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The Mindset Behind Billion-Dollar Ideas | Jeff Hoffman

from The Mo Show | Presented by BSF

1h 43s

The Mindset Behind Billion-Dollar Ideas | Jeff Hoffman

Jeff Hoffman reflects on his journey from founding airport check-in kiosks to launching Priceline, highlighting how personal frustration with inefficient systems sparked his entrepreneurial drive. The early days of e-commerce were marked by technological uncertainty and deep skepticism about trust in online transactions, yet Hoffman saw a market gap in consumer demand—leading to the revolutionary “price line” model that revealed what customers were willing to pay below the surface. He credits his success not to wealth or fame, but to meaningful impact on others’ lives, a realization forged through a personal moment at a funeral where his best friend’s life was transformed by a simple truth. A central belief in his philosophy is humility—being open to learning, feedback, and ideas from anyone, even non-technical staff. He emphasizes that true innovation comes not from individual genius, but from strong team execution and a willingness to delegate. Looking ahead, Hoffman sees profound changes in education, remote work, and healthcare, driven by technology and experiential learning. He argues that traditional schooling systems, with their rigid structures and long durations, fail to prepare students for real-world problem-solving. He also notes how the rise of AI and self-service technologies—like one-click shopping and home-based health monitoring—are redefining consumer experiences. Ultimately, Hoffman sees entrepreneurship not as a career, but as a lifestyle built on curiosity, humility, and a commitment to making a positive difference in the world. His vision for legacy is deeply personal: to live a life one can look back on and say “this was time well spent,” regardless of financial success.

