So, Jon Glasser, I was reading about your story, and I was fascinated, and it reminded me of some things that happened in my life. And that's why I wanted to get you on here because I wanted to understand what it's like for you when you were growing up, the fact that you went to clown school. I don't know if I've ever talked to anyone besides a clown, how it was clown school and how you leverage that in life. But let's go all the way back to when you were in grade school.
Okay.
Something happened to you that I imagine you'd say really changed your life. What was that like?
Well, it's a fair question. I grew up in the San Francisco Bay Area, and my father was consultant, so we spent a couple of summers in Hawaii while he did work. Spent my first freshman year in the British boarding school because he was stationed in Düsseldorf, et cetera. We did some movement around, even though based in the Bay Area. My mother was very bright, my father was too, but very eclectic and unorthodox, and she encouraged us. I did trail crew during the summer and a variety of other things like that. I also went to school in a Jesuit high school, and the Jesuits were remarkable. They taught you to challenge, challenge the church, challenge the Bible, challenge, think about it, challenge. I challenged stuff. So came up with this, maybe not a rebel, but certainly quite willing to be unorthodox along the way. And that led to, I'm sure some of the things we'll talk about, hitchhiking all over kingdom come, getting tossed out of high school, going to client school, etc. But the willingness to be unorthodox and to try things that are not conventional. It's not really risky. I did try to climb Mount Everest.
But nonetheless, things that are a little bit different.
Hey, I like that. It seems like the people that really change the world are the unconventional thinkers. You can't think inside a box and make a big change. I dropped out of college.
Oh, did you?
What you did, I think, is even more fascinating. Tell me about that.
Well, three buddies wrote an underground newspaper called the Bellermann Free Press. It was Cardinal Robert Bellermann, the school was named after? We each wrote a column, and it was about drinking beer and taking advantage of 16-year-old girls. We knew all about drinking beer and had only dreams of girls. That was just not something we were not familiar with at all. We made the mistake of publishing on the afternoon of Parents Night. Mom and dad came down to visit the priest, picked up a copy of this thing, and the roof blew off. Oh, my goodness gracious. It's raunchy stuff. What's going on here? The following morning, we were in front of a tribunal of Jesuits. One by each, my three buddies did the mea-kupa, which is Latin for I'm sorry. I was the last one in. I got in there and there's a little stage nine Jesuits, the principal in the middle, and the principal said, Mr. Glasser, are you aware of the damage done to the school and how this has countered everything we're trying to teach you, find a outstanding Catholic young man. And I got mad, and I said, I'm not sorry at all.
As far as I'm concerned, the Catholic Church is a criminal organization. I said, For thousands of years, you've suppressed science, conducted unjust wars, and I think, frankly, the position on birth control is killing millions of women and children. And I was proud of what I had done, and I hoped it would be the first in a long series of criminal activity on my part in keeping with the tradition of the Catholic Church. And then I just got... I had my throat slit as a result of that. So I got mad at them. I pushed it a little too far, a little too hard. There you go. I wound up in the middle of my junior year out of high school and went off to college because I didn't really want to go to a different high school for my last year.
I mean, wow. You stood your ground. I can tell that you stood your ground. I mean, I don't think most people at that age would have said the things you said in that environment. Like your friends at that time, they told them what they wanted to hear so they could continue. I mean, you break the mold. So then you go to clown school. What the heck is clown school What the heck is Clown School like?
Well, I think from there I went to Duke because my freshman year as a British Board of School, I got enough credits to get out of it. And so I went to Duke. And again, I wanted to go as far away from California as possible. So obviously, North Carolina is pretty far away. And we'll get to the Clown School, but there's some intervening stuff there. So I was a math major. I really like math. It's also where I met my now wife. Been together for 51 years. She and I were in the same dorm. But anyway, at the end my senior year, everybody seemed so certain about their lives. I'm going to be medical school or law school or business, whatever it is. I didn't know. So I took the GREs, the GMATs, the LSATs, the NCATs, the actual every exam I could think of because I figured, I'll never be this smart again. And they're good for five years. And I got out of college and I went to work at Pizza Hut. And then after a couple of weeks of that, I said, Well, that's cool. And then I went to work in Alaska in a salmon canary in our Native American village called South In August, I had six grand in cash, more money than ever had in my life, and nothing to do.
