Ryan Cash

Life passes most people by while they're making grand plans for it

An interview with Todd Garland, founder of BuySellAds

I’ve known Todd for about 5 years now. I first met him when I was working at Marketcircle, buying ads to promote Billings on various design/freelance websites.

Todd is the founder of BuySellAds, a self-serve ad platform that deals with high quality digital advertising. Todd bootstrapped the company himself, and has built it up into a great business.

Todd’s an honest and hardworking guy, and it’s always a pleasure to ask him a bunch of questions. I interviewed him back in 2012, and once before that as well.

Read on to learn more about Todd and the company he’s built.

Tell us a bit about yourself. Where have you traveled to? What kind of music do you listen to? What are your hobbies?

I haven’t travelled much; however, I did live in Brazil for a year when I was 18 and traveled all over Brazil. I’ve traveled in the US a little bit as well, but I still have plenty of exploring left to do. I’m somewhat of a homebody, and enjoy my routine and the comforts of my own home. Outside of work, I don’t have much time for hobbies these days, and prefer to spend all non-work time with my family.

What was your first job growing up?

My first job was as a golf ball retriever at a local golf course. There is a salt-water river (so, perhaps it’s considered a marsh…) that runs through the middle of the course and at low tide you could walk through the mud and pick up the golf balls. The course would pay me $0.05 a ball I think… and I would fish them out of the mud, clean them off, and the course would resell them as used balls for $0.50 each.

Tell us about the early days of BuySellAds. Where’d the idea come from, and how’d you get started? When were you able to hire your first full-time employee?

I started BuySellAds so that I could have an easier way of selling ads on a couple hobby websites I was running at the time. There were plenty of ad companies, tools, and networks, but none that made it super easy for me (and my advertisers) to quickly purchase an ad on my websites. So, I built BuySellAds. I literally just built it. It wasn’t pretty, but it did that one thing really well. We were able to hire our first employee after about 12 months. I was also working a full-time job for the first 11 months after launch.

What’s the biggest mistake you’ve ever made? How did you come back from it?

I’m not a big fan of keeping track of mistakes. I’m sure we’ve made plenty of mistakes, but they all just seem to go away since the process of making mistakes is part of what happens while trying to find success. So, I just think of them a little differently, that’s all. If there ever comes a day when we write the final chapter for BuySellAds, I’m sure I will look back with hindsight and be able to pinpoint and better articulate specific things we did (or didn’t do) that left us short of hitting our goals. Broadly speaking, however, I think most mistakes come from focusing too much on chasing dollars (when you’re not sure if the value you’re providing is actually there) or focusing too much on what your competitors are doing. 

What was the most important decision you’ve had to make at BuySellAds?

I’d have to say deciding not to sell the company back in the summer of 2009. I had some casual conversations going that in all likelihood would have resulted in a sale if I had pursued them a bit more. At the time I wasn’t “done” executing on the vision (still not done…) and ultimately felt as though we would have been selling ourselves short. As it turns out, we most certainly would have sold for far too little. So I’m glad we kept going and tuned out the interested parties.

Can you tell us anything about the strategic acquisition of Fusion Ads? How has the addition of Fusion helped BuySellAds grow?

I have always loved the one-ad-per-page networks modeled after The Deck. There’s simply no better way to monetize a small-medium sized site or hobby project in the design/dev space. Acquiring Fusion really came down to our infatuation with the model, the design/dev community overall, and just wanting to continue on doing what Fusion was great at. About a year later we acquired Drew Wilson’s Yoggrt, Carbon Ads, and Syndicate Ads. Most recently we bought the domain name from InfluAds (they were about to shut it down). So, while we may seem like some large company trying to “own” everything in this space, it’s really just because we love the space. We love working with the advertisers in the creative space. We love working with the publishers, and it’s our way of funneling money from advertisers to creators within the space. These networks are labors of love more than anything else.

When you’re evaluating a new product idea, what’s involved in the research/planning? What’s your favourite part of the process?

It’s really just about talking to customers to find out what we can build that will be valuable to them. We go out to customers with an assumption that there is something we can build that they will find valuable, and we test whether or not their feedback matches our assumptions. My favorite part is when we receive enough data to put forth an effort to build something, and then spending that next week or so with the team executing on a the new product to get to a version 1. It’s a special thing, starting from scratch and having a real working product up and running within 1-2 weeks. We did this recently for our Publisher Pro for DFP product here: http://pro.buysellads.com/dfpselfserve.

How many employees do you have working with you? Do they all work from the BSA office, or do you have remote workers as well? 

We have 17 on the team right now. Three work here out of the Boston office (including myself), and the rest are spread out and remote. More than half of us are on Eastern time, and it works out pretty well.

How do you keep employees motivated? Has it been tougher to manage everyone as the team has grown?

I think it comes down to working on challenging problems. I’m not sure I can say that we’ve consistently kept everyone on the team motivated. There are natural ups and downs to everything. However, we’re here to build products and make customers happy and those two things are generally fulfilling. Our next challenge is finding another winning product that we can all rally behind like we did in the early days of the Marketplace.

