went into a custom-built CMS in 2003 and transitioned into a Template Toolkit site. So, for those techies out there who remember that technology that preceded our WordPress days, when we ran on Template Toolkit until, gosh, probably 2007, mid 2007. And then we migrated to a Template Toolkit site that had an enterprise level content management system. And then finally, WordPress in 2015. And we’re getting ready to launch the next iteration of our WordPress site.

Eric: It’s interesting, when I think about you going through the process of going through technology and working on growing your business, I can’t help but draw the corollary between the fact that this is what Backpacking Light is about, learning to go into the wilderness with gear that supports you in the lightest way possible, which is similar to this journey with the business as well, right? Like the wilderness of business, what gear are you taking with you? Is it supporting you? Is it getting too heavy for the journey you’re making? How can you constantly improve it to be supportive but not causing all these problems?

Ryan: Yeah, I totally agree. And I think we actually got off track in 2015, by creating a website that was so bloated with a bunch of different stuff. And some of that has existed into the design today. And I think our next iteration we’re really going to apply the lightweight philosophy to improve the aesthetics and the region experience, and the user experience in general for our site visitors. So, absolutely, yeah, we apply this philosophy to a whole bunch of different aspects of our lives and doing it in technology is no different.

Eric: Well, looking at your website right now, I would say it’s pretty light weight, I mean, it’s very minimal, not a lot of flash, right? You don’t have too much graphics going on. You’re clearly not doing things when you don’t need to be doing them. So, what are some of the ways that you’re considering improving this? What are some of the things that you don’t like about how the site is currently and how are you thinking about improving them in terms of user experience?

Ryan: I’m glad you see simple because it’s encouraging to me. A lot of our users see simple as well, which I appreciate, but I don’t. So, I think a big part of this is going to be for me to look at it and say, okay, we’re going to build everything from the ground up now. So, if we’re going to look at an article on the page, what needs to be there, and that article is going to be the article content and the photos that go along with the article. And then everything else is going to be up for debate. And so, we’ll see what makes it and survives. And I think we’re going to be simplifying a lot of the widgets and sidebars and ads, and all this kind of thing, to make the user be able to just focus on and digest the content better.

Eric: So, your guiding light, so to speak, in how you’re making these decisions, are your user experience?

Ryan: Yeah, absolutely. And we want to make sure that if a user is on a certain page of the site, they are getting what they need to get out of that page, because ultimately that will make for a more engaged and satisfied user. And it’s really tempting to put banners and gateways into conversion funnels and things like that all over your website and in every possible location, but we’re actually going the opposite direction now. And we really want to provide a solid user experience, because ultimately that’s what’s going to drive membership revenues and retention, versus just trying to capitalize on ancillary forms of revenue like advertising.

Eric: Okay. So, that’s actually one of the things I was wanting to ask you. Because I’m looking at one of your article pages right now, and I notice there’s all these advertisement blocks on here, which obviously… So, let me ask you, is this a good form of revenue for you right now?

Ryan: Not getting enough, no. And I think there’s a huge cost with putting ads on our site. It’s meaningful, but is it something we can make up for by creating a more positive membership experience? And then we’re trying to answer that question and create the data to allow us to make an informed decision there.

Eric: Right. And you’re in an empowered position right now because you’re not just getting started. I mean, when we’re just getting started, say someone who’s just building their site, they may not feel like they can take the path of integrity because-

Ryan: That’s right. Yeah.

Eric: … they’re getting so much information about what they should do, and they don’t necessarily have the experience to push back on things that people say are stuff that are mainstays. But you’re well established, so you’re coming from a unique angle at this, where you can be an advocate for the user experience in ways that a lot of people can’t.

Ryan: Yeah. And that’s how we started. I mean, we’ve been a membership site since 2003. So, at that time, everyone thought it was suicidal to create a membership model and not have ads, and affiliate was still in its infancy at that time. And as a publisher, it was a huge risk for us, but that’s our core. And then we’ve always been about the content. And so, we can return to those roots and invest heavily into user experience and membership and know that it’s going to be okay, because we’ve done this a number of times through the years and have had a positive return from that.

Eric: You’ve had the experience where your members or people have always responded in terms of signing up for your membership and therefore providing the appropriate revenue you need to support the business.

