Mastering the Subscription Model: Insights from a Side Hustlers Multi-Million Dollar Success

This week we’re introducing you to a true entrepreneur and business success story, Ben Aston. 

Ben shares his remarkable journey of transforming a side hustle into a thriving business that generates an impressive $3 million in revenue.

Today, Ben generously shares his valuable insights, experiences, and expertise, taking us through the fascinating process of how he got started and the intricacies of a subscription-based business model.

Ben’s journey began as a passion project, fueled by his entrepreneurial spirit and the desire to create something meaningful outside of his regular job. 

Delving into the world of subscription-based business models, Ben sheds light on the intricacies and benefits of this approach. He shares insights on how he strategically built a business that relied on recurring revenue, effectively balancing customer satisfaction with sustainable growth. 

With his deep understanding of customer needs and preferences, Ben takes us through the thought process behind developing a subscription-based platform that keeps customers engaged and eager to stay on board.

Ben’s story is a testament to the potential for success that lies within your own side hustle, and he generously imparts his wisdom to inspire you to pursue your entrepreneurial dreams.

Whether you’re currently running a side hustle, contemplating turning your passion into a business, or simply looking to gain insights from a seasoned entrepreneur, this interview with Ben Aston is not to be skipped! Let’s dive in. 

This week’s newsletter brings you: 

  • Trends: The subscription business model is exploding all over the world and that trend is set to continue it seems!
  • Strategies: Ben shares his insights, challenges, and successes in this week’s side hustler success story. 
  • Tool of the Week: Want to start a subscription-based side hustle? You’ll need a tool like Chargebee! 

Trends 

Are subscription-based business models just a fad, or are they here to stay? Let’s take a quick look at the numbers!

Digital subscription market (2020-2025)

GLOBAL DIGITAL SUBSCRIPTION MARKET TO GROW BY 2025

According to Statista, the market size of the digital subscription economy worldwide amounted to 650 billion U.S. dollars in 2020.

That year, subscriptions to cloud services accounted for roughly 45 percent of the market, with an estimated value of around 292 billion U.S. dollars.

Meanwhile, the market size of the e-commerce segment is forecast to reach 687 billion U.S. dollars by 2025!

Strategies 

Alright side hustlers, let’s dive into Ben Aston’s inspiring story of side hustle success!

The beginning of Ben’s journey

You’ve bootstrapped a side hustle to a $3 million dollar business. So what was the side hustle and how did it all start?

Ben Aston: So it was actually when I made the move from the UK to Canada and I figured I’m going to be in a new city with no friends. So I thought, okay, well, my plan for the year was to make 12 websites in 2012. That was kind of my big goal.

So the first website I made was called thedigitalprojectmanager.com, and the idea for it was that I was going to create an ebook and sell it online. That was it. I’d write a book, I’d sell it online. 

I never actually got around to finishing the book. That’s still a work in progress. But what I did do was create a whole ton of blog posts because I thought, well, who am I going to sell my book to? I’ve got no audience.

So I thought, well, I’ll drip-feed this book over the course of the year. So that by the end of the year, there are some people who might want to buy it. That was the plan. And yeah, as I said, I never finished the book, but what I created instead was a website that’s become a platform. 

We now monetize through membership. So we have an online subscription, we have online training and we have advertising as well. 

Now we’re at the point where we’re generating upwards of 3 million a year, which is great for something which started when I still had a full-time job. 

So this was something I was doing in the evenings, at the weekends, whatever spare time I had, I’d be hustling to try and build something. And yeah, that’s kind of been the journey.

Did taking action and learning through experience play a bigger role in your current success, or was it more about goal setting and planning? 

Ben Aston: I think the process of making things happen and taking action is so important. I think so many people get hung up on whether or not they’ve got the right idea. They want to be an entrepreneur, but they’re not quite sure what to do, so they don’t do anything. And I think that’s the worst possible thing to do, but if you do something, something will come of it. It’s just a matter of what.

