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Feb. 5, 2025

Time to KILL IT with Your Subscriptions on Shopify 🔥. w/ Matthew Holman from Subscription Prescription

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💡 Episode Highlights:

Subscriptions on Shopify aren’t dying—they’re just evolving! In this episode, we dive deep into what separates thriving Shopi9fy subscription brands from those struggling to survive. Matthew Holman is a leading expert in the space and he shares some of the best actionable insights you'll ever hear to build a high-retention, high-growth subscription business on Shopify. 

💣 The knowledge bombs he drops in this episode are insane! 💣

Key Takeaways – Are You Making These Subscription Mistakes?

✅ Why are some Shopify brands see 20,000 new subscriptions in just 3 months while others are failing?
✅ How can a simple shift in your offer—like quarterly billing—boost retention and reduce churn?
✅ Why are post-purchase engagement and onboarding emails critical to keeping subscribers happy?
✅ What’s the one metric most subscription brands ignore—but should obsess over—to maximize revenue?
✅ How can you turn your best subscribers into true brand advocates and increase their lifetime value?

Subscription Growth by the Numbers

📈 Subscription-based businesses on Shopify have grown by over 100% year-over-year, with merchants seeing 30% higher customer lifetime value (LTV) compared to one-time buyers.
📦 92% of subscribers visit their customer portal at least once—are you using it to drive upsells and engagement?
💰 Brands offering multi-month prepaid options see significantly lower churn than those relying only on month-to-month subscriptions.

🎙️ Host: Jay Myers
🎙️ Guest: Matthew Holman (Subscription Prescription)

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Transcript

Jay Myers: Matthew. I'm here to see the doctor. I have a really bad case of high churn. My low conversion rates, they're flaring up again, and they're really itchy.

My LTV hurts everywhere. Everywhere I touch, my LTV hurts. I need a subscription prescription. Can you help me?

Matthew Holman: Absolutely, Jay. You've come to the right place. I've got, I've got all the tinctures and lotions and pills for you to fix your program and get all that stuff sorted.

Jay Myers: So I, before I get into my diagnosis for all my pains, how did you, do you come from a long line of family subscription doctors or how did you get to where you are today?

Matthew Holman: Well, I will say my my dad is an actual doctor both internal medicine and psychiatry but I'd like to joke that no I can't. I did not follow that path. I went into business entrepreneurship and, and did not decide you know, it's not one of those career paths you think, oh, I'm going to go become a subscription expert.

But I was following the entrepreneur's journey and joined my partner at a company called Qpilot as a marketing co founder of subscription software, primarily on WooCommerce WordPress. And that's where I got my first taste for it. But the fun part is, is the longer we were doing that, we thought I, we started to start focusing on.

Trying to grow our own customers business because if their GMV grew, we made money off them having more subscriptions and that's when I started to get this real kind of one taste for really enjoying this type of business. Problem solving and understanding these problems, but also realizing that there's not a lot of people doing this.

And so as an entrepreneur, both my partner and I were like, wow, there's not really like consultants, a lot of consultants or agencies focusing on this. And we see it's a massive market. So it's kind of how subscription prescription was born a couple of years ago as a newsletter podcast, and now a consultancy.

Right,

Jay Myers: Yeah. I was going to say, I should probably give some context if some jumped right into this episode and didn't know that you, you have a podcast called the subscription prescription and a newsletter your handle on social media is the subscription doc. And so that's a little bit of background there. So, okay.

But so honestly, though, kidding aside, I mean, aren't. Aren't subscriptions dying? Everyone's saying they're tired of them. I went through my, I went through my credit card actually a few weeks ago and I canceled a bunch of subscriptions. So isn't, isn't everyone doing that?

Matthew Holman: I, they, they are. And it's funny. Cause it's like just a little while ago, I was reading a LinkedIn post about somebody talking about 2025 subscriptions are going to die. And I think that they're not like as a model, as a business model, if anything, it's like barely got its legs under it. I think that in many ways it's changing.

I think that a lot of people are canceling unnecessary things. I was looking at like. They're predicting in streaming services are going to do more and more bundling options. So if you, you know, you subscribe to Apple music, you're going to get, you know, you're going to get other apps and services with that, right?

Like, like that happened to me when I upgraded my phone at Verizon recently, they, they got me to sign up for paramount plus and Apple music through them instead of my own, cause I could save money. And so that, I think that's going to continue to happen, but I think what's fun with the physical product side is like, We're just now like unlocking like technology that is makes it really really easy to manage So yes easy to cancel, but also easy to personalize and control so I think the subscriptions are going to are undergoing a little bit of an evolution where it's going from like You know, this lock in, you know, old mentality of like, it just comes when it comes to now having total control over the delivery over the items over from your phone or email or Siri or, you know, an AI assistant.

So I think that they're here to stay. It's just a question of that. They're coming. Going to change and it's becoming more competitive.

Jay Myers: It's funny you mentioned Apple because I have thought for a long time that there should be an Apple subscription. You know, because the strength of Apple products is the ecosystem of products. Like if you have, it's, it's fine when you have an Apple phone, but when you have an iPad and Apple watch, AirPods, a Mac book, it's a really great experience because they all work so well together.

