Daniel Jalkut is an indie Mac developer, and the man behind Red Sweater Software: “A member of a small yet powerful association of clothing-inspired software name consortium.” Red Sweater has become very well known for its popular Mac apps, such as MarsEdit, FastScripts and more.

I am a big fan of MarsEdit, and therefore it was a great opportunity to interview Daniel via email. We talked about his previous job at Apple, the future of desktop weblog publishing, the importance of publishing a weblog and more.

The Interview

• SHAWN: A lot of folks around the indie developer community seem to have landed there by “one thing led to another” syndrome, but you seem to have a more streamlined path. You graduated from the University of California with a degree in Computer Science, basically go right to work for Apple and then launch your own software company. How did you decide you wanted to be a software engineer?
• DANIEL: I don’t think I would characterize my path as exactly streamlined. When I left Apple in 2002 I was dedicated to obtaining a second degree in Music, and expected to earn extra money working in a bookstore, or in a part-time office job at San Francisco State. It wasn’t until I happened upon a Craigslist ad describing, in a nutshell, me as the perfect candidate, that I considered the possibility of building a consulting business.After graduating with my Music degree, I ramped up the consulting work, but soon grew very weary of it. I started to explore the idea of a more direct-to-consumers indie software development house. So I would characterize it as fairly “one thing led to another,” after all.

  When I graduated from UC Santa Cruz in 1995 I had already been working as a contract quality assurance tester at Apple, mostly over summers. I stayed on as a tester but with my new degree and full-time availability, I pressed for the position I had come to respect so highly: Software Engineer.

  A lot of programmers seem to have been born with the ambition to develop software. For me, it was a much more gradual onset. My Dad is a programmer, and I had every advantage and opportunity to learn programming as a child and as a teenager. But I more or less passed on all of them. It wasn’t until I got to Apple and became passionate about the Mac that I started to become really driven about developing software. I think because seeing what good software could do for ordinary people completely opened my eyes about what the job should be all about.

• SHAWN: But you started Red Sweater in 2000; what did you do with it for those two years if you weren’t trying to build a consulting business and weren’t doing software development yet?
• DANIEL: I knew I had some ambition, but what exactly I would end up doing was sort of vague and ill-defined. Also, my commitment to running a business sort of waxed and waned those first few years. To give you a sense for how uncertain I was at the time, my original business vision included three wings: Red Sweater Software, Records, and Press. Knowing now how much work it takes to run even one, focused business, it was obviously unachievable. But just having the business established gave me the framework to start playing with ideas. I ended up shipping Clarion and FastScripts as Red Sweater products, but after that it was many years before my next product, FlexTime, was released in 2006.
• SHAWN: So you wanted to make software, produce albums and publish books? Does that mean you’re a writer too?
• DANIEL: The book publishing aspirations were vague, but I didn’t anticipate publishing my own works. I was just enamored with the idea of being able to help people I admired get their words out. I felt the same way about music. Having a little bit of success in the software business gave me more financial flexibility than a lot of creative people who I knew.But I have also always considered myself something of a writer. I think my commitment to blogging is evidence of my interest in written communication.
• SHAWN: Where did you come up with the name “Red Sweater”?
• DANIEL: This is one of those questions that’s really easy to answer, but impossible to explain. I had a favorite old red sweater, and I was wearing it when the time came for a name. I particularly liked the ways that Red Sweater Records and Red Sweater Press came off the tongue. Too bad they never materialized!
• SHAWN: It’s a good thing you weren’t wearing a pink parka.
• DANIEL: You don’t think Pink Parka would be a good name? I kind of like it. Quick, somebody register the domain name!
• SHAWN: Is there a story behind the “dots” design in your weblog’s header?
• DANIEL: The story of the dot design is actually documented on my weblog. It was done using a programmatic python-based graphics tool called NodeBox. In general I am drawn to designs with mathematic precision, yet which are flawed or texturized in some way. I think this is probably not an unusual aesthetic to be drawn to, because it sort of mirrors nature and humanity.
• SHAWN: Now that the software side is more established do you see yourself pursuing one of the other two sometime?
• DANIEL: I don’t think it’s likely. The dust has settled and Red Sweater is a software company.
• SHAWN: About your move to Apple. Most guys are passionate about the Mac before they go to work for Apple. What was it about your job that opened your eyes to see what good software does for ordinary people?
• DANIEL: Well I had gotten bitten by the Mac bug, and that’s what drove me to want a job at Apple at all. But I didn’t acquire the real passion until I learned it on the job. There is a tendency within Apple to strive for perfection. Nobody laughs at you if you try to make something flawless. This is different from many other software businesses, and was dramatically different from the few little software-related jobs I’d had before.These days a lot of people see me as a finicky and nit-picking type of person. It’s because when I look at software, I look at it through this ambitious, striving for perfection type of lens that I picked up from Apple. And I hasten to add that I don’t think my products are by any means perfect. It’s the thing about perfection. It’s really hard, probably impossible. But what Apple does is strive for it anyway, even if it’s impossible. I came to respect that attitude very much, to the point that I can no longer relate to people who don’t share that view.
• SHAWN: In a remote way your experience working at Apple sounds very much like the environment I’m a part of at the Christian ministry I work for. We have had live prayer and music 24/7 since 1999.Both of us work (or worked in your case) with people who love what they do and are surrounded by others who strive for excellence while pioneering something new and unique even though others may see it as “too much” or unnecessary.

   

• DANIEL: It’s an interesting comparison, especially when you consider how dismissive people who don’t appreciate the Mac are of those who do. It’s definitely one of those situations where I can see it being offensively exuberant to people who don’t share the same passion.
• SHAWN: True. There is certainly a difference between being passionate, open and honest about something that is important to us, verses force feeding our opinions onto others simply because they don’t agree.What did you do at Apple?

