Former Microsoft Head Storyteller David Dwyer

From Microsoft to Mission Field: David Dwyer

Written by Henry Ortlip

He was one of the most influential book publishers during the Internet revolution, he was Head Storyteller at Microsoft, he was living in his dream house in Seattle surrounded by his loving family; and like the fisherman in the Gospel, David Dwyer was willing to follow the Lord, leave the States and go where he felt he was called. In this case, his calling was Chile. Risen caught up this globetrotter to learn more about his upbringing, career conversations, and the true meaning of success.

Interviewed Exclusively for Risen Magazine Point Loma, California

Risen Magazine: What was your childhood like?
David Dwyer: I was the youngest of ten kids and we lived in Cleveland, Ohio, on the campus of Case Western Reserve University. Growing up we were surrounded by college students, not really any kids [my age.] Everyone knew the Dwyer kids because there were ten of us, and we lived next door to a fraternity house. My father left when I was three-years-old; he just totally disappeared.
My father came home one day, gave my oldest brother some money and said, “Your mom’s birthday is coming up. Buy her something nice.” He said he had a business trip to go on, and he just left. It was the last time anyone saw him. He wrote a letter to our family doctor who is a close family friend. In the letter he said he was very stressed and felt a strain in the relationship and with having ten kids, he basically just checked out. He said he would be sending a check soon and that he had some leads on work and it was going well and he encouraged Jackie, my mother, to move to central Ohio to be near her relatives.

David Dwyer (#12) praying with the guys at the Puente Alto Prison in Santiago, Chile.

David Dwyer (#12) praying with the guys at the Puente Alto Prison in Santiago, Chile.

Risen Magazine: How did your mother react under these circumstances?
David Dwyer: It was wild, when she read the letter she knew my dad wasn’t coming back. My mom’s attitude about everything was, “Look, I love your dad and I will continue to love your dad. You kids can pray for him if you like.” [I thought] pray for… what do you want us to pray for? Do you want him to come back, or do you want him to be safe? So I grew up praying, “Just keep my father safe Lord.” I remember as a kid praying that. I don’t remember that I ever prayed for him to come back though. She decided it was time to figure it all out and get on with life without him.

Risen Magazine: That takes some courage on your mom’s part. How would you describe her?
David Dwyer: My mother was a kindergarten teacher. After my father left she ended up taking a job she really wasn’t qualified to get. She got a job at a hospital doing kids arts and crafts therapy; this was a new concept back then in 1966. Her second job was to work as a nurse’s assistant in the afternoon. She worked double shifts most days to make ends meet. My mother was a great example of a woman of faith who depended on the Lord for EVERYTHING… literally.

Risen Magazine: With your mom having such strong faith, what did faith look like for you growing up?
David Dwyer: I was raised in a Baptist church. When my mother would speak it was always about how the grace of God is what sustained us. To me, I don’t remember not knowing the Lord. I guess that’s the best way to put it. I know I made my commitment to Christ for the first time in Sunday school at Cedar Hill Baptist Church when I was in first grade. My life was a life observing this faith. I remember Jesus being very real to me. I remember things happened in my life where the Lord’s hand was very involved in it. The Holy Spirit was always very involved in my life. Though I didn’t realize the power of the Holy Spirit, I knew I was protected all the time, and to me that was a very big deal. So I never worried about things as a kid.
Growing up I thought we were living just fine. It wasn’t until I was an adult that my mother shared stories about how bad things were. She would go to bed at night not knowing how she would put food on the table for us. She knew she had no money in her purse. She said she prayed to go to sleep, and she would sleep peacefully and the next day we would get a knock on the door, or an envelope would arrive. Something would always happen where we would eat. I never realized that, I never saw that side of things growing up.
We moved out to the suburbs when I was in fourth grade and at that point, most of my brothers and sisters had moved out of the house. I would say that my mom became more relaxed. I certainly felt like when I got to high school I was more on my own to make my own choices by myself. I could do the things I wanted to do. However this was a time when we stopped going to church as a family. So I wasn’t attending church on a regular basis. I was going every once in a while with our friends. Soccer was always something I excelled at. I think that was partly due to playing with my older brother growing up and his friends. Playing with the older kids made me a better player at the time. So while I hadn’t rejected my belief in Christ, I definitely was not living for him. I was living for me and earthly pleasures.

The coach was the first man that had influenced wisdom into my life; he spoke things into my life that a father would with his own son.