Starting a subscription-based business model

Tell us about how the idea of the subscription model came to you. What was the inspiration, the challenges, and the opportunities?

Ben Aston: The idea for membership came out of looking at the data and looking at the analytics from the website and seeing what people were interested in. And what people were consistently interested in were the templates that we provided. 

They wanted a template for project kickoff meetings, or they wanted a template for an estimate or whatever it might be. We had a whole ton of great content and a whole bunch of templates. 

And so I thought, well, why don’t I charge people for this? So we made some of the content members-only access because we know people are searching for this stuff. We know that this is what they’re looking for. It gets downloaded a lot. So maybe people are willing to pay for it.

Our membership has been running for nearly 18 months now. The impact of what we did was yes, it creates short-term revenue. So people are willing to pay for access to things that they want. But the challenge is the churn rate. It’s forcing people into membership because they want access to a certain resource. 

It doesn’t mean that they’re someone who’s willing to pay month after month for access to these resources. So what we have found over the past year is our subscription rate is really high, but also our churn rate is really high. And so that’s why we’ve begun to pivot the business model and actually the entire membership offering to try and accommodate for that a bit better.

Are you offering both a monthly subscription and an annual subscription to users?

Ben Aston: Yeah. So we’ve actually just scrapped our monthly membership. So this kind of comes back to our pivot that we’ve just done. Realizing that we don’t want people to sign up for monthly membership and churn after month three, because it’s not worth it. 

So the monthly membership was $15. The annual membership, $150. But what we’ve done now is just scrapped our monthly membership altogether. And we’re pivoting our whole membership model to be less around access to resources and more about being part of a community. 

And the idea is if you just want access to resources, if you just want a template, then we’ll sell you a template. You can just pay $10, get your template and leave.

But if you’re looking to develop in your career, if you want to be part of a community, if you want support, if you want accountability, if you want to grow, then you need to be part of the community. And this is a long-term investment. 

You’re not going to get the value out of it within three months. So we need people to stay in membership for longer, which is why currently the only offering we have is an annual membership, which is priced at $150, but it means that people have made a bigger commitment and so they’re willing to make more effort in giving to the community, but also receiving from it.

Ben’s sales funnel

So how do you get people to sign up for that annual membership? What does your sales funnel look like? 

Ben Aston: Yeah. We haven’t really created a funnel in the classic marketing way…but essentially what we’re doing is it’s a brand experience that we’re offering and providing to people. 

The brand experience includes our podcast and that helps build credibility. People can hear what we’re talking about. And the podcast is completely free. The content on our website, most of the content is completely free. So that’s where trust is built. 

And we know that there are certain trigger points, which help people decide that membership is a good option for them. Things like people getting a new job, things like people looking to upgrade their resume or find a new job. So there are certain points in people’s career, maybe where they’ve got a promotion or they’ve got a review coming.

There are certain points in a digital project manager’s career where they suddenly think, “Oh, maybe I do need some accountability. Maybe I do need some support. Maybe I don’t know what I’m doing.” And so we’ve created a lot of content around those kinds of topics so that people who are searching for it will find our website.

And then from there, we have promos within the article itself saying, “Hey, if you want to be part of the community, come and join us.” 

So it’s a very short funnel, but we’re trying to create content around that obvious user intent where a solution like a membership might be helpful. 

And then with our email also within our website, what we do is when someone becomes a subscriber to the website, we introduce to them to some of our content. We find out who they are by what they click on and what they’re interested in and begin educating them on what we offer.

And as part of that journey, we introduced them to membership. Now, as part of our funnel, it used to be that we offered people a two-week trial, but actually, we found that two weeks isn’t enough for someone to get the value out of membership. It’s not enough time. 

And so actually the number of people that signed up through that free trial and then the people that unsubscribed because they didn’t make use of it was too high. 