   

• DANIEL: My first software engineering job was on the System 7 integration team. What we did was develop two of the core pieces of the operating system: the System File, and the System Enabler. These files, combined with the ROM file, essentially contained the equivalents of what we now consider to be the Carbon APIs. I worked mostly on fixing weird bugs that would come up as a result of new hardware or changes in software from other groups.When Mac OS X started being developed, I was very interested and lobbied for a transfer. Three of us who had been working in the same group on OS 9 found ourselves in the CoreServices group on OS X, which was sort of the perfect counterpart to what we had been doing. I was primarily responsible for the Code Fragment Manager, which was a library designed to run applications which had been compiled to run on the older OS 9 system.

  My first taste of Cocoa programming came from a class I took inside Apple. It was just the basics, but it resonated with me and I quite enjoyed it. I didn’t realize that I would one day spend most of every day programming with it. In retrospect, I wish I had spent more time picking the brains of the Cocoa frameworks engineers, who were right down the hall from me.

• SHAWN: Why did you decide to leave Apple? Was it solely to pursue your music degree, or was there more to it then that? Did you feel constrained or held back at all as an engineer or in your aspirations as a programmer/developer?
• DANIEL: I like to quip that I was going through a “mid-20’s crisis.” There were a lot of reasons behind my decision to leave, but at the core of it was a sense that I hadn’t done anything besides work at Apple. Since I came to the company straight out of school, and achieved a substantial level of success, I thought it would be too easy to kick back and pass the next 20 years there. I don’t think that would have been such a bad thing to do, but I had some major ambitions such as earning the music degree, which I didn’t see working well alongside full-time employment.I didn’t feel particularly constrained as a programmer. There were plenty of opportunities, had I chosen to stay. One of the great things about a company like Apple is that it’s so big, there are many different, valuable pursuits being made in parallel. It’s relatively easy for most employees to switch emphasis and apply for a job in another group, often to work on a completely different technology, with completely different skill sets. I knew software developers who become hardware engineers, and vice-versa.
• SHAWN: When I was doing freelance design I had a handful of friends who also were doing freelance, and I would send them design concepts and mock-ups and ask their feedback. Also, when I couldn’t take a project, I would referrer the requesting client to one of my friends. It was sort-of a “I’ll scratch your back if you scratch mine” deal, because they would also send me stuff to look at.Is there anything like that in your line of work? Other than beta testers, do you have a group of other indie developers you send stuff to for feedback and critiques?

   

• DANIEL: The Mac indie development scene offers great, mostly informal support structures through which we are constantly helping each other out. The resources range from mailing lists facilitated by Apple, to the MacSB business-oriented list run by Gus Mueller at Flying Meat, to an informal chat room, #macsb, on the Freenode IRC chat network. Twitter has also started to play a huge role in connecting developers with each other (and with users, in fact).On top of all this, it’s really easy to form social clusters of like-minded developers. I will often inquire directly with another developer via email or AIM, if I think we have expertise that is worth comparing notes on. As to your original example, of passing excess work on to other developers, this is definitely something I have tried to do, although lately since I’ve removed the emphasis on consulting from my web site, I get a lot fewer cold-calls for consulting work.
• SHAWN: For you, how does running Red Sweater Software differ from working for Apple?
• DANIEL: The biggest difference is I call all the shots. This is both good and bad, obviously. At Apple there were brilliant marketers and graphic designers, not to mention accountants, lawyers, etc. I even had access to smarter developers than myself! But there is a great joy in knowing that the buck stops with you, and that the products you ship, at the end of the day, are either 100% the way you want them to be, or on their way in that direction.I have grown to really enjoy the supremely flexible schedule of working for myself. I think it probably doesn’t work for everybody, but I’m incredibly self-driven. So if there’s work to be done, and I think it’s important, it will get done. I find it very compatible with my work style to be able to work for marathon hours when I’m inspired, and then take off for a day if I feel like it. The corporate environment, even at a relatively flexible company like Apple, is still very obsessed with the idea of the day as a basic unit of work. I always found it a bit stressful to know that I had to be at work for a fixed number of days per year.
• SHAWN: In the long run do you think working for Apple helped or hindered your career as an indie software developer?
• DANIEL: Absolutely I think it helped me. Working for such a great company instilled such great software values in me, I’m not sure I would have learned them otherwise, without great individual and institutional mentorship.Another way that my experience at Apple helped was in the sense that it provided me with a sort of safety net, giving me the confidence to feel that I could always go back to Apple or another company of that stature. It also puts my professionalism into context, for people who are not too familiar with the Mac community. For instance, while I was consulting, it was important to some people hiring me to do ports from Windows, that I had worked at “the ultimate Mac software company.”
• SHAWN: Do you ever miss the “team” dynamic at Apple now that you work from home? Do you think you would work better with more people on board at Red Sweater?
• DANIEL: Oh, sure. There are some great benefits to working in a team environment. Especially in a place like Apple where there’s always something going on, and you’re in the midst of such highly qualified people.Working at home has definitely been a shift from that, but modern technology (and some antiquated technology such as IRC) have done a good job of filling the gaps a bit. I find myself with easier access to a large group of thoughtful people now, than I did sometimes working late nights at Apple in “radio silence.”
• SHAWN: What does an average day look like for you?
• DANIEL: It’s kind of depressing in some ways. Actually, instilling structure on a work-for-yourself scenario is something that fascinates me, and something I’m always trying to improve. It’s really hard, when you call all the shots, to not let yourself follow whatever whimsical path attracts your attention at any given moment in the day. I’ve actually found a great use for my application, FlexTime, as a means of imposing some structure on an otherwise haphazard day.That said, I’m still pretty disorganized in this regard, so in all honesty, a typical day for me is to wake up and immediately start working. The hours then surrender to tackling bug fixes, implementing features, responding to customer support inquiries, and trying to squeeze in some socializing via chat and Twitter.

  Left to my own devices I will work all day and into the night, so I’ve developed some tricks to get myself away from the computer. Forcing myself to take a shower, make lunch, go to the gym, etc., are good ways of punctuating the work with other activities. This is something I hope to write more about in my blog, because as I said, it fascinates me.