Hiring great people is always tuff. How do you find new employees? Are they mostly inbound requests or do you go looking for new talent yourself?

Your best hires will be from existing employee referrals. Referrals will, more often than not, be great hires. The employee referring will be judged by the quality of their referral, and most people don’t like to shoot themselves in the foot.

Do you have any desire to enter the world of offline advertising?

I’d love to do some innovation in the product placement space.

Have you ever had the desire to be on the other end of advertising – as either a publisher, advertiser, or perhaps involved in the creative component?

Not really. We like building software for advertisers and publishers. Building tools to empower both parties is more of our sweet spot as a company.

What’s your hardware/software setup look like?

15 inch Macbook Pro, with Thunderbolt display. Postbox for email, Espresso as a code editor, Cornerstone for SVN, Unfuddle for project management/svn management, and Skype/Campfire for working with the team.

Do you find you need to have a regular routine to get the most accomplished in a day or are you a fly by the seat of your pants type of worker? What’s a typical week look like for you?

Since I have family priorities I tend to keep a fairly set schedule. I typically work from 9 to 5 without much exception. Having the set time allows me to focus more during those hours since I know that it’s “my time” to get stuff done. Anything I don’t get done between 9 and 5 likely won’t get touched until the next day. Constraints breed creativity. From time to time, when I have interruptions during the day that prevent me from staying focused, I will hop online at night after everyone has gone to bed and get some work done between 9 and midnight.

Do you have any advice for aspiring entrepreneurs?

Stop making excuses. Build something. Talk to some potential customers and go for it. Life is short.

If you could spend a few hours over dinner with anyone in the world, who would it be and why?

Easy question – my family. I’d much rather spend my time with them than anyone in the world.

How do you see advertising changing over the next 5 years?

Mobile needs to see some innovation. Traditional banner ads in general need to see some innovation. Consumers are getting smarter and smarter and advertisers will need to find new and creative ways to reach them. That’s a fairly broad set of statements, but in general we’re in a time right now where the medium’s that ads are displayed on are evolving much faster than the targeting and capabilities of the ads being displayed.

Check out Todd’s blog and follow him on Twitter here. If you’re an advertiser looking to advertise in the creative/tech space (or a publisher looking to sell ad space), check out https://buysellads.com.

You can follow me on Twitter here to ensure you don’t miss any of the other interviews in the series.

Filed under Interview BuySellAds Todd Garland Entrepreneur Business

An interview with Dave Caolo, news editor and blogger at TUAW

I first met Dave when I was working at Marketcircle. We met over email discussing one of their products (I can’t remember if it was Daylite or Billings), and have been in touch ever since. Dave’s a news editor and blogger at TUAW, an Apple blog that’s been around since before the first iPhone.

I  the pleasure of meeting Dave in real life as well (something that can be rare these days!), back at a Macworld Expo a few years ago, and he’s just as nice in person as he is online. 

Dave and I kept in touch since I left Marketcircle to start Snowman. He’s always been extremely helpful beta testing both Marketcircle’s and my own products, and helping us get the word out when we’ve launched.

I actually interviewed Dave a few years ago – so it only made sense to interview him again, seeing as though so much changes in this industry in a few years.

Tell us a bit about yourself. Where have you traveled to? What kind of music do you listen to? What are your hobbies?

Travel is my life’s passion. There’s nothing I like more than experiencing a culture that’s unlike my own. So far I’ve been up and own Italy’s west coast (that was my honeymoon), to Paris, Switzerland, Canada and up and down the US East Coast.

My best experience was getting hopelessly lost with my wife in Venice. The streets are so narrow and the buildings so tall, that we got disoriented and wandered around for well over an hour. Eventually we stumbled upon a neighborhood block party. No one there spoke English and we did’t speak any Italian, but they convinced us to stay and we did. The next few hours were spent eating, drinking and laughing as we communicated as best we could with gestures and guide books. It was fantastic.

My musical tastes have changed significantly since I was young. I’ve been playing drums since the 4th grade, and was classically trained on snare drum. Of course, I had a rock and roll garage band as a teenager, and studied jazz at Berklee College of Music. While living in Boston, I got way into industrial and alternative music. Today I listen to instrumental indie, like Explosions in the Sky. I call it “wuss rock.”

What was your first job growing up?

My very first job was delivering newspapers. I had a route that stretched five blocks. The newspaper truck would drop off shrink-wrapped bundles of newspapers that I put into a large canvas bag and delivered door-to-door. Wednesdays were the worst, as the newspapers were huge; stuffed with ads and often bound with a plastic strap in addition to the shrink-wrap. I carried a box cutter on Wednesdays so I could open the bundles.

I got very good at folding the papers into a cylinder that would stay together when tossed onto a porch. Some kids used rubber bands to bind the papers but that was cheating. I had some customers who wanted delivery on the second floor and one way up on the third. I could toss it up there like a pro. Now I’m wondering if I could still do it.

