October 2, 2019

From Simi Valley to Silicon Valley: Stephen Gillett

Today’s episode is with Stephen Gillett, the author of From Simi Valley to Silicon Valley. Stephen is an amazing guy, he is not only the co-founder and CEO at Chronicle, which is an alphabet company born out of X, the moonshot factory, he is also an executive adviser to the CEO at Google. He is one of the youngest CIOs at a Fortune 500 company in history, and he was responsible for leading the tech transformation at Starbucks under Howard Shultz.

He’s also worked directly with Bill Gates as the CIO at Corbis, and he was the president at Best Buy and the COO at Symantec. As you can tell, he has had an astonishing career, but what I love about Stephen is that he wrote this book for his kids. His eight kids. In this book, he shares the lessons that he learned and the remarkable journey that he’s had.

If you want to succeed in business and in life and you’re focused and committed on having a remarkable journey yourself, this is the episode for you.

A Surprising Beginning 

Stephen Gillet: It was the late 1990s and I was a member of the University of Oregon football team. I had been invited to join the team, we had a great year, we were just coming off the Rose Bowl and the internet was also taking off. This was the late 90s, and I had this restriction where I couldn’t be the athlete and have a job. While I was at school I wanted to start working in this technology space. I ended up making an important decision in my life, which is I quit the University of Oregon football team and took a job as a business machine’s associate at the local office depot in Oregon.

That was a great job. I used to set up computers, troubleshoot people’s laptops, and help them with their dialup issues, which was the way you connected to the internet back then. People would come in and ask for help or memory upgrades, and it was a nice setup. We used to have this customer that would come in every couple of days and he would always ask for tech support, but he would never pay for anything. The group of us, the team, started to shun him a bit, but I always helped him because he was an older guy and he reminded me of my dad. I helped him out, he never paid for anything, and he always said thank you. He was nice.

We thought he was living in his car, that was what our impression was. Then one day, maybe a year into my job and having done this for 10 months or so, he comes into the store of Office Depot and he’s dressed in a suit and he has his hair combed and he has a wife for heaven’s sake. We were all shocked, and he walks to the back office of this Office Depot where the manager sits. About 30 seconds later, I get called on the overhead speaker. “Hey Stephen, can you please come to the office,” and I was worried they caught me taking some printer paper or whatever.

I go back to the office in this Office Depot and there’s this customer. He sends out the store manager and now I’m standing in this room, this little office–it’s hot, he’s got an old desk and this customer says to me, “Stephen, do you have a few minutes?” I said sure. He says, “You know, you’ve been helping me out with all my technology needs over the last year. I really appreciate it. You’ve never asked me who I was or what I do.” A 20-year-old Stephen says,  “Who are you?”

He says, “I’m the administrator of what will soon be a part of one of the largest hospital chains in the pacific northwest, from Oregon, Washington, Idaho, and Alaska. We’re building a new hospital just south of where you live, and I’d like you to come be the IT coordinator and run IT for this hospital.”

I’m shocked because one, I’m 20 years old, two, I’m a student and three, I said, “John, I know a lot about fixing your laptop and your printer and maybe helping you connect to the internet, but I don’t know anything about this IT stuff.”

He said to me some words that really stuck. He said, “You have the ethics and the personality that I want working at this hospital and we will train you on the rest.” And then he takes out of his pocket, a little checkbook and he writes a check for, I think, $400, which was a fortune for me then.

He says, “The first part if you accept this job, is to go out to the furniture section of your Office Depot and buy yourself a new desk because you’re going to have a little office down there.” I adjusted my schedule, I quit Office Depot, I called my wife, back then, my girlfriend. We used to pay by the minute on your cellphone, so I talked really fast and basically got the update in a minute.

I quit my job, became the IT coordinator as a 20-year-old kid at this hospital, and true to his word, he brought in the experts on Linux and Windows and networking, and for my final two years of school, I got trained up on all the most sophisticated medical IT systems that this hospital had to offer. It was the height of the .com boom in 1998 and I was recruited directly out of college. My wife was as well, and we moved to Silicon Valley.