I hitchhiked from Fairbanks, Alaska to the Panama Canal through North Carolina. It took me six months along the way. I finally got to Panama and said, I'm tired of hitchhiking, and I miss this woman who now I'm married to, and I'm going to go back to Carolina to be with her. While messing around looking for a job, I said, I'll go to clown school. I'll learn how to be a clown. I still have my makeup in the attic. I could still do a passable juggle, have a couple of stupid Cubscout tricks to do, etc. But it was largely because it seemed like something to do. It might be interesting.
For some reason, I couldn't help but think of Forrest Gump. I don't know why. He runs across. It It is very interesting. Hitchhiking was a thing at some point. It's really hard to imagine. Hitchhiking was an actual way that people got around because obviously for many years... I mean, still, it's illegal and people don't do it, but there was the dangers, I think, of hitchhiking. What was it like back then? I mean, Alaska to Panama? I can't even imagine that.
Well, I mean, there's a route. You can go from Anchorage up to what they call Tope Junction, catch the Alcan, Alaska Canada Highway, down to Seattle. From there, you hitchhike out to Spokane, drop down to Denver, take I-80 or I-70 back to North Carolina, I-40 back to California, and then down the Pan American Highway until you get to Canal. Then the road stops, et cetera. But you have to be smart. Even then, there were some scary people and some scary times. What I would generally do is hitchhike out of truck stops. I'd basically go up to someone filling their tank, and there'd be one of three scenarios. It's either mom, dad, and the kids. Basically, I'm John Glaster. I'm a Duke student. I just had a summer job. I'm heading back east to visit my girlfriend. I'm a clean-cut all-American. They either bought that or they didn't. Or it was a guy with a gun rack and a flag, and basically, I'm bouncing around between jobs, just doing some work up in Alaska, I didn't need to see some other work. I'm basically a blue-collar working guy. Yeah, they're my guy. The third was a bunch of guys with long hair in a microbus and say, Hey, man, got any weed?
I got some money for some weed things. That stuff here. That didn't always work. The truckers wouldn't touch you because there was a liability issue. But first of all, I'll give you some advice. Never hitchhike at night because the Wacko element is up. Never hitchhike within 30 miles of a big city because you want long rides. You want 400-mile rides, not 10 down the road, plus the Wacko elements higher as you get closer to the city. So out of the truck stops during the day and you're looking for the big several hundred mile ride, and sooner or later you'll get there.
I mean, soon there'll be robotics, robot cars that will just drive us for very cheap, so we won't have to even think about hitchhiking. But I did a week on the Appalachian Trail when I was around the same age, and it really taught me a lot of different things. It was a very unique experience. I wish I kept... I could only last a week. I couldn't But at some point, I did think I should have kept going to finish. Did you learn something about yourself or just about life in general while you were doing this?
Well, I think one of the things I learned is at the time, I was really anxious that everybody else, my colleagues, were off to careers, and I was just floundering. And what I learned is it doesn't really matter. I mean, there are lots of ways to make a great life and accomplish a lot, but the fact that you're not traditional, it's okay. But I learned that. The other is you got some really cool rides with some really cool people. And they may have been farmers or mechanics or hairdressers, et cetera, but they were smart. They had sophisticated worldviews. I remember one particular ride I got was going from Seattle to Spokane. It's about 400 miles. I got a ride with two women whose husbands were truck drivers who drove back and forth Seattle, Spokane. That was the route. They would drive the same route, and on the CB radio, chatted up with all the truckers. Jokes and gossip and all that stuff. I thought, This is really fun. They're really cool people, although they're about as innocuous as hell. You learn that there are many people who may not be glamorous, who may not be Nobel Laureates, but they're just really neat, thoughtful people.