I loved that job, though. It took me about 90 minutes to deliver all the papers. I’d listen to music on my Walkman and enjoy being off on my own. I had that job for four years, and I believe it had a lasting impression on me. I still prefer solitary work that can be done while listening to music.

At the top of the last block was a little corner store. Two of my friends, Louie and Michelle, had routes of their own on neighboring streets. Every day we’d meet at that store, sit in the window, eat candy and goof around before finishing up the last few houses. There was a big, old-fashioned radiator in front of the store window, and the owner put a board on it in the winter so we could sit there and warm up while we ate our candy. That’s a great memory. Nick, the store owner, was always very kind to us kids (I was 12 at the time) and would tell us funny stories and get yelled at by his wife.

How long have you been into writing? Was it something you always enjoyed doing in school?

The funny thing is, when in school I had no interest in school. I think it was in junior high that I realized I could not study at all and still score B’s and the occasional A. So, I didn’t study and muddled my way through with a B average. Today I wish I had a time machine so I could tell my 9th-grade self not to do that.

I never considered writing as a career when I was a teenager. Back then, music was my life. When I wasn’t playing my drums I was either listening to music or going to a concert. By the time I was fifteen, I was certain that I’d be a professional drummer. Soon enough I graduated from high school, went to Berklee College of Music in Boston and washed out after three semesters.

It’s no hyperbole to say that the time I spent in Boston was life-changing. That year-and-a-half, more than anything, influenced who I am today. Even though I returned to Pennsylvania to finish my collegiate career (I received a BS in psychology from Marywood University in 1994), it was not as the same person. I’ll forever be grateful for that experience.

Today, I don’t consider myself a writer. Yes, I earn a living with words, but I have no formal training in writing, nor do I have a related degree. The greatest, most accomplished cook in the world is a cook. Until he or she gets a culinary degree, that person isn’t a chef. S/he hasn’t earned it. In the same way, I’m not a writer. I don’t have the credentials to assume that title.

Tell us about about TUAW. How did you get started there, and what’s your role in the company?

I started as a reader. At the time, I was working as an IT director at a Mac-friendly residential school here in Massachusetts. One day they published a call for writers. I applied and got the gig. It was C.K. Sample who hired me. This was back in the Weblogs, Inc. days.

Eventually Jason Calacanis sold Weblogs to AOL. I started to write more regularly and eventually got offered the position I have now. I’m the news editor and my main job is to find and assign news stories to our writers, proof them and publish them. There’s a lot more to it, but that’s the basics. I also make snarky comments in IRC all day.

What are some of the most memorable stories you’ve worked on as a writer over the years?

I’ll never forget when Steve Jobs announced his resignation. I was at AOL headquarters in New York City, working in the newsroom. It was in the evening and fairly crowded. A few writers from some of our sister sites were there, too. We were all working at our machines when someone shouted (literally shouted), “Steve Jobs just resigned from Apple!” The room erupted into an absolute frenzy as we were rushing to confirm the story, contact sources, get the story written and published to our respective sites.

We also knew that something significant had happened. Steve had been ill, of course, and this was his second – and ultimately, last – leave of absence. The excitement of such a big, breaking story was immediately stained with the gravity of what was likely happening: Steve’s health had gotten bad. It was an odd day. I was excited but very sad. I’ll never forget it.

What inspired you to start 52 Tiger? What did you learn from writing there compared with writing for an established brand like TUAW? Can you explain your decision to eventually close the doors?

Oh, boy. 52 Tiger was born out of my desire to be my own man. I wanted a site that I had complete control of and that would generate my entire income. Having full creative control had its benefits, but also drawbacks.

The most vicious lesson I learned is that I have the business acumen of a turnip. Landing sponsors and arranging deals that would keep the site lucrative and afloat was very difficult. I could have used a business manager, but wasn’t in the position to hire one.

A person who works for him or herself must wear every hat. You’re the worker, the HR department, the finance department, the creative department and so on. I was good at nearly half of those things, which wasn’t enough.

It pained me to kill that site, but that’s life, right? You try something and, if it fails, say, “Well, that was that. What’s next?”

How did you decide to write about Apple? Have you ever been tempted to write about another major technology company?

Apple computers are all I’ve ever used. My high school didn’t have a computer lab to speak of and when I got to college, Macs were everywhere. My first job out of school was with a residential school that used Macs exclusively. So those are the machines I know.

I stared reading TUAW many years ago, and when they put out a call for bloggers, I applied. Now, here I am. I guess I could write about Google or Microsoft, but my heart wouldn’t be in it. I love Apple’s products and that makes the job easy.

What do you see happening with Apple in the next 5 years? Is there anything specific that you’re hoping to see from them?

It’s so hard to say. The iPod’s days are numbered. I really want to be surprised. The iPhone was so very exciting when it debuted. A big shake-up like that would be exciting, but I can’t image which industry is next.

What do you think about Apple’s competition?

