Smile Turns 15: An Interview with Greg Scown 

Today marks the 15th anniversary of Smile, makers of tools like PDFpen and TextExpander.

To mark the occasion, I spoke with co-founder Greg Scown about the company’s history, present and future.


1. Tell me a little bit about how Smile got started.

My co-founder Philip introduced himself to me at Macworld San Francisco 2003, where I was exhibiting PageSender, my faxing software. We hit it off, I had an idea for a product, he had the artistic know how, and together we produced DiscLabel, our disc labeling app. We shipped DiscLabel 1.0 at the last Macworld New York in July 2003. DiscLabel won best of show, which was very exciting. I was Smile Software. Philip was OnMyMac. Together, we became SmileOnMyMac.

2. The Wayback Machine has an early version of the homepage (which looks amazing, by the way), but the page shows just two apps: PageSender and HTMLColorPickerX. Were they the first two products? What ended up happening with those apps?

We retired PageSender in 2010, eight years after it first shipped. Faxing was on the decline. Apple’s laptops hadn’t shipped with internal modems for years. We retired HTMLColorPicker X in March 2005. It became obsolete when OS X added an HTML color picker.

Let’s call these evidence of the “change or die” mantra of software development.

3. Back in 2006, Smile acquired what would become TextExpander. Today, that app is one reason Smile is well known to Mac and iOS users, but how did it come into the fold?

We acquired Textpander from Peter Maurer, now of Many Tricks. Smile shipped TextExpander 1.3 on May 23, 2006, and the post you cite does a good job telling the story. It’s a case of, ‘I really need this app for my life, other people must also’ combined with ‘If I make it, I can ensure it will always work for me.’

As for iOS, at WWDC in 2009, Apple announced support for cut/copy/paste in iOS 3. At our Smile WWDC party, Dave and Roustem from AgileBits, makers of 1Password, told us that if we did not produce TextExpander for iPhone, they would.

It wasn’t entirely clear whether or not they were joking, so we built TextExpander for iPhone, which debuted on August 26, 2009. Initially, it could only expand snippets in the Notes section of the TextExpander app. The real game-changer on iOS was when Apple introduced custom keyboards in iOS 8. Now, we’re able to make basic TextExpander expansion available in any app.

4. PDFpen is another well-known app that y’all build. How did it come about?

If the era of fax and PageSender is over, what’s next? We figured PDFs sent via email would replace faxing. Looking at the PDF editor options showed a huge gap between Apple’s Preview, which was read-only at that time, and Adobe Acrobat, which was far too much for an everyday user. We figured we could fit somewhere between ‘free and very limited’ and ‘crazy expensive and can do everything, only a bit of which you need.’

With PDFpen we started by helping users add text and images to PDFs, such that they could sign and return forms and contracts. Then, we built out the feature set, always focused on making it easy for everyday users to view and edit PDFs.

That brings us to this year, when we launched PDFpen 10. Version 10 can do way more than 1.0, but still focuses on making it easy to do the basics.

5. Speaking of PDFpen, there’s another 2006 blog post that caught my eye. In November of that year, Philip wrote about getting the app into Apple retail stores. How was that process? Was it a successful venture?

The retail boxes were not a great financial success. We were relatively late to a declining game. They did serve as good advertising, sitting prominently on the shelves in the Apple Stores. They also helped me convince my grandfather that what I was doing was real.1 I think prior to the retail boxes, he was a bit dubious, not really ‘getting’ the whole Internet thing and downloadable software.

6. What was the idea behind changing the name of the company from SmileOnMyMac to Smile back in 2010?

We had started shipping TextExpander on iOS, and we were planning PDFpen for iOS, so we weren’t Mac-only anymore. We decided it would make more sense to be Smile than to be SmileOnMyMac. This has proved handy now that we also ship TextExpander for Windows. Plus, with the way TextExpander works now, we can expand to even more platforms. It’s good to have the company name match both our reality and aspirations.

7. Fifteen years is a long time, but it is still firmly in the Mac OS X era. How has the Mac and the ecosystem around it changed since then?

macOS has become quite mature and reliable. It wasn’t that long ago that it took a few minutes to restart a Mac, and one needed to do that regularly. I haven’t restarted my Mac in over 19 days, and that doesn’t surprise me. I haven’t needed disk recovery tools in years. (Touches wood.)

There’s the whole “cloud”-ification of everything. Back in the day, you had one computer. I think you can look to Apple’s introduction of the iPhone as the milestone that opened people’s eyes to the possibilities of being multi-device people in a multi-device world. Once you have two devices, you’ll want your stuff on both, and a whole online/sync/SaaS/cloud world has grown into that space now. It’s been exciting to see the Mac become the platform of choice for web app / SaaS development.

8. When Smile started, the iOS App Store was still years in the future, but today, you make apps for both the Mac and iOS devices. How has the addition of the iPhone and iPad changed the company and its products?

They’ve certainly meant more for us to do. It’s not enough to have a macOS app, and certainly not if it ought to have an iOS companion. We’re fortunate to have been grounded in the macOS business, as the iOS business seems much more difficult. We have immense respect for the Omni Group and how they manage to do both platforms extremely well.

Likewise, we understand that not everyone’s experiences with the iOS App Store has been positive. It’s a tough place to make one’s sole business, but it’s an important platform for our customers.

9. Recently, TextExpander evolved from a Mac and iOS app to an entire service, complete with cloud syncing, a Windows version and a paid subscription. What went into wanting to make that change? How has it worked out?

Since around the release of TextExpander 3, sharing had been prominent on the long-term roadmap. After all, we’ve become a multi-device world. We believed that TextExpander had the potential to grow well beyond a single user utility. Teams using TextExpander, similar to our team and how we use TextExpander, were asking for easier ways to collaborate in TextExpander. It took us a while to get there, from TextExpander 3 to TextExpander 6 to be exact.

So we launched what we saw as a cool shiny new thing people would love. And what we found was change is hard. We fumbled a bit on our pricing at launch. We hadn’t anticipated the number of folks who didn’t want TextExpander to be more than a single user utility, or the vehemence with which they would express that to us.

In fact, some of the users who left us have told us they have come back, which validates that we do offer something special in TextExpander and that they do want it. Just, change is hard. And maybe triple think how you present change to your customers.

Fast forward to today. We serve single users, small teams, medium teams, even large organizations. We help users and teams understand how and where they’re saving time with TextExpander. At Smile, we use TextExpander to improve our support, to systematize monthly tasks, and to avoid costly mistakes. Our customers are doing things with TextExpander we had only dreamed of. We feel like we’re just getting started.

10. What can Smile customers expect for the next 15 years?

Flying cars. Isn’t that the standard answer for what one can expect a decade or more in the future? Seriously, though, I think we could have predicted 15 years ago that fax software would diminish in importance, but it’s much more difficult to determine exactly where the next 15 years will take us. I believe Smile customers can expect a company that cares deeply about them, provides excellent service and support, and builds great products they use each and every day. The specifics we’ll have to leave to the crystal ball.


  1. Editor’s Note: I fully understand this struggle.