Risen Magazine: If high school was a time with a little more freedom and maybe a leaning toward sports and self, how did you handle the transition to college?
David Dwyer: I had an outstanding [high school] senior year and colleges started recruiting me [for soccer.] I was convinced I wanted to go to Cleveland State – which had a great [soccer] program at the time – but the coach told me, “We really can’t give you a scholarship, you’ll be lucky if you even play by the time you’re a senior.” I remember looking at him thinking “Seriously?” And he said, “David, you have to make a decision, do you want to be a big fish in a small pond, or small fish in a big pond?” I didn’t realize it at the time, but this was the beginning of the Lord using my passion for soccer to lead me back to him.
There were a lot of small schools approaching me to play for them, but it was the coach of Judson College (now Judson University) that came to my house and met with my mother and promised her that he’d teach me to play for Christ; a concept I did not understand. That ended up being the school the Lord wanted me to attend. Judson was an environment where my faith grew and I became serious about truly creating a relationship with Christ. I had a wonderful coach and Christian guys around me that provided the support I needed to see where my life needed to go. The coach was the first man that had influenced wisdom into my life; he spoke things into my life that a father would with their own son. Soccer was at the center of what the Lord used to lead me back to him; little did I know how this would become so central to my life. I studied communication arts and wanted to be in advertising. I wanted to create television advertisements, clever stuff. Judson is also where I met my wife Michelle.

Risen Magazine: So you get married and begin your career path. How did you get into publishing and then later move on to Microsoft?
David Dwyer: It’s interesting. I never set out with a goal in mind to have X job in so many years, making X amount of dollars. [My wife and I] were thankful for simple provisions and walking in the Lord’s will. The scriptures say not to worry about tomorrow, so we didn’t. The Lord really blessed us. I spent almost all my career in publishing. [Handling everything] from Sunday School curriculum, to some of the best selling books on web technologies. I was the Publisher at New Riders where we published the world’s best selling books on Photoshop with Scott Kelby, web design with Lynda Weinman, and web usability with Jakob Nielsen. It was really cool being part of the emerging consumer web as we know it today and leading the charge on the publishing of digital photography. I got to hang out with some of the most influential people in these areas and publish their books. More importantly, they are friends even to this day. After that run, I spent five years at Microsoft where I was the Chief Storyteller for Windows Marketing. I designed and shaped primarily the consumer Windows story through the web properties at Microsoft.

David Dwyer (left) coaching in Sao Paulo, Brazil.

David Dwyer (left) coaching in Sao Paulo, Brazil.

Risen Magazine: When you look back at your career, why do you think you excelled the way you did? What part did your faith play?
David Dwyer: Everyone I’ve been surrounded by has always had entirely different motivations to what I’ve had. I truly believe when you bless the Lord, he blesses you. I don’t mean that in perspective of trying to accumulate things, that’s not what I’m talking about. What I’m talking about is he blessed me with jobs that I loved, a wife that I love, and places to live that our family loved. And when I share my testimony I always tell people, “Look you’re not going to hear the recovering drug addict story or recovering alcoholic testimony. My testimony is about trying to make Jesus known every day in my workplace.” And from there it was always in the Lord’s hands. We just tried our best to always follow him. Do I have crazy stories in my life? Absolutely. I absolutely do. But that’s not what dictated my life. Let me tell you, I honestly wanted to go to work every day believing it was my mission field. I just did. I believe we are on earth to tell people about Jesus no matter what we do or where we do it. It’s always for the Lord. Just like Colossians 3:23 says, “Work willingly at whatever you do, as though you were working for the Lord rather than for people.
I never focused on money and I never focused on my title. My boss would always play a trick on me and ask me, “How much money do you make in a year?” And I could never answer the question. He’d say, “You need to call Michelle right?” All I cared about was that Michelle was okay with the amount I’m bringing home so that she felt secure, and we had enough to feed the kids, and could pay the mortgage and bills. If she was happy, I was happy. My mentor, God bless him, he’s not a believer, but he realized that the secret to the success of David is making sure his wife’s happy. He is a smart guy. He figured that stuff out early with me. I just wish he figured out some of the other sides of the true happiness of our marriage and of our life together. He knows what I believe; he just chooses a different lifestyle.
It’s amazing to me how people are so free to tell you stories about how stupid they are. Monday morning inevitably sometime during the day you hear the story of, “Man we got so hammered on Saturday night, and you’re not going to believe what I did?’’ And they tell you stories, and if you really sit back and think about it, you think, “Well that was really stupid. Think of all the terrible things that could have happened, and think of the terrible things they actually did.
It dawned on me one day, if these people feel bold enough to talk about how stupid they are and about the things they do on the weekends. Why am I not bold enough to talk about the things that I did on the weekend, and say, “I went with our youth group to play whirly ball,” or “I went to a great Christian concert.” I just started to weave what I was doing in my life into my stories. When someone came into my office and said, “Hey, how are you? How was your weekend?” I would share with them what I was doing. It was a platform. I would put posters up of my favorite Christian bands in my office and stuff. I figured out there are ways to [evangelize] without beating people over the head with it. My faith is a part of me and that’s what you have to be focused on. Your faith can’t be something you use every once in a while, it has got to be who you are. When you do it right it’s not a performance or something you have to put on display. My faith is completely who I am. Your never get to see another side of me. What you see is what you get. Michelle has always been a big supporter of me sharing my faith and going about my life in that way. In the workplace it’s never been an issue to share my faith, or share about Jesus with people that totally disagree. It would always end with, “That was a really cool conversation.” I always tried to take an attitude of love and I never tried to beat anyone over the head with what I believe. It’s always best to let people know what Jesus has done for you and then let them see it manifest itself as they observe your life.

