An Interview with Neven Mrgan

Neven Mrgan is a designer, developer, and writer. He works at Panic, Inc., writes a popular weblog (or two), draws video game graphics in his spare time, and his last name is a bit of a mystery.

In this interview Neven and I discuss graphic design, life at Panic, and other miscellany.

The Interview

  • Shawn Blanc: Until you joined Panic in 2008 you mostly did freelance work building web apps, correct?

  • Neven Mrgan: I did freelance design and development work — mostly on the web — for a few years, and I had more or less interesting day jobs that time as well. I worked as an engineer on very straight-laced business web apps until 2007. This wasn’t terribly fun, and to be honest, I wasn’t too good at it either. Early in 2007 I decided to start sticking to graphic design and UI design, since I was never going to be a kung-fu-grade developer.

  • Shawn: Your job with Panic seems like a perfect match in the sense that you fit right in as another clever, funny, nerd. But on the flip side, now you work in a team setting with a company that builds desktop software as opposed working solo on web projects. What led you to take the job with Panic?

  • Neven: Regarding desktop software, it was somewhat new to me indeed. Sorry to bring up iPhone this early in the conversation, but it was a big catalyst for me in several ways; it was the first time I was doing non-web UI design. That was the roundabout route I took to designing desktop software.

    As for Panic, the fit was just ridiculously good. They build excellent software, and they do so in a genuinely friendly, likable way. That combination is very uncommon. I was a recently married and ready-to-settle-down old fogie of near 30, and was big on leading a comfortable, quality lifestyle, and working on solid, long-term projects. Panic has those same goals.

    Working on a team was a change after a year of clicking around in our home office. It’s hard to complain about the freedom of that arrangement, but I’ll do my best: a chair in your own house can be a pretty inert environment. It’s a bit of a bummer on a purely social level, and it can make your creative muscle slack as well. That’s been my experience, anyway. I’m happy to be surrounded by really smart folk as I click around now.

  • Shawn: Do you ever miss working from home?

  • Neven: I have that option currently and I don’t believe I’ve taken advantage of it more than three times (and even then, only because I had to be home for some reason). I can’t emphasize enough how much I like the vibe at my office. It reminds me of how I’d go to my high school’s super-awesome computer lab on the weekend, in the evening, and whenever else I could. I love what I do, projects and people and desk and all — it’s my job and my hobby.

  • Shawn: You’ve got a lot of projects running — your couple cool weblogs, The Incident, your full-time job at Panic, and more. What does a day in your life look like?

  • Neven: I half-wake up around 7:30 and remain in a hazy, floating, brain-puree state for about half an hour. This is when I get all of my stupidest ideas (like you know how some restaurants menus have a little V next to vegetarian items and maybe a clipart chili for “spicy”; what if they put an F next to “foodie” items? “Can the salad be made foodie?” -“Certainly; we can make it with Pouligny-Saint-Pierre and shave a black truffle onto it.”). Stupid ideas are excellent springboards, boosters for your thought and your daily mood.

    I then check my email and RSS in bed; if it takes longer than five minutes, I save it for after I’m dressed. To do that I pick a Panic t-shirt from the stack I was given when I started (“your employee uniform”) and put my socks on in front of the computer. I briefly chat with whoever is online – usually only Matt Comi, my partner on The Incident. I take the bus to work; twenty minutes of book-reading on the ride, ten minutes of iPod while I walk.

    I work ten to six. The morning is usually time for catch-up, unfinished business from the previous day, or quick production of ideas pickled overnight. Lunch is important because it brings the office together. It’s our most regular team meeting. The afternoon means serious work — Photoshop and Coda — and a snack break around four. I drink Coke Zero and endorse Nuvrei pastries.

    Most days, I try to cook at least one meal; if there’s time to make dinner after work, I’ll give it a shot. If not, Portland has an embarrassment of excellent restaurants. Either way, I eat early and spend the evening working on whatever side projects I have going on. I go to sleep disgustingly late —midnight or 1 am.

    This isn’t a schedule I make it a point to stick to. It’s just how things typically play out.

  • Shawn: What are your favorite pieces of software?

  • Neven: Photoshop, Coda, and Birdhouse.

    I know, I know — give me a chance to explain.

    I complain about Photoshop. Lord, do I. But it’s not only the essential tool for what I do, it’s a great tool also. I’ve done my best to give the competition a shot, and the truth is just that they don’t allow me to make the things I want to make (yet). Photoshop is internally and externally inconsistent, it’s bloated, it’s slow, and it crashes. But I use it more than I use my pants, and for that I love it.

    Coda is an app I work on, so feel free to consider this a shameless advertisement. You’ll have to take my word for it: I used it before I started at Panic, and if I found a better app for web development, I’d promptly switch to it. Life is too short and the web too demanding to be a slave to cheap loyalty. It’s a great app.

    Birdhouse is the only not-preinstalled app on my iPhone about which I have zero complaints. I use it regularly, and I don’t remember it crashing, slowing down, or confusing me once. You could argue that it does a tiny thing, but it does it well.

    Sometimes I think that if this whole computer thing turns sour — if Apple becomes monstrously evil, if the Internet collapses, if I get old and stop grokking new technologies — I’ll switch to farming or cooking or poster design and be just as happy. Maybe that’s true. Some not-so-small part of me would, however, miss the wizardry I discovered some time in 1985 or so as I typed BASIC into my C-64: I can make a screen do things, and do things that do other things, and do different things depending on the things I do back to it. It’s a wonderful game.

  • Shawn: Other than for your lack of development skills, why did you begin doing work as a designer and developer?

  • Neven: Two beliefs: 1) Things should look good, and 2) Computers are cool. For the rest of my life I’ll be coming up with complicated explanations which boil down to those motivating principles.

    So, I’ve really always wanted to be doing this or something like this. This or drawing comics, which I quickly learned was kind of not so hot.

  • Shawn: Was it a lack of drawing skills that led you to computer-based design? (And do you have any old comic book drawings you’re willing to share?)

  • Neven: I’m very happy with my drawing skills!

    I decided to stick with computers because they could do things the real world couldn’t. I’m all in favor of creative restrictions — yay Twitter — but pen and ink’s lack of an Undo function doesn’t challenge me to do better work. It just makes me frustrated.