Being nice to this guy, not knowing who he was, not really expecting anything from him, turned out to be one of the most unexpected detours of my life and career, that set me on a path that would materialize over the next 20 years.

A Book for His Children

Charlie Hoehn: Wow, Stephen, you have an amazing background, and you’ve had a really incredible career, of course, but we were talking before we started recording, about why you decided to write this book, and who it was for. Can you give a quick explanation on that?

Stephen Gillet: Sure, I’m married to my high school sweetheart. I’m 43 years old, and we’ve been together for 26 years, so you can do the math there. We had our eighth child, yeah, that’s eight. Not a mistake there. After being told for many years, you should write a book, you have a lot of this interesting stories and experiences, I kind of passed on that, and never really was inspired to do it. But when I had this eighth kid, I knew this eighth kid was coming, even after the first seven, I thought, how do I capture this unexpected life–the first 43 years of the ups and the downs?

You expected the unexpected, the detours and all the lessons of those years, in a book or in a format as sort of a time capsule, so that these eight kids can have it for the rest of their lives. When they get married and have kids and their families, I always have the story of this period in our life and our family’s life. I wrote it with that in my heart and that in my mind, which is I wanted to gift it to the kids.

As I did that, as I wrote it, as I edited it, as we got editors to help publish and edit and do all the things that you do in the book writing process, I was encouraged strongly to make this book more available. While they were honoring the original intent of it being for my family, the people that were helping me felt like there was a lot of life lessons in here that could be much more valuable to the broader set of people. I agreed with them and now here we are, making it more broadly available.

Charlie Hoehn: I love it. It reminds me of the very first episode of this podcast that we actually did with JT McCormick, who originally wrote his book for his family as well because he wanted them to know where he came from, being the son of a pimp and the son of an orphan mother, and he had no idea where his last name came from, that sort of thing.

I’m curious for you, what was the journey like for writing this book for your family. How did you decide what you wanted to tell them, what you wanted to leave out–what was it like?

Stephen Gillet: You brought up JT, who was one of the first people I talked to. My original decision point was, do I write one book about family, one book about work, and one book about gaming or all the things? Do I do one about business lessons and life lessons? I realized that if I’m telling the story and if I keep my message true to the people that it was intended for, then it’s really going to be a mix of all. Because if I try to parse out work, life, hobbies, serendipity, expected, unexpected–you really deconstruct the actual life that I’ve lived so far.

The original direction that I decided on was how do I weave it in a way that represents and reflects the way I actually lived it? Which means, it’s a little bit of everything in a storytelling mode that kind of moved and weaved in and out of all the things that happened in somebody’s life. I think it’s the combination and the constitution of all of those elements of one’s life that I really tried to bring forth in the book.

Influential Innovators 

Charlie Hoehn: Excellent. Speaking on behalf of maybe the listener who wants to get into the meat of the book, you’ve worked with amazing people, Bill Gates, Howard Shultz, a bunch of other influential innovators. What are some stories you have from working with Bill Gates for instance?

Stephen Gillet: Yeah, Bill Gates–I’ll take you back to 2006 when I met him. I was the head of IT, so the head of technology. Microsoft had been the dominant IT company in my personal and professional life for the 20 years prior to that.

Here I was, not only being recruited to go work for a company that Bill Gates owns but then to have the opportunity to meet the man and meet the legend. This was in Seattle. I was working for one of his smaller companies called Corbis, and we could talk about what that is later. I started in May of 2006 and in June or so, about a month later, I’m going to have my first meeting with Bill Gates because he’s the only board member. He owns the company 100%, and I started to hear stories that the last head of technology which we call a CIO, chief information officer, the last CIO only lasted until that first meeting with Bill Gates and didn’t continue after that. There was a lot of energy, a lot of anticipation around who is this new Silicon Valley guy who had just left Yahoo? How is he going to do with Bill Gates?

I was getting a lot of advice–people telling me, don’t do this, do more of this, don’t look this way, don’t say this word, don’t drink this beverage. I got over-coached. I thought, look, if I try to be something I’m not, if I try to fake my way through this first meeting, if I try to overly orchestrate who I am as a leader and as a person or how I make decisions or what I’m here to do in his company, he’s going to see right through that, I’d expect. I have to be myself, so I pushed aside all of that feedback.

