Retired Partner Engineer at Microsoft Shares Rags-to-Riches Story

Don Tennant
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One of the really cool things I’ve been able to do over the years in this job is speak with people who played a role in shaping the software industry. Those are invariably fascinating conversations, so I had very high expectations when I was invited to speak with George A. Santino, who retired as partner engineering manager after a 20-year career at Microsoft. I wasn’t disappointed.

Santino was one of the early insiders at Microsoft, and the individual who created and led Microsoft’s Enterprise Engineering Center, the lab that expanded Microsoft’s influence from desktop kingpin to enterprise linchpin. His is a rags-to-riches story that’s chronicled in his forthcoming book, “Get Back Up: From the Streets to Microsoft Suites.” After growing up in the projects of South Philadelphia, and with only a high school education, Santino tried and failed at a number of ventures before finally landing a job at Microsoft at the relatively ripe age of 35. But he was nothing if not persistent.

Santino was rejected by Microsoft four times before finally being hired, so I opened my conversation with him by asking him why he had his sights set so firmly on Microsoft. He said originally, it was just to mess with them:

It’s interesting, in that the main reason I interviewed with Microsoft was more out of anger than anything else. I actually didn’t want to work for Microsoft. That was back in the fairly early days of software — the big guys were WordPerfect and Lotus and so forth, and Microsoft was coming on big. They had launched Windows, but it wasn’t doing all that well — it wasn’t until Windows 3.1 that it really took off. Microsoft was the Evil Empire — companies like Ashton-Tate [where I worked] were falling apart. When Ashton-Tate got bought out by Borland, I needed to find another job. So I started looking at other companies in the [Silicon] Valley, and it wasn’t until people from Ashton-Tate told me one by one that Microsoft had turned them down that I realized Microsoft had a presence there.

So I basically really did apply just to kind of mess with them. My assumption was, I would apply, and they would want me, and I would turn them down [saying], ‘Finally somebody you wanted from Ashton-Tate said no to you,’ then I would go on with my life. I was absolutely shocked when they turned me down the first time.

Santino worked on a lot of projects over the years at Microsoft, and I asked him what his favorite was. He said it would have to be creating and leading the Enterprise Engineering Center:

That was an opportunity to really be almost an entrepreneur in a company like Microsoft. I did a lot of entrepreneurial things early in my life, none of which worked out, other than as learning experiences. But to be able to do an entrepreneurial-like thing with Microsoft’s money greatly enhanced the chances of success. Microsoft really at that point had won the desktop — they had a 90-plus percent share in operating systems, word processing, and spreadsheets. But they didn’t own the enterprise — frankly, they knew very little about going after the enterprise.

So we needed to build a facility like the Enterprise Engineering Center from scratch — basically, a lab that would allow us to replicate the network topologies of enterprise companies, and install their in-house applications, our software, as well as our competitors’ software. We could build out these environments and truly get an understanding of how corporations were using our software, and do it at a time when the software was still under development, giving us an opportunity to fix any issues. I’m sure you’re aware that over time, Microsoft would release a product, and customers would report some issues that were missed, and we’d do a service pack. After a while, corporations would learn, don’t install the first one — wait for the service pack, and let somebody else be the guinea pig.

So here was our opportunity to work directly with the enterprises, bring them to our lab, and then ship products that are deployable from Day One. That was an amazing accomplishment, and the fact that the company allowed me to spend that kind of money building something at a time when the market around us was crashing, and companies were going out of business, was just fantastic — it was like I owned my own business, in the middle of Microsoft.

Given Santino’s entrepreneurial spirit, I asked him if he ever considered leaving Microsoft to start his own tech company. He said he didn’t, and he explained why:

I went to work for Microsoft, in spite of the fact that I didn’t really like them, and I learned very quickly that the company was all about results — if you worked hard and got great results, you could do very, very well there. I used to tell people, if you’re going to work in software, there’s no better company to work for than Microsoft. There was no reason for me to go off and try to do something on my own. I was working for a great company that provided me with great support, paying me extremely well — I didn’t need to take that risk. The entrepreneurial period of my life was over. I tried many, many different businesses, some that worked better than others. But now I had the opportunity to have those same sorts of entrepreneurial feelings, but with no risk of having to close the business. It really was the best of both worlds.

I asked Santino if he had it all to do over again, what he would do differently. He said he’d try to get to Microsoft sooner:

All the years I spent as an entrepreneur were great fun, except the way they ended. I learned a great deal from it. But the success and fun and opportunities I had at Microsoft truly were a great experience. It was an opportunity to touch a lot of people’s lives. I’m glad I retired when I did — I was 55, and it was time to do a lot of things that I had been putting off because I was working as hard as I was. I started at Microsoft when I was 35, when a lot of people start there straight out of college. It would have been nice to get there sooner, and be a part of that early growth.

But I really don’t have any regrets, because each one of those things, no matter how much of a failure they felt like at the time, was along that path that got me where I was. Frankly, if the shoe repair business didn’t collapse, and we didn’t declare corporate and personal bankruptcy and load up a U-Haul truck and move to California, I never would have gotten to work for Microsoft. So even though it sucked at the time, it was a very important step along that path.

Santino said now that his book is finished, he’s eager to do some professional speaking:

I want to talk to people when they’re young about the opportunities out there in the world. Sadly, we’re hearing a lot these days, especially from politicians, about how the American Dream is dead, how the deck is stacked against you, how it’s unfair, the system’s rigged, vote for me and I’ll fix it all, because you don’t stand a chance. That’s such bull. I still think that in America, you can get out there, and if you work hard and put in the effort, you can still go from rags to riches. But you have to be willing to take on that ownership, and get out there and make things happen for yourself.

That was a great segue to my next question: What’s his advice for young people who aspire to make it big in the tech world? He said the first thing to do is to get an education.

Though I didn’t get a college degree, the competition out there is absolutely fierce. So get into a decent school, acquire those skills, and make sure you do internships. It’s so hard to come straight out of college and apply to some of these companies. Make sure you get the summer internships, and start to forge those relationships with the company. Once you get in there, bust your ass. Find out from your boss what the company values, and what it rewards. Do those things, and do them better than everybody else. Don’t do anything halfway. Give it your all.

Santino also shared a fascinating inside look at the culture within Microsoft, and how it changed over the 20 years he was there. I’ll cover that in a forthcoming post.

A contributing writer on IT management and career topics with IT Business Edge since 2009, Don Tennant began his technology journalism career in 1990 in Hong Kong, where he served as editor of the Hong Kong edition of Computerworld. After returning to the U.S. in 2000, he became Editor in Chief of the U.S. edition of Computerworld, and later assumed the editorial directorship of Computerworld and InfoWorld. Don was presented with the 2007 Timothy White Award for Editorial Integrity by American Business Media, and he is a recipient of the Jesse H. Neal National Business Journalism Award for editorial excellence in news coverage. Follow him on Twitter @dontennant.

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