    Now here’s a really out-of-context panel done some time in… 1998 or so, maybe?

    Neven Mrgan Comic Panel circa 1998 or so.
  • Shawn: If I ever want a future in art and design it will have to be with a computer. I can never get pen and ink to translate into what I want.

    You’re not alone in with the belief that things should look good and computers are cool. But everyone has their own definition of what looks good and what the best tools for the job are. How do you define when a design looks good? Has that definition changed since seriously began sticking to graphic design and UI design?

  • Neven: One thing I’m learning quickly is to evaluate designs and design ideas in terms of interaction: how they behave under what circumstances, how they work with other elements. That’s sort of new to me, though designing for the web has always been about flexible, unpredictable layouts and such.

    A thing looks good to me when I fall in love with it; that’s test #1. Test #2 is, ok, that’s sweet – what is it? Does it say something, mean something, is it an “it” or an “It”? Test #3 is the more ponderous goatee-rubbing over how the design scales and translates, whether it’s too trendy or too dated, etc.

    Sometimes I learn to eventually accept designs as excellent solutions even if they didn’t hit me right away. And sometimes designs I greet with a WOW bore me very quickly. But it’s very rare that I will love and cherish a design if it has to be “explained”.

    It’s not important that I love everything I design. But hopefully it happens pretty often.

  • Shawn: How would you recommend someone with no facial hair go about completing test #3 as a part of their own design critiques?

  • Neven: There are a number of question you can ask about a design once it’s grabbed you.

    • Will it scale, not just physically, but across cultures, age groups, platforms, ideas? Will your icon idea make sense to a busy person working in a dark room?
    • Can any part of your design be abstracted and used elsewhere? Would anyone want to steal it? (You better wish they would!)
    • If you’re breaking an established pattern or convention, are you doing so with good reason? With what are you replacing what you’re destroying?
    • What if the things you, yourself, like to use were designed in this way? Remember Kant’s categorical imperative, “Act only on that maxim which you at the same time wish to be a universal law.”

    You will add more questions to your list over time; you will also drop some as times change and as you develop your own priorities (the point is not to be able to answer “yes” to every question on the list).

    Now here’s the important thing: DO NOT write down the list. Don’t put checkboxes next to questions and save it all as a file. Don’t print it out. Don’t ask people you work with to start using it. This way lies madness; or at least boredom, burn-out, and blandness.

    My feeling is that many creative endeavors are like this; you should learn specific techniques and aesthetic guidelines, but ultimately you will want to simply do a lot of work and let the aesthetic judgment become a second nature. A good musician can, for the most part, “let their fingers play” instead of focusing on translating each sound-idea into a specific finger movement. A good baker will measure things, but they will only make consistently awesome bread when the dough “feels” right under their fingers. There’s no magic, destiny, or talent at work here, just a gradual process of practicing until the back of your head can do most of the work, not the front.

    So, long answer short, learn as much as you can about the principles of design, about its history, and about other people’s work. But try to let it all soak into your brain through constant creative and functional use, not through cramming or some sort of workflow standardization.

  • Shawn: How much, then, do you suppose good design sense boils down to talent versus practice?

    Can tools and rules, in and of themselves, produce a quality designed product?

  • Neven: I just realized I’ve been harping on the 90%-perspiration thing without going into why the remaining 10% — “the squishy bit” — is important. It’s frustrating to even think about it because it leads me to a mildly fatalistic state where I just throw my hands up and decide that if good design is a matter of talent and destiny, then it isn’t worth doing since most people won’t even know it when they see it. Which is true, in many ways. Why does a designer spend any time deciding between Helvetica and Univers? Most people won’t know or care either way. Or maybe they will, on some unreachable level — maybe Helvetica will appear more generic (at least today it will), Univers more technical; the former, more “design-y”, the latter, more “informative”.

    A designer will obviously have far more opinions of this sort about the minutiae of design. Now, partially these will be a product of the designer’s education and work experience. Maybe they once read Univers was a good choice for signage, or a teacher told them it was a modern classic. Maybe they’re sick of Helvetica.

    But given enough time, these opinions will become more than restatements of other people’s attitudes. Different aesthetic prejudices — sometimes clashing ones — will come together in one head to create a unique taste and signature.

    A great trick I learned from the science writer Matt Ridley: in debates over nature vs. nurture, remember that one is a function of the other, so it doesn’t make sense to say talent “contributes 30%” or some such thing. They’re linked in a much more complicated way.

    To answer the second question a little more directly: no [tools and rules, in and of themselves, cannot produce a quality designed product].

  • Shawn: You’re right that most people won’t know good design when they see it. But in the context of UI design, that’s the point.

    Jeffrey Zeldman wrote a great definition of Web design in an article, “Understanding Web Design“. He said:

    “Great web designs are like great typefaces: some, like Rosewood, impose a personality on whatever content is applied to them. Others, like Helvetica, fade into the background (or try to), magically supporting whatever tone the content provides.”

    Like you said, Neven, the vast majority of people won’t even notice your design. But the very act of them not noticing is (usually) the proof of a good design. On the flip side, of course, are times when the people should notice the design. It’s the Form Versus Function debate that UI designers are faced with every day. The mark of a great designer is one who knows when to chose which side of the issue and how find the balance between both sides.

    The reputation for Panic when they come to a form-versus-function hurdle is to find a simply stellar solution (like Cabel’s 3-Pixel Conundrum). Has Panic developed any official guidelines for working on UI design? Have they ever conflicted with your personal preference?

  • Neven: I work under surprisingly few constraints as far as what must or mustn’t be done. We’re pretty aggressive about staying ahead of the curve, so we insist on certain not-yet-widespread widespread technologies (resolution-independent graphics, for one). We love a good visual metaphor — Coda’s taped pages in the Sites view — but it has to make sense, and it can’t be realistic at the expense of usability, or to the point of sickening cuteness.

    If we’re adding a feature, we almost never go “ah, there’s already a standard control for that, we’re set.” We might just end up using the existing design, but not before we poke it within an inch of its life. Why does this menu look like this? What if we had never seen it before — how would we build it?

