How Income School migrated tens of thousands of dollars to Circle without lifting a finger
“One of the biggest reasons we never changed community platforms was migrating all those subscriptions...that was one of my biggest fears. We were really concerned about that...the migrations team was super helpful and the actual payments migration was awesome.”
Ricky Kesler
Founder, Income School
Overview
0
customers churned during the migration
30
days
from start to finish
1 in 2
Income School members log-in every month
What is Income School?
Income School is an educational platform that teaches how to make money blogging or by creating digital content for YouTube and social media.
Unscalable solutions
When Ricky Kesler and his co-founder Jim Harmer initially launched their course-based membership program on Wordpress, they couldn’t foresee the success they would have or just how complicated managing their business would become.
Fast forward to seven years later – they’d grown to over 1,000 members, achieved seven-figure annual revenues, and produced tens of hours of content that detailed exactly how to replicate their strategies for yourself. From the outside, it looked like their wildest dreams were coming true, but behind the scenes, things were a little messy.
The consequences of one of the first decisions they’d made for Income School—choosing where to host their membership program—was something they grappled with daily. As their business needs evolved, Ricky and his team resorted to layering on various Wordpress plugins to solve the problems-of-the-day, but over time, this patchwork of solutions was neither scalable nor resilient.
“It just got to be all of the different things we had to use, all the different WordPress plugins and stuff, it became this big mess, so we accumulated a lot of tech debt, basically. We [were] stuck in this system.”
Ricky’s a content creator, not a web developer, but he was spending so much time and energy managing and simply maintaining his Wordpress setup that it would be easy to mistake him for one.
“Because I was doing a lot of development work for so long but people weren't really seeing much, they're just like, "Man, is this getting any upgrades? What's going on?”
It wasn’t unusual for their brittle system, held together by wordpress plugins and a prayer, to break down; but it was particularly awkward for a company whose mission is to help people build websites.
“I teach people how to build their own websites, and then I have things breaking on my website. And I'm like, "You don't understand how complex this is compared to what I'm teaching you." But still, that alone was problematic.”
This led to a doubly poor member experience— first due to the platform's bugginess, and then because it continually redirected Ricky’s focus from addressing members' needs to merely keeping the platform operational.
Highly custom, higher maintenance
Ricky desperately wanted a solution that helped them “get a little more professional with how we approach things and consolidate a lot of our technology.” Over the years, they’d accumulated a lot of technical debt – the software equivalent of putting bandaids over bullet holes. And it was taking an awful lot of money – and time – to pay off.
He began working with a team of talented but expensive developers to “essentially rebuild the website and clean things up and be able to try to get a little bit better tracking.” But one year after the project began, it was no closer to being done.
“This was dragging on, it was taking a long time, and it was still pretty complicated. And in the end, we were just going to end up with something incredibly custom, which is also hard to maintain and expensive because it's hard to do ourselves.”
He felt stuck. He knew it was time to invest in a long-term home for his brand but worried it would take a lot of work and even more money to reconstruct, let alone elevate, what had taken him nearly a decade to build in the first place.
- Would he be able to transfer hundreds of hours of course content into a new platform?
- Could he possibly migrate thousands of dollars in member payments?
As Ricky envisioned his current best-case scenario—a highly custom solution that required constant and continuous upkeep — he knew he had to look for alternatives.
He’d already invested a year into building a custom solution; he didn’t have another year to waste.
More value for less money
Ricky first heard about Circle from his friend, Pat Flynn, who gave his full-chested recommendation for Circle. He quickly discovered why – he could get more value, for less money with Circle Plus (including a branded app).
“Holy cow, [Circle Plus] is actually going to save me money and to be a better solution.”
Best of all, the process was smoother than he could have ever imagined.
1. It was fast
Ricky expected moving his course content would be a slog. It was a decade’s worth of work – how could it not be?
“I know if I had just done it myself, it would've taken forever because I just have probably hundreds of videos.”
It wouldn’t be as simple as just reuploading each video either. Each video was a component of a lesson that included text and was part of a detailed course structure, adding layers of complexity to the process.
“Each of the videos is in a lesson, and so there's text content that goes with them. I just expected that to move on to something else was just going to just take hours and hours and hours of busy work, getting everything organized and then rebuilding it on a completely different platform.”
He was shocked when Circle shared the expected timeline – a single month.
“They were like, "Oh, by the way, it's probably going to take 30 days. Is that okay?" I was like, "Wait, are you kidding me? This will all be migrated and done in a month?" It's crazy.”