It’s producing fantastic products. For example, I have a Google Chromecast and I love it. We’ve got a game room set up for the kids with bean bag chairs, the old Wii and room for board games. There’s a small TV in there that’s just a display for the Wii, really. It’s not connected to a cable box or anything.

Last Christmas I got a Best Buy gift certificate and used it to buy a Chromecast, which I connected to that TV. I absolutely love it. Now I use it to watch TV and movies from Netflix and Hulu all the time, with my iPhone as the remote. When we play board games, in that room, we use the Chromcast to stream music from Pandora. For thirty bucks it’s an absolute steal.

Can you explain your writing process? Do you have an ongoing list of ideas you’d like to write about, or do you usually tackle projects one at a time?

Large writing projects start with a mind map. I’ve got to thank David Sparks for that, as I hadn’t heard of that technique before I read about it on Mac Sparky. I used MindNode Pro. Once I’ve brainstormed ideas, I write about each “branch” in the mind map in turn. Eventually I stitch the whole thing together into a completed article. Then I let it sit for a day or two and make a second pass at it, rewriting as I go. At last, it’s off to editorial, where the ever-present typos are removed.

As far as topics, it depends. We have an editorial calendar at work that everyone adheres to. So that’s all pre-determined. If I’m writing something for my personal site, well, that can be whatever grabs my fancy.

What have you failed at in life, and how have you learned from the experience?

You don’t have enough room to accommodate a list of my failures. Dropping out of Berklee was the worst. I also lost a job in 2009 and that was devastating. I spent that whole year scraping by any gig I could get and feeling like a failure as a father, husband and a man. It was awful. I am not a fan of 2009.

I guess I learned that perseverance is key. We’re all going to fail at things. What’s important is your reaction to failure. If you can get to a point where you say, “OK, what’s next?”, you’re good. But that’s not easy.

What’s the hardest part about your job?

The go-go-go nature of it. Everything happens right away and, covering news, you’ve got to be alert to what’s happening and getting it out the door in a timely manner while providing the readers something worth reading. Sometimes I hear the voice of the boss in the Twilight Zone episode, A Stop At Willoughby: “It’s a push, push, push, business! All the way, all the time, right on down the line!”

Are there any parts of your job that you find tedious and boring? What’s your favourite part about your job?

There’s no time for boring! I love writing a post that the readers find useful. That’s my goal. People come to the site to see if an app is worth buying, or to learn how to do something. When we do those things successfully, I feel great.

What’s your hardware/software setup look like? What are some of your favourite iOS apps?

I use an older MacBook Pro that’s connected to a big ’ol ViewSonic. As I said, I use MindNode Pro for mind mapping. Most of my articles (like this one) are written in Byword. I use Markdown because it’s nice and easy. Editing happens in Byword, too.

As for iOS apps, I love Fantastical and that Google app with Google Now. It’s so useful. Apple’s Weather app is really nice, too. I’ve been falling asleep to Ambiance every night for years. Most recently I’ve fallen in love with Beats Music. In fact, I went all in with a paid account. I even ditched Rdio. I’m working on a post about that now.

What’s a typical day look like for Dave Caolo?

Oh, geez. Well, I’m up around 6:00 AM to the kids out the door. After dropping them off, I’m back at my desk around 8:00 and work until 2:00. Then it’s off to the bus stop to retrieve the kids.

I spend 2:00 - 8:00 with the family. For a long time, I struggled with this. I’d either work and feel badly about neglecting my family, or hang out with the kids and feel resentful that I wasn’t working. Today I’ve made peace with the fact that those seven hours are for my family and nothing else. It’s a lot better that way.

How has your family been an influence in your career, if at all?

Hm. Well, when I lost that job in ’09 and I told my wife I’d like to work from home, she was right behind that decision. I appreciate that support tremendously.

When you’re not writing, what are you reading? Do you prefer reading print, or do you use an iPad or another reader device to do most of your reading?

I don’t like reading electronic books at all. I must apologize to all my friends who publish electronic books! This might be my “old man sticking point.” We all have one eventually. I have many books and I hope my kids will take them someday. I can’t imagine giving them a bunch of epub files when I die.

If you could spend a few hours over dinner with anyone in the world, who would it be and why?

I know I’m supposed to say something like “Jesus” or “Albert Einstein” or something, but I’m going to go with my maternal grandfather. He was such a smart, sensitive and insightful man, and I didn’t tap into that when I was an idiot in my 20’s. As a 43-year-old, I’d appreciate a conversation with him.

Lastly, if you won the lottery (say $20 million), what would you do with the money (besides the typical stuff)?

Aside from the typical stuff like eliminating debt and giving some to my parents and sisters, I’d take a year off and travel the world. I’d hire a photographer to come with me and journal the whole 12-month journey. It’d be awesome. I’ve fantasized about that scenario many, many times.

You can find Dave writing at The Unofficial Apple Weblog (TUAW), and on Twitter at @davidcaolo. He also writes a personal blog, which can be read here.

You can follow me on Twitter here to ensure you don’t miss any of the other interviews in the series.

