My Road to Microsoft by 19 Years Old

When I was getting into tech, the industry was much different. Not everyone had computers, and there were no smartphones. The internet was new, and you accessed it through AOL or other similar services. My best friend in school had a computer, and I fell in love with a game called “The Incredible Machine”. I was addicted, and I had to have a computer. At 14, my parents took me to Circuit City, and I got my first computer. It was a Packard Bell 486DX2 with a math coprocessor. It was an actual desktop as in the monitor sat on top of the computer on the desk. This marked the beginning of my journey to Microsoft.

I loved gaming, but I loved optimizing the performance of the games even more. I’d spend my time figuring out the best upper and lower memory configurations for games, edit the config.sys and autoexec.bat, and fiddle with in-game settings. I also loved hardware, and I would upgrade my hard drive and video card from time-to-time. I’ll never forget standing over the computer with my Dad, video card in hand, wondering if we were about to destroy the most expensive thing we owned. We delicately tried to push the video card into the ISA slot, and we could not get it to set. We must have tried for an hour before I finally just crammed it in as hard as I could, and it clicked. I was sure it would never turn on again, but to my surprise it did.

The computer came with a modem, and I spent a good bit of time on bulletin boards before the internet really took off. Once it did in the late 90s, I was hooked. The information overload was so incredibly welcoming to my young sponge of a brain, and I knew that I wanted to be in the technology industry. At the time, Microsoft was not only the biggest kid on the block, they were the only kid on the block. They dominated the industry, and I set a goal for myself that I would one day work for Microsoft.

This goal was incredibly unrealistic in my mind. No one in my family had ever even graduated college, so how was I going to break that barrier and work for a company that employed the world’s most brilliant engineers? I assumed that if I somehow reached this goal, I would be 40 or older before I worked my way up to the point where I would be worthy of the position.

By the time I graduated High School, I had acquired quite a bit of hardware knowledge, and I landed a job at a bankruptcy firm, Wallace and Demayo, as a PC support specialist where I worked while attending a local college. I would field the requests from the call center reps to fix a printer, replace a hard drive, or make configuration changes to Windows. I’d also build new computers out of the parts we had lying around. My boss at the time was a programmer, and he was over the other programmers in the department.

At the time, I thought coding was magic. I had literally no idea what went into it, and I assumed it took some sort of super genius to do it. Remember, there were no online tutorials and YouTube videos to get you started or introduce you to the subject, but I was so intrigued to understand it. I would stand over the shoulder of the developers and just watch them code. Looking back, I realize that I must have been so annoying to them. No one can code with a kid standing over their shoulder! Luckily, one guy didn’t seem to mind, and I would ask questions here and there. A week or so into me asking questions, he realized that I was starting to understand what he was doing. He gave me the confidence to go to the bookstore and get a book on coding. I bought “Learn Visual Basic 6 in 21 Days”.

The language I had been watching him code in wasn’t Visual Basic, but it was a form of Basic called Pick Basic from the 70s. I figured that I should try to learn something a little more relevant, and Visual Basic was all the rage at the time. I never put the book down. I was staying at work until 3am every night, and I finished the book in less than 2 weeks. It came so easy to me. Looking back, I can’t even remember having a moment where it all clicked. It just clicked from the moment I started watching that programmer code, and after finishing the book, I started working on my own version of MS Paint.

Whenever I wasn’t doing my PC support job, I was coding, and one day my boss saw me working on my application. Befuddled, he asked me how I knew how to code, and I told him that I read this book over the last couple of weeks. I showed him what I was working on, and I could tell he was impressed. I didn’t know why because it seemed pretty easy to me. I assumed I knew almost nothing at the time, but what he did next would change my life forever.

He told me that he had a problem he’d been working on in his application for the last 3 days, and he couldn’t figure it out. It had to do with an Attachmate card which was used to talk to the AS400 (mainframe). I don’t recall the exact problem, but he told me that if I fixed it, he would make me a programmer. Challenge accepted! I scurried over to the pile of parts and found an Attachmate card for my computer, and I installed it. I figured out how to configure it and connect to the mainframe then I loaded his code out of Visual Source Safe (old school equivalent of git).