So it just wasn’t worth doing, and it created administration for us as well. So what we’re trying to do as much as possible is look at the numbers, see if things are working, and if they’re not working, get rid of them and try something else. And this game of experimentation is something that’s always ongoing.

Testing out ideas and strategies

So, you’re challenging conventional practices recommended by many, acknowledging that there’s no definitive solution. Is it fair to say that your business requires a constant testing regimen?

Ben Aston: Yeah. And I think so often we can kind of fall into the trap of thinking, “Hey, this guru is clearly really good at something, therefore the advice that they’re giving must be right.” And it might be right for certain instances, but it will always depend. 

And I think what we need to have confidence as entrepreneurs is we know actually better than anyone else, our audience, we have the insights that they don’t have, and there’s not a one size fits all approach to things. 

And to think that you can just … and you see this advertised all over Facebook all the time. It’s like, “Grab my playbook, grab my swipe files.” As though it was just a simple recipe that you could follow and success will just come out of the oven 10 days later. It’s just not that simple.

Whenever I have tried following those things, or even engaging with some so-called experts, they apply their learnings thinking that it’ll work. And I think it’ll work, but it turns out it doesn’t work because they’ve missed a key component or insight. 

That means their whole strategy, their plan, is not very effective. So, my experience has been as an entrepreneur, as someone who knows the business, knows the audience, we kind of have a gut sense on things. And that gut sense is really powerful, and we should rely on it.

Onboarding customers

I’m curious about the onboarding process because I’ve heard that in terms of minimizing churn, the onboarding process is really, really important. So can you tell me a bit about how you onboard?

Ben Aston: Yeah. It’s something that we have evolved as our membership has grown and really, the point of onboarding is to help customers get some momentum early and build on that momentum. 

So we want people to feel like they’ve won, that they’ve got value out of it, that this is easy, this is fun. 

So our onboarding process is partly education, is partly introducing people to the various different parts of the membership that we offer. It’s giving them a kind of heads up on events that are coming up. 

But what we’re trying to do in that early onboarding phase is identify, okay, well, what are the things that people actually clicked on? What type of resources are they interested in? What level, or what stage in their career are they at? And we’re looking at the content that they’re using and then tailoring the journey based on how they interact.

So we’re creating dynamic flows for users dependent on what they’re interested in. And I think that’s super important as is getting them engaged in the community. 

So I’ve talked about how we’re trying to make this transition from being a resource based community, to more of a community that’s built around a shared passion. And so we are trying to get people involved and engaged in our community, our forum, as quickly as possible and showing them, and kind of holding their hand to get through those first hurdles by showing them some really interesting content that might be relevant to them, by helping them create their profile, by showcasing some of our most interesting and trending content. So these are all things. We’re trying to provide value early, get them engaged and get some momentum in place so that they stick around.

Building a movement

So it sounds like you’re not trying to sell a product or resources, you’re trying to create a movement around a common passion.

Ben Aston: Definitely. Yeah. And I think it has a whole lot more longevity. In terms of building a business that is going to be around a decade from now. The products that we create, the courses that we make will be obsolete. 

But if we can successfully create a community of people who have a shared passion, who are engaged, then they’ll still be around in a decade. And I think building a community is really hard work. 

I think the mistake that you might make after listening to this is, “Oh yeah, let’s build a community that sounds easy.” It’s super, super difficult. Trying to get people to engage is really, really hard, but hard things are normally worth doing.

So I think often we default to the kind of easy option, which might produce some kind of short term fruits, but investing in something, building something for the long term, growing things more slowly is less attractive in our startup worlds that we’re used to where we’re trying to create unicorns, trying to get that hockey stick growth. 

Well, actually, if you embrace the fact that you’re not building that kind of a business, but you’re building something that will be around in 10 years time and going slowly, going more sustainably, then I think you can have more fun on the way and take the pressure off yourself to get instant results. So I think there’s just a word of caution there really.

So where do you see your community and your movement going from here?