Filed under Interview Blogger Writer Apple TUAW Dave Caolo

An Interview with Jason Zimdars, designer at Basecamp

Jason Zimdars is a designer at Basecamp (which is a great product, especially when you work with others remotely). 

I met Jason after sending in some UI feedback about Basecamp’s new email UI (last summer). After chatting back and forth a bit, he even ended up beta joining the Checkmark 2 beta testing team. When I decided to start interviewing people, Jason was at the top of my list.

Read on for a little insight into the mind of a great designer – one responsible for working on one of the most popular project management tools in the world.

Tell us a bit about yourself. What kind of music do you listen to? What are your hobbies?

I’m a husband, dad, and software designer at Basecamp (formerly 37signals), based in Chicago. I work from my home office in central Oklahoma surrounded by my family, dogs, books and toys. I listen to music constantly while I work, mostly indie rock/folk bands that have a high probability that all of its members are sporting beards. I’m also really into movie scores and an Italian composer named Ludovico Einaudi. I dabble with some fine arts type stuff occasionally in my spare time (drawing, painting, ceramics), but more recently I spend my spare time looking for ways to decompress. Tinkering in my garden or playing video games are especially effective ways to turn off my brain for a bit. 

What was your first job growing up? When did you decide to get into design?

Growing up I was the kid who could draw so “commercial art”, as we called it, was how you made a living if you were an artist because artists can’t make a living…or so went the advice I was given at the time. I did things like t-shirt designs and cartoons for the school newspaper but I never really worked in design until the last few years of college. That’s when I did my first internship and got a full time design gig just before graduation. Up until then I had mostly worked the typical retail/service jobs that everyone has starting out.

Do you have any formal design training, or are you mostly self-taught?

I went to art school at a large 4 year university, majoring in Visual Communications. I had no idea that I made a good choice until years later but here I was at The University of Oklahoma where they inexplicably had this great design program. The faculty had ties into Carnegie Mellon, the University of Cincinnati and professionals like Paul Rand and Malcolm Greer. And they were old school. The program was in the Bauhaus model where students from every discipline took a year of foundations art courses. Drawing, painting, mixing colors, photography, criticism, drawing type, art history. The program was broad and flexible enough that I was able to explore design for the web, too. I was really fortunate to stumble into such a great education.

Do you have any role models, or people that you really looked up to when you started working as a designer?

In college I read and re-read everything I could find by Paul Rand. I admired the fun in his work and his pure philosophy about design, his stance against the purely decorative. As I moved into my professional career I looked up to the people pushing the web forward at the time: David Segal, Jeffrey Zeldman, Jason Fried, Joshua Davis, Amy Franceschini. The web was where I wanted to work so I absorbed everything I could looking for that secret sauce. 

Can you tell us about your work at Basecamp? What kind of stuff do you get to work on there?

Earlier this year we made a big change to the company. We retired the name 37signals, began to step away from our other products and went all in becoming “Basecamp” the company, makers of the product by the same name. This probably seemed like a big change from the outside but behind the scenes we had been focusing almost all our attention on just Basecamp for a long time and I may have been doing so longer than anyone. That’s why about a year ago I took over product direction for Basecamp. For the last few years I’ve been working on mostly big projects. I spent over a year (starting with the initial proof-of-concept) working on the new version of Basecamp that launched in 2012 and have been all-in on the product ever since continuing on to the mobile web, iPhone, and Android versions. Big projects and app launches are the exception, though. Typically my work is about helping our development teams design and build new features and improvements where my involvement can be any of these: design, development, review, direction.

How many other designers do you work with on a regular basis? How do you guys collaborate when working on a new project?

Roles at Basecamp are a little loose but we have two designers who lean more towards graphic design and focus primarily on our marketing websites and campaigns, three others are dedicated product designers who work directly on the actual product,  and finally three more, myself included, who are designers but also have a managerial role. Our designers are a tight-knit group but we don’t usually work on projects together. We like projects that can be done with a tight scope and a small team consisting of a designer and one or two programmers. I’m often involved in a mix of concurrent projects, maybe one where I’m the designer and a couple more where I’m more of a project manager setting high level goals, reviewing the work and helping teams get through roadblocks. 

What’s your design process like? Where do you start, how do you iterate, and how do you make it all come together?

37signals’ book, “Getting Real”, is still relevant to the way we work even today. Our process is heavily tuned to make real things that can be clicked (or tapped) in the app, in a web browser as early as possible in the process. Our designers are all very skilled with HTML, CSS, Javascript and Ruby on Rails so that they can work directly in the app code along with the programmers. We typically move quickly from loose concept sketches to prototypes or even real working code in the browser. The closer the design is to the real thing in actual context the more accurate it can be evaluated. It makes for super-tight feedback loops and fast iterations from there. We skip formal wireframes and pixel-perfect Photoshop comps in favor of iterating. We may do hundreds of tiny iterations on a feature before discovering the final design starting at the very epicentre of the design. Starting with the most core part of the feature before moving on to the next piece. Take a typical sign-in screen, for example. The most important part of that is the username field, the password field, and the button that sends them. We’ll get that working before thinking about additional concerns like sign-out, forgot password, error states, etc. When you’re working with wireframes it’s tempting to try to figure everything all out at once and think you nailed it only to be surprised the first time you see it in the browser. Taking this approach means we are getting the most important things done right early in the project so it’s easy to make decisions later about what to leave out if time runs out and secondary features naturally take a back seat (as they should) to the primary goal of the design.