Ryan: That’s right. Yeah. Yeah. And the rest, advertising and affiliate and some of the sponsorships and partnerships we’ve done in the past with other companies, those have been just gravy. It’s been nice because that allows us to shore up the coffer so we can do further development. And I’d be foolish to think that advertising and affiliate revenues are not contributing right now to our ability to fund the next era of the website for us. But at the same time, we see our most profitable growth and it always has been in membership.

Eric: We spoke earlier about your approach to affiliate revenue. And I think you definitely do a lot of gear reviews and talk a lot about gear on your site, but you don’t always make those affiliate links. Can you talk a little bit about how you decide when you’re going to make something an affiliate deal?

Ryan: This is really challenging. I have a love, hate relationship with affiliate. And my love for it is that I can’t build automated tools in the backend to automatically create affiliate links without our editors, our content editors, getting their hands dirty in affiliate, so to speak, and causing conflicts of interest. So, I really appreciate that it’s easy to separate from our editorial coverage. The frustration I have with it is that, it has now become such a foundation of the content publication industry and it’s across several industries, but it’s very pervasive in the outdoor industry. So, that now when you try to search for a product review or an article that offers a gear guide or something like that, almost always it is driven by affiliate marketing content generation concepts. And so, being able to tell the difference between something that the reviewer has actually used in the field, test it, has the qualifications to test it, versus a publication that is publishing a gear guide or a product review solely for the purpose of generating their primary source of revenue, which is valid income, it’s really difficult for users to sort out.

Eric: Yeah. Which I imagine your established reputation helps you out with. But it basically is a barrier to entry to anybody like you coming in, new people who have basically like a strong natural desire to talk about these things. Because they’re competing against people who, like you said, don’t have the direct experience, but they may have the skills and the tool set for advertising, driving traffic and all this other stuff.

Ryan: Yeah. Yeah. Right.

Eric: So, basically ends up, the content on the web that’s getting promoted more, isn’t necessarily the most useful content from the user perspective. It’s just the most prevalent because people with a profit motive and with experience can push it.

Ryan: Yeah. You bet. And that’s why it’s so important for us to invest into our membership and creating value for them, whether it’s in front of, or behind the paywall.

Eric: Yeah. And jumping around a bit, there’s just all these questions that are naturally popping on my mind. And I imagine you get a lot of organic traffic and you have a lot of people who come to your site and maybe aren’t members. What is your approach to how you develop the relationship with people who are visiting your site, and then ultimately incentivize them to become a paying member.

Ryan: The commonly accepted gateway drug to all conversion funnels is your email list. Right? So, that’s where we try to start an actual two-way relationship with people. And I get a lot of responses to email and I’m able to respond to some, I’m not able to respond to others. But just making that connection via email, it’s still, that’s our gold mine. And it’s not a gold mine in that you can just turn it on and create this foster revenue, but it’s where you start your relationship, it’s where you can start delivering free content to educate your customer and bring them to the website to see more depth or breadth in the topic they’re studying. And so, email is always the first thing. And so, we have hopefully, email widgets sign up, which it’s on every page and we can capture their attention right away.

Ryan: Now, in the absence of that, SEO is definitely the number one driver to traffic. I mean, we have one and a half million posts in our database. And so, that’s a huge SEO footprint. And most of it is, of course is long tail keywords. And people come here for a variety of obscure reasons, but that is the primary reason they do visit the website. And then once they’re on our email list or they drop in at the bottom membership level, which gives them access to forums and participating with our community, and then the relationship can flourish from there.

Eric: Yeah. And I notice that you’re using a Backpacking Light handbook, which I imagine is a downloadable PDF in exchange for email address, which now, but it says first edition, 2020. So, were you doing something like this before?

Ryan: Yeah. We had been doing an online seminar, video seminar. It was about 15 minutes long. It was just to introduce people to the ins and outs of what Backpacking Light is and how to go lightweight, backpacking if you’ve never done this before. And we still have that, it’s still in our email new member funnel. And so, we just added this resource because people were asking for something they could print out and read on the couch and take notes on and think about. So, that’s why we created the PDF.

Eric: Perfect. So, people subscribe, they opt-in, give their email address, they get the handbook, and then you have a funnel where you’re sending them emails over a period of time. And then one of the other things that they get is this seminar and probably some other things. And sprinkled in there, you talk about the membership.

Ryan: Yeah. Later on in the process, we do. We’re actually rebuilding our email funnel now because we’re trying to educate people into what Backpacking Light has to offer, which is a huge challenge for us because we have several thousand authored articles and a million foreign posts in our database. And it is a difficult website to try to get in and get a question answered. So, we’re trying to change things a little bit in our funnel, so that we’re actually educating people about how to find stuff at our website. And secondarily, helping them solve the main problems that brought them to us in the first place, which is, how do I reduce my pack weight without sacrificing safety and comfort.