Risen Magazine: Everyone wants to feel valued for the work they are doing and your bosses knew money wasn’t your top priority, so how then did you approach them or handle promotions or raises?
David Dwyer: I’ve never had to pursue a position; I’ve always been offered them. Therefore I’m always in a position of choice, “Do I want to move up, over, or out?” [Laughing] I’ve never had to sit in a job review where I’ve had to argue for more money, or argue for a new title. I wouldn’t know how to do it. However, there was a time when I did something phenomenal while working for Addison-Wesley. I only received an average raise that year. They said, “We can only give you an average raise.” I thought, well this is the one time of year we talk about these things; I’m not happy about this; and my wife will not be happy about this so I told my boss, “Look, I’ll agree to the raise, but I want you to promise me something today.” She asked, “What’s that?” I said, “The day I leave this organization and I resign please do me a favor. Don’t ask me the question. What will it take to keep you here?” I said, “Just don’t insult me that way.” She said, “Are you planning to leave?!” I said, “No, you’re not hearing what I’m saying. I love what I do and I’m going to continue to do it the way I do it, I’m just saying, don’t insult me when I go to leave here by saying what will it take to keep me here. Because if I go to this extreme to advance the company and its an average raise, what am I supposed to tell you? I would prefer to stay at a place that’s going to reward extraordinary work.” That’s just the way business is sometimes and I understand that. I just do not like playing games so I wanted to be sure to set my expectations for the future.

Risen Magazine: When did the idea of becoming a missionary enter your mind?
David Dwyer: Things were wonderful in Seattle when we were at Microsoft. Honestly, we were living in our favorite house, probably our favorite city, we were skiing and snowboarding together as a family, and we had an awesome church family. We really got plugged into our church immediately, the pastor and I became great friends, and everything was really in tune. The job was great every day and I was pinching myself because I had a dream job at a great company. Life was grand; life was really grand. We had always been mission-minded, so we were pouring back into the church, and the kingdom of God.
We were sitting in church; it was mission’s week. Our pastor did a sermon at the end of the week on the calling of the disciples. He put the story into modern day context. He points to me in the audience. He says, “Hey, sitting out here is the guy who runs the Windows website. Over here is one of the pediatricians on the plateau.” He was using the examples of these successful people in the audience, and he was explaining why people like fishermen [in the Bible] were the equivalent. The disciples made good money because being a fisherman was not a casual blue-collar job. If you owned a fishing boat, and you owned the nets, then you were in a great position. The fishermen would probably sustain multiple generations of their family. So the pastor says, “Picture this. Jesus walks down and tells them to follow him, they drop their nets and they follow him.” The pastor continues, “Let’s have that linger here a moment. Think of the controversy around their dinner table that night. Their families probably were saying, ‘How are we going to eat?’ The pastor says at the end of the sermon, “If we are in this world to proclaim the name of Jesus Christ, and this is the sole purpose for being here, then if Jesus walked into Microsoft, or walked into your doctor’s office, or walked into your construction site and said, David, Joan, Billy, stop what your doing, drop it all and come follow me, would you?
For [the next] two weeks, I’m sitting in meetings at Microsoft. I can’t even begin to tell you what they were about. I’m sitting there thinking, what if Jesus walked in this meeting right now. Then he says, “Can I interrupt for a minute? David, would you come with me?” I thought, would I have the nerve to really do it?
I had never felt so alive in the kingdom of God. I was going through these mental exercises with God for two weeks. I just remember thinking, “Wow, Lord I’m not ignoring you. I’m not, this is just a really heavy question,” because, we were 100 percent confident we were walking in his will. We had it together as a family. But after a couple of weeks going through this, I went home, and I said to Michelle, “We need to talk.” She said, “I think I know what you’re going to say.” I said, “You have no idea what I’m going to say.” We sit down; she has this sly smile on her face. I said, “Remember that sermon a couple of weeks ago when Bud was closing missions week?” She smiles and says, “I do.” I say, “That is all I have been thinking about for two weeks in every minute of every day. Michelle, the Lord is asking us to answer the question and we have to answer it! I don’t what that means or how we do it, but we have to answer this question.” She looks at me and says, “I’ve been thinking the same thing these past two weeks.” We laughed at each other, and we said, “What do we do now?
We met with our pastor, which lead to us going on a short-term mission trip to Chile. Our environment when we arrived was pretty raw compared to the Pacific Northwest, it reminded me a lot of inner city Los Angeles – very urban, lots of graffiti and stray dogs everywhere. I looked out the window of the rundown school bus we were on and said (in my head), “Lord if you’re trying to show us international missions is what you want us to do, I’m not sure this is what I would be showing Michelle.” The moment I finished that thought, Michelle turns to me and says, “I could live here.” I said, “What?!” She said, “I’m just really feeling a peace about this.
The big question for me was, what would I do in the mission field? I wasn’t a pastor, and most missionaries were pastors and church planters.