Ben Aston: Yeah. So we’ve grown the community now to about 800 paying members right now in the course of about 18 months, which is great. I’m happy with that growth. I think there’s a ceiling actually to the size of the community that we can have, and it still be rich and engaging. So there’s a bit of a cap on that. 

So what we’re trying to do now is actually launch other communities in other disciplines as well. So we’ve created a site for product managers called theproductmanager.com. 

One for E-commerce called theecommmanager.com, one called People Managing People, which is kind of HR related, and one called The QA lead, which is all about quality assurance and quality engineering.

So the way that we’re scaling is by building communities in other disciplines and other niches as well. So the digital project manager’s our flagship and as things work and as things are successful and we hypothesize and we test and we learn and we optimize once we get to that point where we think we know what we’re doing, we then roll it out in these other platforms on these other sites. 

So yeah, we’re actually this year about to embark on a project to unify the sites together under one platform so that we can more easily publish and share content and really get some of those efficiencies of scale. But yeah, that’s what we’re doing. We’re growing new communities.

How do you go about keeping your content and training relevant and up-to-date?

Ben Aston: Yeah, that is super difficult, but we’ve been quite intentional right at the beginning. In focusing less on the tools and more on the higher level frameworks and theory that you can apply that stay relevant from one year to the next. 

So I think, yeah, if we were creating courses on how to run your next Facebook campaign and Facebook changes its interface every second week, we’d find it super difficult, but our overriding kind of principles for content is to make it evergreen. 

How can we create something that, yeah, we can come back to and update next year, but isn’t going to require rewriting. Because what we want to do is not have a churn of content. We don’t want to be a new site. 

We want to create stuff that’s evergreen that will be relevant next year. Well add relevant next year as it is this year, maybe with a new section on something. So yeah, we try to steer clear of ephemeral content and try and find those evergreen areas that we can write about.

Building a community

What are some tips you could share regarding being an entrepreneur in a digital world and building a community? 

Ben Aston: I think probably the most relevant thing to anyone starting or maybe for someone whose side hustling at the moment. I think one of my regrets is not leaving my full-time job earlier, and waiting so long. 

I’m not really sure why I waited so long other than I just had the comfort of a full-time job to fall back on. So yeah, if you’re thinking about making a jump, make the jump is something that I would recommend. 

And I think one of the really important things that was impactful was my first hire and then every subsequent hire after that. And I think sometimes we can be reticent to hire when we think, “Oh, we’re adding overhead.”

But my experience has been hiring great people who are better than you is going to really help you grow your business faster. And there’s no way that we would have grown the way we have, if I hadn’t hired really great people. 

So build that team as early as you can, make sure that you’re not settling for B-grade candidates, but hire the best people you possibly can and build the team that is going to help take you to where you want to go. 

And then I think it really comes down to … We’ve been talking about this a lot today. I’m a massive fan of things being good enough. If it’s good enough, ship it and then build things, tests, and then learn from it.

I think all too often, we get caught up in perfection, as we talked about. And it is our concept or idea of perfection, which doesn’t always play out in the real world at all. We can spend hours laboring over something and we might be creating the wrong thing altogether. 

So I’m a big fan of building things, testing, and learning. Once something is good enough to test rather than create perfect things. 

That way you’re able to see if something works and pivot much more quickly. So build a great team, leave your job, and start testing things. Don’t just assume you know.

Tool of the Week

Thinking about setting up a subscription-based side hustle? 

Chargebee is a popular subscription management platform that helps businesses automate and streamline their subscription billing and revenue operations. It offers a comprehensive set of features and tools designed to handle the complexities of subscription-based business models.

With Chargebee, businesses can easily set up and manage recurring billing for various subscription plans, including different pricing tiers, billing frequencies, and add-ons. The platform supports a wide range of billing models, such as flat-rate, metered, usage-based, and more, giving businesses flexibility in their pricing strategies.