Eric: Right. Now, here’s an interesting question, because you’ve gone through many site rebuilds. Now, people may launch a site. Things may not be working out, right? In the first three months. And they’re like, “Oh, my funnel’s not working. So, I need to redesign it. I need to redesign my site because it’s not doing what I needed to do.” How have you determined when the right time is to do a redesign, where you’re not making the mistake of just not having given it enough time or maybe implemented it wrong to begin with? Basically, how do you avoid making the mistake of thinking that you’re just redesigning for the sake of the fact that something’s not working and really, it’s not time to redesign? It’s maybe time to ask more questions. What isn’t working for people? Maybe do some more discovery work. How have you made the decisions on when to do the redesigns?

Ryan: That’s a great question. The discovery is never a point in time. I would encourage anybody who’s listening to consider discovery as part of your ongoing process, because that’s the only way you’ll identify the trends that your users are experiencing as they engage with you over a period of years.

So, when we built our first enterprise site in 2007, it was going great until 2015. I mean, this was eight-year-old site. It was fast. It was easy to use. We had control over a hundred percent of the code so we could do whatever we want to. And then the company that was hosting the site and maintaining the code base for us announced that they were going out of business, and we had two or three months to build a new site. So, this was a reactive response, right? Moving to WordPress for us. And so, that happened in 2015. We didn’t have time to structurally develop what we wanted. We were in a mode where we just had to get the new site up and replicate the accessibility of the content on the old one. So, we launched. And as you mentioned before, this was a buggy mass for three to six months. And it took us a while to level it out.

But then we got to that point where we’re like, “This isn’t what we wanted.” But this is not the site that we had before. And this is not the direction that we wanted to go. Right? This was our stop gap. Unfortunately, it turned into a four year stop gap, because at that time we were still recovering from the recession of 2009 to 2011. We were conserving cash, paying off debt. And so, we knew that we needed to save on the order of tens of thousands of dollars to invest into a decent web redesign. And so, we hunkered down, fixed what we could, deal with some of the bugs that were critical, and then saved as much cash as possible. And that’s where we’re at today. So, we had to make some short-term painful decisions to have a long-term healthy economics for our company, as well as being able to be in a position today where we are ready to do what we want to do with the website now.

Eric: Yeah. I mean, if you have to make a reactionary decision, it’s basically all bets are off at that point, you just got to do what you got to do.

Ryan: Yeah. But back to your discovery question and how discovery is ongoing, we have built into our process, so to speak, regular surveys and feedback mechanisms where our users can communicate with us. And then we track that and we log it and track it in spreadsheets. And I’m able to see trends and user experiences, and frustrations and things like this. And so to me, that is like, man, that’s the goldmine, right? That is the ability to say, “Okay, here’s where our user base is going. And here’s how we need to respond.” So, that we can start picking up trends early, before they become disasters and do long-term planning.

Eric: It’s essential. And I know in the course of MemberMouse history, we’ve always had an active discovery process. But our ability to respond to what we’re discovering has waxed and waned over the years. Like you said, sometimes there’s just periods of time where other stuff is just bumping up ahead and priority just because, your host shuts things down and you just got to respond. Somebody who’s a resource quits and you don’t have a… All sorts of stuff happens. So, the ability to respond to discovery is part of the challenge of running the business. However, there is that constant listening process is essential, because the members and the community will tell you, especially with membership sites, will tell you where you need to be going to increase retention, which ultimately is the lifeblood of the business. I mean, if people are coming through your funnel and signing up, that’s great. But if they’re leaving just as quickly as they’re coming, that doesn’t help.

Ryan: Yeah, for sure. And I think the biggest thing I’ve learned in discovery is that my approach to how I view the website on a practical and an emotional level is very, very different than how my members view it. And it’s vital that you integrate those two things, so that you can create a common vision moving.

Eric: Yeah, for sure. So, just to be clear, the site that’s currently up now, is this is the stop gap?

Ryan: This is the stop gap. I mean, it’s our three versions into that stop gap. So, it doesn’t have the all of the structural problems that the old site had, but there’s still some legacy ones existing.