Your faith can’t be something you use every once in a while, it has got to be who you are.

Risen Magazine: So when you decided to leave Microsoft how did that go down?
David Dwyer: We had just launched Windows Vista when our family went back to Chile for the second time. The missionaries there had told us they wanted to talk to us about some opportunities. We discussed the opportunity which was something we could do very easily because it involved hosting teams and doing technology. So when we got back to Seattle we were trying to figure out timing to leave.
After a key product launch, your bosses are carefully monitoring the status of their key employees – the ones they want to be sure to retain in the group as opposed to moving them to a different part of the company, or worse yet, to another company. Since I was the only one in my group who did what I did, and was the first Chief Storyteller in the history of Windows, I was one of the ones my boss wanted to keep in the group. My General Manager’s boss, who would have had no reason to know me except that I had won a couple of awards when he had started (I was the only two-time winner, which is why he knew my name.) So J.B., my GM, goes into a meeting to report on the status of his group to his boss [and it goes something like this:]

JB:Hey, we are losing Dwyer
Boss:What! How are we going to retain him? What’s your tactic? Are you using stock options? Are you going to do a raise? What are you going to do? You have to convince him this is the place to be.
(So JB gets an earful in what he already knows)
JB:It doesn’t matter what we throw at the guy he isn’t staying.
Boss:Don’t even tell me… is he going to Google?
JB:No, he’s not going to Google
Boss:Don’t tell me he is going to Apple?
JB: [Laughing] “No he’s not going to Apple.
Boss:Well who are we competing with here?!
JB:We are competing with Jesus Christ.
Boss:Aww man, we’re ——!

Risen Magazine: Wow. That is a hilarious story! They knew they couldn’t compete with Jesus Christ. How then did you find your role as a missionary?
David Dwyer: When I am asked to speak I make sure to say the following… “I believe that when we come to the realization that everything we have, everything we have ever done, and everything we are is from the Lord, and we take the big step of truly giving it back to him, for his glory, then we will live transformed lives for the glory of the Kingdom of God.
That’s what we did when we went to the mission field. We said this is all yours [God] and we stand here today giving it back to you so we can truly find out what it is you want to do with us. He surpassed any dream we could have ever dreamed by taking us to Chile. We are so humbled and happy to experience this journey with the Lord. He prepared us especially for this. I believe that everything I have ever learned in the professional world has helped me as a missionary. It’s a bit different going to the mission field in your mid-40’s.
We ended up in Chile working as the hosts and planners for short-term teams that came to work with our host mission IberoAmerican Ministries at our church plants in Chile, Ecuador, and Peru. Our entire family participated in that part of our calling by helping the teams and translating. In addition to this work, I personally re-worked the web presence for the ministry and do a lot of tech support.
About three years ago, I was chatting with my best friend, Roberto, in Chile who heads up our futbol ministry at our church and asked him what he thought about taking the ministry outside of the church. Long story short, that led us to begin work in Chile with Ambassadors in Football– a global soccer ministry with more than 20 years of experience. It became evident very quickly that this was something that I needed to lead, and now we do work with children and have a prison ministry that is really taking off in Santiago. Roberto heads up our youth team that participates in tournaments and the coaches in our kids programs. Our dream is to see the work continue to grow throughout Chile and into other parts of South America where Ambassadors doesn’t currently have futbol ministry.
A cool side note is that I am also using all my branding, technology, and even publishing experience with Ambassadors at a time when the Lord brought us all together. So even when you pursue your calling, don’t get too comfortable or you’ll miss other opportunities that the Lord continues to prepare you for. I was 47 years old, living in the mission field when we were then called to begin a new futbol ministry. It’s a journey we are on…not a destination we have arrived at.

Exclusive interview originally published in Risen Magazine, Summer 2013



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