That's what you learn. The other is in Central America, I had never seen poverty like that. I said, Wow, this is... You come from an up-white, middle-class, suburban kid. You're not really seeing people who are basically on the edge of starving, if not starving. I experienced poverty. Frankly, the last thing in Panama, at the time, there was great tension between the US and Panama over the canal. I had never experienced prejudice because I was a gringo. I had never been on the receding end of hatred because of the color of my skin and where I was from. Wow, I didn't like that at all. I can imagine people who... That's their daily reality.
Wow. It's something I always tell people is travel and experience the people. I don't really travel, and I don't go to museums necessarily anymore. I've been to so many museums and churches, and I've seen so many things that feels the same. But what I like to do is I like to travel. I want to sit down with people. I want to understand the culture. I want to see how they live. Because for me, that's been just absolutely changing in my life. It sounds like for you, the same.
Absolutely. You're different in ways it's hard to describe, but you are because of all those experiences.
It's very interesting because you obviously are very intelligent. You went to Duke, which This is an incredibly challenging school I've been leading to get into. You are now teaching at Harvard, one of the hardest schools in the world, one of the most prestigious, if not maybe the most prestigious school in the world. Everyone in the world knows about Harvard. But you've also thought very differently. Did you see throughout time how education and thinking outside the box, did those go hand in hand? Or have things changed where schools are more open to it?
Well, I think most schools, particularly when you get to university, college and graduate school, if you say, I want to do the following, and it's not typical, they usually can accommodate that. They say, I want to put together a major. They're used to people want to be econ majors in chemistry, but they're pretty accommodating. They just want to make sure you've thought about it, et cetera, and to go off and to do these things. I think there is a willingness to do that. When I was in graduate school, I went to the University of Minnesota, I got a PhD in medical informatics, and all my buddies were computer scientists, but I was a sociologist because I thought that actually the hard part of getting this technology to be used by doctors and nurses was not the technology, but was managing people and managing change and things like that. I was going to study that. Very unusual for someone in that program to be a sociologist, but they were willing to accommodate that. They said it makes sense. If you're willing to grind your way through it, I produced this monster of a dissertation, 467 pages, which was just this of a thing like that.
But anyway, I do think in the colleges, if you want to try something different, they're open to it, just as long as it's thoughtful.
Yeah. It's interesting how people are like, If I want to be successful, I need to get a computer science degree, where, like my wife, she has a psychology degree. She never was anything in... She wasn't a psychologist or never went on to be a psychiatrist, but she's used that in sales, for example, or management or leadership, understanding people, which I think there needs to be a big push now. I mean, computer science might be the worst degree that you get. I mean, it might be replaced by AI tomorrow. It almost seems like people going back for these liberal arts type degrees or Anthepology or you use sociology. These might be very useful for understanding how to navigate people.
Yeah, and I think there's not only book learning you can get in those courses that teach you that, more so than taking a course differential equations, for example. It's also life experiences. It's the way you were taught. It's by your parents. And also the experiences you have. I have three grown daughters. In high school, they were all on teams, soccer and lacrosse teams. They're Okay athletes, they're not great at it. But the point is they were on teams, and teams teach you something, how to get along with others, how to work together, how to handle disputes, et cetera. So it's a series of experiences of dealing with other human beings and how to work together and work well. At times, you turn into a leader, but not always. I think that that thing is absolutely incredible in terms of making sure or giving you the ability to thrive.
Hey, I like to talk to professors. My dad was a professor. He just retired. I think he was sad when I dropped out of college, although I did go back many years later and graduate because my then-girlfriend said, I will not marry you unless you have a college degree.
Oh, there you go. There you go.