Eric: Right. And so, with the redesign that you’re approaching, I understand you’re making the solid investment. You’re basically saying, “Okay, we’re going to do it this time. We’re going to do exactly the way that it needs to be done. And it’s going to take whatever investment it takes.” But the goal is to build something that is exactly what you need. So, we talked a little bit about user experience. What are some of the other things that you’re really looking to improve in the new version that’s coming?

Ryan: I should say that we’ve been building this now for about 18 months already. And it’s not being built in a way that’s visible to the public. But in order to scale and create a stable platform, we knew we had to invest into the server. And so, the last 18 months we’ve spent studying the database and collecting data on how to optimize queries for a million database records, which is an enormously challenging problem. I had no idea. And then building a server environment and a hosting environment that was, number one, secure, number two, stable and number three, fast. And so, we’re still in that process, but we’re coming to the end of that. And things should be pretty dialed in by August or so, when we start building the new site, the UI UX on the new site. With those three things in place, stability, security, and speed, then we have a good solid foundation where we can do whatever we want with the user experience. And that’s the exciting part. That’s the part where the public gets to enjoy the fruits of what we’ve been doing for the past few years.

Eric: So, your database of content, you’re not doing that in a WordPress database?

Ryan: We have the databases stored on a completely separate server. I doubt if your listeners will be interested in the technological implementation of it. But the goal is to get it off the host server, so that the queries can run fast and in an isolated environment where the other things won’t disrupt them.

Eric: But so, for example, when I ultimately, in the new design, when I click to view an article, that’s not a WordPress post, that’s coming from a custom database, from a specific server that’s designed with this infrastructure to serve things up really quickly, right?

Ryan: No, they’re still WordPress database, is that they’re being stored in a separate hosting, in the sense, than the rest of the site.

Eric: Okay. So, you’re actually going to have, essentially two WordPress databases. One that has your content, and then one that has your front-end user experience, that’s delivering the UX stuff like that.

Ryan: That would be the simple way of looking at things. So, right now we have 175 databases. The thing that’s really challenging is for example, our forums database, where we have 150,000 forum topics and 1.1 million posts or replies to those topics. So, those are going to have to be separated out into separate databases, and then a custom index made so that the queries can run past and things like that. It’s a really challenging engineering problem.

Eric: And an interesting question. Okay? So, you have 175 databases. I totally understand why from a technical perspective, you start with a WordPress site, you’ve got all these plugins. It’s everything’s great. A couple hundred, couple thousand posts. No problem, everything’s fine. But yet you’re getting to millions and now you’ve got your forum plugins, or whatever’s running that software, that’s got a database of millions of things. You got your posts that have millions of things and whatever else is going on there. So, you’ve come to a situation where you have all of these databases distributed, but ultimately, to try not to make this picture too complicated, but ultimately there’s one delivery mechanism, from a user experience standpoint. They’re going to backpackinglight.com. They’re clicking on to request an article. They’re browsing your forum, regardless of the fact that behind the scenes, that those are coming from distributed databases on different servers, their experience is one site.

Ryan: Absolutely. And they don’t care about the databases.

Eric: Exactly. So, what is the mechanism you’re using between the one client experience and the distributed databases?

Ryan: Those are connectors that you have to custom build, because anything that comes out of the box is going to try to solve too many problems to be efficient and require too much server resources to do it efficiently. And so, this is the kind of thing you just, you have to rewrite the database queries from the ground up.

Eric: That’s awesome. I love that. So, okay. You basically have a middle tier, right? That you’ve custom built. In architecture, in software architecture, we call the piece that’s not the client. The client experience is basically what the client experiences, that’s the client layer. And then there’s the middle tier, which is the piece that stands between the client. So, the client makes requests. When I click a button on your website that generates a request. Now, the middle tier in enterprise software, the middle tier handles the request. So, for me to translate as a software engineer, what you just explained, you’re custom building your middle tier.

Ryan: That’s exactly right.

Eric: So, when somebody clicks on a button on your site, the middle tier you’ve developed custom software, that here’s what was requested by the client. And then knows the existence of where the data lives, and basically processes it in the most efficient way to request the data from the specific database of where it lives on a distributed server or wherever.

Ryan: That’s exactly right. Yeah.

Eric: So, the thing that you’ve been spending the last 18 months working on is that, a, where all the data is going to be stored and what databases and where. And b, the middle tier that can handle the requests from the client, so that it can talk to and request the data from the databases.

Ryan: Right. And creating the hosting architecture that provides the data security and stability when these enormous queries run. Yeah.