One of the things I had to do was a PowerPoint presentation and the first slide had to introduce myself. The first draft of the slide was all my resume, and my degrees and I looked at that and I said, “Who cares about that? You think Bill gates is going to care what my grade point was or what project I worked on at some company?” I said, “I’m going to introduce myself in a new way.”

Back in that same year, I had been named one of the top guild masters in World of Warcraft by WIRED magazine, so there’s a big article about me floating around. I decided to put on my first slide of my PowerPoint and my first meeting with Bill Gates–my introduction slide, but it wasn’t an introduction to Stephen, it was an introduction to my gaming character in World of Warcraft. My paladin.

I had a picture with flame coming out of his eyes and this huge sword that was glowing blue and all the stats of everything that our guild had accomplished. Then I went into who Stephen was.

Fast forward a month, I’m sitting there at the Microsoft Campus, we used to do our board meetings over there, and Bill Gates is on the other side of the table. I’m nervous, I felt like I was a duck. A duck in the sense that above the water, I look calm and calculated and deliberate, but below the water, man, those feet were pedaling. I sit with Bill and my turn comes to introduce myself and go through my PowerPoint, so I pull up my slide and he’s looking at it and he’s looking at me and he’s looking at it. I’m talking about World of Warcraft and gaming and questing and our achievements, and all that stuff that brings the online world into that room.

After the intro, he says to me, “You know, I’ve been reading a lot about these guild masters and it’s nice to finally meet one.” That moment set off the next several years, in which I met with him nearly every month, usually for multiple hours, and had one of the most exciting and interesting and humbling chapters of my professional career.

Charlie Hoehn: That’s a great story. What surprised you about working with Bill Gates, what kind of things did you learn from him that maybe a normal person wouldn’t do?

Stephen Gillet: Well, one, he is very deliberate in the kinds of questions he asks and he has this ability, in my experience with him, to create a kind of a mental model or a mental construct of the conversation that we’re having, and move it around in his mind. When there’s a weak point in that construct, usually that’s the question he’s going to ask you.

You learn very quickly, when you work with him, don’t fake it. If you don’t know something, just say you don’t know. Don’t talk too much about something that you don’t feel that you have a deep competency to talk about. He’s very nice–he was very nice to me, and we ended up having a great relationship over those years. He really was going to point out and push on the one thing in your presentation you hope nobody asks about–he’s likely going to be the one to ask.

Charlie Hoehn: How were you transformed in your work with him?

Stephen Gillet: Well, it’s interesting. If I can set the stage a bit more, you have Bill Gates, he’s at Microsoft, he’s the chairman, I think, or maybe just the final year of his CEO. He’s also running the Bill and Melinda Gates Foundation, which is his philanthropic. And then he’s got this little tiny sibling in the middle, called Corbis, which is doing online photography. All in the historical archives, in black and white photos, and making those available to the world.

Often times, I found that the technology that Corbis needed to adopt or needed to buy might not necessarily be the stuff Microsoft is selling. During my conversations about technology strategy or technology procurement, what applications we buy, what services we buy, oftentimes, I’d get in very detailed, very heated, not bad, but just very heated technology conversations about the future of Corbis as IT strategy. Sometimes I would not converge with what Microsoft was doing. Sometimes it would.

I learned over those years, when you have that confidence and you have that ability to understand these capabilities in terms of technology or business processes, and you’re sitting across a table from Bill Gates, one of the most legendary leaders and this is overall but in that space in particular, is first, a sense of humbling and intellectual humility, but then you start to be confident and he pushes you and he molds you and he shapes you to really have passion and belief about the things you’re asking.

I think that would be the lesson I took after those years working with him.

Charlie Hoehn: What did that look like? Him pushing you, molding you–tell me more.

Stephen Gillet: What would happen is we would go in to a meeting and we’d have a particular technology we needed to purchase or an architecture we needed to design, and you would walk right into what I talked about–that mental construct where he immediately gets all the elements of what you’re saying, you don’t have to tell him things twice. The conversation then goes to, in some cases, why are we building it this way and are we using the right services and technology solutions if indeed, that’s the way we want to build it?