Which is sad because I really didn't... I wanted to just have a Lamborghini that said no degree. That was my goal in life. I wanted to prove that... I didn't really want to have a Lamborghini, but I wanted to prove that you didn't need to have a degree to be successful. But I did have to go back, and I think that was a great day for my father. I think he was happy. When we look You said you met your wife over 50 years ago, or you've been married for 50 years, right?
No. Well, 51 years ago was the first time I told her I loved her.
Amazing. Okay, so 51 years ago, you said, I love you. I mean, people aren't even together for five years. There's so many people I know that don't even have a relationship at all. They're already in their 40s and up, and they're struggling. What did you do or what helped you to balance this, and then you had three daughters, but then also a high-level executive career.
Well, I think there's a separate question, and I'm sure people have talked about, what is love? And what makes durable love? Over a very long period of time. There are some times that are not always easier, where you're changing a lot. Golly, we met when she was 18 and I was 19. That's a lot of change you're still going to go through. Anyway, how does that work? That's a separate conversation here. I do think everybody wants to have it all. They want to be a good parent. They want to have a good spouse. They want to serve their community. They want to grow themselves. They want a job, whatever, whatever. They want to do it all. And it's not possible to do it all. Not as well as you would like. There are trade offs along the way. So it's this constant low-grade anxiety. I have the right balance. I'm going to miss a kid's soccer game because of a conference or a tournament. Is that the right thing to do? And so you try as best you can to balance knowing it's highly imperfect, and you will do it again. I do think what you can do and should do is a conversation with the principal, your spouse and your kids, is, look, I'm trying as hard as I can to balance all this stuff.
I won't always get it right, okay? But I don't want you for a moment to think that that's because I don't love you. I love you dearly. It's just that I will be a human being, and I will try. And if you think I've got an imbalance, you let me know. So you try hard, you bring them in as part of the solution and as part of the balancing act, and you ask for honest feedback about whether My wife, remember one time when I was traveling, she said, I get lonely when you're not here. That's all she had to say. I said, God damn it. It was too much. I've skewed to the right too much. I need to get back to the basics.
Would you say then that communication might be the single most important thing?
Yeah, I think there's a... It sounds like you're sure you have your own speciality of this. Communication and being very candid about this. Now, there are certain things your spouse will do that irritate the hell out of you. At some point, there's no point saying it over and over again. It drives me nuts when you do it. Okay, leave it alone. Get on with it, et cetera. So communication, and I think the other is mutual respect. I respect you, what you do and how you go about that. And the other is the willingness to give in and to say, I know it's important to you, so we will go do this less important to me. Picking where do you go for a vacation? You might say, I want to go this country. She says, I don't want to go that country. I want to go another. Okay. You know what I'm saying? There's a give and take that goes with the communication and goes with the high respect.
I feel like I can really appreciate that because I feel like I many times go with the flow. It's not because I don't have my own opinions. It's because I don't really care so much to have an opinion because I know she's going to choose something. We like the same things. So she wants to go visit here. I'm great with that because I can only make so many decisions in my mind. I don't even like to make decisions, to be honest. So I'm like, I would rather someone else make that decision than me making that decision. But I really enjoyed what you said. Now you've written eight books. I don't know why the heck... I wrote one book over here. I don't even know why the heck. Why would someone even want to write another book? It must have been that important to you.
Well, first of all, I like writing. I mean, I just enjoy the act of writing. So I think if you don't like it or it's a grind, then you're not going to do a lot of it. Or if you did one, you said never again. That was too terrible. So I wrote a textbook with two colleagues because I thought there was a generation of leaders of these organizations that just doesn't really know how to do this technology well. Actually, it's the most widely used textbook on the topic in the world. It has been for many years. So that was great because there was a need for it. There was one book I wrote, which is I used to write College for various Trade Press. I've had 16 articles in Harvard Business Review over the years. So I just pulled them all together. So this is this compendium of writing of them. We did a book on AI and a book on strategy. The four non-professional, one was this 101 questions, which is the we'll talk about. The other, as I mentioned, I've written a letter to my family every week for 35 years. And what I did is I took a five-year block of letters when the kids were little, so they're six, seven, eight years old.