Eric: Awesome. So the last step, which is essentially, usually the only step that people think about, have to think about, is actually the look and feel of the site, what the user is experiencing as they navigate through things and stuff like that. So, I’m really excited about that, hearing about how you’re approaching that. Because it’s definitely not something that only 5% or less of our clients ever have to deal with because of the scaling issues and the challenges. So, I just wanted to paint the picture a little bit, but certainly this’ll get out of the realm of feasibility to go deeper into, on the forum like this from this point. But I certainly wanted to share with people to get a bit of a picture more and for my own understanding what you’re dealing with, because it’s pretty cool.

Ryan: You bet. Yeah. So, I use a hiking analogy here. One of my favorite things to do is just mindlessly hike on a trail. It is restorative for the mind because you’re not investing in mental and emotional energy on where to go. You’re just following the trail. And then you might come to an intersection that gives you the chance to go one way or the other. And usually at this time, you look at your map and make a decision and you go. 

Near my house, there’s a couple of trail intersections, where literally four trails combined in one spot. And it connects to this massive network of, it’s like a spider web of trails. And so, you can create an infinite number of journeys in this particular national forest area. It requires a lot more mental energy to do that. And I see web design as very similar.

When somebody comes to a website, I have to believe that they’re coming not to just hang out with the website. They’re coming to solve a problem, seek some information or engage with your community. Those are the three things that people come to our website for. And so, do I want them expanding their mental energy on making the decision of where to go based on what page they are on? And the answer is always, no. I want them to find what they’re looking for and then spend their mental energy digesting what they find. Right? So, in terms of UI and UX design, our goal from here is really to reduce the friction people have in working with their website, so they cannot be distracted and get to where they’re going more easily.

Eric: And that’s a process that you haven’t necessarily started with pen to paper yet for the new site, or have you started doing wire frames?

Ryan: Yeah, we have. Yeah.

Eric: You have. Okay. So, what’s some of the most interesting, or unique user experience elements that are going to be on your new site that you’ve come to because of your dedication to this approach?

Ryan: Yeah. So, one of them was how we acquire leads for our email newsletter. So, we come from a publishing and news background. And so, I always had this vision that, “Well, I want my website, the front page to look like the New York Times,” which has this really beautiful, elegant news website with this amazing diversity of content that you can explore. Right? And then in January we did an experiment where we said, “Okay, if you’re a new visitor to the site, who’s not a logged in user, what is the first thing and primary thing we want you to see? We want you to see our newsletter promo.” And so, we installed that for non-logged in users. And our email conversions went through the roof in terms of signups.

So, we tripled our email signups per day. And that has actually already had a huge impact on being a solid return on our investment because those emails subscribers eventually convert to paying members, right? So, that was really eye-opening experience for me. And it allowed me to see, okay, for a new visitor, what do we want them to have in their hands? It’s the handbook, because once they’re in the handbook, they’ve got access to this tremendous resource of free information that they can then, practically put into use right away. So, it engages them with value. It gets them on our email list. And it keeps the first visit experience really, really simple.

Eric: And also, you’re starting off the relationship and building a relationship with them by giving them something as opposed to asking them for something.

Ryan: Yeah. And it doesn’t stop with a one-time gift, right? I mean, you’re in the process of cultivating a relationship with a customer that you hope will last years. I mean, we still have members who have been with us since the day we opened membership in 2003. And it’s so cool to see that someone has stuck with us for 17, going on 18 years. And it’s, I want more of that because that ultimately is what creates the foundation fabric of your community. So, cultivating relationships with customers, it takes a lot of time and you have to build trust over a series of weeks to months to years. And it’s not a one-time gig.

Eric: If you just even take a little bit of time to think about it, that’s how all relationships work. I mean, we’ve all met people who we know want to get something from us, whether monetarily, emotionally or whatever. And it feels like a burden upfront, and we want to get out of there as quickly as possible. But yet, when you go to a lot of sites, I mean, that’s sometimes the way that it feels, that immediately I’ve just gotten here, but already you want me to make a decision and do something.

Ryan: Yeah. I know from personal experience, when I go look for… We obviously use a lot of software as a service products. And so, when I go shopping for something, the first place I almost always go with a company like that is their blog. I want to see what they’re contributing to the broader market. And if I liked their blog and get value from it, I’m far more inclined to consider their product than just going to the pricing page and seeing what the features are.

