Smile Celebrates 15 Years

15 Years and Still Smiling!

It’s 2003, two men walk into a bar. They greet each other for the first time and have a conversation. Fast forward to July, at Macworld a new company called SmileOnMyMac launches their very first product.

15 years later and here we are today. Greg Scown and Philip Goward have built SmileOnMyMac from a team of 2 to a team of 20+ staff, contractors, and consultants. Together they’ve launched 6+ products across 3+ platforms (depending on how you count (¯\_(ツ)_/¯).

  • 15 years
  • 6+ products
  • 3+ device platforms
  • 12 Macworlds with 8 awards
  • 50+ MUGs
  • 3 MacMania Cruises

We’ll be taking the week to look back at all the products which make up Smile’s catalog, as well as those which have been retired (faxing just isn’t what it used to be).


It’s been a long and eventful ride, one that wouldn’t have been possible without the support of our customers and friends in the Mac community.

So celebrate with us! Send us a Self Addressed Stamped Envelope and we’ll send you birthday stickers 🎉.

  1. Get 2 envelopes
  2. Put stamps on both
  3. Address one envelope to yourself
  4. Address one envelope to us
  5. Fold the envelope to yourself in thirds, and stuff it in the envelope to us.
  6. Mail it!

Our mailing address is:

Smile, Inc.
PMB 278
350 Bay St., Suite 100,
San Francisco, CA 94133

Now for a little stroll down memory lane.

In The Beginning…

After being converted to the Mac platform in college, Greg did a stint as an Apple engineer before setting out on his own to launch a company. After a stutter or two, 2002 saw him successfully running his one-man-shop and selling the faxing software, PageSender.

Philip, also of an entrepreneurial spirit, had left his previous venture by 2002 to get back into a passion of his, developing on the Mac platform. Having fallen in love with the Mac the very first time he saw one in 1984, he was eager to find a new project in that space.

Both attended Macworld San Francisco 2003, Greg to exhibit PageSender and Philip to search for ideas. Macworld was “the” spot to mix and mingle with both users and press, though NCMUG/MCE also put on a good trade show. It’s at this time that Greg’s friend and former boss, Judy MacDonald Johnston, an entrepreneur several times over and collector of people, suggested that Greg meet up with a friend of her sister’s, Philip.

It’s in conversation with each other that they learned their skills were complimentary. Greg had the know-how to make the backend of his idea for disc and package labeling software but lacked the special mix of technical and artistic skill Philip possessed to build the frontend. With Greg as Smile Software, and Philip as OnMyMac, they combine to create SmileOnMyMac.

A busy few months later and SmileOnMyMac was winning Macworld New York’s Best Of Show award for DiscLabel.

Early Days

Clearly, they had something. With both PageSender and DiscLabel, it only made sense to keep launching a new product each year for Macworld 😱.

2004 saw the launch of the PDF editor, PDFpen. PDFpen came about from the slow decline of faxing and the rise of emailing PDFs, as well as general annoyance at having to run a business without a decent, easy-to-use and affordable PDF editor to help.

2005 saw the birth of short-lived photo album maker PhotoPrinto.

group photo MW2005

Macworld 2005: Sean Newman (Friend), Greg (Smile Founder), Jean MacDonald (former Smile PR), Philip (Smile Founder), Brian (Smile Engineer)

2006 saw the launch of two separate products. First, the critical-for-support text expansion tool TextExpander (more on that in a later post), as well as the short-lived visual search history, BrowseBack.

group photo MW2006

Macworld 2006: Philip (Smile Founder), Brian (Smile Engineer), Jean MacDonald (former Smile PR), Jane Pellicciotto (Allegro Designs), Greg (Smile Founder)

By 2007 perhaps they’d come to their senses, as they launched no new products, but did launch PageSender 4.0 and DiscLabel 5.0.

By SmileOnMyMac’s 5th birthday in 2008, there were 6 products; 2 going strong, 3 retired, and faxing just wasn’t what it used to be.

How can just two people keep up this grueling pace of development, especially with a business to run? They get help. They brought on Brian for engineering, Anderson for support, plus a full-time marketing and press relations person in Jean MacDonald. Currently of Micro.Blog, Jean is the sister of the Judy mentioned above, a web designer, press relation-ist, and fan of SmileOnMyMac.

Bringing on a public relations person is still a bit of a rarity for a small tech company. Jean helped to spread the word of SmileOnMyMac to user groups and conferences near and far, racking up well over half the 50+ MUG appearances and all 3 MacMania cruises.

Going Mobile

2007 is notable as the year that changed how we interact with our devices. It’s the year Apple launched the iPhone. This directly leads to the next wave of apps from SmileOnMyMac, all mobile: TextExpander for iPhone (now TextExpander for iPhone & iPad), PDFpen for iPad and PDFpen for iPhone (now PDFpen for iPad & iPhone), and PDFpen Scan+ (now retired).

More products mean bringing on more developers and more support staff.

group photo MW2009

Macworld 2009: Brian (Smile Engineer), Maia (Smile Marketing), Philip (Smile Founder), Lorene Romero (Friend, NCMUG), Angel (Smile Support), Greg (Smile Founder), Jean MacDonald (former Smile PR), Sean Newman (Friend)

The inclusion of iOS apps with Mac apps leads to the company rebrand. If SmileOnMyMac is no longer just On The Mac, it makes sense to drop the ending and just be Smile, as it is today. This allows the company name to encompass the Mac and iOS platforms as well as any others, such as when TextExpander for Windows rolled around.

And It Continues

In the coming posts this week you can read about the story of each of our products.

Let us know what you were doing in 2003 @SmileSoftware and on Facebook, and stay tuned for the next post.



Smile Marketing/CX
Hat Enthusiast