[98] Why I Stopped Selling Digital Products on Squarespace
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This transcript was generated by Descript AI and may contain errors.
[00:00:00] Speaker 3: If you teach people about Squarespace, why don't you sell your digital products on Squarespace? It's a valid question and one that I've gotten quite a few times throughout my career, and that's exactly what I'm going to be talking about in this episode. I'm Becca from Inside the Square, and in this podcast, I share my tips and tricks for creating a Squarespace website that you're proud of.
[00:00:19] I have been selling digital products for years. That is the core of my business here Inside the Square. But only the first year or so did I actually sell them using Squarespace. For there are three distinct reasons that I moved to different platforms for selling my products, and that's exactly what I'm going to be sharing with you in this episode.
[00:00:38] For a transcript of this episode, along with the links to the resources that I'll mention, visit insidethesquare.co/podcast. I also want to mention that the term Squarespace is a trademark of Squarespace Incorporated. This content is not affiliated with or endorsed by Squarespace Incorporated. This is just me sharing my experience as a Squarespace user to help other Squarespace users out there make the most of the platform.
[00:01:00] So let's get into it. If I sell digital products, why don't I use Squarespace to do it? Back in twenty nineteen, I made a 34-page PDF of my code collection, the codes I collected as a Squarespace designer. I started selling it to other designers. And doing so through Squarespace, I ran into some roadblocks almost immediately.
[00:01:20] First and foremost, you have to share a file, a physical file. And converting a code collection to a PDF turned into quite a hot mess. It took me a few weeks to really dial it in. When you copy code out of a PDF, it might change the formatting. It could add spaces, add line breaks where they didn't need to be, insert commas in places that didn't need to have commas.
[00:01:44] Copying code out of a PDF back in twenty nineteen was not an easy task. So right out of the gate, the way that I released my product opened up my inbox for quite a few support emails. People had purchased code, and it didn't quite work as intended. So that was the first thing I needed to find a workaround for.
[00:02:01] If I'm sharing a file, and it has to be a file, how can I sell a file on Squarespace that's easy to copy from? What I ended up doing was creating a single page PDF, and if you clicked anywhere on that page, it would take you to the digital version of that file, so you could easily copy the code and add it to your Squarespace website.
[00:02:20] But I ran into another snag. When someone purchased this digital product on Squarespace, they'd immediately be given a link to download the file. That link expired in 24 hours. Yep, 24 hours. If you've ever purchased a digital product, you might be like me, where you purchase it, click on the link to download it, then forget where the heck that file is.
[00:02:43] Or maybe you get distracted by something else and you wanna hop back into that project a few days later. Well, unfortunately, anyone who purchased this digital product from me, if they clicked on that link after 24 hours, they would get an error message saying the link was invalid. Now, to be fair, Squarespace has made some updates, and when someone clicks on a link for a digital product that was purchased more than 24 hours ago, the system is supposed to generate an email to send them a new link.
[00:03:10] Now, I'm honestly not sure if that was the case in 2019, but I am positive that I got quite a few emails every single week from people who had purchased a digital product, click on the link, and it was now invalid.
[00:03:23] Managing the support for that digital product was a big time suck for me, and I lost a lot of hours just tracking down orders and sending over links. I was more than happy to do it. I wanted to make sure people had what they paid for, but I knew that there had to be a better way
[00:03:38] I wanna pause on that for a second because I think there's something in here that goes way beyond digital products. To be fair to Squarespace, the system now does the right thing. You click on an expired link, it sends you a fresh one, problem solved, technically. But here's what actually happens. Someone buys your product at 11 o'clock at night.
[00:03:58] They're excited, they go to bed. Thursday rolls around, they've got a free hour. They dig back through their inbox, they click the link, and the screen says invalid. And what does a person do when they paid you money for something, and they try to access it, and all they get is an error message? They do not read the next sentence.
[00:04:16] They do not sit around waiting for another email to show up. They find your contact form and they email you, or they reply to the receipt that they were sent automatically saying, "Hey, I just bought this and it's not working." Even when the system is set up to send them a refreshed link, the customer is still going to panic, and that panic will be associated with your business, potentially the first interaction they have with your business besides consuming the content that you've published.