Sometimes, most times, he advances the dialog past your understanding of it. Meaning, you leave learning a few things that you didn’t walking into that room. But sometimes, you’re in the right, and you have got to push back and when you push back, you’re not going to be received by a docile voice, you’re going to be challenged as well. Those conversations I found the most interesting.

This all ended up, in the end, creating much better outcomes for me, for the company, and for him in the kinds of solutions that we were bringing to bear for those particular sets of technology issues. Over the two or three years that we were having those conversations was a very powerful influence on how I then, later in my life and career, interacted with people on my own.

Starbucks Technology

Charlie Hoehn: I want to dive deep into each topic, but I know I have to jump around a bit. Let’s shift a bit to leading the technological transformation of Starbucks under Howard Shultz. What was that like? Tell me some stories?

Stephen Gillet: If Bill Gates influenced me on how I think of myself as a technologist, as an IT professional, and as an architect, Howard went above and beyond that in many ways. He taught me, over the many years I worked for him, how to lead with the humanity of your leadership and your person, your being.

I remember distinctly in my years with him, lessons learned that we can talk about, but if I go back to the first chapter when an article had leaked. Howard Shultz was the author of a memo that leaked about how Starbucks had lost its way. I think it was late 2007.

He wrote this very compelling memo on how it had lost its original third-place intent, which is between home and work you have this third place. I was at Corbis, and I read this memo in the press too. I ended up getting connected to him because he ended up coming back as CEO and started to form his executive team. Through a very long and difficult process, I ended up in the final interview with Howard Shultz before being considered their chief information officer. The same role I had at Corbis working for Bill Gates would be the same role I had at Starbucks.

The interview with Howard was mostly about my experience having visited a store before the interview. So, my assignment was, I would visit a local Starbucks in Seattle and I would come to the interview with Howard and be able to talk about what I observed in that interview. I had gone to my local Starbucks, and I wasn’t even a coffee drinker at the time, I had never had a latte, and I tried everything on the menu over a few day period–chai teas and lattes and Americanos and cappuccinos.

I came prepared and I wrote a bunch of notes down about what I observed in the store. When I got into the meeting with Howard, the ice breaker, the first part of the conversation was me gearing up to tell him what I saw on my visit to my local Starbucks, and he stopped me from talking and he himself talked about his experience at his local Starbucks.

He did it in the most beautiful founder-esque CEO way, about the environment and the smell and the sense of community, and the wonderful wood grain tables that brought people together, and it was just beautiful. Here I am shrinking as he’s talking, because I pull out my paper and it’s about you know, bad WiFi and not enough plugs, and the bathroom was kind of dirty and it smelled like burnt cheese because someone was cooking a sandwich.

I thought, after this long grueling set of interviews, that I just bombed with Howard. We proceeded to talk for the next couple of hours about my experience, and what I had seen and what I’d done, and how I make decisions and what kind of leader am I–how do I encourage others to be their best? I ended up getting the job, and for the next four or five years, he shaped me, he originally took a bet on me that my resume never would have supported.

I didn’t know anything about retail, really, and I wasn’t a coffee drinker but because I had this technology background and he was willing to take a bet on me, he single-handedly reshaped my life overall, and the next several years at Starbucks, he really taught me how to be that kind of a leader.

Charlie Hoehn: So, you say he reshaped your life, tell me more. What happened next?

Stephen Gillet: Yes, I joined the company. I went from being a midlevel manager to now being one of the executive team members of one of the most iconic companies in the world. We instinctively knew and he instinctively knew–I’d give him the credit for–he knew that when Starbucks was going to go through a transformation, technology needed to be at the core of enabling that. So, he wanted somebody who had maybe even a generational proximity to the way current technology was being used in the world with consumers, with corporations, and with the back-office stuff.

In the situation where my resume and my experience in retail would never have justified getting that job, the fact that he brought me on and didn’t just leave me to the masses to figure it out, but coached me and shaped me and challenged me and taught me. He refined instincts that I may have had or may have used to say, when you are leading people, he said to me once, “The guy who sweeps the floor should pick the broom.”