And I pulled out the parts that dealt with them. And I created a book called The Father's Collage. And I said, This is what your father remembers. This is camping trips. This is science projects, et cetera. And it's a written photo album. I said, This is my present to you, my memories of you. I published it. And then five years later, I took another five-year block and did the same thing all over And then actually, you may, I don't know if you have kids or not, but we used to do bedtime stories and Elizabeth adventures. And we make up a story, and I wrote them all down and published a book called The Elizabeth adventures, all these things. I said, This is the stories we used to tell. And then the most recent one is 101 is they'd send me questions, and I'd write an answer. And so far, we took 101 in one book, I'm now up to 180. And they run the gamut from what's the scariest time in your life? Fair question. But on the other flip side is, what were your favorite cartoons growing up? So anyway, there's books, partly because I like writing, partly because I felt like the field needed it, and I could be right or wrong, and partly because with my children and my spouse, to be great, I want them to know, This is your father, and this is father.
This is what he believes, and this is what he remembers about you as a little kid.
I need that book because I'm always looking for really unique questions. I like that. What scares you the most or what scared you the most before?
Well, in the answer to that question, when I was the Chief Information Officer at the Brigham and Women's Hospital, we had one day where the systems went down, and they were down for a very long period of time. I was getting scared because somebody was going to get hurt. A doctor or nurse was going to make a mistake because they couldn't get a test result or it couldn't do this, and someone was going to get hurt or die. And you remember talking to the technical Wizards. You always got these technical Ninja Wizards who make this thing sing. And I remember going into the computer with Bob, who was our Ninja Warrior Wizard. I said, Bob, what's going on? Do we know what's wrong? He said, No, we don't. And you could feel your intestines the size of a golf ball because they could fix it in one second or maybe not at all. I said, Oh, my God. And here's my chief smart guy. He didn't know what's going on. He didn't know what's happening here. And I remember being scared at that particular time. And I'm not smart I don't know enough to give him any real advice.
I tell you what I did to him. I said, Bob, tell you what, how about if I go get a priest that will do an exorcism? And he looked at me this stare. And I think he's trying to think of one or two things. Get him out of here. I got work to do? I got this moron who's talking about an exorcism. Or what the hell? We've run out of other options. We'll get a little holy water and incense down here and see what we can do to make the whole thing work. But that was the scariest time of my life because I thought we were going to hurt somebody and maybe even kill somebody.
When you look back, Did you ever have a thought in your mind when you were younger? I want to achieve this. And then what was the feeling if you achieved it? Or it doesn't even have to be when you were a teenager or in your 20s. It could have been two weeks ago, and now Was there something there where you were like, I really want to achieve this. And if so, did you achieve it?
Yeah, I wanted to go to Duke, and I got into Duke. I wanted to get a PhD, got that. I wanted to get certain jobs along the way. I was very active in professional societies in the digital health field, and I wanted to create one, and I wanted it to thrive, and it did that. To give you an example, one of the questions I think all people should ask themselves, let's presume you've got five minutes left in your life, and you look back on your life, what do you want to say about your time here? I said, I want to say five things when that time comes. That I'm as madly in love with my wife then as I am now. That my children will have lives as blessed as mine. They'll have their own paths, but blessed. The third is that I'm scared of crushing poverty, pain, racism, etc. But if I'm not, then I deal with it with the courage. The fourth is that the people I work with will say that I inspire them, talk them, and led them well. And the fifth is that the industries and organizations I serve are better because I was here.