And especially if you use iCloud, everything just syncs automatically. So like I get a new phone every probably two years, I get a new laptop, maybe every four years and you know, whatever. There's a, there's a. I would pay a certain amount per month to have a Apple subscription. And you could have different tiers, right?

A 300 a month, a 900 a month or whatever. I I'm surprised I haven't launched that yet.

Matthew Holman: I would love that because it's funny that you mentioned four products and it's like, I have, I'm using AirPods watch filming with the iPhone and watching you on my Mac book, so

Jay Myers: so you would be a prime candidate for this.

Matthew Holman: I would love that. Cause I think about that regularly. Like, do I need to upgrade my watch? Do I really need to upgrade my phone?

But so it does happen. Like, I think I'm on a similar. Schedule to you. I do think it's like, that's a quick, cause I get asked that question a lot about non typical subscription industries. Like, how do I create a subscription? And I think it's always like, how well do you know your consumer? Like, how well do you know what they value or not?

You know, service based businesses, like how, how nice would it be if somebody could drop in whenever they want to get a question answered? Like, that's, that's the kind of screams membership as opposed to like paying you hourly. So, like, there's actually like, you know, law firms that are exploring this kind of idea.

Like, you know, there's other businesses that are and again, I think it just comes down to, you got to know your customer and what they value and what would be valuable to them. That also happens to work with your business model.

Jay Myers: So if some subscription brands are doing well, there's probably, there's a lot that are failing. What are, what is the, what is the real secret to subscription growth?

Matthew Holman: Yeah, I think what's so fascinating, this is a question I ask online all the time is, which do you think is more important acquisition or retention? Because I'm a subscription guy. So you might think that my answer is going to be retention. And there's a ton of retention people on Twitter. So I always get that kind of response, but I think the truth is like understanding that it's actually a complete system.

So understanding that how acquisition can actually lend itself to success. So On retention. So, like, one of the simplest ways to think about this is, is if you normally just sell a monthly subscription to say pet food, there's a lot of different ways to, to buy pet food. And that has very little value other than a little bit of a price discount.

If you're starting to add a gift with purchase, or every time we ship a bag of pet food, we ship a new treat or a toy for your dog, or, Hey, we're going to offer you a quarterly subscription or six months. If you commit six months. Right now we'll give you 30 percent off instead of 20 percent off. So there's you can start to think about like there's a lot of ways to frame a subscription Offer on the acquisition side that actually lends itself to better retention So I mentioned like the gift with purchase like those types of orders tend to do better in over time A six month commitment does better than a monthly subscription even quarterly So like with all our clients we push really heavily to have a quarterly option on the product page and on upsells Which i'm sure we'll talk about more but And if you see the churn numbers that I've seen from brand to brand to brand, I have not yet seen one where a three month month over month subscription has a better retention rate than a quarterly subscription at that first renewal.

They always have a better renewal rate. So just things like that, where you're starting to think through, how can I acquire somebody that lends itself naturally to keeping them around? Those are the brands that are really, really thriving today.

Jay Myers: It's interesting. You know, when you, when you install iPhone apps, now there's always the option. It's like 9. 99 a month or 10. 18 for the year. It's like, or something, something just ridiculous discount, like 93 percent off if you pay annually. I know one, I mean, obviously iPhone apps are very, they've gotten very savvy at how you subscribe.

You know, they're, they're all free in the app store, but then you subscribe once you're in the app. And it's so easy to unsubscribe because it's all done. And that's why I think that it's not like, but I, I do, I mean, we see the same thing, obviously the annual subscriptions do drastically better than monthly subscriptions.

So when you say quarterly subscriptions, you're still shipping monthly billing quarterly.

Matthew Holman: It can, it can be both ways. So like, say like a, so, so like I break it down like a subscription box, you know, say like you're doing battle box, say, right. And you're doing monthly battle box. You're not gonna, I'm trying to convince, I say this, cause I'm trying to convince John to test this idea. Cause he's a little reluctant to get into the longer commitments, but that, so I say that a little tongue in cheek, but the idea is you might pay six months at once, and then you're going to get the monthly box because the box only comes monthly, right?

But say if I'm buying skincare. You could try to, I've seen both methods. I, from an environmental standpoint, it makes more sense to like, Hey, I'm going to ship you six months worth of product all at once because it's skincare and it's a couple of bottles. You, you put them in your closet. It's not a big deal.

You can't do that with pet food because like, you know, nobody's going to keep six giant bags of pet food. Right. So, so it does depend on like what's most convenient for the customer. What makes most sense from like a shipping standpoint, but you can do either way. What, like if you do the six months at a time, getting one month, shipments that's typically viewed as it's called a prepaid subscription as opposed to like, a six month where you get all the product at once is just like a six months recurring subscription.

Jay Myers: Interesting. So when you, okay. So you, you said you are retention and acquisition both matter. You're now, I On the retention side though you mentioned some things around acquisition. What, what, what are some of the biggest lifts you see for improving retention? Obviously how you acquire them, you mentioned that like better acquisition, better customers.

But other than that. What are some things, ways you can improve retention?