[00:04:42] I don't think that's a good thing, and I think that was actually pretty detrimental for me as I was growing a business for so many people to have that experience and that interaction. So I want you to keep that in mind if you're considering selling digital products. If there is any part of the customer experience that feels disconnected or panicky or stressful, or if there's any part of the customer experience that requires them to read the fine print to feel better, that is not going to be a good customer experience, and you might not want to have that associated with your business Another thing that was a little tricky was the follow-up emails that people would get after making a purchase.
[00:05:21] At the time of selling this content, I was able to alter a little bit of the content of the email, but selling more than one digital product meant I needed to send more than one message. I could use Squarespace campaigns to do this and set it up through different automations there, but that would mean multiple emails for every purchase.
[00:05:39] They would receive the link to download, they would receive the invoice or the receipt, and then they would receive an additional email with additional information. That was definitely not ideal. I didn't want to send anyone multiple emails for purchasing one thing. So that was another workaround that I needed to work through.
[00:05:57] I wanted to find a system where I could sell individual products and have a custom message sent to the person after purchasing that specific product. So here we are. We're looking for a link that doesn't expire, we're looking for an opportunity to sell just a link and not an actual file, and we need an opportunity to customize the immediate message that was sent to someone after purchasing an item.
[00:06:20] At the time of selling in 2019, those features were just not there within Squarespace. I also wanna talk about memberships for a moment, and this one is really important not just for the Squarespace users that are listening, but for the designers. Creating memberships, whether it be a members-only blog feature or a members-only digital course, you can technically set these up for your clients inside Squarespace, but I want you to know what you're walking them into.
[00:06:47] When somebody buys a membership through Squarespace, I want you to think about what has to happen. They have to create an account, they have to complete the purchase, and then ideally, they're gonna get a welcome email about all of the things. That, in Squarespace, is three separate emails for one decision, all landing in the same inbox within a few seconds of each other.
[00:07:07] So I want you to put yourself in that person's seat, the person that just joined the membership. You paid for something. You've got three messages sitting right there, and you don't know which one is the real one. One of them seems like a receipt or an invoice. Another one seems automated for creating an account.
[00:07:22] And then there's another one that's a welcome email. Which one is the link to log in? Do you need to open all three? Do you need to save all three? What's the most important action to take? So again, we're kind of hitting that confusing customer experience, just like we talked about with the link for a digital product.
[00:07:38] If their initial reaction is, "Let me read into the fine print," if it's not something that's, they instinctually know what to do next, that can be an issue for anyone that's brand new to your business. Someone just invested money, and you're already making it hard to work with you. That is not ideal, but it's technically how the system was designed So I wanna be really fair here because nothing about this is technically broken, okay?
[00:08:03] Money moved, access got granted, the technology did exactly what you said it would do. It's just the effort required. Effort on the setup side, effort on the customer side, effort on cleaning up the confusion for both sides. And if you're just starting out or you're a solo business owner like me, that effort can be kind of unsustainable.
[00:08:24] It's something that technically works, but if it costs you 20 minutes a day and a steady stream of confused customers within their first purchase, that's not really working for your business. That's when I think it's time to start looking around, not necessarily at fees, but at follow-up. But on that note, let's go ahead and talk about the fees.
[00:08:42] I started doing the math. My products are always lifetime access. You buy it once, you get it forever. I tried doing limited access once. It was a hot mess. I'm never going back to that again. Lifetime access is my jam. So if I was selling a product that was, say, $34.99, which was the original price of that 34-page PDF I had to pay a processing fee for that purchase.
[00:09:06] Then I had to pay a processing fee to this credit card company, and I was not getting a lot back on that particular digital product.
[00:09:13] I don't have a clear memory of the exact price point back in 2019, but I know that when I did the math, I started looking to some alternatives because, again, I had a low price point product at a fairly high volume.
[00:09:25] And for a struggling brand new business, that was definitely not the way to go. Now, it'd be very easy for me to end this episode sounding like Squarespace doesn't care about people that sell things, but that is not true at all, and I want to be crystal clear about it. It's just what they've been building lately isn't for me and my business, but they have a lot of features that can work for a lot of different business models.
[00:09:47] Last month, in July 2026, they released a whole suite of new features for selling limited quantities. So we now have a reserved cart option where an item gets held for someone during checkout with a countdown timer, and if they don't finish, it goes back into your shop. We've got quantity limits, so one person can't sweep through and take your entire inventory.