I want that. I want to be able to say that when I'm done. If I went in the next five minutes, I could probably say that. So along the way, there are things that you accomplish and you feel great about. And there are big things and there are little things along the way. What I find is as cool as those are, the feeling is fleeting because you then move on to, now what? I remember when they came out after I might be attending my PhD, and I make you leave the room in the committee debate. They come out, laelgate with my advisors, they Congratulations, Dr. Glass. I thought, Son of a God, four years of work, and I got it. I thought, But I'm no different. I'm no taller, I'm no smarter, I'm no more athletic, I'm no better look. I'm the same person as I was before. In some ways, it was sobering to often to do that. Anyway, I think their accomplishments are great. There are things that are greater than that.
I think I've heard this before from other people, like athletes or somebody exit their company. I was just talking to someone this morning. They exited, but it didn't feel like a void. The void was still... They were the same person, and they were very depressed for many weeks, if not months later, because they thought it would completely change, not the monetary gain, but just change everything in general, and it didn't. They were just the same person. So it seems like this is something as humans. Do you think it's because we still have a... It's like technology has adapted much further than us. Our brain is still like a... Was it Neanderthal brain or lizard brain or whatever? Do you think it's because we haven't really adapted, our environment is adapting much further or progressing much faster?
Well, I think it may be fairly fundamental, which is when most people, when they wake up, if they're excited about the day, say, Why are you excited about the day? Well, I really like working with my colleagues. I enjoy the work that I do. I feel good about it. I like the organization that I serve, et cetera. It's the journey, as they say, that is It's a treasure, not the arrival. It is the every day, day in and day out. It feels really good here. When you find people who are retired and they walk away from their professional career, it's the long walks, it's the crafts they take, it's the involvement in the community stuff, it's the things that fill their day, that give their day meaning, that are the things. It's not necessarily, if they get an award, that's great. Everybody likes that. Golly, get your picture taken, people clapping, that's terrific. But that's not the real... In some ways, that is hollow, which is one of the reasons I think you got to be careful. If you believe that your goal is fame or wealth or whatever, you'll get there. I don't doubt that.
But then you'll get there. And if that's it, I'm the same as I was before. And to the degree my life sucked, it still sucks, even though I'm a I'm wealthy as hell now. I think it is more that we enjoy the journey. For me, sitting on the couch next to my wife, that's the greatest. I'm not saying much of anything, just sitting there is the greatest. Anyway, you get what I think, get my point. It may be technology-oriented, but I think it's very fundamental. It is the moment that is the treasure.
Yeah, I travel quite a bit. I have to say, when I am just sitting with my wife on the couch watching Netflix, there's a lot of satisfaction there, just as if I'm traveling somewhere. So I can see that. Sometimes those moments I'm happy that I'm just here with you, relaxing, because it's just always a constant go, go, go. So, John, I need to get a few of those books, but I need to get the questions because I need the really, really thought-provoking questions I need. And then I love the idea of the collage. I mean, the fact that you're executive in residence at Harvard Medical School, I I mean, it's insane. That is my goal one day is I just want to go to Harvard. My wife went to Harvard. I want to go to Harvard so I can get my sweatshirt there. And then I would love to attend a class. That's my goal one day. I just thought of it, John. I want to sit in a class at MIT and Harvard just to see.
You know what's the coolest part, though, is when we teach this class. Yeah, so great. You got the crimson, the Latin in all nine yards. But I sit in this class, and I'll give you two examples. And so there are the students. One student, for example, is a physician from India, and she's got a project she's working on, which is to reduce the teenage suicide rate in India. And she said, It's the highest of any country is a teenage suicide. I said, Wow. Why is that? I said, Well, because usually the pressure on the Indian kid to be a doctor, a lawyer, or whatever, and the kid just wants to be a musician. But the pressure is excruciating. She was going to go off and dedicate her life to reducing teenage suicide rates in India. I thought, Wow, that is cool. That's what makes Harvard special, because People like you become students. Another one is a woman who is a scientist in China who has a set up, works for a company that does medications for kids with very rare genetic disorders. And they can give that kid the therapy for one-tenth the cost in the US.
