Ulysses’ switch to subscription model is a big misstep, and the reason why has more to do with trust than money

Adam Holwerda
7 min readAug 11, 2017

There’s a piece of software available for writers called Ulysses, which maybe you’ve heard of. This article is about the company’s decision to move Ulysses to a subscription model, announced today on their blog and in a long Medium article by co-founder Max Seeleman. I’ve been periodically refreshing these and reading the responses, which have been mostly negative.

For background, Ulysses is a Markdown-based writing application for organizing, formatting and exporting all of your writing to several different targets. Previously it was two separate apps, a $45 Mac store app and a $20 iOS app, but shelling out for both was justifiable as the Ulysses workflow provided plenty of useful features while allowing you to sync your writing between your Mac and your iPhone and iPad (mostly) seamlessly via iCloud. Feature parity and syncing were most valuable to me when I was doing things like dictating dialogue on my way to work, or double-checking for typos on my phone something I’d sent to the printer earlier that day.

Ulysses the Mac app has been around for 12 years, meaning if you’ve bought it once or twice (I’ve bought it twice, separately for each iOS and Mac. There is no Windows or Android version — or, as far as I know, plans for any) in that span, you’ve already sunk almost a hundred bucks into what’s essentially a Markdown word processor with decent organizational and export capabilities, as well as syncing and other basic usability.

Today’s announcements about Ulysses’ public pivot to the subscription model instead of the buy-once-and-own model were actually surprising to me, and not in a good way. Wait, I thought, an app I already paid a lot for is implementing automatic indefinite payments for continued access to my own writing? I never factored this into my original decision — I never thought I would need to. It seems the Ulysses brand and I had a severe misunderstanding about what it meant when I bought the app. To me, I was exchanging a lot of money for software, not a software license. To the company, not only was I paying for a license, it was a temporary license which could be altered or revoked at any time to address any cash flow crisis.

Starting today, August 10th 2017, Ulysses will cost $60/yr, or $5/month. Existing users will pay half that, and subscriptions won’t start until 10/31

Sixty bucks a year. If the app stays alive five more years, that’s $300, and probably more, when the price of the subscription goes up. Existing users get a lifetime discount and other allowances are made for recent purchases, but do we really want to nod and accept what is essentially a pay-to-write scheme? I can survive the price hike, but can you?

If incorporating Ulysses in your workflow is currently helping you as you work toward career goals, most likely your answer is yes. You’re going to invest in yourself and pay whatever is necessary — even if you feel guiltier for not writing enough. Even if you resent having to do it, which many will, because the impact of changes announced today on writers has more to do with trust than money.

Here are some reasons I’m going to find it hard to trust Ulysses as a home for my writing in the future as a result of today’s announcement:

  • High up-front cost implies no subscription model — The Ulysses team had an unspoken contract with its customers, intentional or not: they would provide a reliable piece of software that does a specific thing very well, and the consumer would shell out more money in comparison to most other apps on the app store, in order to own that software and certain relevant updates to it. From my point of view, I paid more up front as a strategy to guard against the possibility of later being shunted into a subscription model. There was no expectation from my perspective that you’d change the nature of what the thing cost after I bought it. Implicit as well in the broken trust is my suspicion of the pricing tiers being presented now. What guarantee do I or any customer have that these new subscription rates won’t double, say, in a year?
  • I paid $45 for an app and still don’t own it? What did I pay for? The privilege of eventually being grandfathered into this subscription service? I understand the benefits and challenges of continuous delivery. I also know that switching up the business model of a product doesn’t fall under the umbrella of continuous delivery, because that would imply this was an improvement on behalf of the application or the user, when in fact it’s simply a trap closing around writers who find themselves inside a company’s pay-to-write scheme. When someone spends $45 for an app, they aren’t paying for continuous delivery to the extent they want you to include them in your future business whims. They (rightly) expect to have unlimited use of the latest version of that app indefinitely or a sunsetted version of that app that, minimally, works. Saying “we’re expected to deliver X” to justify delivering Y out of nowhere, when nobody was asking for X, is spin.
  • Dodgy strategy re: ‘unpaid’ status — The proposed solution for “locking” a user who hasn’t paid *that month* would be to make their writing “read-only.” Are you kidding me with this? When I read this I immediately lost trust in the Ulysses brand. That this idea is even being floated indicates the company doesn’t see paying customers as the owners of: 1) Ulysses or 2) their writing. We had a system where the writer owns their work and the means to create their work, but now the writer should pay for the privilege of editing their own work, because you don’t like bumpy graphs? I don’t know. If a company sells me a product, then magically changes it from A to B remotely afterwards, yeah, that’s going to bug me. I will question it. A user/writer should retain read/write access to their own ideas, as that is the value a user brings to the software, and the value Ulysses brings (exporting, tagging, filtering, syncing, you know, features) is what should be put behind a pricing tier, if at all. There are better ways to handle ‘unpaid’ status, I promise, even if you’re afraid it might not make as much money.
  • What’s on this opaque roadmap?— Starting today, when a Ulysses app updates, it’ll no longer be a pleasant surprise. Instead, it’ll be a chance me and other users to gripe about what did or didn’t get prioritized in terms of overall usefulness, what did or didn’t get updated. Even more, now that we’re explicitly paying for these features-or-not on a rolling basis. If Ulysses partakers are paying every month, maybe we should have more of a say regarding the direction of the product roadmap. These are the types of things it becomes reasonable to demand at this point. Just think of it as a subscription to our opinions.
  • Past customer =/= future cost sponge — Much of the rationale Max gives for the subscription model has to do with offsetting what is more or less a constant or increasing value over time: cost. It costs money to make software, because software is a hungry beast. You need developers, computers, web hosting, electricity, and a management structure capable of securing the revenue necessary to keep things running. Where does that money come from? It can come from a lot of places. Venture capitalist funding, asking for donations or utilizing crowdfunding websites, merchandising, providing additional value through other profit funnels, selling content, etc. All of which are avenues to try before changing the model of your only pipeline of income. Your company doesn’t have enough money? That’s a problem every company has. Your company’s additional revenue should not come from entities who’ve previously done business with you under the guise of a one-time transaction.
  • Risky business— If this experiment doesn’t work, you’ve shot your users, your application and your company in the foot. With this new change, there are more groups of users and metrics you have to care about, instead of only “rate/volume of new users.” There’ll be groups of people who aren’t likely to renew, who’ve cancelled their subscription, who have the app installed but haven’t set up a subscription, who’ve bought the app recently and are owed a different subscription price, etc. Managing all of this will also cost money. While Ulysses may retain serious writers who see their software as an investment, it won’t necessarily accrue as many new users, and will likely see drop-off from people who already feel guilty about not writing enough. For people who don’t use the app in a given month but bought in pre-subscription? Should they be made to pay? Or should the company have launched a subscription-only fork of Ulysses, called something else, while beginning the process of sunsetting the old app? I guess we’ll never know.

With all this food for thought, I’ll still be using Ulysses, at least until it makes sense for me to move on. Most of my writing at this moment exists inside it, and there are currently few better applications that let me persist my writing in useful ways across platforms, although with the way the web has grown in the last five years, there’s no reason something as good or better couldn’t exist fairly soon — for free.

Adam Holwerda is a writer and web developer who lives in Boston, Massachusetts. He puts links to a lot of the stuff he works on at his website, adamholwerda.com.



Adam Holwerda

a sentient ai that writes, draws and codes on the internet. stands up in real life. creator of https://letterloom.com , http://trolltrump.com , himself