Meaning don’t be overbearing, don’t come in with all the answers. Know that everyone we work with has, in many cases, a family or a spouse or a partner or someone they love, and this is the humanity of the company. Never lose touch, as you are making decisions that will impact the company on the technology side, to never lose touch with that humanity that is thriving across all of these countries we operate in, and all of these people and partners that we employ.

That really stuck with me in a way that is truly mission-driven, and then we had a wonderful set of years together.


Charlie Hoehn: You know it is something I have noticed in flipping through your book is and you mentioned this on the cover as well as the word serendipity keeps showing up, would you say that serendipity has been the driving factor in your career in your life?

Stephen Gillet: I wouldn’t say it was the only factor, but I would say over the last 20 years of at least my professional career, but it even goes to my personal life, there have been these moments–whether it was Office Depot and the serendipity of this customer being this executive who offered me a lifetime opportunity, whether it was meeting Bill Gates and going from a traditional resume to talking about my gaming and it happened to be the same month that article came out about World of Warcraft, whether it was Howard Schultz and him releasing that Starbucks had lost his way and that technology happens to be at the core of what he felt would help transform the company, and I was available there in Seattle. There are a whole set of moments or short periods where serendipity, timing, luck, and grit converged to totally change the trajectory of my life and career. That was why I put this on the cover because I try to capture and dissect and analyze those moments, now in retrospect.

When I get asked about, “Well, how did you get to where you are? How did you end up doing family and work successfully?” These moments kept coming back that defined key periods along the last 20 plus years what ultimately shaped what I am, and who I am, what I’ve done today.

Charlie Hoehn: Wow, and your career, your life, kept advancing. You went on to become the president of Best Buy, correct?

Stephen Gillet: Yes, so after we were going into our fifth year, and I will talk about the details of this transition of the book, I ended up joining Best Buy. At this point, I had a really good run at Starbucks. My life had been changed by Howard and the culture and mission and what we did together as a team over those years to really get the company back on track. I am humbled to say I had a small part in that.

Best Buy, from what I know, hired a consulting firm. They were going through some difficult times in 2011-2012 and they had hired a consulting firm in order to, “Tell us the companies over the retail landscape that have had a successful transformation in which the use of technology in digital was a key catalyst,” and so the researchers went out and found two companies who were at the top of this, Domino’s Pizza and Starbucks, and so they said, “Find us the person in Starbucks who did it.”

I got the call one day and that started my chapter at Best Buy as the President of digital marketing and business operations. They brought me in to be that next-generation voice in the leadership team to help the company to move and compete in the new era.

Charlie Hoehn: Before we talk about your time at Best Buy, what were the big accomplishments you had from a technological standpoint at Starbucks?

Stephen Gillet: So, prior to Starbucks, I had a career in IT in Silicon Valley. I worked at CNET and Yahoo. I was a very accomplished, confident, and experienced internet technology IT executive.

Starbucks really refined the other part of my career. So, while we had great technology and great digital, I also learned how to be a better leader. I learned how to bring those elements into my leadership style, and I would be remiss not to give kudos to all the tremendous people at Starbucks in marketing and digital and IT, who I happened to be the ambassador for, but that collective team, over that four or five year period developed some of what, I would consider and I think the world may consider, some of the most innovative technology solutions for a retailer. It involves a world-class, highly successful loyalty program and moving to free WiFi, and how you get people on WiFi in one click, and fast and high performing in all of your stores.

How do you get mobile payments set up? A lot of people pay with the devices that they are bringing into the local Starbucks. Then there was all of the backend IT inventory management, labor scheduling, store point of sale. Most people think that, “Wow you went to free WiFi and mobile payments and loyalty,” and that is all great and transformative, but I would argue that some of the most transformational IT work that was done at the company has never been written about in a magazine or showed up on the cover.