And she says, I'm going to open up a business where the kid and the parents come to China to be treated because they can't afford it. It's not coming by insurance. It's a zillion dollars. And so it makes it special. Yes, the name is special, but those two people are examples of the 75 people in this class. They said, Wow, you guys are really cool. The world's going to be better, a lot better, because of the work that you do. And for me to be part of that and to help you do a better job, that's what makes us special. That's what makes this place special is it can draw that, draw that talent in.
But, John, this has been great. So if people want to get in touch with you, they want to look at the books, they want to follow along your journey, how can they do so?
Well, I think a couple of things. One is there's the website for the books called Books by John Glasser. It's all one word. The other is you can find me on Facebook. I put out a weekly post on Facebook, which is a series of vignettes or whatever from writing. So come on in and be my friend on Facebook. And you can find these books on Amazon, too. But anyway, I look forward to, if they want to, people to be part of the broader community. It's fun. There's a lot of good stuff. It's a lot of humor, but also some insight, periodically. I mean, I wrote one post on Facebook a couple of weeks ago, is what are some of the pearls of wisdom that I pass on to this class about leadership. I'll give you one example. People give you permission to lead them. You cannot impose leadership on people. They will look at you and say, I will let you lead me. Because if you try to impose it, they'll sandbag you, they'll quit, whatever. Just remember, leadership is a voluntary act on their part. It's not something... Just be sober and thoughtful about that.
Anyway, that stuff is being posted, but I've been a light of either Facebook or through the website or whatever. I look forward to having them part of the broader circle of people who are showered with wisdom from Jon Glasser.
I love it, Jon. I can tell a lot. You have a few years of wisdom in you, and you are now dedicated to making the world a better place? It seems like you've been doing that for a while and that's an obvious importance to you in your life. The next five minutes, I'm going to ask this question to everyone. I'm going to ask this question to every single person that scares you and then that question, and then I'm going to come back to you with their answers. But, John, this has been great.
I'm going to give you two other questions that ask people. What's the scariest time of your life? Second, what's the hardest thing you've ever done? Third. And then the third one, because we talked a little... A kid came to me and she said, How would I know I'm in love with this person? How would I know if this person is the one? What does that love look like? And that's a good question. Anyway, ask your people, what loves the best of them? What's the hardest thing they've ever done and when they've been the most scared? They'll get some very interesting answers.
My mind is blown.
Thank you, John. All right, big guy. You have a good one. Say hi to everybody in Southern California for me.
Daniel Robbins interviews John Glaser about the unconventional experiences that shaped his worldview long before his career in digital health leadership. From Jesuit schooling and getting expelled to hitchhiking across continents and later teaching at Harvard, John shares how curiosity, nonconformity, and human understanding became central to both his life and leadership.
Key Discussion Points:John shares how a rebellious streak, encouraged by an unorthodox upbringing and Jesuit teachers who taught him to question everything, led to his expulsion from high school after publishing an underground paper and refusing to apologize. He reflects on his hitchhiking journey from Alaska to Panama, describing what it taught him about poverty, prejudice, and the unexpected intelligence and richness of ordinary people. The conversation then moves into leadership, where John explains why people “give you permission” to lead them and why sociology, communication, and understanding change mattered more to him than pure technology. He also opens up about marriage, parenting, writing books for his children, and the five things he hopes he can say about his life in his final moments.
Takeaways:A major theme in this episode is that unconventional paths can produce extraordinary leaders because they teach empathy, perspective, and comfort with uncertainty. John’s reflections show that success is not found in titles, awards, or milestones alone, but in relationships, meaning, and the daily journey of how you live. His views on leadership, love, and family are especially powerful because they come with the honesty of someone who knows balance is imperfect, but still worth pursuing with respect, communication, and humility.
Closing Thoughts:This Founder’s Story episode feels less like a career interview and more like a life conversation with someone who has seen enough to know what actually matters. John Glaser leaves listeners with a reminder that the most interesting lives are rarely linear, and that meaning is built not through perfection, but through courage, curiosity, and deep connection with other people. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.