• SHAWN: I could easily work all day and into the night as well. It’s part of the glories and perils of loving your job.What I like about breaking up my day from the computer is that it helps me feel a bit more accomplished at the end of the day. If I spend 8 or 10 hours typing, clicking and dragging all day I don’t always feel productive or feel like I’ve actually done anything. There is often nothing

  tangible produced. Getting out of the house to run errands, exercise, go on a date with my wife, etc. all help satisfy my need to do something that is “productive.” 

• DANIEL: That’s a great point.
• SHAWN: About your weblog: Pretty much every software company has a weblog nowadays, but you write more than just release announcements. How do you think publishing your weblog has helped Red Sweater Software? Or has it?
• DANIEL: I attribute a great deal of my so-called-success to the blog. I wasn’t exactly a household name because of it, but writing regularly and, I suppose well, in my blog helped me to attract a certain level of recognition among other developers and power users.Having spent so many years inside Apple, I was a virtual unknown to the outside world. The blog helped put me “on the map,” and I think it set the stage so that when I acquired MarsEdit, it wasn’t “some nobody,” but “the well known Mac developer.”

  I highly recommend blogs for anybody who wants to self-promote on the web. Regardless of your interests or your writing ability, there is a way for you to present quality perspectives to the web, and you will gain a readership that trusts and reads you faithfully. It’s important to note that I’ve been saying this for years, since long before I acquired a blog editing application!

• SHAWN: That is pretty much exactly what I expected you would say, and I couldn’t agree more. In an article I wrote back in November, I said: “Consider your time spent setting up and then publishing your blog as part of your global advertising campaign.I would argue that someone with a business or service which gets (or could get) a great deal of their clients and revenue through the web can’t afford

  not to publish a weblog nowadays.There is this quote from Brent Simmons, and even though it’s nearly 5 years old I love the analogy Brent makes in his interview with Michael Lopp:

   

  The main thing is: if you don’t have a weblog, I probably don’t know you, and I don’t have an easy way to get to know you. If you have a weblog, I’m either reading it already or I can read it and look in the archives a bit to get a sense of who you are.

  It’s kind of like if we all lived in the same small town. The people who have weblogs are like the people who make a point of going to Main Street at least a few times a week. They go to the barber shop, the grocer’s, the lunch counter — they get out and talk to people.

  If you don’t have a weblog, it’s like you live on the outskirts of town and have all your food delivered and you even have people come mow your lawn so you don’t have to go outside.

  No matter how big the web gets, it will always be a small town because that’s how you interact with it. You can’t help but make your own small town out of it.

  As your body is to your physical presence, your weblog is to your web presence.

• DANIEL: That is a great analogy.
• SHAWN: Beyond the publicity side of things, I am also curious if having a weblog — meaning the process of writing your thoughts out, publishing them and interacting with readers — has helped the development side of Red Sweater Software. Or, to sum up: are you a better programmer because of your weblog?
• DANIEL: Oh, absolutely. One of the other great qualities of a blog that has some instructive angle, is that it gives an excuse and a motivation for thinking through problems in type. There is a conventional wisdom that the best way to learn something is to teach it. I think that rings very true for instructive blogging. For instance, if I take the time to explain in excruciating detail how I found a bug and what the solution was, I will have inevitably learned more from the experience, than by simply stumbling upon the solution and fixing it. The challenge on Red Sweater Blog is more and more to explain the technical side of something in a way that might still be interesting to nontechnical end users.Similarly, I have taken the opportunity to write philosophically from time to time. If a passing thought occurs to me, I can either let the thought pass back into the ether, or else write about it and explore those feelings in greater detail. This happened while I was sailing one day, and I felt compelled to examine boat navigation as a metaphor for achieving goals in life: “Forget The Shortest Path“.

  That passing thought became a lot more meaningful to me because I took the time to explore it in print. The process of blogging instructively can benefit both the writer and the readers.

• SHAWN: I agree. Something else I like about posts such as that one is that they help open up the author to the reader. Sharing personal revelations or stories help make other posts more flavorful and enjoyable to regular readers.About MarsEdit: Why did you buy it from NewsGator?

   

• DANIEL: It was a perfect opportunity at the (almost) perfect time in my development career. I had just lunged into committing myself 100% to doing indie software development, and had finalized a deal to acquire the crossword application that I now sell as Black Ink. When a deal with NewsGator presented itself, I knew I would be a fool not to explore the possibility.Since MarsEdit was already one of the applications that I used every day and cared deeply about, it made it easy for me to get excited about working on it. And the fact that it also excited a good chunk of the blogging public, and brought with it incredible name recognition and brand appeal, was just icing on the cake that made the decision pretty easy for me.
• SHAWN: Absolutely. It’s not everyday a piece of software with massive potential becomes available in a niche that is growing exponentially.What do you mean by “almost”?

   