Matthew Holman: Yeah. I think it's like, it often feels like it's, it's funny sometimes cause they'll do these workshops and like whiteboard with brands about this stuff. And it's often kind of like this funny experience of like, Like a, it's not rocket science in some ways, but, but sometimes you need to hear an outside perspective of like, do you really know all the commonly asked questions about your product?

Do you really know all the common reasons why somebody doesn't like your product or doesn't have a good product experience? Like I bought something recently, it was a sleep supplement and I had to, I had to DM the founder to ask him like, when's the optimal time to take the supplement? Is it an hour before bed or 30 minutes?

Like, and so it's like, just that's that basic of a question. If that's not being addressed, you open the door for like negative experiences. So like the best way to think about it is, is once the purchase happens, you have this delay between when somebody has bought it and when they're getting your, your subscription delivered to you.

Right. And so. You need to be engaging in an onboarding and education series that addresses commonly asked questions, right? Related to how the product works. How long does it take to see benefits? What's coming? Like those types of things, depending on what you're selling, educate them on the ingredients on the founder story.

And then once it's there, make sure there's a great initial product experience. A brand that I'm a huge fan of Because I'd use their stuff on Shopify, but also just because I just love this is called X endurance. It's a supplement company. And they basically say, once you get it, we actually don't want you to start taking it right away.

We want you to go do your normal, like big week workout that you would do and make sure you track that time and that effort. Then start taking our supplement for seven days and then go do that same workout again, so we can prove to you that our product works. And so, not everybody can do it that way, but it's like, you know, if you're doing skincare, like, if you're not prompting somebody to take a before picture, Like you open the box.

I've got this new skin care product. Take a before picture, upload it to us or email it to us or whatever you want to create some or just save it on your phone. If that's worst case, start using the product. Okay, go look at that picture. Now, 2 weeks later, 3 weeks later, how what that time from is like.

Make somebody prove like you can prove it to them if you have a good product. And so whatever that is, if it's tea, like I had this match of tea experience where it felt like I was kind of in Japan with the way they were because it was like very much that kind of like vibe. And so it felt really cool drinking this match of tea, feeling like I had a Japanese tea experience and it wasn't like I'm not saying it's not cultural appropriation, but the idea is I felt like that.

And that positive first experience is so critical for the, because subscriptions are the fact that somebody is using your product for months and months. And if they don't use it right away, and don't have a positive experience right away, then they're not going to be around.

Jay Myers: Yeah. You know, I think you can probably email someone three times the day that they place a subscription. Like there's, there's so much excitement. And it's, they actually have done studies on like brain waves and endorphins and dopamine hits. And like the peak moment of excitement in the shopping experience is right when you click checkout.

Like we've talked about this before. And like, I've, I've, I've, you've probably done something similar where like you're excited and you're placing a big order with your wife maybe. And you're like, come over here. I'm going to click checkout. Okay. Let's click it together. We're buying this expensive thing.

And it's, there's a moment there and. And then most brands, it's just like a boring, plain order, confirmation email, but anything like if it, it, anything you sell the value is only what the customer perceives of it. And so like, you've got this window of opportunity, like you could send them an email the second they like the supplements, like what, what it's made, how it's all natural, organic ingredients.

One hour later, send them another one. Three hours later, they're not going to click spam on the first day, cause they're excited.

Matthew Holman: And I think it really is. And that's why actually I'm a huge proponent of like post purchase surveys as well. Like, you know, like I'm a huge fan of like no commerce is because As a brand, as a generally subscriptions are doing something that's a little life altering like, yes, there's mundane stuff, but we're talking about skin care.

We're talking about supplements. We're talking about people caring about their pets or their kids. So there's like a compelling reason why they bought this. And so you ask a post purchase more more questions than just attribution. You ask them like. You know, if it's, if you're selling a weight loss supplement, like, and you don't know your, the goals of your, of your, of your subscribers, like, are they newly divorced trying to get back in shape?

Is it, is it like a health thing? Is it because they're going to go do their first marathon? If you don't know those core reasons, like you're missing out on a massive opportunity to build retention, because if you know that your, your weight loss supplement or people that are newly divorced, and you don't have that mentioning.

You don't have talk about that or talk about like, how about like, you know, getting yourself back or, you know, like all those types of like marketing messaging you could engage in. Like you're missing out on a massive opportunity. And so similarly with like pet food, if like you're selling fresh made pet food or it's different than the competitors and you're not reminding.

So that's a big, I'm a big proponent of as well. It's like in your transactional emails for upcoming order notification. If you're pet food and it's, you know, Ethically sourced and healthy in this. And you're not reminding people of that. You're, again, you're missing out on, on, on, on that touch point.

And that's, those are the places where we're seeing after the offer. So after the way, like somebody buys from you, the next most impactful thing you can do is just look at all these communication touch points and remind people about why they bought and why the product is valuable to them.

Jay Myers: Yeah. I mean, the way I think about it is they buy from you. They're not actually a customer yet. Like they're the, the, you know, the jobs to be done, like what, what they're actually doing is they're trying the product. They're, they're, they're trying it. And so like, when you see that new subscriber sign up, it's not actually a subscriber until month two, month three.

They're still trying it. They still, you got to educate them. You got to learn more about them and you, you have to sell them to become a long term subscriber, then turn them into an advocate and other things. But

Matthew Holman: Absolutely.