Where have you traveled to? Do you ever find inspiration in your travels that translates into your work? Is any of your work inspired by other offline influences – whether it be nature, film, or music?

Most of my travels have been inside the US to the kinds of places you go on vacation with your family, though my wife and I did visit Rome a couple of years ago. It was our first trip to Europe and the immersive history of the place was personally inspiring. Standing in the shadow of massive, beautiful architecture that was built hundreds of years ago you can’t help but wonder if our modern cultures are making anything so significant. That reminded me that it’s important to making things that are useful. It’s a great joy to hear from customers how Basecamp has made their job so much easier or their team more effective. I feel like I can take some pride knowing that the software we make helps people plan cities, build buildings, create products, organize events, and make music, games and movies.

What do you see happening with technology in the next 5 years that’ll change the way people use your products? Is there anything you’re hoping for, either as a designer or a user?

Five years? In this industry that can feel simultaneously like a few seconds or an eternity. Seconds because everything is moving so fast that it feels like nothing is static; eternity because so much changes in 5 years that it’s impossible to predict and difficult to imagine. The shifts from desktop to mobile, and email to messaging, are the most relevant to us today but they are so quickly moving into the mainstream to be almost past tense. If I had to bet I’d say that the next shift is going to be in the way that products like Basecamp move from being tools you just use to tools that do things for you. We’re seeing this already in phones with things like Google Now that push relevant information to you when it’s contextually appropriate. Why search when the information you need is just there when you need it? Why check Basecamp to see what James is working on when Basecamp can let you know when he’s done getting things done or appears to be stuck? The challenge for us will be continuing to evolve with the changing expectations of our customers. 

What’s a typical day look like for you? Do you find you need to have a regular routine to get the most accomplished in a day or are you a fly by the seat of your pants type of worker?

I wake up most days early enough to see our kids before they leave for school. I have some breakfast while catching up on email, Basecamp and tech news on my iPad. I try to clear the backlog so I’m ready to start the first task of the day when I switch over to my computer. I’m pretty habitual and get up at the same time most days, even if it’s the weekend and I’m not working so it’s rare that I’m not working by 8am. Like most of us at Basecamp, I don’t live in Chicago so I work remotely — almost always from my home office. I like that it’s quiet and that I have complete control over my environment. It’s great that I’m home when my kids leave for school and when they return in the afternoon and most days I’m able to have lunch with my wife. I typically work until the family needs me whether that means dinner is ready or the dog is tugging at the back of my leg to play ball anywhere between 5pm – 7pm. I work a solid day with big blocks of time for focus so when I check out I try to shut down completely – no checking email or Basecamp. 

What’s the hardest part about your job?

Basecamp is a small company — intentionally small, it’s part of our culture. That means it’s always a challenge to be working on the right things, the most important things, and the things that make the biggest impact for the effort. With big teams and limitless resources it’s so easy to drift away from the problem and make all kinds of features that over-shoot the problem or just don’t deliver enough value. Often you can deliver 80% of the value of a feature to 80% of your customers in the first 20% of the effort. The hardest work, with the lowest payoff is trying to nail that last 20%. I’m generalizing but we’re always looking for that sweet spot where we can get the most impact for the resources spent. We have a word for that here, we challenge each other to find a *judo* solution (see http://signalvnoise.com/posts/312-lingo-judo).

How has your family influenced your career, if at all?

Other than being endlessly patient and supportive, my family keeps me in check. When you love your work, especially the kind of work that requires complete focus, it’s easy to just work all the time. Time gets away when you’re chewing on hard problems — there’s always just one more idea to try or one more to-do to complete. Having a family that matters more than work means that I have to work reasonable hours and sometimes that means a hard stop. It’s healthy and the constraints make me better. When your time is limited, when you absolutely have to be at the soccer field by 6pm, it’s easy to focus and work on only what’s important.

What’s your hardware/software setup look like? What kind of software do you use to get your work done?

It’s pretty simple. I have a 13” Macbook Pro, a 24” LED Cinema display and a standing desk. I’ve been doing a lot of work on mobile apps recently so at any given time there are an array of phones and tablets within reach. Almost all my work is front-end web development and design so I use Sublime Text 2 all day long with occasional dips into Xcode and Photoshop. Aside from that there are a couple of scratch-pad type apps I always have open when I’m working: iA Writer for sketching with words and Soulver for quick calculations. I use Paper by 53 and Procreate for quick visual thinking on the iPad, too.  