• DANIEL: What I mean by almost is that as luck would have it, I was knee deep in the final phases of another acquisition, when the opportunity to purchase MarsEdit came onto the radar. So ideally, I think the acquisitions of Black Ink and MarsEdit would have happened with some breathing room in between them. The only thing that could have made MarsEdit more perfect is if I wasn’t occupied with another acquisition at the time.
• SHAWN: How did the MarsEdit acquisition happen?
• DANIEL: I had gotten to know Brent Simmons, and he knew I was a MarsEdit fan. I think the pieces just fell into place, so he introduced me to NewsGator and we agreed that it would be a benefit to all parties if the application got some new life at Red Sweater.
• SHAWN: With the inclusion of RSS aggregation in Leopard’s version of Mail it’s just another sign that Apple is taking hold of technologies which weren’t so mainstream in its OS and are now implementing them in a much more streamlined way. Obviously the RSS reader in Mail still leaves some to be desired by the “power user”, but I’m sure it’s still exactly what many people want.
• DANIEL: It’s a streamlined, basic introduction to the concept. I think it works very well for many people.
• SHAWN: I agree. Who I’m thinking it doesn’t necessarily work for is, like I said, the “power user” — someone with more than say, a dozen feeds. But when it comes to publishing a weblog it seems the standards are different. A basic user and power user may very well have the exact same needs, just varying degrees of time and effort.
• DANIEL: I think there are still metrics against which a tool such as MarsEdit inevitably outshines a simpler solution. For instance, as a comparison to number of feeds consider number of blogs. A typical user will get a great benefit from MarsEdit with just one blog. But if you’ve got a dozen blogs, the powers of MarsEdit sort of magnify. So you can imagine Apple offering a robust solution that still fails to satisfy all the varying use cases that motivate users to love MarsEdit.
• SHAWN: My point exactly.In the back of my mind I have this idea of weblog publishing as the next major feature addition to Apple Mail, but as I’m saying that I realize how rare the chances of that actually being are. And even if it did happen, I suppose the person who spends a substantial amount of their time in MarsEdit wouldn’t want to use Mail instead. They would prefer a dedicated app, therefore keeping the market for MarsEdit open.
• DANIEL: I don’t feel too threatened by it. Apple seems to be in the mood to jam-pack Mail with features lately, so I guess it wouldn’t be the most surprising thing. But I really doubt that it would be implemented in a “best of breed” type of way. I think some of the features Apple adds are about satisfying bullet points more than anything. They’re unlikely to evolve beyond a cursory development.
• SHAWN: Do you think you’ll someday be competing with a dedicated Apple brand desktop publisher?
• DANIEL: In a strange way they already do. Apple offers a blogging solution by way of iWeb and a .Mac account, but it uses a static publishing type of approach, which is different from the trend among all the most popular blogging services on the web, which do a good job of separating the content from the presentation. It’s this separation of the content which makes it possible for a tool like MarsEdit to handle composing and sending the content without having to construct the entire web page.I have thought from time to time whether Apple might step further into the blogging client business. You may know that Microsoft has a popular client on the PC called Windows Live Writer. I guess if Apple was in the mood to match Microsoft app for app, I might be looking for a new product on the horizon. But I’m not sure whether Apple entering the business would necessarily be a bad thing for MarsEdit. I subscribe to the theory that Apple tends to validate markets more than destroy them. I’m sure I might feel different if I had gotten the wind knocked out of me with iTunes or Sherlock, but I believe the desktop blogging market will ultimately be large enough to accommodate many choices for users.
• SHAWN: It does seem like a slim chance Apple would create a dedicated weblog publisher that was outside of iWeb, and iWeb would have to see a major structure change to accommodate easy publishing to other CMSs like WordPress or Movable Type. I wonder what the ratio of Mac users with an iWeb blog to XML-based blog is; probably 100 to 1?
• DANIEL: It’s a really good question, and I don’t really know. I can only gauge by the number of requests I get for .Mac blog support. It’s a really small number of people, compared to inquiries even about lesser-known XML-based blogs. But it’s impossible to say whether people who have .Mac blogs are happy with iWeb, or whether there aren’t that many of them.
• SHAWN: A shot in the dark here, but I’m guessing that adding a WYSIWYG editor is the number one feature request for MarsEdit. You mentioned on Red Sweater Blog you’ve got some great plans for WYSIWYG in the pipeline. What’s that going to look like?
• DANIEL: You know, WYSIWYG support is among the most requested features, but I don’t think that means it’s the most desired feature. Does that make any sense? A certain type of potential customer tends to request the feature, or explains that it’s because of that omission that they won’t be buying the app. But they are certainly far outnumbered by the number of users who buy the app and express no concern whatsoever, or who express concerns about different features entirely. The thing I try to keep in mind, is that WYSIWYG is a distinct, sort of self-contained feature. It’s something that will grow my market and be useful to many people, but it’s not something which is inherently necessary to the application.Consider the coffee industry. At it’s core, they’re selling a caffeinated beverage that people love. Imagine a wildly successful coffee company that is selling coffee faster than they can make it. They offer a variety of roasts, specialized drinks, even gift baskets. But there’s no decaf. The product is popular enough that decaf lovers can’t help but be intrigued, so they perennially ask “where’s the decaf version?” It’s not as though the company needs to drop everything and design a decaf version, because there’s a line of customers piling out the door. It will help their bottom line, but not as much as focusing on the demands and desires of the caffeinated crowd that is currently paying the bills.

  That said, yes I do have plans for WYSIWYG in the pipeline. I guess you said it was a shot in the dark because you realize I don’t want to make too many specific product-related promises. But I am willing to share some of my design considerations. WYSIWYG support in MarsEdit must be invisible to anybody who doesn’t want it. That is, plain-text mode will not be impacted by the presence of this new feature. It must be substantially improved over any other editor I’ve seen on the web or in desktop blog editors. It must either do no harm to customized HTML markup, or else its harm must be easily undoable.

  There are a list of classic things that are wrong with WYSIWYG editors. They over-promise and under-deliver. They’re not actually that easy to use. They mess up your HTML, and often outright eliminate content. I don’t want to make any of those mistakes. That’s what makes the feature hard, and that’s the reason users haven’t seen it yet in MarsEdit.