2. It was easy
The content migration was a completely white-glove experience that required almost no work on Ricky’s end.
“When the migrations team did the actual content migration, I did need to do a little bit of work to organize things ahead of time, but then they just took it. They just had a tool that pulled it in, and overnight it was all moved over. It just made it very easy.”
Besides simply passing on the need-to-know information, he was free to relax and focus on his business, saving himself and his team hours of busy work.
“What probably would've been, for at least one person on my team, a full week of just busy work, we just didn't even have to do. That was well worth any cost that we paid for Circle.”
3. It streamlined his business without ever disrupting it
One of the biggest obstacles that stopped Ricky from moving platforms sooner was the fear that he’d be risking the business he worked so hard to build. It’s difficult to transfer customer payment information, and asking members to re-enter their details is a big step that can lead to bigger drop offs.
“That was one of my biggest fears. One of the biggest reasons we never changed off of that WordPress plugin we used was migrating all those subscriptions. We were really concerned about that.”
A mishandled migration presents a critical moment where members reconsider whether their subscription is truly worth it. Given that one of the reasons Ricky was switching platforms was because of technical issues, he needed to assure members that this new choice would indeed be an improvement.
Before, managing subscriptions alone was a constant headache, as WordPress plugins would frequently disconnect members subscriptions and disrupt members’ access.
“One of the things we've always had to deal with is with the WordPress plugin we used, we'd run into random things where somebody's subscription would disconnect from their account on our website, and then they'd get charged, but they'd lose access or they'd try to cancel, but it wouldn't actually send the cancellation over to Stripe or PayPal, and then it was just a mess.”
Thankfully, the Circle team ensured his fears were unfounded. The concierge migrations team, led by Sarah, provided clear and tactful guidance throughout the process.
“Sarah, the migration specialist, gave me clear instructions on what was needed from me. I was slow on a couple things, and if I worked outside of her system, she's like, "Okay, great, you did this. All right, well here's this document again. Now let me know when you've completed these steps." And kept me on track. And that was great.”
This personalized support made the transition smooth and stress-free, significantly increasing Ricky's confidence in his decision to switch platforms. In the click of a button, Circle transferred thousands of dollars in payments without losing a single subscriber.
“The Stripe migration went very well. I was amazed they were able to bring over all of those subscriptions. Just no issue. The customers didn't have to do anything. No churn concerns there.”
Income School’s members—and business—were not even a little bit inconvenienced. On the contrary, many were pleasantly surprised by the seamless change
“On the Stripe side, people didn't even know. They're just like, "Oh, we're on a new platform. Cool. I love the new look.”
The outcome is a superior member experience that simultaneously reduced Ricky’s administrative burden.
“That's done. It's gone now. We don't even have to deal with that, so it's really nice.”
Ricky couldn't hide his enthusiasm when discussing how pleasant of an experience he had with Circle. Initially, he had braced himself for what he assumed would be a long and stressful process. However, the reality was a delightful surprise.
“Honestly, I'm super impressed with the product but also just with the timeline, how quickly that was able to happen. You guys have your processes down really well. And every single person I've worked with at Circle I've had very positive interactions with.”
The future is bright
At the end of the day, Ricky values saving time and money—like anyone—but his top concern has always been his members' experience, which he’s been able to uplevel thanks to Circle.
“Our members were really excited about [the branded app]. What we had before… the website and all the course content…it worked really well, but it wasn't the same. Now it's a full app.”
Every piece of the member journey is seamlessly integrated, from courses and conversations to live coaching calls – and it’s all accessible via the app.
As a result, engagement has skyrocketed. 45% of Income School’s members log-in to the community at least one time a month – 3X higher than the average for a community their size.
Ricky is both proud and excited about the transformation his business has gone through, not just for himself but what it signifies to an industry undergoing deep disruption. Innovation is on the move, and you can either lead the charge or get left behind. By investing heavily in his members' experience and how his own content business is perceived, Ricky’s made his choice clear.
“It’s been a crazy time for our industry anyway, and so there's been a lot of uncertainty and stuff, and so seeing this change made it really clear to people that I'm actively investing in this business. I'm very active in it. Because I was doing a lot of development work for so long but people weren't really seeing much, they're just like, "Man, is this getting any upgrades? What's going on?" And so this big change and happening over such a short time, it re-instilled in people confidence that I'm actively working on things for them and trying to make things better. It's instilled more confidence in current members, for sure.”
