You CAN Teach an Old Dog New Tricks

In this first of many more articles that I will be publishing on this site, I thought it would be helpful to chronicle my entrepreneurial journey.  I hope you enjoy this walk down memory lane with me.

Running a Business in College

When I was in college, I found out that students were either too busy or too lazy to go out and get food. So I organized a food delivery service for the college dorms. I sourced about twelve to fifteen food places and got them to agree for me to take orders and deliver on their behalf. Then I put up posters with my phone number and started receiving calls. I got a minimum of ten bucks, or up to ten percent surcharge, for every transaction. That means even if they ordered less than a hundred bucks, I would still get ten and all I had to do was go to the dorm room to get the money, so I could buy the food and deliver it to them.

Surprisingly, I saw a lot of rich kids who could afford to pay someone ten bucks to buy them McDonald’s and bring it back to them. Of course, it got pretty tiring after a while, because the more successful it became the less time I had left for school activities. So there goes my first foray into having my own business.

Goodbye to Jobs

My first two jobs, and the only time I was employed by another company, was with Apple Computer and then Microsoft.

At Apple, I was a Product Support Manager for the Apple III and then the Lisa, both of which failed. So when I was offered to be a Product Support Manager for the Macintosh, I turned it down and left the company.

During my stay at Apple, I had the opportunity to learn about Excel for the Macintosh, and I was able to use that to get freelance Excel programming jobs after resigning. I helped financial professionals by getting their work done on spreadsheets and by doing macro programming. Eventually, that helped me land a contract job at Microsoft, to work on Excel version 1 for Windows.

That was when I was officially exposed to software. I saw how Microsoft had grown by focusing only on software, and I realized that that’s what I wanted to do. So that got me venturing into software technology entrepreneurship.

My First Real Startup

Ironically, my first real startup did not involve software. My friend and I founded MicroRain, a manufacturer of desktop computer furniture, by raising US$250,000 from angel investors in Seattle, WA.

That was quite a bit of money in the 1980’s, but we managed to pull it off. We produced furniture for the Macintosh, so that people could store their computer accessories around their new Mac.

The company did well in the beginning. We were able to generate US$500,000 in first-year revenues, which is quite phenomenal for a startup at that time.

Fast forward to eighteen months later, our business went bankrupt. We did not realize that we were spending more money than we were making until it was too late. In hindsight, I really did not know what I was doing, which is why it had gone bankrupt and ended up in failure.

Selling My Second Startup to Microsoft

I went back to freelance consulting work for the Macintosh after MicroRain went bust. I discovered that there was a demand for custom software development for the Macintosh, so I began my second startup called Match Data Systems in 1998. But it became increasingly difficult to retain my programmers because Microsoft and other big companies kept attracting them away from me.

So in 1991, I decided to set up shop in the Philippines, as there were already a lot of programmers in the country and they cost less than hiring from the US. We were actually doing offshore outsourcing even before it became a term. All the development work was done in the Philippines, but the customers were all in the US. Match Data then evolved from being a custom software development company to a software product company, and we became a partner of Great Plains prior to its acquisition by the latter in 1999.

After a couple of years, Great Plains was acquired by no less than global software company, Microsoft. The entire process of Match Data’s inception to exit took eleven years. In hindsight, that took way too long to happen; it really could have happened a lot sooner if I knew what I was doing.

Tempting Fate with My Third Startup

Two years after Microsoft acquired my company, I tried to retire in 2003 for a few months.  But I could not stay retired, so I began working on my third startup – a company that we know today as Gurango Software.

We initially set out as an outsourcing firm, providing .NET development for US-based clients. By 2005, we decided to become a software product company and we have been developing business software solutions ever since.

Succeeding at Startups Like a Boss

It was in 2010 when I started learning about Lean Startup. The following year, I met some like-minded people in the Philippine Software Industry Association. Together, we co-founded the Software Products Incubation Group of the Philippines or It aims to nurture and support the growing software startup ecosystem in the Philippines.

Since I learn best by teaching, I applied the same Lean Startup techniques to my own business and passed on my discoveries to guide other startups as well. I learned that there is a scientific method to determining a startup’s success or failure. These have been documented in Eric Ries’ book “The Lean Startup.” There is also a scientific way of looking at a startup business and this has been well covered in Alexander Osterwalder’s book “Business Model Generation.”

These two books have sort of become my bible for creating software startup companies. It has helped Gurango Software and it also proved to be useful when I co-founded two other software startups last year.

Just an Old Dog Learning New Tricks

I have been in the software business since 1988, and for the first 22 years I had no idea that scientific methods existed for growing a software startup company. This is just a three-year old learning for me, but I really wish I had known these things back in ‘88. I may have had an instinctive knowledge about growing software startups, but now I am more equipped from a formal academic perspective. If I had known better, I would probably not have done a lot of the things which contributed to my failures. And, I would most likely have put more focus on the efforts that could have accelerated my successes.

So, yes, it is possible to teach an old dog new tricks. You can teach not just young people, but also those who have been around for a long time, on how to go about having a successful software startup. Anything is possible as long as you are willing to learn.


Joey Gurango is the CEO of Gurango Software and the president of the Philippine Software Industry Association
Connect with Joey on LinkedIn



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Joey Gurango has a solid track record in forming and running successful software companies. He founded Match Data Systems (MDS) in Seattle WA USA in 1987, MDS Philippines in 1991, and MDS Australia in 1996. In 1999, he sold MDS to Great Plains Software, which was acquired by Microsoft in 2001. Joey served as the Asia Pacific Regional Director for Microsoft Business Solutions, before he left in 2003 to form Gurango Software. In 2007, he was inducted into the Hall of Fame for Microsoft's Most Valuable Professionals, in recognition of his mastery of software technology and business. In 2006, the Philippine Center for Entrepreneurship acknowledged him as one of the country's Ten Most Inspiring Technopreneurs. In addition to leading Gurango Software as the most successful Microsoft Dynamics partner in the Philippines, Joey has co-founded several other software start-ups, and is the President of the Philippine Software Industry Association.

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