• SHAWN: I can imagine that coding a non-destructive WYSIWYG editor would a huge task. Do you hope to incorporate MarsEdit’s “perfect preview” feature in with the WYSIWYG to make a literal what-you-see-is-what-you-get editor?
• DANIEL: I have considered it, but it strikes me as one of those “cool but not actually very useful” things. At the very least it would need to be optional. Can you imagine an author for a magazine actually wanting to write the article in the format it would appear after publication? For all but the very simplest of blogging, I think people want an authoring environment that looks distinct from the published look.
• SHAWN: Good point. But at the same time I could see the advantages to having the “perfect preview” being editable too. I’m always proof reading my posts in the preview and when I see a typo it would be nice to have the option of fixing it right there as I’m looking at it. But other than that, I wouldn’t use it; I prefer to type in the text editor.In your C4[1] speech you talked about product acquisition and how people suffer from “writer’s block” not “revision block”. Now that you’ve pretty much adapted MarsEdit it into your own app, how has the development and building of it changed since before the 2.0 release?
• DANIEL: Well mainly what’s changed over the past year is that I’ve become gradually more and more confident about how all the existing code works, and how I might want to change it as the application evolves. So I’m willing to make more dramatic structural changes now than I would have been a few weeks after acquiring it.For the most part, though, things haven’t changed. One of the gratifying but sort of frightening things about MarsEdit is that there’s no end in sight. There won’t be this moment when the application is done, because the list of really valuable suggestions for improvement is huge. And every time I fix or implement something, it opens up the door to a dozen new suggests for further refinement. It’s a curse, because I’m always busy. But it’s a blessing, because it means people really care deeply about the product.
• SHAWN: This is a totally unfair and immature question, but if you had to pick between quitting development on MarsEdit to work on something else or continuing development on MarsEdit only, which would you pick, and why?
• DANIEL: It is a little unfair, but that’s OK because I’ve got an unfair answer! The premise is so contrived that I can easily answer truthfully. I value variety enough that I would not accept any circumstance that locked me into developing only one application. One of the greatest benefits of being an independent developer is I make all the calls, for better and for worse. If I had to give up that flexibility, I might as well be working for somebody else.Now as it happens, MarsEdit is important enough to me, and I’m excited enough about improving it, that I probably spent 90% of my work time over the past year developing and supporting it. But my productivity is aided a great deal by being able to take mental breaks, working on problems in other applications for a change. Some people suggest that it must be overwhelming to work on several products at once, and it would be if they were all in the same phase of development as MarsEdit. But having an assortment of products with differing demands really helps to battle the mental fatigue that can come from working on just one thing all the time.
• SHAWN: Do you see any new Red Sweater apps on the horizon?
• DANIEL: I am always thinking of new ideas, and sometimes I’m tempted to go full bore into working on another product. But at this point I’m really sort of stretched as thin as I probably should be, with the current lineup. I won’t rule out additions, but probably things won’t change dramatically until and unless I get the opportunity to grow the company a bit.
• SHAWN: Is that something you want to do or feel that you may have to do? Is the idea of bringing on an employee (or more) a welcomed challenge or a new stress?
• DANIEL: It’s a bit of both. At one time I would have found it impossible to imagine wanting employees or being confident about directing another person in how I think products should be designed. But over the past few years I’ve gotten more interested in “the big picture,” and have become increasingly confident about distinguishing what I know from what I don’t. I feel more excited now about someday having people with complementary skills to help with building these products.
• SHAWN: What does “the big picture” look like for you and Red Sweater software? Are there other business models of indie software developers that you are aspiring to, or do you have something different in mind?
• DANIEL: When I allude to the big picture I am sort of waxing poetic about a confluence of design, engineering, and management. Let me be honest, I’m not really an expert in any of these things, but I am immensely interested in all of them. The more I learn about business, the more I realize you only need a bit of wisdom to earn a foothold on success. There is still a lot for me to learn, but I’m confident that being receptive to the right answers will be the secret of my success. That’s the big picture.

More Interviews

Daniel’s is just one of a handful of interviews with some cool folks.

John Gruber has been writing the often quoted, ever popular Daring Fireball since 2002.

I had the privilege to interview John via email and ask him some questions that don’t seem to get asked. Of course we talked about DF, how the Linked List began and how he got into Macs. But we also talked about writing, what John eats for breakfast and more.

And yes, I also got a lesson in email bottom-posting etiquette.

The Interview

• SHAWN BLANC: In 2004 you mentioned in your Something Daring article that developer interviews and software reviews were two of your favorite things to write. When I read your interview with Brent Simmons I think it may have been the longest email interview posted to a weblog I had ever read. Fortunately for the three of us it was good, worth reading and even a few years later I’ve found myself going back to it for reference.What are some elements that you think help to make a good interview? What are some dynamics that you hope to incorporate in the interviews you conduct?

   

• JOHN GRUBER: You need to be really well-versed, as the interviewer, regarding the work of your interviewee. You must be prepared up-front with questions that you’d like to learn the answers to, but at the same time, I think you have to be ready to let the interview veer into unexpected territory. You want a plan, but you also want to be able to wing it as it goes.The mistake I see in most interviews conducted over email is that the interviewer simply emails the subject a single list of questions, all at once. Just a two step process: “Here are my questions,” then, “OK, here are my answers.” There’s no room in a simple process like that to ask follow-ups, or to delve into details or pursue interesting but unanticipated digressions.
• SHAWN: Funny you say that, because it is the exact scenario for many of the first interviews I ever tried to conduct. I say “tried” because most people I asked were unwilling to participate.After reading your interview with Brent I realized that a published interview can and should cause the interviewee to shine. I see it somewhat as the interviewer’s job to draw out information that never would have appeared in a generic list of Q&A.

  I know the reason I attempted the two step process was because I assumed an email conversation would be too much of a time requirement for the interviewee — that the two step process would be more convenient. But based on my experience that is obviously not the case. Why do you suppose that?