    As Cabel has mentioned, we’re big on weenies: elements that make a design stand out immediately. There’s nothing wrong with a simple metal window, but there’s nothing great about it either, and more things should be great!

    This is the designer’s nastiest temptation — over-designed, needlessly custom chrome which neither fits nor improves the platform. This is the land of Windows Media Player skins. Often we try to “fit the OS better than it fits itself”, if that makes sense; if we think an Apple widget betrays the hand of an intern, we’ll draw our own, better one. This is the thing people notice the least, but it’s a great personal victory.

    To get back to rules and guidelines, nothing is off the table, really. I realize that when I say that I’m excluding things obviously off the table: round windows, animated toolbars, blue chrome, scripty type. Part of this intangible, complex, wavelength-syncing soup we as a team live in is the baseline of quality and aesthetic we all appear to share: let’s not do Thing X, ever.

    As for my personal preferences, I’m probably more conservative than the team as a whole. I’m seeing that (slight) difference as a learning opportunity, so I’m happy to report there have been no freak-out arguments over shades of green. You’ll just have to take my word for it, our tastes are creepily aligned — if we weren’t such motormouths, we’d get along fine with an occasional nod or frown.

  • Shawn: Has the process of completing a design project changed for since joining Panic? Is there a boss or an Art Director who signs off on your work?

  • Neven: “Sign-off” is, like most things with us, a matter of conversation and feeling out people’s reactions more than a structured process. I’m the sort of person who has to get total agreement from others before I’m fully happy, so I usually gauge everyone’s feedback as I work, and this hopefully results in a universally accepted design by the time I’m done.
  • Shawn: I have done freelance work from my home as well as being a designer working with a team in an office environment. When I freelanced I had a handful of creative friends whom I could send drafts of my work to and ask for their feedback. Ultimately if my client liked it and I liked it, then it was a done deal.

    In the team dynamic, I enjoy having the ability to tap a friendly co-worker or two on the shoulder to get instant feedback and dialog about the project I’m working on. But there can, at times, be a downside to that setting insofar that more people need to sign off on the finished piece — it’s not just me and the client anymore.

    I prefer the team setting significantly more because it helps me stay more productive, more creative, and more dynamic in approaching problems. But (and maybe it’s just me. But) it can be frustrating when there is not universal head-nodding approval for every project I’m working on or leading.

  • Neven: I find that a team of our size — about a dozen — is a really good middle ground between the isolation of working alone and the tar-pit indecisiveness and slowness of focus groups, market research, surveys, and gigantic corporate meeting fests. I am constantly getting new ideas from the team (while bouncing them off everyone). At the same time, I don’t have to sit and wait for a design to make the rounds and get approved by a chain of people.

    Other than company size, a few other things about Panic help make this possible. We’re close in age, interests, and general attitude about life and work. Everyone is great at their job, and this makes it very different from working for clients. The client’s preference and criticism may or may not come from actual knowledge of the product, the audience, and the technology we’re talking about.

    Here at Panic, I know I’m getting feedback from a tech-savvy person smarter than me who is also a regular user of the product. If they have a complaint — and I should also mention they’re good at knowing what matters how much when it comes to design — it means there’s likely a real problem I should solve. Maybe there’s something I forgot; maybe the design should be a little more polished. Or maybe my idea was crap to begin with. I am far less likely to defend the design by simply saying “I think it’s good”. Keep in mind that this often happens when working for outside clients, and it’s not good for the designer. Not letting yourself get challenged will keep you from exploring new ideas. The trick is to be challenged by knowledgeable people you like and respect.

    I don’t know of any online resource for those, though, so… Your parents/karate instructors were right: there are no shortcuts, it’s going to take time!

The End…

Thank you, Neven.

For more interviews with extraordinary designers, developers, writers, and web nerds, visit here.

An Interview with Neven Mrgan

Mr. Hines and the Unpublished, Unfinished Interviews

A few months ago I was asked by Ian Hines to conduct an interview via email. Unfortunately that interview was never completed. I am a slow correspondent, and just recently Ian had to end the interview early because he was taking his weblog down for professional reasons.

Ian was a fantastic interviewer, and I was not the only person he was chatting with. He also conducted interviews with Pat Dryburgh, Kyle Baxter, and Jorge Qunteros. All of which had interviews that were never published to Ian’s now-dissolved weblog. So instead, these three gentlemen posted their interviews with Ian onto their own sites. And so I’ve been provoked to do the same.

The Interview

  • Ian Hines: Let’s start at the beginning: How long have you kept a weblog, and what made you get started in the first place?
  • Shawn Blanc: I remember writing that first post as if I published it yesterday. I so clearly recall the first time I felt the novelty of writing something combined with the adrenaline rush of publishing it. Even now, four years later, I still feel that same novelty and that same rush every time I publish a new article.

    That first post was written on January 27, 2006 during a trip to Colorado. I wrote it on my 12-inch PowerBook G4 and published it on Blogspot.

    (Back then, all my blogging friends used Blogspot. Randy had been publishing his weblog for like 6 years already, and Josh was going on three or four I think. About six months later I migrated it to WordPress (version 2.1 I think) because the WordPress WYSISYG editor seemed way better than Blogspot’s.)

    I have always considered myself a writer, despite the fact that until I began publishing a weblog in 2006 I had barely done any writing. (Funny how it works like that.) So perhaps that is why I still recall that first post so much — because I was finally writing.

    Publishing a weblog has been the best thing I could have done for my writing. It is a format that really works for me: I enjoy it, I’m challenged by it, inspired by it, and frustrated by it. I love it and I hate it. Some days I cannot wait to sit down at my keyboard, while other days I consider quitting altogether and spending all that new free time building furniture. And but so the blend of emotion is sort of my proof that I ought to keep growing and writing.

    But if I ever did quit, I know I would miss it. Blogging in its purest form — when I’m not being influenced by stats, etc. — is really enjoyable to me.

