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Ulysses is one of the most popular writing applications for macOS and iOS. The application started its life in 2003, more than a decade ago. In 2011, Max Seelemann and Marcus Fehn decided to start anew with a clean slate. It took the team eighteen months to create version 1.0, but the result was well worth the investment. In 2016, Ulysses won a prestigious Apple Design Award.

A few months ago, I talked with Max Seelemann, one of the founders of The Soulmen, the company behind Ulysses. We talked about the early days of Ulysses, how the application has evolved over the years, and what it’s like to run a software company that focuses on macOS and iOS development.

Mentioned in the Interview

Transcript

Bart Ulysses is a product I’ve been using for quite a while and I’m curious to hear Ulysses’ backstory. My first question is a bit of an obvious question. What’s the story behind Ulysses? How did it come into existence and why did you decide to create Ulysses?

Max Well, it’s been quite a while back, I think 2002. I was on a mailing list, and some guy there wrote “I have an idea for an app. I’m looking for someone who can do it.” That happened to be my partner, Marcus, and I was the person that said “Yes, let’s do it.” Then, he came up with an idea for a writing app. We started working on it, and released Ulysses in 2003. That’s how we got started.

Marcus wanted to write a book at that time, and he was looking for apps, but couldn’t find anything, so he came up with his own idea. I was in school, and he was a full-time web designer and making graphics. That continued like that for a while, actually, until it was 2011. So, we had done it as a part-time thing for like eight or nine years.

And then, when I was finished with my university, the Mac App Store came out, and we put up our old Ulysses that we had at that time, on the Mac App Store, and it was a blast. We actually made almost a year of the previous revenue, within the first two weeks. It wasn’t too much, I mean. Don’t imagine any big sums, but it was like “Well, we don’t need much. We can eat a little less, and then, from the money we got, we can finance three months of living. Let’s give it a shot!”

That’s when we decided to make it into a full-time job, and into a company. So, I started a Ph.D. and aborted it, and Marcus was just finished with his parental leave, so we were good to go, and we started. Our next side project was an iPad writing app, Daedalus, and that came out in that year. That gave us sort of a financial backing to start over with Ulysses again.

So, this is what happened. We had old Ulysses that was around all the time, and then in 2011, we decided it was time to make a new Ulysses. There was too much evolution in the market around it, and the product, as a side product, as a hobby thing, didn’t take enough evolutionary steps that would have been necessary to have it keep up to pace. So, we decided to scrap it entirely, and start over completely new. It took us one and a half years to release just 1.0 of the new Ulysses, and that was in April 2013.

Bart That’s very interesting. I’m sure you know that the Mac App Store has received a fair bit of criticism from developers, especially the last few years. But from what you tell me the Mac App Store was a turning point for Ulysses.

Max Absolutely. When I saw the announcement, I think it was an Apple special event or something, and we were extremely excited about it, because this was a new way to gain visibility for our product. Having a central place to acquire apps seemed so much more logical than the way it was before. Because before, you had to sort of find an app by accident. You couldn’t just go and look for apps in a way that was accessible to the regular user.

I mean, you could go to some version tracker sites, or MacUpdate, and find out about apps there, but that was sort of, I would say geek stuff, and the Mac App Store was the access point for regular consumers. That was a huge new marketplace, and as soon as we got on it, it was a great platform for us.

Bart You mentioned that it took about 18 months to release version 1.0, the version you released in 2013. What were some of the biggest hurdles? You already had a version of Ulysses. You knew what the problems were and what the challenges were. What was it that took so long? It’s of course a complex application, I’m not underestimating that, but what were some of the issues that you ran into along the way?

Max When we set out, and said “Let’s make an entirely new app,” we had our time estimates, and those were in the range of five or six months, for a team of two. Eventually, it took us 18 months, with a team of four. So, we completely, completely mis-estimated what would be needed, to make this app.

I guess there were a bunch of reasons. One was that we’d never worked on something full-time, so we thought that working on something full-time would make different estimates, and maybe it does, but our additions were so much larger than before, that we just weren’t able to make any good estimates. If we had known that it would take 18 months, we might not have pursued it, actually.

The other thing was that we sort of, in this process, we had to learn how to focus on the things that are most important. When we set out, we had a concept of what’s very, very big, very fully-featured, and we actually started developing in that direction. I had a colleague of mine, a friend of mine, come on the team and work with me, as a second developer, and he started out building a framework for the export from the app, that turned out to be way, way too complex, for what we actually needed in the end.

But at that point, there still was a plan to have something very complex, and very capable. We realized later on, that this wouldn’t be needed, so we sort of mis-developed, also. We branched into some complex feature settings that turned out, later, to be unneeded. So it’s a bunch of reasons.

And then, the hardest part was that we ran out of money during that time, and we really, really badly ran out of money. We had existing products that were selling, and we had our development of the new app, but if you focus just on the new app, then you can’t develop any further the old products, which means that those will see less and less sales. This is, of course, a problem, if you need to finance a new app. The issue being that, when building apps and selling them, just like the traditional way, you need to do the development first, and the money afterwards. And the bigger the development, the more you need to spend, before getting any income.

