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

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

Branding and Naming Strategies with Mike Pile of Uppercase Branding – Small Business Show 226

uppercase branding interview small business show

What’s in a name? Everything when it comes to your company or brand! As founders, owners, and stewards of Small Businesses, we all know how important your company or brand name is. Joining us today on the Small Business Show, Mike Pile, Founder of Uppercase Branding discusses his own business as well as sharing tips and methods for coming up with great names.

Mike discusses how prioritizing tasks and projects when you are the boss can be one of the most challenging adjustments after leaving a corporate job, along with being sure to disconnect at the end of the day to keep your creative juices flowing. We then move on to discussing how Uppercase got its start and what marketing methods worked the best for them. You might be surprised to hear what traditional methods produced the best results.

Later on the show, we spend time talking about how to come up with a great name for your business or brand with some examples of good and bad.

Listen in to your co-hosts Dave Hamilton and Shannon Jean and then post your comments and questions to our Small Business Support Group on Facebook!

(Original broadcast date: March 15, 2017)


00:00:00 Small Business Show #226 for Wednesday, June 5, 2019
00:00:25 SPONSOR: gets you 20% off your first year
00:01:50 An Interview with Mike Pyle, Founder of Uppercase Branding

Mike Pile from Uppercase Branding joins us today
“Verbal Identity Consultancy”
Pulling out stories from companies
Prioritizing tasks and projects
Being your own boss: scary and liberating
Disconnecting to keep your creativity flowing
Marketing YOUR B2B Marketing business – using existing connections
A gift in the mail
“Brainstorming is a waste of time” Strategy and discovery
“A great name won’t help a bad business model” A bad name can be a distraction
Vetting your name is just as valuable as creating one
Norman Awards – Great new brand names.
“Adwash” – Samsung. Not so good: “Scion” – Hotels
Set a big stretch goal
00:33:41 SBS 226 Outtro