Twenty Years of SmartDraw turned 60 last month. It felt like a milestone. Even though I feel as young as ever, sixty-something sounds much older than fifty-something.

The last time I felt this shift was twenty years ago when I turned 40. At the time, I was making a very good living as a hired gun writing Windows and Mac applications for software publishers, including Microsoft. I worked at home. Life was good. But I had an itch: I wanted to sell a product of my own.

Twenty Years of SmartDraw
A timeline of Twenty Years of SmartDraw.

My 40th birthday was the shove I needed to get serious about it. Somehow 40 didn’t sound like a young guy with a limitless unknown future ahead of him. It sounded like a warning. So exactly twenty years ago, in November 1993, I started writing SmartDraw.

The Web did not exist yet. My plan was to distribute the program using the burgeoning online services of CompuServe and AOL. Users could download shareware (as it was called) for just the cost of the connection time. Payment to the author was an honor system: If a user liked your program they sent you the purchase price and you sent them a user guide and some backup diskettes. Sounds crazy but it worked. The beauty of this system was that I didn’t need capital to build a sales force and distribution and I could keep my day job.

SmartDraw 1.0

It took me about eight months of spare time to write the first version of SmartDraw and another four to create the symbols, write the user guide, help system, installer and test it. (Note to future software entrepreneurs: There’s a lot more to shipping a product than writing the program itself!) I uploaded SmartDraw 1.0 to AOL and CompuServe in November 1994 and collected my first payment the very next day. (Thank you Mr. Jones, I still have your order form framed on my wall!)

My goal with SmartDraw was to create a MacDraw-like program for Windows 3.1 that was both elegant and easy to use. I had written lots of Mac software, including two graphic editors, and had recently been switching these to Windows for my publisher clients. Most of the drawing software for windows was (to my mind) awful at the time. In CorelDraw in 1993 you had to enter text into dialog instead of directly into the shape. Yuck!

I also wanted to aim the product at business users, because businesses were more likely to pay for shareware than consumers, so I added support for flowcharts and other business diagrams.

SmartDraw 1.0 was a simple drag-and-drop drawing program. It supported anchoring lines to shapes (used for flowcharts, etc.). It came with libraries of symbols for a variety of diagram types. It was very similar in functionality to the new crop of drawing apps for web browsers like Gliffy, Lovely Charts and many of the free drawing programs you can now find on the web.

The Web Arrives

SmartDraw 1994-2014
The first SmartDraw user interface (1994, at top) compared to today’s version.

By 1995, the web was born and spreading far and wide. It was clear that SmartDraw’s future was in distribution from a web site, rather than AOL.

I wrote the first web site using Microsoft Word. Within weeks most of our downloads came from our own web site.  At the time, SmartDraw was one of just a few products that were conceived with online distribution in mind. (I like to say “before it was cool….”) It was small and easy to download. Then the question became, “how do we get more sales?” Web marketing was born.

SmartDraw was a pioneer in almost every form of web marketing. Our techniques (and our website) have been widely copied and we’ve been very successful, with millions of downloads every year. Web marketing is fun. It’s a constantly changing landscape. The innovation never stops. It’s one of the things I enjoy most about the company.

SmartDraw Evolves

The product itself has developed enormously since 1.0. My goal in improving SmartDraw has always been to make it as easy as possible for an average person to quickly create diagrams that look like they were drawn by a professional. SmartDraw‘s automatic formatting of flowcharts, org charts and dozens of other diagrams is the culmination of that.

What’s Next?

Today SmartDraw remains an application that runs on the Windows desktop, but we all increasingly use multiple devices and we want one set of files available on all of them. Last year we added the ability of Windows SmartDraw to share files with your phone, tablet and web browser. The next step is fully functional SmartDraw on every device: Windows, Mac, IOS, Android, and any web browser, with full file compatibility across all platforms.

Did I mention that I am now programming in JavaScript?