Jay Myers: okay. I, I want to get the whole point of the show is to get some really good. Takeaways, hopefully for some people.

So the best brands you work with a lot of brands, what are the brands that are just killing it in subscriptions? Like there's, there's, there is brands that are absolutely killing it. And yes, what we talked about earlier, there's some that are dying a slow death, but no, the subscriptions are not dying as an industry it's growing.

And trust me, like we both work in it. We see them, the ones that are really winning, what are they doing?

Matthew Holman: Yeah. A couple of things. And I'll mention like one of my clients, they launched like three months ago and they're already at I think just eclipsed 20, 000 subscriptions.

Jay Myers: zero to 20, 000 in three months. Holy cow. Can you

Matthew Holman: So yeah, subscript no, I can't, I

Jay Myers: you? Okay. No, wait, no worries.

Matthew Holman: yeah. But they're and it's, it's, well, it's a, it's a hydration brand.

And so it's like subscriptions aren't dead. Like they're, when you nail the product, when you nail the branding, when you nail that off. So I will say this, that the biggest thing that I'm seeing, like really move the needle is, is experimenting with the offer, right? So this is on your product page or on a landing page.

How are people buying? There's a couple of different examples and websites. I'm actually working on like a replo template right now that I can just give people so they can see the similar design, but offering a quarterly option. A monthly subscription option and a six month option, just so that you can have three choices to see.

And a lot of people are falling on that quarterly middle option as well as the one time below that. So creating a product page that has a couple different buying options is actually increasing conversion rate, higher LTV, higher AOV. And, and better, better retention. So that's like the first thing is like spending a lot of time, like getting into the, the offers and then also experimenting with this idea of like, am I going to give a free gift?

Am I, whatever the other little extra incentive can I put to put like, it's like the cherry on top. That's, that's, what's really moving the needle for brands right now. It's like, if you're getting like, like, it's like the butcher boxes of the world. If you subscribe in a butcher box. You're interested in getting that monthly shipment, but you're also buying chicken wings for life.

Or you got a Thanksgiving turkey at Thanksgiving, right? Like, like you're doing something extra on top that feels, it just has to feel like you're getting. A really good deal, even though you might be shelling out 200 on some quarterly subscription. So that's, that's the first thing. And then the second thing is like brands that are really engaging after the fact.

So this is one of the biggest opportunities I see is, okay. You do that onboarding email, the education we talked about, but starting with like month two or month three, like, how are you engaging with subscribers? So a very simple way we're using a tool called Zamo. It's available on Shopify integrates with Klaviyo.

I'm a huge fan of it because we're putting in the upcoming order notification email, an option to upgrade from a monthly to a quarterly. So if somebody likes their subscription, lock them in, get them to do three months or six months, like give them an extra 10 or 20 percent off another item like that.

And we're doing that in the transactional email. So the take rates we're getting one and a half to 2%. Of the subscriber base each month upgrading to a quarterly subscription, which is

Jay Myers: And what type of discounts do you offer on, or do you

Matthew Holman: another, an extra 10%,

Jay Myers: like it's okay.

Matthew Holman: Yeah, I would say like from a financial standpoint, the quarterly is really compelling because it's less shipments.

So you're spending less on shipping. So the shipping is more affordable. You're usually locking people in better. So you're, and you, and the cash flow you get up front. So it's better, it's better for cash flow. So you can afford to give, say like if you're monthly subscribed and save, it's 20%, 15%, 10%, you could do quarterly at another 10% and, and not blink an eye.

So that's, that's one little option there. And then if you have other products starting to create a chain of where you're introducing people to other products, and that's where. If you don't start educating, educating people up front about the product and how it works, they're going to ignore you.

They're more likely to ignore that those communications. So if you make it kind of normal, that it's okay for us to talk to you a little bit about our products. Then when we email you a couple months down the road, again, I really liked the portal experiences we're seeing where you're seeing offers and banners, like, you know, between I mean, you know, as well as I do, there's so many different compelling ways to show, like click this to upgrade, add this to your next order, doing that kind of stuff.

Like it, I think that the brands that I'm, that are struggling are the ones that are afraid of the subscriber. They're afraid they're going to cancel.

Jay Myers: Yeah.

Matthew Holman: And those ones are kind of like, it's a little bit more tenuous, but the ones that are like leaning heavily into, Oh, our subscribers love us. So we're going to message them about a new product or a new offer or a new option.

We're going to increase that LTV of those subscribers and not, and yes, we might lose some people because of that, but overall it's much, much more beneficial for the, for the brand.

Jay Myers: Yeah. You will, you will lose people, but you'll grow your existing subscribers. You'll turn them into better, more happy customers that are more likely to refer friends as well too. And you mentioned the subscriber portal and you know, that's, we, we know that 92 percent of subscribers visit the subscriber portal at least once.

So like, it's a, it's a super valuable page and you, yeah, we've seen people that want to lock it and make it so customers can't go and they have to phone to cancel and like, no, no, no, that's the exact

Matthew Holman: tricky. Yep. Yep. Absolutely.

Jay Myers: Okay. I want you to imagine you're launching a subscription brand, a, you like health and wellness.

