Interview with Greg Scown of Smile Software – Small Business Show 227

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We constantly talk about maximizing our time on the Small Business Show and how using our time wisely is one of the key aspects of being successful as a Small Business owner. Automating processes and using tools to manage repetitive actions is part of a system to increase your productivity each day.

Today, we get a chance to talk with Greg Scown, Co-Founder of Smile, creators of life-changing and time-saving software applications like PDFpen and TextExpander. You’ll recognize TextExpander as a frequent sponsor of the show and software that both of your hosts use daily. 

Join Shannon Jean and Dave Hamilton as we try not to geek-out over one of our favorite pieces of software and focus on the business story of Smile and how they have found success by focusing on the productivity niche while transitioning one of their core products to a subscription model. There are some great lessons about communication, customer service and authenticity in Greg and Smiles story.

Listen in and then visit the Small Business Support Group to ask questions or share your own story.


  • 00:00:00 Small Business Show #227 for Wednesday, June 12, 2019
  • 00:01:17 Greg Scown from Smile
  • 00:02:13 The Apps Came First!
  • 00:03:27 PageSender Fax Software ships in April 2002
  • 00:04:06 Meeting Philip Gower and DiscLabel
  • 00:05:14 PDFpen: The Riches are in The Niches
  • 00:06:53 Stick with your goal
  • 00:07:40 Accepting and Letting Go of an Eroding Product
  • 00:08:45 Be Honest with Your Customers
  • 00:09:23 TextExpander goes to a Subscription Model
  • 00:14:08 The Business case of Subscriptions
  • 00:15:21 When you see change coming, go there first
  • 00:16:09 SPONSOR: Linode. Instantly deploy and manage an SSD server in the Linode Cloud. Get a server running in seconds with your choice of Linux distro, resources, and choice of 10 node locations. Visit and use promo code sbs2019 to start with a $20 credit.
  • 00:18:50 SPONSOR: The Alternative Board. TAB is a group of business owners & experts in your area that you can turn to for advice. Visit to apply for free today and find out if if there’s a board seat available in your area!
  • 00:20:09 Sustainability
  • 00:20:42 Best mistake: Over-committing to yourself
  • 00:24:16 Be less diverse: don’t hire jerks
  • 00:25:17 Podcast sponsorships to build a business
  • 00:26:51 Ask your customers “Where did you hear about us?”
  • 00:28:03 “Generally our Experiments run Six to Twelve Months”
  • 00:29:45 “Love and Respect Your Customers and They Will Love and Respect You Back”
  • 00:30:16 SBS 227 Outtro

The post Interview with Greg Scown of Smile Software – Small Business Show 227 appeared first on The Small Business Show.

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