Eric: Right. And this, I think comes down to something that I’ve heard you talk about before, which is the long-term process, the long-term vision versus a short-term gain, right? We’ve touched on this just now a little bit, but what are some of the downsides you see from people looking for and how they make the mistake of going after that short-term gain or the quick return, or the home run or something like this?

Ryan: I mean, snake oil salesmen have been around for centuries, right? So, the modern-day version of that is the internet marketing home brand, where you create a product, you buy paid ads to drive traffic to the landing page. You convert, you squeeze the lemon as hard as you can to get as much juice out of it as possible. And then it fizzles. And then you’re done, and you then send and repeat, right? So, I’ve never been drawn to that for a number of reasons. As an entrepreneur, I always felt that you have to provide something to somebody that provides long-term value that actually allows them to change their life and give them some life satisfaction. And it goes beyond the quick hit. And that’s always what has driven our decisions. It’s never been, “Okay, what do we need to do in the next three months to survive and pay our bills?” It’s how are we going to be in this business for the next 10 years? And I’m looking at the next 10 years right now.

Eric: But the thing is like, clearly there’s always going to be snake oil salesmen. There’re the people like we were talking about earlier, the affiliate marketers, who are essentially just following a formula, know exactly how to do it, don’t necessarily care about the subject matter or do so to different varying degrees. But there are people who do have the intention of what you just talked about. They do want to actually help people. They do want to share their knowledge. But they lack necessarily the models, the correct models, because there is a lot of courses out there. Snake oil salesman, selling how to be a snake oil salesman. But if you don’t have the experience, you don’t necessarily know if you’re falling into that trap. So, I ask that question more from the perspective of, there’s someone who has that intention, they want to do it for the long-term, but they don’t necessarily have the experience to know that something they’re choosing to do right now is actually about choice.

Ryan: Yeah. And that’s an enormously challenging problem for all entrepreneurs. And I think the way that my wife and I have addressed this through the years is we want to do this. We want to give it a shot. We know it’s going to take longer than five years to see if it’s going to work. So, what can we do to make sure it’s going to work? And so, we both went all in on it with our time and finances and everything, and then made the decision that we’re going to apply the Backpacking Light ideology to our own personal lives, so that we can maximize our chance for success. And that meant not bloating the business with things that were unnecessary, and not bloating our personal lives with things that were unnecessary, including personal expenses and the houses we chose to live in and things like that. And so, that being able to live a lean life to us was the absolute secret sauce that allowed us to be in this for the long-term.

Eric: Yeah. And not for nothing. I mean, that’s getting to a point like that, is not necessarily also super straightforward.

Ryan: No.

Eric: Like you said earlier about hiking, you mindlessly walk a trail. Well, to you, now that’s second nature. But to be mindless at any point in time, isn’t necessarily easy, right? But there’s a relationship that you’ve developed through consistency of doing the hiking. This is a really interesting topic to me. I do tea ceremonies. And I feel like my tea ceremony is like you’re hiking, because it’s something I do consistently. It’s a very simple process. Like hiking is you put one foot in front of another, essentially you walk on a path, with tea, you put leaf in a pod and you pour water on it. Through the mechanism of consistently engaging with these practices, there’s something magical that happens where you start to learn to listen more at a deeper level. And I think trust comes out of that. And from the position of trust, that’s where you can become mindless because you’re releasing control.

Ryan: This is one of the hallmarks of a meditative practice. I mean, if you can’t be personally vulnerable enough to experience the emotions that you’re going to experience in this journey, because it’s difficult being an entrepreneur, right? And then being able to let those emotions go is a practice that requires an enormous amount of discipline over a long period of time to really get into a grove. And you have to realize that it’s not going to be perfect all the time, and that’s okay too.

Eric: Or that it is going to be perfect. But what perfection looks like is not what you want it to look like.

Ryan: Yes, right. That’s a great point.

Eric: Again, like walking a trail like, “Oh, I wish this trail wasn’t so steep.” Well, is the trail not perfect or is the fact that you want to avoid obstacles?

Ryan: That’s exactly right. Yeah. When I went through courses with the National Outdoor Leadership School, one of the things they teach is a tolerance for uncertainty and adversity. And I can’t think of two better lessons that every entrepreneur needs to just grab hold of.

Eric: Well, in life in general. I mean, entrepreneurship is great because you’re at least entering into the realm of opening yourself up to improbability. For example, as opposed to a 9:00 to 5:00 job, there’s a little bit more predictability now. There’s definitely arguments against that. But let’s just say, things are consistent about it. You know how much money you’re going to make each month, you know where you’re going to be at certain times, you know how much vacation time you get off, et cetera, et cetera. But because of that predictability, you’re actually, you’re losing the tests that can allow you to learn more about yourself.