[00:10:08] We've got low inventory badges, pay links you can just text to someone or drop into a QR code, express checkout. And the way that they framed this was around empowering sellers to move away from constantly discounting and move towards a more curated, exclusive release, which honestly I think is a really good read of where independent selling is going right now.
[00:10:29] It's a strong feature release. If you make ceramics, for example, or you're a tattoo artist opening up your calendar, or you're running retreats with capped seats, these new features are for you, and this is a genuine upgrade all of those updates are definitely awesome, and I'm very excited for the clients I work with that sell physical products and offer services because I think we have some really cool things to integrate into their business model.
[00:10:53] In the show notes for this episode, you'll find links to three alternative platforms if you decide that Squarespace is not the right place for you to sell your product. But it might be perfect for you. If you have a high price point, if you have a zip file of content, if you're already on Squarespace, the learning curve is a lot shorter if you're comfortable using the platform, so maybe it is the right choice
[00:11:14] For anyone listening who's selling your own products or the designers listening who are ready to help their clients find the right platform, here's what I actually want you to consider. Three specific questions, and yes, the order matters, so stick with me here.
[00:11:28] The first question: what are you selling? If the answer is physical products or bookable services, Squarespace is a great choice. Go check out those new limited release tools that I just mentioned and explore some example sites that I'll have linked into the show notes. There are some really cool people selling really cool things on the Squarespace platform.
[00:11:48] So again, physical products or bookable services, you've got some amazing options and brand new features to check out. So definitely consider Squarespace as a good choice. Now, question number two is what's your volume? I want you to run the numbers on this. Take one month of sales or your ideal sales numbers and work out the transaction fees, then the processing fees, and compare that to different platforms.
[00:12:12] Would it be better for you to upgrade your subscription to Squarespace to a higher level to avoid the percentage fee for the digital products that you're selling, or would it be better to look at an alternative for selling your products? I clearly have my website on Squarespace. I just happen to sell things using a different platform, and that is totally an option.
[00:12:31] So do the math and find out the actual sales volume and percentage of your profits that are going toward using Squarespace as a system for selling those digital products. Spend a few minutes with a calculator. If math is not your thing, hop into your favorite AI platform and ask it to run the numbers for you.
[00:12:48] Is sticking with Squarespace for your digital product the right choice based on the volume? You could also discover that leveling up your subscription to something slightly higher in Squarespace would actually save you even more money than the cost of that subscription. So definitely something important to keep in mind.
[00:13:05] Now, the third question is one that I really should have asked myself in the beginning of this. What happens after the sale? If you've got one file and one transaction that's the whole relationship, Squarespace is great for that. The platform can handle all of it. But if you've got a course or a membership, tiered access, anything where you need to do a follow-up, a check-in, an onboarding process, that's where the work starts to compound.
[00:13:29] Now, to be clear, that happens in just about any platform that you use. But the more control you have over the messaging that happens after a product is purchased, the better the customer experience will be. So think about that customer journey after they make the purchase and how you can support them.
[00:13:45] Make sure that your support system doesn't rely on them reading the fine print
[00:13:49] So one last thing before I let you go. My thoughts in this episode are all based on the product that started it all, my CSS cheat sheet, which was once a 34-page PDF that I started selling back in 2019. That product has grown into a Notion database full of hundreds of selectors and snippets for customizing Squarespace, and I'm actually retiring that product at the end of the month and taking my business in a different direction, which is a genuinely strange thing to sit with while I'm recording an episode about where you should put your digital products.
[00:14:22] The thoughts in this episode are based off of experience, a very long firsthand education in what selling a digital file can actually cost you in your business. Squarespace might be the perfect platform for selling the content that you're going to sell for your business. Or you might want to look at an add-on service that can really enhance the product offerings that you have available on your website.
[00:14:44] Inside the show notes for this episode, I've listed some of my favorites that I think work really well within my Squarespace ecosystem. Because again, huge fan of Squarespace in general, and that is where my website will be for a very long time. Thank you so much for tuning into this episode. I'm Becca from Inside the Square, and if you have any questions about Squarespace or all the cool things that it can do, send me an email.
[00:15:06] My inbox is open 24/7. hello@insidethesquare.co. I'd love to hear from you. Thank you so much for tuning in. I hope you enjoyed this episode. And most importantly, have fun with your Squarespace website. Bye for now
If I teach people how to use Squarespace, why don't I sell my digital products on Squarespace?
Fair question.