So let's let's say it's a, like, a mushroom supplement for energy or some, some sort. And you got to, it's day one, you've got zero subscribers. I want to know exactly what you would do from a strategy standpoint to launch your subscription brand.

Matthew Holman: Yeah. And I'll tell you, I think about this a lot because yeah, at some point I'm going to launch a brand and probably in the health and wellness space for me, I'm thinking much more strategy around branding and lifestyle. So if I'm say we're doing a mushroom an energy supplement. Then I'm going to start thinking through like, okay, how, how am I going to be talking about this and how, how can I touch more than just a mushroom coffee or a mushroom drink?

Right. I want to be talking to new dads. I want to be talking to like people, like founders that are, that are That are working all hours of the day, people or moms that are feeling worn out, like they're being pulled in 10 different directions. And I want to start thinking through, like, for me, I think the thing that gets me really excited is I'm trying to think through a communication and engagement strategy that makes more sense than just a product notification system.

So meaning, Hey, would you like to sign up for daily affirmation texts on like, get like, Taking charge of the day,

Jay Myers: hmm. Mm

Matthew Holman: you know, carpe diem, right? We could call it the carpe diem program. So you're going to get, you can, you can opt into a daily text reminder with motivational quotes or, you know, we maybe we'll have a membership group or a Facebook group or something like that.

That's, you know, trying to create some empowerment and have other people share their energies, you know, generating secrets and stuff like that. So I'm trying to think through what can I add? Because that to me, from a cost standpoint is not that much to like. Yes, the cost of sending those SMS messages and yes, the cost of like writing some of that stuff, which you could do in batches that as a value add would be really, really massive for certain people, which those are the people that I want to get because those are the people that my hypothesis would be would stay subscribed longer.

So I'm trying to think through like ways I can be engaged because then if I want to start introducing new products. If I want to upsell them to other things, if I want to collaborate with a partner, I already have an audience that actually likes to hear from me and appreciates hearing from me and is following me on Tik TOK and Instagram because of that, those like video.

So I'd want also like video content and stuff like that that goes along with that. Otherwise I feel like it just becomes a really competitive space and it just becomes product to product, which ultimately lands on price to price.

Jay Myers: What I'm hearing from that is you would focus on building the relationship that comes with a, like has a subscription offering. Like it, it very much sounds like. Build relationship, build community, build the texts, build the, build the video content. Oh, and you have a subscription too. Like it's not like

Matthew Holman: a lot of time asking people about what would be helpful for them. And I think the other, I think the hard part too, for a lot of brands that I work with and talk to are, is like, not every customer is going to be the same. So the example I like to use is like, I've been a dollar shave club subscriber for like going on eight years now or whatever, and I never buy an upsell.

I never touched my, like a couple years ago, I got my, Razor shipment dialed in the way I liked and I just leave it alone and I get a replacement handle every year or something like that. I am the lowest touch, but maybe not like the most ideal. Cause I don't buy all their stuff as opposed to other people.

I know that like buy their like grooming kits and like all these other things. And those customers LTV, but, but there's, but I like the brand and I like the product and I'm going to keep buying it. Those are two different customer types. And same thing with my experiences, like there might be people that just like the mushroom coffee.

They like the brand, but they don't want the texting and they don't care to follow me on social that's, that's fine. Like I can create an experience that works for both, but I know that people that buy the more premium experience or see value in that are going to be more worthwhile, more profitable to me down, down, down, downstream.

So that's why I think sometimes as a brand, it's like, it's okay that people pick the monthly option instead of the quarterly, or it's okay that people have bought the one time versus the subscription. I have systems in place to try to get them to upgrade, but if they don't, they don't. I'm just not going to lose sleep over that segment.

I'm going to spend more time and effort and energy and resources on the profitable segment. What can I offer them? What more value can I unlock from them? That's the secret to like making the subscription business profitable.

Jay Myers: Yeah. We talked a bit about this when we were at sub summit it's and I remember a couple of people coming up to us after, well, one person particularly came up and said that was the most valuable 30 minutes of, of sub summit. Because I remember we asked, The audience, like, does anyone know their net dollar retention rate?

And it's not something that a lot of brands think about. And so for those listening, that dollar retention rate is you have, there's user churn and there's dollar churn. So you can get a thousand subscribers a month. And if you lose. A hundred of them, that's 10 percent user churn. But if your existing subscribers upgrade, add more products, become essentially spend more money, you might not have dollar churn.

You might actually be at a point where you are losing 10%, but your existing subscribers become 10 percent more valuable. And then you have a net dollar retention of what would be a hundred percent. It's, it's, it's. It's it's flat. I, you know, Shopify has a net dollar retention of it's, I think something like 121 percent because even though they, they actually have, I would say a very high churn rate, but what Shopify does really well is they have a path for a store to sign up for 29 a month and eventually be paying

Matthew Holman: Right.

Jay Myers: 000 a month on plus when, what, you know, so like there, there's that even, and that will account for hundreds of stores that churn.

And. It's something that I think a lot of brands probably don't like, I don't know if you think about the brands you talk to, like, if you said, Hey, what's your net dollar attention, would they know that number off the top of their head?