  • Ian: It’s interesting that you mention the tension between loving blogging and thinking of quitting; I gather that that is a common feeling among dedicated bloggers. I’m curious how your blogging influences your professional and personal life, and visa versa? Would you say that you continue blogging in spite of it’s impact on your offline life, or because of it, or… what?
  • Shawn: Publishing my website influences my home and work life much the same as any other pursuit would. Growing up and all through school I studied Martial Arts, and it effected my whole life. I trained five days a week, and everything I did or thought revolved around Tae Kwon Do. My friends were in Martial Arts, we only ever watched fight movies, I read books about weapons and Japan and ninjas (seriously), and I made sure to buy clothes that would be most appropriate in case I were to get in a fight in a back alley.

    After that it was playing the drums. From my senior year of high school, on through college, and for my first five years on staff with the International House of Prayer I was a full-time drummer. My best friends were my bandmates, I visited drum websites, watched drum-solo videos on YouTube, spent all my money on drum gear, and listened to a lot of Carter Beauford.

    It was in 2007 when I began transitioning out of my life as a drummer and into a life of graphic design, writing, and much higher interest in technology and software.

    Obviously it’s not as cut and dry as I’ve made it sound — I am still a Black Belt, I still own my drum kit, and I was writing and designing and being nerdy before 2007. But my point here is that there are seasons of my life which can clearly be earmarked by what hobby or pursuit I most had going at the time, and usually for a decade or more. Each of these pursuits had a profound impact on my daily life.

    So to answer your question, I write both in spite of, and because of, the impact on my offline life. I mean, of course it impacts my offline life. If it didn’t it would mean I wasn’t putting enough of myself into it. If I didn’t want my online writing to have an effect on my offline life then I suppose I ought to go find something which I would.

    The reason I sometimes consider quitting is probably just like anyone else who considers quitting something they do. There is always that feeling of the grass being greener on the other side. Will I be publishing my site 10 years from now? I don’t know. But I do know that for this season of life I have the time and the energy to write and I want to make the most of it so that when I look back it won’t be to see time wasted fiddling around on the internet.

  • Ian: Well said. But how about we flip it around: how does your offline life influence your writing?

    Back in early February you published a piece about titled “A Job Should Also Be an Education” in which you said:

    My uncertainties, struggles, and discoveries as the director of a marketing and creative team are something I’d very much like to talk about more here on, but I honestly don’t know where to begin.

    I started to briefly in “Marketing Shoes” and in my responses to Cameron Moll’s questions on leading an in-house design team. And posting my 1:1 form was another attempt at it.

    But talking about management, leadership, marketing strategy, and creative solutions from a corporate-feeling, non-profit organization’s standpoint is something I don’t feel very smart in. (And I generally prefer to only talk about things which I feel very smart in.)

    I, for one, would love to hear more about your work at the International House of Prayer, your hobbies, etc., but that doesn’t seem like something you’re inclined to focus on at SBnet.

    I guess what I’m really asking is: how do you decide what to — and what not to — write about?

  • Shawn: Well, I primarily decide what not to write about by wimping out — sometimes before I even get started. Or sometimes mid-way through.

    I think to myself: “Self, nobody cares about this crap. It’s not worth your time to write it, and it’s certainly not worth anyone else’s time to read. You and they both have something better to do.” Perhaps I’m being hard on myself at those times, or perhaps it truly is the voice of reason. We may never know.

    How do I decide what to write? No clue. I just write it I guess. There is no content strategy or research plan. I just write whenever I have a clear thought that I’d like to communicate. If I get stuck during the process of working out that thought then I’ll save it as a draft in MarsEdit and re-visit it later. More often than not I do come back to that post, finalize it, and publish it.

    And actually, I am inclined to talk more about my work on my weblog. Although that inclination has yet to translate into actual posts. As of this writing I have a handful of draft articles started which are not related to Apple or technology at all — they’re about marketing, the creative workflow, and management. Hopefully one or more of them will get finished and published soon and will pave the way for more of the like to follow.

  • Ian: Hmm… That leads me to an interesting thought: roughly how many draft articles do you have in MarsEdit right now? I tend never to have more than a few at a time, mostly because I find that when I get an idea it gnaws at me until I publish it.
  • Shawn: Roughly 30. The oldest dates back to February 2008. Some of the drafts are only one or two sentences, and are simply the start of a thought. Others are hundreds of words yet still incomplete, and a few are would-be links.
  • Ian: Do you find that — at least in your personal opinion — you write better when the idea pours out of you or when you take more time to write it in drafts?
  • Shawn: I guess it depends on the definition of writing better. If I have an idea that just pours out then yes, the initial foundation for what I’m writing is certainly much stronger than an idea I’m unclear on and trying to winkle through. But a piece that I were to write quickly and then publish would not nearly be as well written as one I took the time to write, edit, re-write, and then edit some more.

    In my opinion, my strongest articles are ones which I spend a significant amount of time on (sometimes several weeks) before publishing. Some of those articles started as an idea that just “poured out”, but some of them didn’t.

  • Ian: Makes sense. I’ve never really been much for drafts in any context; even major academic papers are usually just written in one go-through. I tend to edit as I go (for better or for worse).
  • Shawn: Yeah, I tend to edit as I go too. And I hate that I do that. It slows me down and I don’t think it leads to a better first draft.

    When I edit as I go I have too much focus on writing well and not just writing. That’s Natalie Goldberg’s big thing in her book Writing Down the Bones — she’s always saying to just write. Write. Write!

    The trouble with editing as I go is that I lose track of where I’m going because I focus too much on where I’ve been. Even now, as I’m typing this answer at this moment I’m editing it as I go. (!!) For me, it’s a habit I want to kick but it’s easier written than done.

  • Ian: You are, I’d wager, best known for your glowing and fantastically spot-on app reviews. In fact I feel like I’ve seen you refer to yourself as a software evangelist. How did you come to start writing those?
  • Shawn: Thanks for the kind words, though I can’t ever remember referring to myself as a “software evangelist”. I certainly do like the stuff though.

    How exactly I fell into writing those winded reviews I’m not really sure. Though I do know it all started with my review of NetNewsWire. I wanted to write something of length that had a storyline, yet was chock-full of nerdy content. A review of an app that I love seemed like the perfect solution. And it was.

    For me, writing a software review isn’t so much about giving the ins and outs of an application. It’s about telling a story and sharing a point of view from my eyes and then weaving the piece of software into that storyline.