That was a huge problem, so we had really low wages. We had some of the employees even took pay cuts for two months, so it was really, really difficult. We were working like 60, 70 hour weeks for half a year. It was really killer to the health, and I was sick for months afterwards, after the release, so it was a really, really tough time, and I won’t be doing that again.

Bart I can imagine. But in the end, it was worth the effort, I suppose, because for example, a few years later, I think it was last year, you got an Apple design award for Ulysses. Across the board, Ulysses has been very well accepted in the Mac community, and also in the iOS community.

Looking back, if you could do anything differently, what is it you would do differently? Is it the initial feature set, for example?

Max From this very hard time of doing this new 1.0, we learned the hard way, that starting small is king. If I would do it again, I would do it in smaller steps. Of course, right now, we do have a completely different financial situation. We have a product that does make a good revenue, so we do have some money to spend, and we do have some reserve, so that we don’t run out of money like next week or so. So, we would have more peace of mind on it.

But then, I would also start smaller. I would do it in smaller iterations. I would maybe release a partial product first and then turn it into a full product step by step. Because you realize you have ideas, and you add them to the app, and your customers probably like them, but they also give you feedback, and the feedback almost always changes the features again.

So, the more you build without any feedback loops, without any direct contact with your customers, and the customers actually using the product, the further away you get from what the customers actually might be needing. So, getting in touch, getting something out early, is really key to getting the product in the direction that your customers actually need.

Bart That’s something I’ve heard before. It can be very useful to have that feedback loop.

Max Right, right. Absolutely. This is also something we’ve switched to in the aftermath, like making smaller releases, small feature sets, and then, when we are ready to share a preview, then we do a beta version, and look for feedback from the users, and what they like and what they dislike. That really helps us tremendously, in improving the quality and the usefulness of the app.

Bart Earlier, we talked about the Mac App Store, and how it helped Ulysses in the beginning. The Mac App Store hasn’t changed a lot over the past years, which is one of the things that a lot of people, especially developers, are a bit disappointed about. Also, quite recently, with the new releases of the MacBook Pros, the Mac ecosystem also received a fair bit of criticism from especially developers and pro users. How do you feel about the current state of the ecosystems, especially the Mac ecosystem?

Max It’s difficult. I see all the points you mentioned. I mean, there could be more new hardware, of course. And there could be more love and more attention to the Mac, as a platform. I absolutely would put my name under those wishes. But on the other hand, the Mac is also a very stable platform. If you’ve been with the Mac for a long time, and if you’ve been with the Mac for the times of 10.1 or 10.2, or 10.3, you would have seen an operating system that was barely usable. It was crashing all the time. It was slow, and it was really difficult to use.

If you compare it to the modern OS’s, they are so much more stable, they are so much more refined. I find there’s a bit of less pressure to actually advance it, because it’s quite good, actually. It’s not that the Mac platform itself is falling behind or something, it’s the desktop platform overall, that has matured, and is now at some certain point where the development is going a bit slower.

And regarding the hardware, look at what gets released, or what got released, recently. The new MacBook Pros are only barely faster than the devices that shipped two years earlier. When you look back at the times like ten years ago, every year, the machines would get so much faster. When I remember the time around 10.2, you would replace your computer every two or three years, because it was not usable anymore, because the advancements of the hardware were so radical, so fast, that the old machines were just not usable anymore.

Right now, you get some computer, and maybe you upgrade it to an SSD, but it can easily run for seven or eight years. The life span of the computer is also lengthening, so I also see there, there’s less pressure. There’s less to be gained from a hardware update, and there’s a longer lifespan of the product that exists. So, I can totally understand that there’s not that much pressure on Apple, to actually put more in there.

Bart Yeah, exactly. I think us Mac users are maybe a bit spoiled, expecting new things all the time, every year, especially with the iPhone. I agree that it’s not as bad as most people make you believe.

Another question I wanted to ask is about marketing. Ulysses has established a solid positioning, I think, in the community, as a solid writing application, with a lot of possibilities. Do you do any type of active marketing, such as advertising or content marketing, or is it all word of mouth? Do you have a plan in place for marketing?

Max We do have a full-time marketing position, since three years. We have one person that does nothing but working content marketing, or press contact management, and all that kind of stuff. There is quite some energy going into marketing. We didn’t always have, or didn’t pay much attention to, marketing. But then, at a conference, a good friend said to me, “Marketing is what keeps up the sales between the releases.”

So, when you look at a classic release, and then sales numbers, and from people that post it online, you see big spikes during the initial release, and then it falls down to almost zero. If you want to get those baselines, after a release, up, then you need to do marketing. That’s what the friend said to me, and he also said it takes years. We started doing marketing, and we realized it takes years, but it’s really worth the effort.