Matthew Holman: No, it's not how a lot of them think about it, which, which I think is the right way. Like, I think you can think about it in terms of average LTV. I think you can get close to it, like thinking of it that way, but it's still not quite the same. I would say like an interesting example of a brand we work with.

Came to me recently said, Hey, cause they sell both monthly and quarterly options. And they do a lot to try to prioritize the quarterly. And they're seeing churn the monthly subscription churn is really high. And so like the first question I'm asking as I'm looking at this problem is. Is not how, because they're saying, how do we stop monthly churn? And my question is, is do we have a process for getting people that like monthly to upgrade to quarterly? that's actually my first response because I get that people leave because there's but oftentimes it's they're a bad customer. They're a bad fit. They had a bad experience There's actually a lot of things that are completely out of your control

Jay Myers: hmm.

Matthew Holman: If I'm not trying to upgrade people, if I'm not trying to figure out out of a thousand new subscribers this month, who's going to be my premium six month year lifetime subscribers.

I don't have that system in place. I'm missing out on the real opportunity. And then yes, that's where I think of like classic retention effort is email and some of this other stuff to try to get people to use the product and win them back. That's how you like work with a high monthly churn of trying to like.

Get some of that to be better. But if you don't know how to upgrade then you're missing out on, I think on, on the real opportunity.

Jay Myers: Do you have a subscription company? If someone said what's the best subscription company I can model after that I can go and I can look at everything they do. I can look at their product pages, their customer portal. I can sign up. I can read their emails. I can see how they market to me, talk to me, cross sell me, upsell me educate me on the product.

Like who is The creme de la creme of subscription brands that if someone said like, you know what, I got 50 bucks a month. I want to go to subscribe and become a student of a brand in

Matthew Holman: is a really good question. And when I not, I mean, I get asked about other good brands at times, but like. So I'll, I'll list a couple, like, I think that, oh man, there's, there actually is quite a few, so I'll, I'll, the first thing I'll, I'll, I'll, the problem is, is I usually think about brands for specific reasons.

For, well, the, and like say like, so like Battle Box, I mentioned 'em already. I think Battle Box does one of the coolest things ever, which is they send a content video about what's in the box. After the box ships. So they're, so you, so you get teased about what's in there and get really excited and they use, they have an amazing content game.

And then, but like, they're not like, you don't swap out stuff. Like there's not like a lot of like versatility with the way you might think of a normal subscription. So it's not like they're an ideal for that type of scenario, but they're really great at content and experience. But like, there's some skincare brands like Tiege Hanley.

Like, I think like they do a really great job of that. I was, I was talking to No, now it's my newborn baby brain. That's making me forget this brand name. I had another skincare brand that they were Oh you know, I interviewed Brian McDonald from almost pride in my podcast and he was talking about, they actually spend a lot of time on education as well, like talking about product differentiation, differentiation.

Jay Myers: And he's a perfect example for it because they, they really need to, right. It's raw dog food. So it's

Matthew Holman: right. I do think like a lot of the big ones, I think like, I'm trying to think of it like another the, the product page example, I keep, I throw to everybody I'll say is respire. com. It's a, it's like a hostage. It's a hostage tape, respire. com. Their product page, I think is beautiful and shows the, the The monthly quarterly and 6 month option.

I also really, really like the way human H. U. M. A. N. N. You can't, you have to, you have to Google it to see a landing page. Cause their landing page offers a little bit different than their product

Jay Myers: Right. And, and probably click on one of their ads, I imagine

Matthew Holman: yeah, yeah, you got, yeah. So sorry, sorry, humans by

Jay Myers: I'm sure they're

Matthew Holman: but go look at their, go look at their offers because they show like, they'll sell you a six month supply while they're selling you a four, a six month supply for the price of a four month supply.

So it's like, you get six, you get, you buy four months and they give you two months free. So like they're doing something really, really fascinating with, with that piece. And there, there actually are a lot of, a lot of brands that are doing a really, really good job just depending on the space that you're in.

But again, I think it's part of that too, is the technology pieces. Now it's, it's a lot easier for somebody on bold, on skio, on loop, on recharge to like, They're like implementing new features. The portal looks better. That's, that's where I think something's really. And then again, I'm super bullish on Zamo.

If anybody is like thinking about tools, being able to automate. It's, it's a one, it's an embed, it's an embed tool. So like inside your Klaviyo notifications you can send a transactional email. Cause I just mentioned all this stuff that's good for the portal, but honestly, I would rather somebody doesn't go to the portal if they don't need to.

Jay Myers: a hundred percent.

Matthew Holman: Right. So if I can put the skip feature or a delay feature or an upsell feature in an email, that's like one click change. Then great. So like, you know, get our poo was doing this for a while. And now Zamo is kind of, I think, taking it to another level. So it's like all about that customer experience standpoint, but a lot of skincare brands, like I think that they're just amazing at, so, so it's funny.

Skincare brands are amazing at unboxing. I think pet food brands are like great at like. Personalizing and talking about your pet and asking more questions about your pet, which is something I think more brands should steal from, regardless of what you're doing X endurance is a supplement brand that I really like.