I fixed the issue he had the very same day, and he kept his word and made me a programmer. Four raises later, I went from $8 an hour to $40,000 per year within the first 12 months of being there. In that time, I taught myself Pick Basic, SQL Server, and a myriad of other long forgotten technologies. It was the late 90s, and I had acquired a skill at 18 years old that not many people had. The industry was in the middle of the bubble, and I took every advantage of it. I left to make $56,000, and then I left that job 6 months later to make over $100,000 per year as a consultant at 19 years old.

I was making more than my parents had ever made, and I moved out of my parents house. My mom said that an apartment would be “throwing my money away”. She was hoping that would keep me at home, but I just bought a house instead. Sorry Mom! I’m pretty sure my parents thought I was selling drugs or something illicit. I look young now, and I looked incredibly young back then. My Dad came to the closing with me, and they kept addressing him about the documents. He looked at them and said that he wasn’t buying the house, and that I was. I’ll never forget the incredulous looks we got from the attorneys. It was priceless.

I was loving life. I took a Visual Basic class in college, and my professor would give me half the class to teach while he took the other half. I dropped out after that class. I wasn’t getting very much value out of college, and I didn’t see how it could help me in the future. The technology industry doesn’t put a lot of merit in college. If you can do the work, they’ll take you in. The dirty truth is that completing a Computer Science degree doesn’t make you a good programmer. Curiosity and drive does, and you can’t teach that.

One day as I was driving home from work, I got a call from a recruiter, and he asked me if I wanted to work for Microsoft! I was shocked. I told him that was my dream, and he set me up with an internal Microsoft recruiter. She was going through my resume and asking questions, and I stopped her half-way through. I told her that I didn’t have a degree, and the job says that it requires a Bachelor’s Degree. She laughed and she told me not to worry about it. She said, “Bill doesn’t have a degree either. It’s fine.”

She laughed and she told me not to worry about it. She said, “Bill doesn’t have a degree either. It’s fine.”

The next step was to do a phone screen. The position I was interviewing for was a Technology Specialist for .Net, Microsoft’s brand new (at the time) development platform. As a consultant, I had been implementing solutions in C# while it was still in Alpha (using notepad and the compiler), and they needed someone who could go to their biggest Enterprise clients and give presentations to development teams on the massive changes coming their way. I can remember the stop light I was at in my car when Keith Sharpe, the technical screener and future colleague, told me that he was going to push me to the next phase of the interview process. I was in shock.

After that, I got an email inviting me to Charlotte, North Carolina for an all day in-person interview. I had never flown before, but they set it up with a hotel and rental car ready for me. When I arrived, I met the two other candidates. One had his Master’s in Computer Science, and the other had his Phd. I thought to myself, “at least I got a free trip out of it!”.

I was put in a room where a different interviewer came in every hour to ask questions that ranged from technical to riddles like “Why is a manhole round?”. Books have been written about interviewing at Microsoft. I wish I knew that at the time! One interviewer, Geoff White, asked me to code an application on the whiteboard. It was a simple banking application that processed transactions. I did it in Visual Basic, and I later found out that I was the first person he had ever asked that question to that provided a working compilable program. He was entering my code into Visual Studio as I wrote it on the whiteboard.

At the end of the day, I had to meet with everyone I had interviewed with and present to them. It was a whiteboard architecture session, and they laid out the details of the system I was to design. I drew everything from databases, firewalls, servers, and network configurations, and they tried to poke holes in my design. I fielded all the questions, and I actually felt pretty good about it. They sent me on my way and told me they would get back with me.

As I was leaving, the recruiter I had been working with took the elevator with me. He asked me how it went, and I told him that I thought it went ok but there was no way I would get it over the other candidates. They were so much more qualified than I was. He smiled and looked at me, and he said, “I’m not supposed to tell you this right now, but you’re going to get an offer. They loved you.”. I almost broke down in tears right there in the elevator. I was shocked, excited and going absolutely crazy inside. I couldn’t wait to tell my parents. They would finally know that I wasn’t a drug dealer 😉

The moral of the story here is that if you want something, go and get it. It’s not going to come to you by chance. You have to prepare yourself for the doors that open in your life, and my initiative to teach myself to code prepared me for the day that the Microsoft recruiter called me asking if I wanted to work there. I was ready for my moment. Are you ready for yours?

After spending 10 years at Microsoft, Matt left to create the digital marketing company, Platypi. While at Platypi, he created Alabama’s first coding bootcamp, Covalence, which has now expanded across the country. Follow Matt on his entrepreneurial journey at mattlanders.com.

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