On this episode we talk with Greg Scown, founder of Smile, which is behind apps such as TextExpander and PDFPen. Greg discusses how he got his start, why you should include time for curveballs in your product launch, and the modern day role of conferences. He also covers how to handle competition, lessons learned from acquiring software, and much more.
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Show notes

Greg Scown: Twitter
Smile
TextExpander
PDFPen

Transcript
Alexis: Greg, thank you for coming to the podcast.
Greg: You’re very welcome. I’m excited to be here.
Alexis: So before we get down into the rabbit hole of Smile Software, TextExpander and PDFpen and then iOS apps and the Mac Store and all this good stuff, let’s start with yourself. Give us a bit of background on yourself.
Greg: Sure, I’m originally from Pawtucket, Rhode Island and I got involved in computers around age nine.
In fact, it was kind of funny. My father moonlighted teaching investments at a little community college and they did a stock market game. I was fascinated with this; I played the game and really enjoyed it.
I convinced my dad that I should invest a portion of what I had in my savings. So being a kid, and the wisdom is invest in what you know, I bought some shares of Ideal Toy Company.
About six weeks later Ideal Toy Company came out with this neat thing called The Rubik’s Cube, so I tripled my investment and made enough money to buy a computer, which was really what I wanted to do at the time. I hadn’t really anticipated it working out quite that well.
Alexis: Before we get too far from this investment thing, I have to stop you here. Did you continue your wild investment streak?
Greg: I have not continued my investment streak with that degree of success but I am a lifelong investor. That is true.
Alexis: Okay, I just want to make sure because you can send me an email whenever you feel good about a toy company.
Greg: I’m pretty sure that stuff would go directly to spam [chuckling].
Alexis: Alright, so you got your first computer.
Greg: Yes, it was a TRS-80 core computer hooked up to my TV. That was how I got started. Fast forward a bit, graduated high school, I came out to California to go to school. I took a degree in Computer Science from Stanford which kept me out here.
I did an internship with Apple my junior year and went to work for them in my senior year – after I graduated, rather. I worked for Apple for four and a half years. My last 18 months, I ran a small research and development group in mainland China.
Alexis: Oh wow.
Greg: That was really fun. They closed the development group because it wasn’t exactly great financial times for Apple but it was a fantastic experience for me and I really enjoyed it. We actually managed to ship several things from that site, so that was fantastic.
Alexis: Was that Chinese language stuff?
Greg: It was actually general purpose. There were two groups there. There was a group that was doing Chinese language software and I was no expert in the Chinese language so I was no help to that group, but I did help with engineering practices and such.
The other group did generally software so they did a Kodak image format plug-in for QuickTime, we did File Exchange 3.0, which was the system software that managed reading and writing PC desk formats on the Mac. I’m pretty sure we did on other thing, but it escapes me at the moment.
It was just fantastic to be able to ship software. I worked in Cupertino for three years and shipped nothing, then I worked in China for a year and a half and I shipped three different products, so that’s fantastic.
Alexis: What led you to think, “I want to strike off on my own and I’m going to build my own software.†Was that an immediate thing after Apple?
Greg: Apple drove me to it, seriously.