I mentioned as well as they have a membership offer that I think is really interesting to look at and pay attention to. Yeah,

Jay Myers: Yeah. And so different ones. Do you, do you take a bit of budget, your, your month, personal monthly budget and subscribe to things just because you want to. It's the experience or you just subscribe

Matthew Holman: and no. Like I get, I get, I get free product often, which is my wife complains about. But I do like I do. Yes. For me. It's like, I'm a little bit more of a particular, like, I'm curious about what this looks like. I want to see what this is like. Like, for example, this brand isn't on Shopify, but my wife had a custom hair care subscription.

They're on Magento. So. which I think was part of the problem. And she like loved the product and hated everything

Jay Myers: About the subscription.

Matthew Holman: And it was like, if they were on Shopify, all of that, I think would have been so much more seamless and, and, and easy to use.

Jay Myers: Well, I, I don't know if that leads into my next question, but you could use that one if you want. My next question was going to be like, given the choice of any brand in the world, who would you like to work with with your consultancy? Like if you could pick a brand and so like maybe it's a brand that's actually like doing pretty good despite themself.

Or just a great. A great brand that you think maybe has an amazing opportunity for subscriptions, but they're not. Who'd be your ideal brand?

Matthew Holman: Yeah. That's a good, that's a really good question.

Jay Myers: You need it up on your vision board, Matt.

Matthew Holman: I do. I do. I, I needed, I needed a little bit of that. So, so honestly, so my, my wife up until she was pregnant was, is a, been a subscriber of Lola for a long time. I actually would love to work with Lola and, and help them figure out. I think, I think there's some opportunity there with how they're managing their subscriber experience and managing their upsell portions product swapping.

I think when you have a product that it needs to be used, But there's a lot of different reasons why there's different SKUs, why different women are using different SKUs, that there's some, there's some experience opportunities there. Honestly, I would love to spend some time just with Dr. Squatch, just because I think that that brand is so cool and their purchase experience is so amazing.

But I do, I do see anybody with Like in Utah, there's a couple of brands, big brands here, like Dime Beauty and Just Ingredients that you know, I don't mind talking about it cause they know, cause I've been bugging them. We've been having some strategy chats, but so I would say any brand that has a big, a diverse SKU count to me feels like Greenfield.

It's like most likely you are not prioritizing certain products. You don't probably don't have much of an upsell or a good swap strategy, other than in the cancellation portal. So that's kind of where it's like, if you have a lot of, if you have more than a one hero product, to me, that's like actually really interesting because then we can start looking at like, what's what products perform better.

So like, I'll tell you a very quick anecdote story of, I did a, I did a consult call, like just a one hour once with a brand that had three products. And they were prioritizing all three on the homepage. And you and I have done homepage teardowns before, so you'll know exactly where I'm going with this.

They had three products that they prioritized. When we looked at the LTV of all three, one product had twice the LTV of the other two. And so my proposal to the brand was. You need to pry. You need to become this product company that needs to become your homepage or landing page. That's the lead in these other two are just upsells. And the founder was like, nah, we want to keep selling all three and prioritize all three. And it's like, Hey, the data supports that one of your products is twice as effective. Just naturally without you doing anything is retained twice as better as the others. And so that's what I mean is when you look at like diverse skew catalogs, people are selling tons of different flavors or styles and stuff.

It's like, Oh, wow. Now I can find out what's actually like, Hey, we need to be selling this more. Hey, when these two get bought together, you, you have subscribers that are bundling these two

Jay Myers: Bundle subscriptions.

Matthew Holman: right? Like all that stuff. It's like, to me, that's like green field of like, cause it's kind of chaotic.

So it helps to have somebody come in and say, this is what we're going to do. Anyway.

Jay Myers: Yeah. Bundle subscriptions are amazing. Like we, we see that when anyone subscribes to more than one product, their LTV goes up drastically. Like

Matthew Holman: It's much more than the dollar, the difference in AOV. It's there's a, yeah, no, you're right. There's a retention element. Like.

Jay Myers: Yeah. I don't know what it is. I guess they're, they're bought in, they're using more of the product suites, they're something, but it's, I mean, if you can get customers to, to bundle together in a subscription, it's, it's a game changer.

Matthew Holman: Oh yeah.

Jay Myers: What would you say is the hardest thing that you have to sell brands on when you're consulting them and you're trying to convince them to, to do something, to change something about how they operate what's, what's the hardest sell or that you get

Matthew Holman: Yeah. I think the hardest thing is I've mentioned a little bit, so I'll say two things. One is just the mindset of the, you know, the the loss versus gain mindset of I'm, I'm worried about keeping the subscribe. How do we keep subscribers longer as opposed to how do we acquire better subscribers or how do we keep.

The good subscribers happier. How do we make the good subscribers happier? So again, this idea of like, if I, if I have 20 percent first month churn, a lot of brands are freaking out about the 20 percent and I'm

Jay Myers: Mm hmm.

Matthew Holman: what's happening to the 80 percent month over month. What does it look like three, six months from now?

So that's, that's one thing. And then the other thing is just, I think that I see a lot of, I'd see a lack of experience. I see a lack of like the retention piece. It's just part of the Shopify is like. Brands are putting massive resources into acquisition and to branding and styling and all of that stuff.