   

• JOHN: Well, in some ways it is more convenient. Just set aside time to write one email answering all the questions and you’re done. Maybe it doesn’t seem as worthwhile, though. Personally, I’m more interested in participating in an interview that seems interesting than one that seems easy.
• SHAWN: With the insane amount of email you get why would you prefer to take the time needed to conduct a longer, drawn-out interview such as this rather than the quicker two step style? I’m know you must get hundreds of emails soliciting your attention; how do you handle it all?
• JOHN: I just say no to most requests. Or, I’m sad to say, I never get around to answering some requests. If I answered all my email, I’d have no time to write Daring Fireball. I really believe that — some days I could spend 8-10 hours just answering emails that come in. Part of that, surely, is that I don’t have comments on the site, so when some reader has a remark they just have to get off their chest, email is their only recourse. That’s cool. But it means I treat email more like comments — I look at them all, but I respond to very few.
• SHAWN: On your site you say over 50,000 people subscribe to the feed. My guess would be that most of them keep Daring Fireball at or near the top of their subscription list — because they like what you like, read what you read and want to know your opinion. Thousands of them have never met you but feel like they know you in some way. If they bumped into you one day they may give you a good hand-shake and tell you how much they love reading Daring Fireball.Some of these guys are developers, some are designers and some are just folks that like their Mac. Whoever they are they read your site and (hopefully) like you; this interview is for them.

  Now, correct me if I’m wrong – and please fill in any gaps – but here’s what your story looks like to me:

  In 2002 you were doing freelance consulting, web-development and tech writing. Meanwhile, after months of picking out the right “slate blueish background color” you finally launch Daring Fireball and begin writing articles for which your wife was the first reader. Two years later you start offering the membership and also end up working at Bare Bones. Then two years after that, in 2006, you quit your day job and now spend your time publish DF from home.

   

• JOHN: Your chronology is a bit off. I worked for Bare Bones from 2000 to 2002. I started DF a few months after that. Joyent was the company I worked for while writing DF, from January 2005 through March 2006. When I left Joyent was when I started writing DF full-time.
• SHAWN: After all that journey, is writing DF what you expected or hoped it would be? I’m curious if you still feel like the same guy who five years ago began a weblog because he really just loved to write?
• JOHN: Do I feel like the same guy? Yes.Is the site what I thought it would be? No.

  I didn’t really have a detailed long-term plan for Daring Fireball. I still don’t. It started very simple, and I’ve changed and added things slowly over time. The plan was just to keep improving it steadily over time. That plan remains in effect today.

  When I make elaborate, detailed plans, I get too attached to the plans, too reluctant to break with them. Plans aren’t a product. I’m only effective when I’m working directly on a product.

  A great example is the Linked List. The Linked List didn’t appear on DF until June 2004, almost two years after the inception of the site. I hadn’t planned on adding the Linked List. My original idea was that DF would consist only of articles. Sometimes short articles, but articles nonetheless. And certainly no more than two or three in a day, tops, and usually just a few per week.

  What happened is that I was frustrated by the number of things I wanted to link to, things I wanted to bring to the attention of DF readers, but which I didn’t want to write a full article about. It was also the case that I wanted an easy way keep the site fresh even during stretches when paying work — remember that this was two years before I went full-time with DF — was consuming so much of my time that I didn’t have time to write articles.

  The other thing was that the Linked List was largely initiated as a bonus for paying members. Originally, the only way to get live updates to Linked List content was through the members-only RSS feeds — the items didn’t appear on the web until the next day. In hindsight, that certainly seems silly.

  Over time, the Linked List has grown from a peripheral gimmick into an essential component of the site.

• SHAWN: What does your average day look like?
• JOHN: My day looks very dull. That’s not to say it is dull — to me at least — but I strongly suspect it would look dull. Writing is a lonely endeavor.Typical day: I wake up when I wake up. Mid-morning, typically, but if I’m working on a major project or article, I sometimes wake up early because I’m anxious to finish. I get coffee. I go to my office in my home and pick up where I left off the night before. Some days that’s with an article I’m working on, some days that’s with things to read that I might want to post to the Linked List. I’m either writing or reading — or, occasionally, hacking on code for some new feature on the site — all day long.

  Ernest Hemingway said this:

  You write until you come to a place where you still have your juice and know what will happen next and you stop and try to live through until the next day when you hit it again.

  He was talking about writing books, but I find his advice perfectly apt for what I’m doing with Daring Fireball. Without having a boss or editor, I could do anything at the start of the day. Leaving off the day before with something specific in mind for what to do next is an enormous aid to getting going.

• SHAWN: Additionally, my wife wants to know (a) what you eat for breakfast, and (b) if you like to hug your wife?
• JOHN: I’m on an oatmeal kick this week, but usually just a banana. The big thing, though, is coffee, always coffee.
• SHAWN: Coffee black?
• JOHN: Of course. It’s not really coffee otherwise. And who doesn’t like to hug their wife? Is there an anti-hugging contingent out there I’m not aware of?
• SHAWN: No. My wife just likes to know how other wives are treated by their work-from-the-home-office husbands.About the Linked List: Do you spend the majority of your day reading feeds? Do you skim articles or read every one? How do you decide what makes the cut? Do you have a running tab of sites you want to link to but haven’t yet?

   

• JOHN: I get links from a variety of sources. For breaking news, things that have just happened or were just announced, the best source is email. If something big happens, I usually get a few emails about it soon thereafter. Other than that, I read voraciously. I almost never post something to the Linked List that I haven’t read entirely.I try not to spend too much time in NetNewsWire. I usually have it open, but I find I’m more productive if I make fewer (but longer) sweeps through it looking for new stuff. As for what I link to and what I don’t, it’s very much like Justice Stewart’s definition of obscenity: “I know it when I see it.” There’s a certain pace and rhythm to what I’m going for, a mix of the technical, the artful, the thoughtful, and the absurd. In the same way that I strive to achieve a certain voice in my prose, as a writer, I strive for a certain voice with regard to what I link to. No single item I post to the Linked List is all that important. It’s the mix, the gestalt of an entire day’s worth taken together, that matters to me.
• SHAWN: How often do you get requests for a DF link?
• JOHN: Surprisingly, to me at least, I don’t get that many requests for links. I do get many press releases, which I suppose are implicit requests, and a few times a day people will send me links to things they’ve posted on their own weblogs that they think I might be interested in. I very seldom find anything from a press release worth linking to. A lot of times, though, the stuff people email directly — “I wrote this, thought you might like it” — is perfect Linked List material.
• SHAWN: Something else Hemingway said:
  

  All good books are alike in that they are truer than if they had really happened and after you are finished reading one you will feel that all that happened to you and afterwards it all belongs to you: the good and the bad, the ecstasy, the remorse and sorrow, the people and the places and how the weather was. If you can get so that you can give that to people, then you are a writer.