Mr. Hines and the Unpublished, Unfinished Interviews

The Daniel Jalkut Interview

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.

The Daniel Jalkut Interview

John Gruber: A Mix of the Technical, the Artful, the Thoughtful, and the Absurd

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 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:

    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.

John Gruber: A Mix of the Technical, the Artful, the Thoughtful, and the Absurd

Interview with Cameron “i/o” Hunt

There’s a shortage of well-designed tumblelogs on the internets these days. And like a one-man brute squad, designer Cameron Hunt has been putting up an inconceivable fight to help dispairing websites.

Cameron has released several Tumblr themes, and his website,, is recognized all over as a well designed website and a pillar example of tumble blogging.

I had the chance to interview Cameron via email and talk with him about tublelogging, web-design and a few other tidbits.

The Interview

  • SHAWN BLANC: Let’s start with the weblog: why did you start publishing?
  • CAMERON HUNT: I’ve had a website since I was in high school. I love websites, I love having a website. It’s my passion. For a long time I considered a different career because I love making websites so much, I really didn’t want to make them for anyone other than me. I guess that sounds a little selfish. Both my parents were involved in journalism, and in high school I was heavily involved in my school’s newspaper. I love publishing, and I love writing about what I love. Blogging is all about doing what you love, forget the rest. You blog because you love it, not because you want it as your career, or because Google Adsense might make you rich. It’s like being a rock star, but less cool, and no one knows you.
  • SHAWN: Interesting response to your own passion for designing sites: You love it so much you didn’t want to do it. Though oddly, I know just what you mean. And I couldn’t agree more with your thoughts on blogging. I think it’s the passion that makes or breaks a weblog. Of course I’m sure that not everyone who publishes a weblog does so because they love it, there’s always going to be the guy who thinks he can get rich overnight with Adsense. So, besides your Tumblr themes, what other web designing do you do?
  • CAMERON: I do freelancing here and there. I’ve done some print design, mostly posters and brochures. I used to work at my college’s Marketing and Communications department; I worked on web and print projects, and I was one of the few people who understood both at my job. I was also one of the only people at Marketing and Communications that understood HTML/CSS and design. I always underestimate my talent and skill for understanding and implementing a design into HTML and CSS, it’s because I know so many web designers online who are good at it. But in the real world, it’s an uncommon skill. A lot of people can design, less can web design, and even less can design a website with beautiful markup. Besides tumblelogs, I haven’t designed much that’s online. I designed Nick Douglas’s tumblelog which was the job that started my freelance tumblelog services. Most of my web design until 2007 were my own personal projects.
  • SHAWN: I haven’t studied your code or anything so I can’t say about your developer skills, but you clearly have a great eye for classy design. And you are certainly making a name for yourself lately. I see your name popping up all over the place, and primarily it seems like it’s related to your use of Tumblr and the look of cameron i/o. Why did you pick Tumblr as your CMS?
  • CAMERON: There’s a lot of reasons, but I’d have to say the biggest is ease of use. I got interested in tumblelogging in 2006. I ran a website called “shrimpdesign,” it was my portfolio and blog rolled into one. I got interested tumblelogging in late 2006, so I added a tumblelog to my blog. They were just little snippets in my regular blog posts. Eventually I wanted to separate my blog and portfolio, so I set out to make the same kind of website that I have now: a regular blog mixed with a tumblelog. Except I made it with Textpattern, which didn’t work so well. It was hard to update. And I hacked Textpattern to get it to work the way I wanted to, so it was a hatchet job.1 I found Tumblr a couple months after abandoning Shrimpdesign. I was resolute in dropping my silly online identity of “shrimpdesign” in favor of a respectable and mature identity. I played around with Tumblr for a while, and in less than a month, I bought a domain name for my Tumblr powered tumblelog. Tumblr was incredibly simple to use, it was a breeze to theme, a joy to post. Tumblr’s bookmarklet was really the turning point for me. Above all other easy-to-use Tumblr features, the bookmarklet is their pride and joy. The bookmarklet is the easiest way to post something you found. If Steve Jobs demo’d it, he’d say “boom” at least 4 times, and “like butter” at least twice. It’s really good.
  • SHAWN: How has changed from its original launch to what it is now?
  • CAMERON: I’m not sure how to answer that question. In my mind, cameron i/o doesn’t change. I change. This website is a representation of myself on the internet, my endeavors and passions. I change over time, and my website reflects that, but my website will never change in it’s extension of me.
  • SHAWN: I can’t think of a better motivation to publish a tubmelog: The concept of a website being an extension of yourself. That would make a fantastic ad campaign for tumblelogs. And not that this is related, but I’m reminded of how parents are now registering their newborn kid’s namesake URL on the day of their birth. Regarding Tumblr, I have to admit that I’ve done virtually zero research. What exactly is Tumblr?
  • CAMERON: It’s a tumblelogging engine. “Tumblelog” is a term coined in 2005 by this guy named “Why.” He’s sort of the crazy uncle of the Ruby community. Anyways, he used the term to describe Anarchaia and the term stuck. Wikipedia will tell you that Anarchaia is the first official tumblelog. That’s bull. Tumblelogs have been around, but there’s never been a term. I believe that Daring Fireball and, some of the most popular blogs on the internet, are tumblelogs. I’d even call a tumblelog. The real definition of tumblelogging is this: different presentation and format for different types of posts. Back to Tumblr. Tumblr is currently the easiest way to start a tumblelog. Although it doesn’t get credit for being the first tumblelogging engine. Ozimodo was probably the first tumblelogging engine, it was written in Ruby. Tumblr is a lot like Kleenex, they are the standard because they set the standard. Every tumblelog engine since Tumblr has pretty much copied them (not in a bad way, mind you, but in a competition-helps-users way).
  • SHAWN: Would you recommend Tumblr to someone that ran a primarily ‘article focused’ blog, but still wanted to post a linked list?