And then you'll have like a junior level retention market or mentioning a 40 million, managing a 40 million business. And so, so I think that's often where there's like, kind of like a gap. And so that's where it's like, Hey, if you already have an email team, you already have an e commerce manager. You have some of those pieces in place.

Like, let's add a little bit of strategy to the subscription component. Even if it's just like, I'll just. Give you some insights on where you could go. Then the rest of the team can go execute. Cause I think that's often what's hot. People just don't know what we should be working on. Like, should we be sending this email?

Should we be doing building this flow? Like, so that's kind of like where it's like often like. You know, you need to put a little more effort in here, especially when you've seen this, it's like brands that are have like 60 percent of their monthly revenue is coming from subscriptions, like recurring customers, 80 percent of their budget is on that 40 percent that they're trying to acquire every month.

And so that's, again, I'm not saying it doesn't have to be drastic, but shift a little bit more. I think you'll see better, better, stronger returns.

Jay Myers: I love that. Have you heard of, probably have the concept of your thousand true fans? Have you heard that talk or read that book?

Matthew Holman: No, tell me

Jay Myers: Okay. You just, you reminded me of it. So you, you subconsciously, it

Matthew Holman: maybe I've heard it and

Jay Myers: like, it sounds like you know it. It's, it's so, you can, there's a book about it. You can just Google it.

There's YouTube talks about it. But the concept is that you, you might have like, Tens of thousands of customers. You really only have like a segment that is your true fans. They're like the super users of your product. They're the ones that can't live without it. They, their retention is really high.

They're referring people like if it's a software company, they're, you're, they're logging into your app every day. They're just like really, really good users. And a lot of times as brands or whatever, whatever you sell, you, You, you look at the 20 percent that is first month churn, or you look at the customers that are turning and you're spending all your time, you've got like cancellation flows and you're trying to win them back and you're worried about the ones that are losing.

But what you should be doing is finding, you know, your thousand true fans, which it doesn't have to be a thousand. That's just kind of a metaphor. You find your true fans. Find out what makes them your true fans. Like, why are they so good? Are they a certain type of a person? Do they, do they work in a certain industry?

Do they, are they, do they have a certain health problem or do they, whatever, whatever, what makes them so good? And then go out and find more people just like

Matthew Holman: better like that.

Jay Myers: Don't worry about the rest. And we spend. So much time painting all our customers with the same brush. And we just say, Oh, I've got 30 percent churn.

You might actually be doing amazing with your segment. So don't stress about losing those. Go out and find more of people just like your thousand true fans. And this is not a concept I've made up. You can Google your thousand true fans and there's a, there's a kind of a whole book about it, but like you, you kind of said it and that was like,

Matthew Holman: Well, it's i'll answer this with this question It's like okay for anybody listening And you want to take one takeaway from this like go do this one thing because I can guarantee you if you're a subscription brand You do cancellation surveys Are you doing surveys when somebody hits three, four, five, six months about why they like the product?

Because if you're not, that's a massive opportunity to figure out why they like it, ask them if they can remember why they bought in the first place, but then also ask them why they keep it, why they're using it. What they love, what they hate, what could be better, what could be more valuable. That's where like, again, we've seen it.

Like that's where we start seeing like, Oh my goodness. Like we're not offering this upsell. Like, Oh my goodness. They don't know, like they love our product catalog, but we only send an email upsell email once a month to these guys. Like, what are we doing? Like that all the time.

Jay Myers: Yeah. And even just reaching out, like you think of the brands you mentioned, X, X endurance and those other ones, like if, if you've got an email saying, what can we do better? What can, how, what can we improve? Like even just knowing that they care would make an impact on your, yeah, absolutely. I mean, I got a list of probably 20 more questions, but I know you have to run.

So, this has been, this has been really, really good. What do you If someone is, you put out a ton of amazing content, like I'll just go out and say, if you're not following Matthew on, on, I think primarily LinkedIn would be the main, cause you put

Matthew Holman: and Twitter, but

Jay Myers: LinkedIn and Twitter,

Matthew Holman: best one.

Jay Myers: Follow him on both of those channels.

He, I, I listened to all his podcasts. I, I can't say I read every single newsletter because I'm more of a listener than a reader cause I can listen and go to the gym at the same time. But I listened to every single podcast and honestly, like I learned something every single podcast and you put out such good content where I'll put the links in the show notes, but where would you like to send people to

Matthew Holman: Yeah, definitely. You can definitely check me out on LinkedIn, Matthew Holman, subscription doc or subscription prescription. And then the subscription doc. com is my website, which is getting a little bit of a brand left right now, but you can find all our links on there too.

Jay Myers: Amazing. Thank you so much, Matt.

Matthew Holman Profile Photo

Matthew Holman

CEO

Matthew Holman is one of the foremost thought leaders in the subscription space. He's helped Shopify subscription brands add hundreds of thousands of subscribers and worked with some of the most popular and fastest growing subscription brands!

Matt did not plan on being the subscription doc, but after working as the marketing leader at a subscription startup, he and his partner kept seeing a lack of expertise in the space. They first started a newsletter, podcast, and then full consultancy to help brands figure out subscriptions.

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