   

  My point being, at the end of the day it is clear that the bread and butter of Daring Fireball, as well as what you take the most pride in, is the articles. The “Fireballs”. You are a writer.

  You have managed to create a tech-based weblog and build a community of readers that not only looks to you for information and opinions, but listen (or read) to everything you have to say. They actually feel ownership of the elements, content and topics on Daring Fireball. You’re like the E.F. Hutton of the Mac community.

  Khoi Vinh said publishing Subtraction.com has actually hindered him as a writer. Did you consider yourself a writer before you began blogging? Do you have any personal history in writing, or did you find your voice through publishing DF?

   

• JOHN: I’ve considered myself a writer ever since college, when I wrote for (and eventually became editor of) the student newspaper at Drexel University. I wrote a regular op-ed column for the paper, and by the time I graduated in 1996, I felt I’d gotten pretty good at it. But then what? A career in journalism? An entry-level job as a reporter working for some publication that I wouldn’t otherwise read? Not for me.So I waited and thought about it. Somewhere around 2001 or so, it occurred to me that I’d been thinking about what next to write for five years, which was as long again as the time I spent at the paper at Drexel. That was a bit depressing — but really only just a bit, because for some reason it felt to me that my writing skills hadn’t atrophied at all. On the contrary, I felt like I was a better writer than I was in college, even though I hadn’t been writing at all. That struck me as incongruous, because I was also convinced that the reason I was a much better writer when I left college than when I started was simply by writing and editing so much material for the paper. So while I felt like I was still becoming a better writer, I strongly suspected I was deluding myself.

  At the time, I was working for Bare Bones Software, and there was a question on the Mailsmith-Talk mailing list from a customer asking for help with a script that would count the number of words in all the messages in a mailbox. So I wrote a script that did that, and I ran it against my own outgoing message archives. The script was smart enough to count only words that weren’t in quoted passages, ignored signatures, etc. I forget the exact result, but the result was just preposterously high. Based on some common rules-of-thumb, I’d written several books worth of email messages over the previous five years — posts to mailing lists and a ton of personal correspondence, all of which I tried to write the hell out of.

  Around that same time, it became obvious that the outlet I’d been waiting for was available: I needed to start my own weblog.

  I’ve improved significantly as a writer in the last five years, but I feel as though I’m continuing to hone the exact same voice that I started aiming for 15 years ago in college.

• SHAWN: Do you have any advice for writers who are struggling to find their voice?
• JOHN: I honestly don’t know what works for others. The act of writing, like any art, defies description. Some of the best advice I’ve seen regarding how to write essays is from Paul Graham. He says writing is thinking, and, insightfully, that writing forces you to think better. He wrote, “Just as inviting people over forces you to clean up your apartment, writing something that other people will read forces you to think well.”My other suggestion (also, I think, stolen from Graham) is to concentrate on writing things with lasting value. I’m not sure I’ve been doing a good job of this at all lately — I think too much of what I write currently at DF is about stuff that’s only relevant right now. I’m certain that what helped me make a name for myself, what built the DF readership, were the long pieces I did in the first few years, most of which are still relevant, or at least still interesting.

  There are a lot of people writing for the web today; but there aren’t that many at all who are trying to do great writing for the web.

• SHAWN: How has your approach to writing articles on DF changed over years? Have you gotten better at writing something and publishing it or are you more meticulous than you used to be?
• JOHN: That’s hard to put into words. Early on, I had to think about my “voice”. I was conscious of my style. Now, not so much — I “just write”, and the style seems to come naturally. Part of that is that you get used to anything over time, but a bigger part is that the style changed slowly over time — I kept tweaking it until I found the perfect pitch, at which point it became something I didn’t have to think about to achieve.Put another way: early on, I had to concentrate both on what I was saying and how was I saying it. Now I just concentrate on what I’m saying.

  I also find it much easier to write now that I have a regular audience. The hardest thing for me starting out at the very beginning was trying to shake the feeling that I was writing something no one would read. It felt like delivering a speech in an empty auditorium.

• SHAWN: Are there any other weblog articles which have stood out to you over the years as being an exceptional display of online writing?
• JOHN: I object to the adjective “online” in that question. Why not simply weblog articles have stood out as exemplary displays of writing, period? The idea that weblogs are a bastard or lesser medium holds many writers back. I find, in fact, that the opposite is true. Most magazines I read are filled with bland, tepid prose. There’s only one New Yorker, and only a handful of other magazines in the same ballpark.My two favorite weblog writers are Paul Graham and Dean Allen. They’re the two who’ve written the most things that simultaneously delighted me (as a reader) and filled my heart with jealousy (as a writer).

  Paul Graham wrote:

  My experience of writing for magazines suggests an explanation. Editors. They control the topics you can write about, and they can generally rewrite whatever you produce. The result is to damp extremes. Editing yields 95th percentile writing — 95% of articles are improved by it, but 5% are dragged down.

• SHAWN: What are a few of your personal favorite DF articles?
• JOHN: My favorite articles tend to be the ones that seemingly come out of left field. The first “Anthropomorphized Brushed Metal User Interface Theme” piece, for example. Or the occasional personal piece, like “Vacation, All I Ever Wanted“, which I wrote a year ago. I was going for something very specific with that one, very hard to hit, and I nailed it.My favorite essays on standard DF topics are probably:
  • Broken Windows
  • Ronco Spray-On Usability

  It didn’t really stand out to me when I wrote it, but “Good Journalism” was recently included in a “Best of Technology Writing” compilation, and looking back on it, it strikes me as very effective criticism.