We do content marketing by running a blog, and having a newsletter that gives our users, or potential users, new content, and we check our app, to have better onboarding. We manage our press contacts, and we do sponsoring, for example, NaNoWriMo, if you know it? It’s a writing challenge, and we’ve been sponsoring it for the past three years now, to gain visibility.

So, you need to take some money in the hand, and spend it here and there. We don’t spend too much. I mean, I think we could spend a lot more. We try to spend it only on things that we really feel make a difference for the people, where we can offer something substantial. But yes, we do quite a lot of marketing.

Bart That’s great to hear, because I think content marketing, it indeed takes some time, but I’m a big fan of it. After a while, it really, really pays off. It’s a very interesting approach, I think, especially for a company like yours, that’s been around for several years.

Max I still don’t know exactly what is the right way or the wrong way. It’s just that we’ve been doing some things, and some things we’ve been doing get direct feedback, and some things don’t, but overall, it has made a huge difference, so that is what I can say. It’s difficult to look for the direct impact of something, and I still struggle with seeing “This is worth the money we spend, and this is worth the money we spend, but this is not.” This is a very difficult decision to make, and I still struggle with it. But overall, it really, really made a huge difference.

Bart Switching topics, I noticed that a few years ago, you released an iOS client. What I like about that is the price, to be honest. As a developer, it really pleases me to see that it’s not a $5 application. How important is the iOS client for your business? For your customers, I can imagine that it’s key that they have something for their iOS devices, but from a business perspective, how important was it, and is it, for you?

Max The business is quite crucially linked to our customers, so what is important for our customers is also important for us, as a business. Having an iOS app, so we started with an iPad app and last year, we released the iPhone version. Having those just makes the product so much better, that we can access so many more customers. This alone has a huge impact.

And then, we sell about the same number of copies on the Mac and on iOS. Maybe, on iOS, even slightly more. The iOS app is only half the price of the Mac app, so you can calculate it. It’s like a third or something, maybe 35% or 40% of our total business, so it’s very, very important.

Bart That’s nice to hear. It’s really great, I think, that they complement one another. The Mac app complements the iOS app, and vice versa.

Max Yeah. The iOS app is actually the full app. I mean, there’s a tiny handful of features that are not on the iOS app, that are on the Mac app, but overall, it’s the exact same app. That’s really what our people, our users, love, is that they can do the same thing on their telephone as on their desktop Mac.

Bart Do you think it would be more difficult to release Ulysses today, with a lot more competition? For example, I’m sure you’ve heard of Bear.

It’s taking off like crazy, and it looks like every day, there is a new writing application. Do you think you have an advantage, that you have a long history, and that people already know about Ulysses? Or would it be possible to launch Ulysses today?

Max I think it would surely be possible to launch Ulysses today. I think it would be a bit different. It would be taking a slightly different direction, but overall, I think it would be possible, yeah. If you release a product in a relatively small market, like the writing apps market—it’s not the biggest section of the whole App Store—if you release a product in a relatively small market, and it gets a lot of attention, then of course, it influences other products as well, just the same that our product is influenced by the products that are already there, or that are coming out.

So, the app would be different. Maybe not much, maybe a bit more, but I think it would be possible, yes. I mean, there’s a lot of competition now, but it’s still good to see that there is new competition coming up, and the competition can make a living, so the products are done well. So, I don’t feel like the market is over-saturated or something.

Bart That makes sense. I have one final question. It’s more of a personal interest. The Apple Design Award, what impact did it have on Ulysses? I mean, Ulysses was already successful at that time, so it wasn’t that you needed a big break or anything, but did it open any doors for you that were previously closed, or how did it impact Ulysses?

Max I think it did open a few doors, especially inside Apple. We will have to see, in the longer run, if those doors are just open for a short time, or if they will remain open. But it’s definitely a way to make our communication with Apple a bit stronger. So, if we say something that we want, if we have a feature request or something, or if we are in need of something, then Apple is very, very helpful. So, that is very important for us.

And then, outside of Apple, it has provided us with some interesting attention. Because before, nobody from the local press, for example, would care about us. Nobody knew that we existed. As soon as we got this award, I mean it went through the German press and got published in a lot of newspapers, and the local press caught on to it, and did interviews with me, as well.

We have sort of emerged into a pretty well-known local business now. That’s very interesting, because we get a lot of invites to go to fairs, or to do talks, or for an Open House day, that kind of stuff. It’s very interesting that we now get a lot of recognition locally, but we didn’t get anything before.

Bart Yeah. That’s nice to hear. If people want to know more about Ulysses, or about you, where can they find you?

Max Just go to ulyssesapp.com. You can find out everything about the app. There’s a team page, where you can find me and email me, if you need to know anything.

Bart Okay, that sounds good. Max, thanks a lot for your time. I learned quite a bit more about Ulysses, and I look forward to the next release.

Max Thank you very much.

Bart Take care.

I hope you enjoyed my conversation with Max Seelemann and I encourage you to check out Ulysses at ulyssesapp.com. You can follow Max on Twitter at @macguru17. Thank you for listening.

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