And the mistake I think people do when they want to enter into something that they see they’re doing it for the fruits, like, “Oh, I want to be an entrepreneur because I want to make as much money as that person. I want as much freedom as that person has.” But they don’t want to do the work. They don’t want to actually take the journey. They want to go on the hike, but they’d rather a helicopter take them to the peak so that they could get the picture at the summit without having to walk the trail, which loses its potency, basically.

Ryan: You bet. You bet. Yeah. I think there’s a lot of different motivations, people work in the corporate world versus becoming an entrepreneur. And some of them are the same. It might be to make a lot of money or it might be to participate in a career that gives you some personal meaning. But for me, the entrepreneurial journey, the motivation was always, I have a problem in front of me, and it’s a business problem. It’s a societal problem. It’s a problem that people have with how they practice recreation. And I want to participate with the broader community and solve a piece of that. And so, the ability to do that is, I think that’s where you get to the end of your life and say, “Did I help people?” And that to me is a more powerful motivator to keep going than exiting the company for a big payout someday.

Eric: And was that always the case for you, because I know you have a PhD in engineering?

Ryan: I do. Yeah.

Eric: So, was there a point in time… By the way, what kind of engineering?

Ryan: Biological.

Eric: Was there a point in time where your plan was different?

Ryan: Yeah. I mean, my career path at the time I graduated with my doctorate was to be a university researcher and primarily in the areas of biopharma. And I did some projects in oil field recovery as well. And those industries come with so much societal baggage that I was having a difficult time reconciling what I was doing, which was basically performing research, so that these publicly held corporations could make enormous amounts of money, and do so in a way that has some societal benefit, but they’re also perceived as being sharks in the overall scheme of corporations. Right?

And so, I was trying to figure out a way to, okay, my options were to stay in academia and do this. What I really wanted to do was teach students engineering, but that, unfortunately when you’re a researcher, that’s second to bringing in grant money for university. And so, I could do that or I could go into the corporate world and actually work for one of these large corporations, which I had almost zero interest in just because some of my peers had done that. And they had told me how good the pay was, but how difficult the environment was to be creative and to do things where you had a say in how problems were solved.

Eric: From what I’m hearing you say now is, it’s very clear that you’re purpose driven. You want to make an impact. You want to leave a legacy of a kind that has a positive impact on your community, your immediate community, and your larger community. So, after you got your doctorate, was that the first time that you were aware of this discrepancy, or were you not yet so clear about your purpose driven aspects at that time?

Ryan: I have to admit, I wasn’t as clear about it. It came somewhat as an accident. Backpacking Light was founded in 2000. My wife and I, we got pregnant about a year and a half later. She actually gave birth to a stillborn baby in 2002. So, at that time we were waking up to what is going to be important in our lives. And this was about the time I was in a tenure track position and working 80 hours a week and writing all these grant proposals. And I realized that, okay, there might have to be an alternative here and how we pursue the career, because I don’t know if I want to squander those in the lab all day. Right? So, I went back to Backpacking Light at that time, looked at some of the traffic data and things like that. And we were absolutely growing like gangbusters. And so, we made the decision to make it a commercial venture in 2003. And here we are today. And it’s been challenging, it’s been hard, but I can’t say I regret it.

Eric: Yeah. And it sounds like you were already doing 80 hours a week in work. I mean, it wasn’t like it was a new thing for you to be busting.

Ryan: Yeah. But the advantage to being an entrepreneur is that sometimes you can’t walk away from it, right? There’s a lot of drama in your business and you have to address it, whether it’s with your own staff or a website technical issue, or something else. But at the same time, you can decide the extent to which you invest into your business in terms of personal energy and time. I suffer from the opposite. I’m more likely to burn 10 or 12 hours a day working on the business because I enjoy it so much. But there’s this balance you got to strike with the rest of your life. And it can be very difficult at times.

Eric: And what does your team look like these days? Have you done a lot of delegation and hiring over the years?

Ryan: We’ve focused on that quite intentionally, in the past three years. We’re developing a smaller team than we’ve had in the past, but a team that’s more engaged and stays with us for a longer period of time. And that’s been the biggest difference in staffing for me. We, at our peak, we had a team of about 15 employees and we all went to work at an office every day, and it was a very stressful time. And so, now we’re all distributed. We come from different backgrounds. We’re at different locations across the US, but there’s less of us. And it’s just, it’s a nicer environment to manage, and everybody is more engaged. And I think we’re getting a lot more work done as a result.