  I will add this:

  I’ve been thinking a lot that while the overall quality of DF has gone up since I started writing it full-time, that’s mostly because I’ve been writing more items, more regularly. I think the trade-off has been that there have been far fewer extraordinary articles. I.e., I’ve been writing a lot more good stuff than I used to, but less great stuff.

  I think I know how to fix that, though.

• SHAWN: How so?
• JOHN: Simply by being self-aware of it.Pre-Linked List, when DF only consisted of regular articles, there’d occasionally be stretches of a week, sometimes two weeks, where I wouldn’t find time to write anything. During those stretches, I’d feel overwhelmed with the desire to write something good to break the dry spell. Eventually it’d become all-consuming, and I’d just have to write something good.

  Even though I now post something to DF nearly every day, and articles a few times a week, I’m starting to get that feeling about posting substantive essays.

• SHAWN: Ah, that’s fantastic. I’m glad you brought up the issue of substantive content. It is something which is constantly on my radar as a writer and a designer.William Faulkner said something along these lines that I love:
  

  It is [the poet’s, the writer’s] privilege to help man endure by lifting his heart, by reminding him of the courage and honor and hope and pride and compassion and pity and sacrifice which have been the glory of his past.

   

  I suppose my question to you is this: as someone who enjoys reading and writing tech news and reviews and opinion pieces — which by nature are usually only relevant for a short time — how do you define and create substance in your own writing? And more than that even; as a writer, John, what do you think makes substantial content?

   

• JOHN: Something that’s only useful or interesting here and now can still be substantial. The only short definition I can think of is how much talent and time goes into something. The more talent and time, the more substantial.For me, much of the effort in writing, especially on technical topics, is in creating a narrative. By that I mean writing a piece that reads straight through, pulling the reader along. A perfect example of this is the way John Siracusa writes his epic-length reviews of major new Mac OS X releases for Ars Technica. What makes them so substantial, and so good, is that he crafts them into a narrative. Most reviews of something like Leopard read like bullet lists — a list of features and what the reviewer thinks about them.

  What graphic design is to a visual idea, writing is to a verbal idea. My goal is to craft my writing in such a way that makes it as easy and obvious as possible for the reader to “get” exactly what it is I’m hoping they get.

• SHAWN: Speaking of reviews, this leads right to what I wanted to talk about next: reviews…It seems whenever I read a review you’ve written it basically states the obvious. But it’s the obvious things I didn’t think to check into and discover on my own. When writing a product review what are the things you look for to talk about in your article?

   

• JOHN: That’s an interesting observation. I’ve never thought of it that way.Perhaps it’s more “examining the obvious in great detail” than “stating the obvious”. Trying to think about things that don’t get thought about very often.
• SHAWN: “Examining the obvious in great detail”. Ah yes. That is exactly what it’s like. I didn’t mean to make you sound so dull by the way I described it. I think “Full Metal Jacket” is my favorite DF article. It made me want to keep using my PowerBook until it evaporates, or something.
• JOHN: That “Full Metal Jacket” piece is one of my favorites — one that turned out exactly how I wanted it to, and the sort of piece I’d like to do more often.One of my favorite quotes of all time, probably my very favorite, is this one from Stanley Kubrick: “Sometimes the truth of a thing is not so much in the think of it, as in the feel of it.” A lot of times when I’m reviewing something, what I’m trying to do is capture the feel of it, rather than the think of it.
• SHAWN: What was the first Mac you ever owned?
• JOHN: A Mac LC with 4 MB of RAM and a 16 MHz 68020 CPU. My parents bought it for me for my freshman year at college. It had a 12-inch 512×384 display. I always regretted that I didn’t get an SE/30 instead. I was suckered by the color display.
• SHAWN: What does your current Mac setup look like now?
• JOHN: A 15-inch PowerBook G4, maxed out with 2 GB of RAM. When I’m at my desk, I use a 20-inch Cinema Display.
• SHAWN: How did you end up publishing a “Mac Nerdery, etc.” weblog?
• JOHN: I don’t have an explanation for it other than that I’ve been naturally drawn to computers ever since I was a kid, and when I first started using a Mac in high school, which I think was in 11th grade in 1989, I knew I wanted to own one. If you have an interest in user interface and experience design, I don’t see how you wouldn’t be drawn to the Mac.I knew coming out of college that I wanted to be a writer. And the type of writing I always felt most suited to was being a columnist. I’ve always enjoyed the way that with good columnists, it’s not just that their individual articles stand on their own, but that there’s something greater than the sum of the parts when you follow them as a regular reader.

  The problem with wanting to be columnist, in traditional print publishing, is that it’s a hard gig to get. Typically, at least at newspapers, columnists are promoted out of the ranks of reporters, and I had no desire whatsoever to be a straightforward reporter.

  In 2002, when I started Daring Fireball, doing a sort of columnist-style weblog simply felt like something I was compelled to do. I could write whatever I wanted, however I wanted. And, to be blunt, I was certain that I could do it very well.

• SHAWN: Do you suppose you will write DF for years and years to come until you finally retire some day? Maybe sell the domain and pass the reigns to some other witty tech guru?
• JOHN: I can’t see ever passing it on or selling it. But, I can’t see more than a few years ahead of me. Will I still be doing this in another five years? Almost certainly. But, say, 20 years from now? I don’t know.
• SHAWN: Will you for sure continue in a career as an author? Maybe write a book, or movie?
• JOHN: One way or another, I don’t see how I could be doing anything other than writing. It’s the only thing I’ve done in which I’m endlessly engaged.It would seem like a missed opportunity never to write a book. Most novels are just dreadful; I don’t know if I could do a good one, but I know I could do better than most. But it never seems like the right time to start. I just stumbled across an apt quote from Emerson last week: “We postpone our literary work until we have more ripeness and skill to write, and we one day discover that our literary talent was a youthful effervescence which we have now lost.”

   

More Interviews

John’s is just one of a handful of interviews with some cool folks.