  • CAMERON: You can use Tumblr for anything you want. You can post text and links exclusively. There’s no way to have a “more” link where some of a post’s content is reserved for the permanent link. I’d recommend Tumblr and Chryp to anyone who wants to start a tumblelog and blog hybrid. Tumblr is the best hosted solution (if you want simplicity and no hassle), Chyrp is a hosted solution with more customization and control.
  • SHAWN: What are you doing on your site then when you write an article and post a link to it on your homepage with the “read more…” link? Is that hand coded by you each time, or are you doing something special on cameron i/o?
  • CAMERON: Yes, I hand-code it every time I post an article. I’ve got a lot of reasons to switch to Chyrp, and that’s one of them. Nothing against Tumblr, but I need complete control over my website. With Chryp, I’ll be able to customize and automate my site like never before.
  • SHAWN: You’re pretty involved in the Tumblr community. How has it grown and evolved since you first started using it?
  • CAMERON: I missed the first version of Tumblr. I started using it somewhere between 1.0 and 2.0, it’s hard to tell because Davidville had no official release date for 2.0, my guess is it happened over the summer sometime. There were only small updates before the release of 3.0 on November 1st. Tumblr 3.0 is a great service for anyone starting a tumblelog. Everyone associates me with the Tumblr community. I love tumblelogging, and Tumblr is the biggest tumblelogging community, but I’m not married to Tumblr. I’m planning on moving from Tumblr this year. I love Tumblr, but I’m a complete control freak when it comes to cameron i/o. I’m going to move to Chyrp once it stabilizes and a few key modules are released. I have minimal knowledge of PHP so I can control cameron i/o more fully than Tumblr. Of course I’ll still use Tumblr for some things, and I’ll probably keep releasing themes.
  • SHAWN: Like you said earlier, the main idea behind a tumblelog is that different posts have different styles: One style for quotes, another for links, another for articles, etc… Unfortunately, the majority of Tumblr websites I come across look very ugly to me – they are cluttered, choppy and messy. When you design a tumblelog theme, what are some key style guidelines (if any) that you try to implement?
  • CAMERON: I am very adamant about distinction between posts. Tumblelogs are jumbled; their content is pulled form a variety of sources, the content itself is varied since you can post several different types of media. The key in tumblelog design is to bring order to the jumble. Since the content is jumbled more than most websites, the design has to compensate. This can be done in a few ways, my favorite would be icons and subtle styles for each post-type. And a good structure that all posts conform to, and normal text sizes. A lot of tumblelogs have different font sizes for different posts, for instance; photo captions would be slight larger than regular text posts. It drives me crazy because it’s all body text. Headers and quotes should be larger, but the body copy should be standard. I’m also very adamant about typography.
  • SHAWN: I agree with your views about typography but I don’t share your zeal for distinction between posts. Feel free to talk me out of this point of view, but I honestly don’t see a major need for distinction between posts in a tumblelog. Although I suppose that completely contradicts the definition of what a tumblelog is. I think slight “tip-offs” can add to a tumblelog’s design, but I don’t see it as a necessary component. I would rather see no variation in types of posts than the often gaudy typographic nightmares I usually see; i.e. what I’m pretty sure is the default Tumblr theme.) What I do like are sites such as yours, Sam Brown’s and Phil Bowell’s where colors and icons are used as a tip off for a different post type while the headers and body text are the same. But other than being pretty, is that really necessary? When I am reading a tumblelog I’m not scrolling down looking for “quotes” or “links”. I am just reading it. If something catches my attention it’s not the type or classification of a post, it’s the content which in that post.
  • CAMERON: I guess I phrased that wrong and mislead you a bit. I was talking about distinction between posts, not post-types. For instance, I’ve seen some tumblelogs that simply jam everything together, and it’s very hard to tell where one post ends and another begins. I think that’s awful because there’s no structure. No offense to David Karp, but some of the default themes are fairly schizophrentic in their typography.
  • SHAWN: “Fairly” may be an understatement, but yes, we’re agreed then. Designs aside for a second, one thing I very much like about Tumblr – and tumblelogs in general – is the easy on-ramp it has created for many people to start blogging. People who used to think, “There is no way I could write an article every day, thus I’ll never start a weblog,” are now realizing that they don’t have to write 500 words or more every day in order to publish their own site. I’ve said before that I think everyone should blog, and so I like what Tumblelogging has done in that regards.
  • CAMERON: Exactly! Tumblr takes out almost all the overhead in blogging, and focuses on content.
  • SHAWN: True. Of course, on the flip-side of that coin is the issue in which tumblelogging has created a vast amount of insipid weblogs where people simply post links and YouTube videos and random pictures with zero of their own commentary. Thus creating posts and links with no personality.
  • CAMERON: There’s the rub. I don’t think there’s any way to stop it, though the Tumblr folk are placing good restrictions to limit misuse. It has always been like that with blogging, there’s no easy answer or cure. It’s comforting to know blogs with good content are always highly respected.
  • SHAWN: I’m curious: If you could only post a “link-blog” or an “article-blog” which would you choose, and why?
  • CAMERON: I would, without question, choose an article-blog over a link-blog. Articles give me a higher amount of quality than a blog simply filled with links and descriptions. When I post a link, it’s just a link. When I post an article — a long form post that I’ve crafted from nothingness — I’m downright proud. It’s a greater sense of accomplishment. Not to say posting a link-blog is trivial, I’m just more passionate about my articles.
  • SHAWN: When posting links, is there something specific you look for? Is there a “criteria” that has to be met for you to link to or quote something? What’s the deciding factor behind what makes it on your tumblelog and what doesn’t?
  • CAMERON: I don’t have any specific criteria, it just needs to be interesting or thoughtful and within the scope of cameron i/o’s topics. It has to be incredibly interesting for me to post outside of my loose topics.
  • SHAWN: I notice that your site is almost completely text-only. Do you purposefully not post the common tumblelog elements such as YouTube videos and pictures?