Eric: Yeah. I find that too with MemberMouse that I’ve never had a brick and mortar situation with people who worked for the company. But I’ve actually found a lot of people through just meeting them through things I’m passionate about like tea. So, there are a number of people who work for the company and have for a while now, who I’ve met first outside of business. Has that happened for you? Are there some backpacking people?

Ryan: Yeah, for sure, it’s through the years. Although, I would say most of the people who are on our public facing side, the staff who’s creating our content or moderate in our forums, they’ve been recruited out of our community. So, that in and of itself has been a very satisfying thing that, okay, one of your members is now one of your employees. And I think as an employer the thing that strikes me the most today is that, if any one of my core team members left, I think I’d be heartbroken because we’re friends, and we’re engaged in this common purpose. And we share a lot of common life values. And that’s been super cool.

Eric: Yeah. I agree with that. So, you mentioned in the beginning that your son is about to go to graduate school.

Ryan: Yeah. I hope he starts at The Hartt School of Music this fall.

Eric: Oh, amazing. So, what’s he going to be studying?

Ryan: He is a violist and a composer, classical music composer.

Eric: Awesome. I compose orchestral music as well, myself. I played the violin for nine years.

Ryan: Now, very cool.

Eric: That’s awesome. I’m so glad that he is doing that. The world definitely needs more music in it. So, I hope that he has great success. Is there anything that you two talk about and share in terms of advice that you’re giving him as he approaches his graduate journey as you have?

Ryan: Well, fortunately he is a much better minimalist than I ever was. And so, I think he’ll be more successful younger in life than I was.

Eric: He had a maybe a better starting point too for minimalism.

Ryan: For sure, we learned a lot in the last 30 years.

Eric: That’s great. Wish him the best of luck. And Connecticut is a great state. My older brother lives there. He lives in Southbury. Which is a couple of hours outside of Hartford.

Ryan: Yeah. Yeah.

Eric: So, is there anything that we haven’t talked about that comes to mind that you think would be valuable to share with people?

Ryan: As I prepare for this next era of Backpacking Light, I’ve really been studying the concept of how do you do what’s essential with as little as possible. And one of the books I’m reading right now, that I’m actually on my second read through it, because it was so powerful is called, Letting Go of the Words by Janice Redish. She writes from the perspective of website copy. And realizing that you can provide a fast, efficient and powerful and engaging user experience by saying less, is probably one of the most transformative things I ever learned about communicating with people in general, but on the web specifically. And so, that’s a resource I want to leave you all with and highly recommend it.

Eric: Yeah. That sounds like something that I would be really interested in. So, before we sign off here, first of all, I want to personally thank you so much. You’ve been a customer, remember Ryan, since you made the move to WordPress in 2015, I think.

Ryan: Yeah.

Eric: And so, I really appreciate you being with us and being a part of the supporting what I do here and my team is doing. So, thank you so much for that.

Ryan: Thank you as well. We’ve learned a lot from watching you guys.

Eric: Awesome. Well, I’m glad to hear that. Probably a lot from our mistakes as well, just like we have. So, we’ve touched on already, but if you still just don’t want to share where people can learn more about you.

Ryan: Our website is at backpackinglight.com. And we’re on social media at Instagram, and Facebook at Backpacking Light, and Twitter at Backpacking, and YouTube at Backpacking Light USA.

Eric: Awesome. Well, thank you, Ryan so much for joining us, and I hope you and your son have a really great time on your upcoming backpacking trip.

Ryan: Thank you so much. I really appreciate being on the podcast.

Eric: All right. Bye, Ryan.


Thank you so much for listening to my entire conversation with Ryan.

I hope you enjoyed this episode and are now walking away with a more expansive perspective on what long-term success looks like in life and business.

I’d like to extend my sincere thanks to Ryan for coming on the show and sharing from his many years of wisdom and experience.
To get links to all the resources we talked about in this episode, you can head on over to SubscriptionEntrepreneur.com/155.

There you’ll also find the complete show notes and a downloadable transcript of our conversation.

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Thanks for Listening!

Thank you so much for listening to this entire episode of our podcast. We hope you learned a lot from our conversation with Ryan and now have a much clearer picture of what it takes to build a successful subscription site.

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