If you were to picture yourself in a career outside of the design world, what would it be?

I’ve always admired these guys that run fish hatcheries. They’re usually beautiful, quiet places. Sun-dappled running water, fresh air, the movement of schooling fish. No stress, no notifications just peaceful, solitary work in nature. 

If you could spend a few hours over dinner with anyone in the world, who would it be and why?

I’d love to sit down with Pendleton Ward. Adventure Time is seriously great and the team putting that out is absolutely killing it. I’d love to hear about how they generate ideas and how they’ve managed to keep the quality and creativity so high for such a long time. It’s common to root for the underdog but honestly I’m a bigger fan of excellence. Many people turn off a football game when the score is lop-sided but there’s nothing I’d rather watch than a team executing at a high level. Michael Jordan in his prime, Apple under Steve Jobs, shows like Adventure Time that get better ever episode… these are historic runs by people doing absolutely the best work in the world. How can you not be a fan of that?

Be sure to follow Jason on Twitter and read his posts over at Signal vs. Noise. And if you’re looking for a great project management tool, be sure to give Basecamp a try – it’s free for the first 60 days.

You can follow me on Twitter here to ensure you don’t miss any of the other interviews in the series.

Filed under Interview Designer Basecamp 37signals Jason Zimdars

Announcing my Interview Book (sort of)

About a year ago I started working on a fun side project – an interview book.

I decided it’d be really neat to interview a bunch of interesting people, and package it all together in a nice book. These people included developers, designers, business owners, writers, marketers, videographers, photographers, game-makers – pretty much anyone in the tech or creative space. 

Unfortunately, I didn’t foresee how much work it’d be, or how busy I’d get with other things. I just can’t realistically create what I had set out to create, and so today, I’m announcing that I’ll be publishing these interviews here on my blog (much like I used to do).

So if you’re interested in reading my interviews with some really cool people (fourteen in total), you should follow me on Twitter and stay tuned in the coming weeks.

Check out the first trailer for Alto’s Adventure, an upcoming iOS game we’ve been working on at Snowman.

Checkmark 2.1 is here and it’s on sale

Yesterday we released Checkmark 2.1 in the App Store, adding Snoozing, improved Recurring Reminders, and more. You can read more about the release on the Snowman blog here.

To celebrate the launch, Checkmark 2 is on sale for 70% off for a limited time only.

Download Checkmark 2 on the App Store

I was thrilled when I saw that Apple had featured us under Best New Apps, Locally Developed, and Made In Canada. Thanks Apple!


Announcing Alto’s Adventure

Last month we announced Alto’s Adventure, the biggest project we’ve ever worked on here at Snowman. We’ve been working on Alto since January 2013 and it’s great to finally break the silence.

Because I’ve been so busy I forgot to post about it on my personal blog. I’m mostly writing this entry for myself – so that I can look back on it in the future.

Cult of Mac posted an exclusive look at the game earlier today. It’s worth checking out, as there’s some never-before-seen artwork in there ;)

I can’t say anything more about the game just yet, but what I can say is that this is the best thing I’ve ever worked on. I’ve never been so enthralled with something I’ve been working on, and it feels great. It keeps me up at night – but it in a good way.

You can follow along the adventure (pun intended) by following us here:

Twitter: @altosadventure
Instagram: @altosadventure
Facebook: facebook.com/altosadventure


Checkmark 2 for iPhone is here

In case you missed it the other day, we launched Checkmark 2 in the App Store this past Tuesday. And we’re having a launch sale.

For a limited time you can download Checkmark 2 for $2.99 – 50% off the regular price.

But hurry, the price is going up to $5.99 soon.

Checkmark 2 features an all-new design and tons of new features to make you more productive than ever.

You can learn more about Checkmark 2 and all of the new features here.

Filed under Snowman Checkmark Reminders App Store iOS Tasks To-do

Announcing Checkmark 2 for iPhone


Ever since Apple showed off iOS 7 at WWDC last summer we’ve been hard at work building a brand new version of Checkmark.

Check out our teaser page here: http://builtbysnowman.com/checkmark/

We had already planned to add a bunch of new features, but with the introduction of iOS 7, we decided to go back to the drawing board and start over.

We wanted to make sure Checkmark felt at home on iOS 7, but at the same time, we didn’t want to sacrifice any of the simplicity and usability speed that we spent so much time developing for the first version. 

Checkmark 2 features an all-new design, with a sidebar-style navigation system, a brand new compose view, lots of fun little animations, and some brand new notification sound options.

But that’s just the aesthetics. 

We’ve kept the task creation workflow entirely intact from version 1, while adding a ton of handy new features and a great new UI along the way.

I want to take a second to highlight some of the major new features, starting with the biggest one – Lists.


We’ve added a third major component alongside When and Where, and we’re calling that feature Lists. 

Lists are great for managing projects, thanks to our powerful Headers feature. Headers let you categorize your list, so that it’s not just a long and daunting pile of items. 

In this screenshot, you can see how an architect might use the Headers feature to organize a to-do list for a New York building project.