  • CAMERON: There’s a good reason for that. I used to post any picture or video I came across and I found interesting. Recently I prefer to only post a video or picture if I’m the creator. If I didn’t make it, I link to it instead of reproducing it. It’s my policy now because that’s how I would like my content treated. Do unto others, and all that.
  • SHAWN: Talking more about web-design… As we touched on earlier, you have designed a handful of Tumblr themes. When desiging a theme what are some of the key components you integrate? Also, what impact on your own site have your themes had?
  • CAMERON: Well, it’s typically the other way around. I use concepts from my own tumblelog for my themes. For instance, when I began tumblelogging, very few people had a wide-layout for their tumblelog. My tumblelog had a wider layout and smaller text than most. That’s been reflected in my themes. A lot of my themes have the photo description on the side of photos instead of beneath. Other than that, nothing really comes to mind. I’ll be releasing a couple themes soon that use recycled designs from cameron i/o.
  • SHAWN: Actually, I was talking about traffic. What sort of impact has releasing Tumblr themes had on getting more readers and “followers” to your site?
  • CAMERON: A lot! There’s basically three reasons the majority of Tumblr users follow people: 1) They’re famous, or popular already; 2) Their Tumblr looks cool; or 3) You know them. I fall under number 2. Being a themer actually really made my Technorati rating completely out of proportion because it counted every Tumblr blog using my theme as a link to me, so I’m in the top 10,000 blogs on Technorati, but it doesn’t really matter since Technorati is going downhill.
  • SHAWN: I think that makes for an extremely valid argument as to why it’s important to have a well designed site. Of course, I suppose it’s not that people want to have a poorly designed site, they just don’t realize they have one. And I’d say it’s fair to assume the ratio of ugly Tumblr themes is much higher than other blogs ratio of ugly sites.
  • CAMERON: At least the majority of Tumblr blogs that are popular are also well designed and maintained. See, that’s another thing. You can have a beautiful theme, but if you format the text in an incoherent way, it looks terrible. A lot of the ugly comes from text formatting.
  • SHAWN: Well put. Now regarding Chyrp. With the recent hiccup on the Tumblr servers will you be migrating sooner now? Other than being able to install Chyrp on your own domain, are there any other incentives for switching?
  • CAMERON: There’s a lot of incentives. Right now cameron i/o is fractured. I got a Tumblr blog, two Textpattern installs for Articles and Projects, and a plain html file for my Colophon. It’s a bit painful to update. With Chyrp, I can manage my complete website from one Chyrp install. And I can have a search, which is something I really wanted for my tumblelog. And I can make my own post-types with a bit of PHP code. Also, I can finally exit sub-domain hell, and use my website like a normal person. My articles will be at, and my Mint will at last be in it’s rightful place at /mint/. Really, it’s all about the control. I can tweak everything with Chyrp, it offers me more control. I’m very picky and particular about my site.
  • SHAWN: Why not just use Textpattern for everything, or use Tumblr and put the full post in your main page’s stream?
  • CAMERON: First off, currently everything from Articles and Projects gets posted on my Tumblr. I like to keep the front page succinct, and if someone wants to explore an article (or project) further they can click a “more” link. Tumblr doesn’t really have support for the “more” link which is why I use Textpattern to supplement, and then I have to manually post each project and article. As for using Textpattern to power my whole site, there’s problems with that. Like I said, I’ve tried it before and Textpattern just isn’t made for the kind of site I want. First, no bookmarklet for easy posting. I really like Tumblr’s (and by extension Chyrp’s) bookmarklet. Second is post-types. You can fake post-types with Textpattern’s sections, but it’s not a perfect replacement for Tumblr or Chyrp. Third, Textpattern’s admin interface needs an overhaul. You can only edit your theme files in the Admin interface in a textarea. Also, Chyrp has a Tumblr importer. Which means the switch to Chyrp will be seamless, I bet most of my readers won’t even notice.
  • SHAWN: I’ve seen you mentioning you want to quit college and start freelancing. What would the ideal situation from here to there look like?
  • CAMERON: I’ll finish my current spring semester right now, and then quit. Basically, I’ll do the same thing I’ve always done, just with more of my money staying in my pocket, less debt and more time. There’s a lot of hoops you gotta jump through, and I’m just completely sick of it. Every time I work on a design project for school, I think “I could be designing for a real client right now.” So that’s what I’m going to do.
  • SHAWN: What do you want to do in the world of freelance web-design?
  • CAMERON: I want to design quality websites. I want to work on projects I’m excited about, and so far I am. I can’t wait to show off the stuff I’ve been working on.
  • SHAWN: What would an ideal job look like for you? Front-end design? Back-end development? Both? Weblogs, corporate sites, etc…?
  • CAMERON: Most of my design is front-end right now, but I’m trying to learn a few programming languages so I can at the very least understand what is going on behind the scenes. I always dreamed of working at Apple, like many nerd-designers do, but I have a feeling that’s not for me. I don’t think I could work for a large company. The ideal job for me is self-employment; designing, writing and creating what I’m passionate about.
  • SHAWN: Do you have any plans to start advertising on cameron i/o?
  • CAMERON: If I do, it’ll be small and discrete and not just an ad service. It’ll be catered to my readers and audience.
  • SHAWN: How much ‘work’ have you generated from your Tumblr themes? Meaning: Do you spend much time on pro-bono troubleshooting?
  • CAMERON: I don’t spend much time on that. I actually get more support requests for Tumblr. For instance, there was a tumblelog currently stealing content from a PS3 themes website, basically copying theme entries and hotlinking. So the owner of the website visited the tumblelog and assumed it was me since my name was in the footer. It happens more than you think.
  • SHAWN: Interesting. Cleaning up someone else’s mess is something I never even considered. I’ve thought about releasing a WordPress theme but don’t have the time to support it and don’t have the heart to tell people “sorry, can’t help you.”
  • CAMERON: I haven’t done much support. Most people who want to change the theme around do it on their own. I get a few requests, but not probably as much as you think. Although I need to update my themes for new Tumblr features.