I actually did when I started.
Back in 2019, my first digital product was a 34-page PDF full of Squarespace code. And almost immediately, I started learning the difference between a system that can technically sell a digital product and one that works well for the way you want to run your business.
For me, the biggest issue wasn't actually checkout.
It was everything that happened after someone bought.
The customer experience became the problem
My original product contained code, and copying code out of a PDF was messy. Formatting could change, spaces appeared where they shouldn't, and suddenly a product meant to save people time was generating support emails.
I found a workaround, but then ran into another problem: Squarespace's digital download links expired after 24 hours.
Squarespace handles this better now. If someone clicks an expired link, the system can send them a fresh one.
Technically, problem solved.
But imagine buying something, coming back a few days later when you finally have time to use it, and seeing invalid link.
Are you calmly reading the instructions underneath?
Probably not.
You're wondering why the thing you paid for doesn't work.
That's the distinction I eventually started paying attention to: something can technically work and still create a bad customer experience.
The same issue showed up with follow-up emails.
With digital products and memberships, customers can receive multiple automated messages for one purchase: a receipt, an account email, a delivery email, a welcome email.
Again, nothing is technically broken.
But now your new customer has several emails and one question:
Which one am I supposed to open?
If someone's first experience after giving your business money is confusion, that's worth thinking about.
Then I started doing the math
My products have traditionally been lower-priced, lifetime-access products.
As sales increased, transaction and payment-processing fees mattered more — especially when I was also spending time answering support questions and managing workarounds.
That's when I started looking at other platforms.
This doesn't mean Squarespace is a bad place to sell.
Far from it.
Squarespace has been adding some genuinely useful commerce features, especially for limited releases and physical products. Reserved carts, quantity limits, low-inventory badges, pay links, and express checkout can be fantastic for someone selling ceramics, merchandise, appointments, retreat spots, or other limited inventory.
Those features just aren't particularly important to the kind of digital-product business I run.
So should you sell digital products on Squarespace?
Maybe!
If you're deciding where to sell — or you're a Squarespace designer helping a client make that decision — I think there are three questions you should ask.
1. What are you selling?
For physical products and bookable services, Squarespace can be an excellent choice.
It can also work really well for straightforward digital products: a ZIP file, photography, fonts, templates, or something where the customer makes one purchase and downloads one thing.
And if you're already comfortable with Squarespace, keeping everything in one platform has an obvious advantage: there's very little learning curve.
2. What's your sales volume?
Don't compare platforms based only on their monthly price.
Run the numbers.
Take a realistic month of sales and calculate what you'll pay in transaction fees and payment processing. Then compare that to the cost of upgrading your Squarespace plan or using another platform.
You might discover that upgrading Squarespace saves you money.
You might discover that another checkout platform makes more sense.
And remember: your website can stay on Squarespace even if your checkout doesn't.
That's exactly what I do.
3. What happens after the sale?
This is the question I wish I'd asked from the beginning.
If someone buys one file and that's basically the entire transaction, you probably don't need a complicated system.
But what if you're selling a course? A membership? A resource that gets updated? Something that requires onboarding or ongoing communication?
Ask:
How do customers access what they bought?
What message do they receive immediately afterward?
What happens when they come back six months later?
What happens when something goes wrong?
The more complicated the relationship becomes after someone clicks buy, the more important the system behind that purchase becomes.
What I use instead
Today, I prefer Flodesk to sell my digital products, I like having checkout, customer segmentation, email marketing, and follow-up automations working together in one place. If the experience after the sale matters just as much as the checkout itself, this is where I'd start. Get a discount if you sign up with my affiliate link: https://flodesk.com/c/INSIDETHESQUARE
Two other platforms worth exploring are SendOwl, which is specifically built around digital-product delivery, and Payhip, which offers a flexible lower-cost entry point for downloads, courses, memberships, and subscriptions.
There's no universally perfect platform. The right one depends on what you're selling and what you need that platform to do after the sale.
My original little 34-page PDF eventually became my Squarespace CSS Cheat Sheet, a database containing hundreds of selectors and snippets. Seven years later, I'm retiring that product and taking my business in a different direction.
Squarespace might be exactly the right place for you to sell your digital products.
Or your Squarespace website might be the perfect home for your business while another platform handles the sale.
Choose based on what you're selling, how much you're selling, and what needs to happen after someone buys it.