All of the usual drag and drop to prioritize works here, even with entire Header sections.

You can quickly create new tasks for a particular Header using the + button to the right of it. Use Return on your keyboard to continuously enter tasks at lightning speeds!

When you’re creating simpler lists, such as a list of movies you want to see, you don’t have to use Headers – they stay out of the way. 

So lists are great for projects, but they’re also awesome for everyday use.


Location Groups let you add multiple locations to one place, e.g. add 3 different supermarkets to one location group called “Groceries”.

Setup one reminder and be notified when you’re at any of the locations in the group. Create location groups the same way you create app folders on iOS – just drag and drop one icon on top of another.


Another big focus we had when designing Checkmark 2 was figuring out a better way for users to reschedule reminders when they’ve gone off but are unable to act on them.

With Checkmark 2, when a reminder has gone off (or before or after), you can push it ahead by few minutes, hours, or days with just one tap. Now it’s easy to reschedule things when plans change.


Now in Checkmark 2 you can create daily, weekly, bi-weekly, monthly, and custom repeat reminders – you pick the days of the week. You can, for example, create a reminder for every Tuesday, Thursday, and Sunday. 


One thing that was missing in Checkmark 1 was the ability to assign a date to a location-based reminder. We’ve added that in Checkmark 2.

You can still add timers to location-based reminders, even with a specific date.


We’ve added iCloud sync so that your important data is always backed up in the cloud.

(Note: Checkmark is still an iPhone-only app at the moment).

There are a bunch of other new features, but you’ll have to wait until we launch to find out.

Speaking of launching – we’re just putting the finishing touches on the app, but we expect to release it in March if everything goes well.

Make sure you sign up for our email list so that we can let you know exactly when we’re launching – so that you can take advantage of our special introductory pricing. And of course we’ll be back with another funny video ad…it’s F’ntastik!

(This post was reposted from the Snowman blog)

Filed under Snowman Checkmark Reminders App Store iOS Tasks To-do

The end of the Facebook era

An interesting post by Chrys Bader about Facebook and how it’s evolved and where it’s heading. I’m not sure I agree with eveyrthing Chrys says but he definitely raises a lot of good points.

I’ve definitely noticed a trend amongst my own circle of friends. Facebook’s great when you’re young and in college, looking to meet as many people as possible and connect, party, and have fun. But once you’re past that point in your life, when you’re settling down, starting a family – that sort of thing, it becomes less and less of an interesting place to spend your time.

Just a few years ago my newsfeed was full of parties, vacation photos, and funny links – now it’s shifting towards baby photos and people ranting about their jobs. Needless to say, it’s not as interesting as it used to be.

When I compare Facebook to other social networks with family members not in the tech space, I tend to label it as “everyone you’ve met since kindergarten”. When I talk about Twitter on the other hand, it’s a “place to connect with people that have the same interests as you”. Flickr is “a great place to share and store important photos in high resolution”, and 500px is “a great place for photography”. 

Social networks are whatever we want them to be – we decide who to follow, who to friend, and what to like. But there are definitely trends and social shifts and nothing can last forever. Or can it?

Rise Alarm Clock for iOS 7

I’ve been beta testing the new version of Rise for a few weeks and am really enjoying it. Keep an eye out for the update – it’s quite nice.

In the meantime, check out this charming little video they put together showing off some of the new features.

Behind the scenes: selling your own iPhone case

Ever wondered what it might be like to sell your own physical product? Jon Wheatley shares the results of his yearlong experiment selling his own iPhone case called Peel.

I wanted a case that had a very low profile and also one that was branding free. After a lot of back and forth with a few different factories, I managed to find one that could do what I wanted. I placed an order with them then signed up to Shopify. I had a working store in about half an hour. I then tweeted about it and the orders started to trickle in.

Some good insight into how much work shipping your own product is, and the importance of good packaging design.

This was also very nice to see:

Returns aren’t worth the effort

On the rare occasion that a case arrives damaged or defective, we either send people a full refund or a replacement. Dealing with returns just isn’t worth the effort for us and it’s also a pretty horrible experience for the customer. People are nearly always pleasantly surprised that we don’t require them to return the item before getting a replacement or refund. That makes them happy. We chalk this up as a marketing expense and move on.

Via Oliver Cameron

My favourite tiny tweak in iOS 6

Here’s a minor iOS 6 tweak that was just pointed out to me:

When you’re choosing a wallpaper, images are automatically resized to fit the full display – since I assume most people don’t like using only part of an image as a wallpaper (I certainly don’t).

Here’s what it would have previously looked like (in iOS 5) if you chose an landscape image to use as a wallpaper on your iPhone:

Instead, iOS automatically fills the screen with your image, like this:

You can of course shrink the image down if you like, but it’s nice not to have to play around pinching in and out if you just want your image to fill the display vertically.

Hat tip to @amelia_rosebell for pointing this out!

Filed under iOS 6 Apple iOS iPhone Wallpaper Photos