More Interviews

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

  1. A link to the “Hatchet Job” website.
Interview with Cameron “i/o” Hunt

The Dan Pitts Interview

Dan Pitts – like many of us – works a 9 to 5 and does freelance on the side. He’s a great guy and does some equally great work. His freelance gig flys under the name of e210 Design.

One thing I love about Dan is his passion towards design. On his bio he says, “Design is more than making something that looks great or sells, it’s a way to encourage and serve the client.”

There are many designers out there whom are creating with no purpose or passion behind their work. Dan on the other hand is really seeking to enhance his own art, and bring something quality and worthwhile to the design community.

I had the chance to ask him some questions about the work he does and (of course) the Mac he does it on. Enjoy.

  • SHAWN BLANC: Hey Dan. Tell me about what you do that your bio page doesn’t say.
  • DANN PITTS: Currently I’m working a full time job that I have had for 9 years now. At my 9-5 we focus on catalogs and gift books with some book covers. After my first son was born I found that my creativity (and my wallet) needed a boost so I went out to find some different kinds of work. So for the past four years I’ve built up a network of clients and other designers and have gotten to the point where I have steady work coming in. I am limited to how much and what kind of work I can do since I usually have to work at night. I have chosen to focus on book cover and web design. I’ve found that variety really brings a joy to designing and a boost to creativity.
  • SHAWN: When you first stepped into freelance design work on the side what was the biggest challenge you faced?
  • DAN: The quick answer is finding work. The details of that answer is that I had to set up a website portfolio that I could point people to. Problem was I didn’t have much work (and no book covers) to post. At the time I didn’t put anything from my 9-5 on there and all I had were a couple logo’s I had done for friends and a website I had worked on for our church. So I had to create my website (which has been the hardest client I’ve worked for) and then create these covers that were going to show what I could do. I kept running into a wall where I felt they just weren’t good enough or could be improved but eventually I just had to get the site posted and some covers up to start the process. Looking back they were pretty weak but you have to start somewhere. Thankfully for me the first batch of emails I sent out looking for work produced a client I really enjoy working for and they have sent me many projects so now I can post actual work.
  • SHAWN: Why Book Covers?
  • DAN: First, I was already doing it at my 9-5 job so I had some experience in it. Second, from a business standpoint it’s really a great niche, if you can get in with a publisher and they like your stuff they will probably give you repeat work. Most important for me is that it’s a single piece of art and it’s goal is to catch your attention and lead you into the book. So each book is a new challenge with new solutions and is inspired by the work someone else has done so it kind of has that team aspect to it. I also like the finality of being able to see a project that is printed (as opposed to the web work I do).
  • SHAWN: Why Web Design?
  • DAN: Well web design is obviously the future, if the future isn’t here already. The ability to communicate information on the web is so amazing, I wonder if we don’t take it for granted already (and I’m still amazed when I run across companies that don’t have a site or they have a bad one and it’s not a priority for them). It’s relatively inexpensive and can be so current you can do things you could never do with print; podcasts, video podcasts, pdf documents you can download, it’s all so amazing. Then to think that the only thing that changes between the fortune 500 company and a church website or a small business of 4 employees is the content, that makes the design that much more important. I’m comparing it to print where a major company might print something out on a huge press run with high weight, glossy paper, special inks, embossed and a church is making black and white copies in there office. Not with the web, each site is viewed on the same computer with the same browser.
  • SHAWN: If web design is the future, what do you think that will mean for print?
  • DAN: Well there are people with a lot more experience and knowledge that I would look to for that answer but here’s my take. I’ve seen it effect some areas of print already. My 9-5 job, one of their main clients is a catalog company and the web has effected their business dramatically. I don’t know if print will ever go away but I think it will serve more and more as a way to lead people to websites. Print can never keep up with the web when it comes to current content, but there is something to be said for the ability to hand someone a business card rather than sending an email. For books, I have a hard time imagining the day when a 200-400 page book is sold in an electronic format and tens of thousands of people buy it. I know some of the reference books I have worked on come with a cd that has the information in pdf format also but that is an extra aid, not the main product. Even writing this though I have that feeling that if I see this in 15 years I will look back and laugh. Who knows, I guess that’s why I try and have my feet in both.
  • SHAWN: That’s a great answer. I think the concept of using print to point to web is excellent. This allows for more focus on design with printed material, allowing the content to be primarily web-based. Changing topics a little bit. Let’s talk about your workflow. For starters what does your Mac setup consist of?
  • DAN: Right now I’m nearing the end of a good run with my G4 20 inch imac, 160gb hard drive with 1gig memory. I’m in need of upgrading the programs and computer but here’s a screenshot of what I’m using now.
  • A Screenshot of Dan Pitts' Workstation.
  • SHAWN: What other Apple gear have you used?
  • DAN: I remember my dad getting one of the first macintosh computers for christmas when I was younger. In high school that’s all I used and in college being a fine arts major I didn’t have to use the computer a whole lot so I always found the mac lab, just happened to pick the right profession I guess. I started freelancing on the first generation imac, went to a G3 powerbook with a seperate monitor (the 21 inch apple crt’s which weighed about 200 pounds). Then got a hand me down G4 titanium powerbook from my dad before the imac. The imac has been with me the longest.
  • SHAWN: I have always loved the titanium PowerBooks. I remember when they first came out. That was actually my first time in an Apple store. They will always be a classic to me. So when you do a freelance project for print, like a book cover, what does your workflow look like?
  • DAN: Right now it’s usually make client calls on my way home from work. Then after being a father and husband for a while I start working around 9 or 10. I’ll start by sketching out stuff on paper and trying to ask, what problem am I trying to solve. Then I’ll look at websites or books, try to gather information, scans or images I might want to use, nice fonts, anything. Then if possible I like to let that kind of soak in and have a direction before I start working on the computer. Usually that direction will then move into other ideas but I found that if I don’t have a place to start and focus I can go anywhere and waste a lot of time on ideas that don’t work. An important part of my workflow seems to be the time that elapses between sending the first round out and then getting the corrections back. I like having that time to detach from the project and come back with fresh eyes, and usually the art director will narrow it down to what comp they want to work on. I have to refine and keep polishing it. I hope time and experience will change that a bit and I can provide great stuff first round, but I have a ways to go still.
  • SHAWN: So if you work a 9-5, and do freelance work starting around 9 or 10, how much sleep do you normally get?
  • DAN: Sleep? Usually if work is moderately busy I’ll get 5 hours a night. If it’s really busy maybe around 4. I’m not one of those guys that can pull an all nighter (not even when I was in college). At a certain point my eyes just stop working and I have found that I’m not really productive anyways. No matter how much Mountain Dew I drink. I could handle it better when we just had our son but now I have twin girls (a year and a half old) and it’s been much harder. Every now and then I need to go to bed at 10:30.
  • SHAWN: I bet that’s something we can all relate to.
The Dan Pitts Interview