It is all the backend IT that allowed the company to operate and be more efficient and connect with the users and with internal employees in new ways. I believe that is what gave us the currency, that kind of capital to then go do these consumer things that everyone knows of today. If you just tried to jump right to the digital or the consumer piece without giving their back-office structure, I don’t think it would be as much of a success today. I think it is in the combination of those two. So, all of that had been done by the time I got to Best Buy.

Charlie Hoehn: When you came to Best Buy, what type of work did you start on? Were they wanting you to do backend stuff for them as well, or the front-end consumer-facing?

Stephen Gillet: Well, for the first time in my career I stepped out of just being the CTO or the CIO with technology, and now I was running it. I had a CTO, I had a CIO, but I was also running marketing and supply chain and HR and all the other functions of a company. The CEO at the time would have me over for dinner when he was recruiting me, and I had this notion that I wanted to go somewhere where I mattered.

If I had gone to another Silicon Valley company or a big successful consumer company, maybe my work would get noticed, but at Best Buy they were at this critical junction where they had spent a decade competing against other retailers like Good Guys and Future Shop and Circuit City, and they won that war. They won the war of consumer electronics retailers. Their goal was how to get someone to leave their house and drive past a Circuit City and come to Best Buy. They won that war.

Now, they were competing against Amazon and Apple, and not even having to leave your house–totally e-commerce and mobile commerce. Their whole system and the whole structure was geared around the physical retail world. That is the serendipity that brought me to their attention, which is wanting to bring in a leader who could help them transition from the analog bricks and mortar world, which was still important and critical but also compete in the digital online world. That was the narrative of which I ended up joining.

Charlie Hoehn: Now with each of these transitions, it really feels like you are leveling up each time in some way, shape or form. How did it feel transitioning into these new higher roles? Going from CIO to CTO to president is a huge deal. What did that transition feel like for you? How did you mentally get yourself in the right place?

Stephen Gillet: Well, if I had tried to go from Yahoo to that or from Corbus to that, I think I would have had a more difficult time. I have to go back to the time I spent working at Starbucks and frankly working for Howard. Over those four or five years, the confidence and the learning and the observation and the chance to be supported in what I was trying to do and what the team was trying to do, I think gave me a momentum and a confidence that I didn’t have in the earlier years.

I was much more insecure about my business understanding and my financial understanding. I ended up getting an MBA that helped that along the way, but it was at Starbucks and particularly it was with Howard, that polished my uncertainties and my insecurities. It taught me how to be that kind of a leader that would allow me to go on to be successful. It was that momentum that I had going into Best Buy that I think gave me the ability to view their world and what they needed to do with that same sense of confidence and humility, but with the understanding that we can do it and we can compete to be successful in the new world.


Charlie Hoehn: So, tell me a story about your time as President at Best Buy. What stands out?

Stephen Gillet: Well there’s two. One, it was a short chapter and I will give you a little bit of the flavor for that, but the full story is in the book. The first thing that happened was they had reached out to me, and I was entertaining external opportunities while I was at Starbucks, for various reasons that I outlined in the book. Best Buy called and I said, “Best Buy, wow, you are going to have trouble. I thought you’re going under.” I didn’t know what was going on.

So, I met with their team, and I met with the CEO. I had a great dinner here in Silicon Valley. I went home that night to my wife, Asia, and I said, “Hey, I just had that meeting with Best Buy, and it was wonderful. I didn’t realize it was a Fortune 50 company and that they were number one or number two in every important consumer electronics product, and they had 50 billion in revenue,” all of these things I didn’t know about the company that had come out in this meeting.

I am going on and on about this and my wife is just staring at me. I remember my wife and partner just staring at me. I told her I wanted to go out to Minnesota and really learn more. She said, “There is only one question I want you to ask while you’re out there, which is, is there anything worth saving? Is there anything worth saving at that company or are they just a person or a company of a bygone era that is now moving online?” and that shocked me.

I had never asked a CEO, “Tell me why you’re worth saving.”  It was all about the company and the business and the products. It was Asia who gave me that laser beam focus and said, “If you go out there, and I am supportive of you going out there to talk to them more, go figure out if their company is worth saving. Because we just went through this in the last several years in Seattle. It was worth doing and we are happy, but we don’t want to go to that again if at the end it is with a company that no longer needs to be here.” I got armed with that and flew out to Minnesota and had quite an interesting week out there.

Charlie Hoehn: It led to you being the president at the company, so obviously there was something worth saving there. There is so much I want to cover, Stephen. You have such an incredible story. What I find most incredible about you, of course, is the fact that you have eight kids who will now have a book that they can learn about their father, and all about everything that you have been through. What are one or two lessons, if you have to leave everything else out of the book?

Stephen Gillet: I think looking back now, all during that it may have been more difficult and more emotional, but from some of my best-planned ideas, I have some of the biggest adversities. Some of my most unexpected moves, I’ve had some of the biggest successes. I think it is the moments in your life where you allow unexpected things to happen, and you take some risks, and you make decisions based on the best information you have at the time.

I think that on the professional side, one of the lessons is be available, be open, look around corners, try to let unexpected things happen, and push yourself in situations where these things can happen to you. The other part is about the family, especially in this era we live now, it is very odd for us anywhere, especially in Silicon Valley, to say we have been together since high school and we have eight kids. People are like, “What’s wrong with you or something? Is there something we need to know?”

Don’t sacrifice family and children and the moments that make that special. There is one story where I was in the middle of my heyday at Starbucks. It was probably 2009 or 2010. We were going through a lot of changes and challenges and everyone was saying that we were going to fail. It was a really stressful time. I remember sitting in my office in the building in Seattle, and I was taking lunch. I opened up the New York Times.

They had this full spread online article and the moment of this article and the timing of this article is perfect, serendipity again. It was a summary article about this Hospice company. Hospice is an organization that goes into the home and takes care of people as they’re near the end of their life, it was very sad, but you know we all deal with that. This company I think was 100 years old. So, it was like 1909 to 2009, or something along those lines.

For the first time ever, they released the same two questions they asked people as they are about to die: What do you regret most? What do you wish you did? The same two questions. They released the answers of the last 100 years of what people said. I remember that, in the middle of this maelstrom in the business world and family and everything going on, silence as I read these answers.

You could click on 1952, and here are the answers. 1928, here are the answers, 2005 here are the answers. When they asked people on their deathbed, as tough as that sounds, what is it that you regret most? What is it you wished you did more? It was all the things I tried to live by and try to live by even more since then. It is things like–I wish I had buried the hatchet with somebody who I had strife with. I wish I had that second or third child. I wish I had gotten reconnected with my faith. I wish I had called my mom because we weren’t talking.

It is the same answers, the human condition that spans 100 years in a way that is eerie. It is the same answers and the same categories, whether it is the high-tech industrial age we live in now, or it is near the turn of the century and that hit me like a brick. Never lose focus on what’s the most important thing in your life, which for me is family and love and children, and it is in that that I tried to write the book. It is in that that I would give them the lesson of how to live their lives.

Charlie Hoehn: I have a few more questions for you. The first one is what is the best way for listeners to potentially either follow you or even connect with you? Say they like something from the podcast or from your book and they want to share their thanks, what is the best way for them to do that?

Stephen Gillet: So, I included that in the book. I have an email address, [email protected]. I am on Twitter @stephengillett. I am on LinkedIn–I am everywhere that you need to be on social media. If you want to talk or chat or connect or tell me how great something is or how bad something is, you can email me. I think that is the best way.

Charlie Hoehn: Excellent and the final question I have is what I ask every author, give our listeners a challenge. What is the one thing they can do from your book this week that will have a positive impact on their life?

Stephen Gillet: I got to ask this question when I wrote the book, which is, who is it for? Is it for business professionals, is it for students, is it for gamers, is it for parents?

So it is the ups and downs of life but look through that when you find one or two things, whether it is about a career move or being a parent or being a gamer or making a big and tough decision or going through adversity as a family, that you talk about that and you keep a sense of optimism that no matter what life throws at you there’s always going to be a dawn. There is always going to be a way for you to overcome that.

With the right people and the right mindset and the right optimism, as far as what I have seen, you can accomplish and overcome any adversity that hits you in life. I think that would be my message to them.