Transcription

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English
Bismillahirrahmanirrahim. Welcome to a new episode of the most show podcast. Jeff Hoffman, it's an honor to have you on the show. Well thank you so much for having me here. We're good forward to this conversation. Yeah, me too, me too, fascinating story. I definitely want to take you back to your earlier days with priceline, which is a name that is still ingrained in my mind. You know, early internet days, it really was the place you would go to by anything, travel, tickets, planes, hotels. It was Expedia priceline, if my memory serves me right. Looking back on those inception days starting it off, how hard were those early days in getting the business off the ground for you? So you know, it's interesting because you had two battles to fight that were really hard. First of all, the internet itself was brand new, right? The technology. So no one had really built--we were one of the early companies that was actually generating revenue on this new thing called the internet. So the technology was one challenge. There weren't people trained in TCP/IP protocols and all the internet stuff. Everyone that had written code and built things before, built it in different paradigms. So you have a technology problem, which is creating an e-commerce site before there ever was an e-commerce site. The harder one I think it turned out was the marketing problem. If your whole life you've literally gone into stores and talked to humans or picked up the phone and called them and now think about the travel business, right? I pick up the phone, I call a travel agent and we chat for a while. We talk about hotels and what's available or what flights and what costs. And I'm talking to a human. And at the end, that's the person that I give my credit card number to and assures me everything's fine and I can call her back, there's all that. Now, all of a sudden, overnight, we're saying, look, you can just look on the screen, click on something, enter your credit card and we have to convince you to trust that when you land, it's all going to be okay. When you get to the hotel, even though you've spoken to no people, are they going to have my reservation? Is it going to be paid? Is it going to be, by the way, the hotel or whatever it is that the resort looked like, what I thought it was going to look like? So those were the challenges. Tech was the lesser one, but it was one because e-commerce was new and marketing and convincing people to trust a transaction that was fully online without a human involved was really hard. How long was the working on the infrastructure of the platform? How many years did you spend on that before it eventually went to what we know as price line? Yeah, so actually it was shorter than people think, considering today with all the tools you can launch really, really fast, but it was really just 96 and 97, 1996 and 97. Early days. Where the building days of it and then launched in 98. So the platform went live in 98. So it was really less than two years total to build everything and then launch it in 98. This is like one of the OG names. It must be up there with the America online, the Google, the inception of Google. The Time magazine did a thing early on and they said the internet's big three and it was Amazon eBay and price line because it was the first, some of the first companies to be up and running and running a business and generating revenue with customers. So yeah, we were definitely in that OG list back then. Was that your most successful, made-it venture, would you say? Was that one of the, let's say, the first time where most people heard of you for the first time? Your made-it moment? Actually, for me, no, in my industry in travel because years before my actual first startup on my first product was the back in the day. You had to wait in line at the airport to get a ticket agent to give your boarding pass, right? They'd check your ID, they'd print a boarding pass and hand it to you. And I stood in one of those lines an hour and a half, 20-something years old, and I had quit my corporate job. So 20-something years old and unemployed, so the price of a ticket was a big deal to me. And I missed the flight standing in that line. It was an hour and a half on a Friday afternoon. And I got upset that we wait in line for an hour and a half and all they do is hit print and hand you a boarding pass. And I was like, why don't you just put the printer over there? Why do I have to wait for you to print someone? Everyone's yelling at me, get out of line, move, right? The woman's saying it doesn't work that way. And the people behind me saying, yeah, it doesn't work that way. And I'm like, it doesn't work that way because you accept that it doesn't work that way. So I went home and started doing some sketching. The idea was, can't you just put a kiosk in the airport and I'll check myself in. And so those kiosks were really my first startup. We created the airport check-in kiosks and started marketing them to airlines and airports. And because it was my first real startup, but it gave me like, for example, back then they did these awards like the, every year they would pick the 20 most influential people in travel and tourism worldwide. And it was like horse, who was the CEO of Ritz Carlton, right? And Bob Crandell, the chairman of American Airlines, and then me, some 20 something year old software engineer, people were like, this has to be a clerical error. What are you doing on this on this list? So in the industry, they were like, you know, meet this guy because we think he's going to change the way you travel. And so that's not what was relevant. What was relevant to me was never having built a startup and having no idea from day one, how are we going to deliver the kiosk, how are we going to service, install it, the whole thing of building a business, the fact that we pulled it off, that was my favorite business. By the time the group got together that launched price sign and you know, move later to booking and everything else, none of us were rookies anymore. You gained experience from that. Were you able to patent that tech? Yes, we got patents on the tech then, so which we were able then later to do an acquisition, we were able to sell the company. So the self-check-in, almost like how ATM machines. That was the model. The idea is not too dissimilar from that. No, I was sitting there thinking, I don't have to go into the bank anymore. I can just stop it in ATM. So why do I have to go up to the counter any hour? So that was exactly the model. Fantastic. Where does this come from, Jeff? Where does your knack to want to challenge the status quo, if you will, and come up with such ideas as opposed to maintaining course like everyone else did in that line you were in for an hour and a half. Where does your knack for wanting to venture off the beaten path come from? It's funny that you asked that. My mother, who just passed away two years ago, would have loved that question because my mother told me my whole life that I am the most impatient person she ever met. However, I remember this realization I had and this realization was in school. When our teacher said, "Who knows what a Shakespearean tragedy is?" And I did not know. And so she said, "I'm going to tell you guys why they're called that." And she said, "What Shakespeare understood about humans was that the single greatest strength, the characteristic of your personality that got you where you're going is also the one that's going to kill you." So I suddenly had this realization. Here's what's going to happen to me. My impatience is why I have constantly said, "Come on, this is ridiculous." And I'd be the one saying, "How is this line so long? What are they doing?" And everyone's yelling at me, "Shut up, it's just long." And always my impatience, I was like, "I'm going to figure out a better way to do this." But I also know that one day I'll be standing on a corner in New York City, I'll step into the intersection, a bus will kill me, and people will say, "He couldn't wait 10 seconds for the lights to turn green." That was Shakespeare's tragedy. "My impatience will be my undoing." But it's also the reason that I just, when something's inefficient, I go nuts until I can fix it. You still have that today? I do, yeah. A lot of the things that we've done over the years have been focused on efficiency. It still drives me crazy when I can't figure out why something is inefficient as it is. And obviously in the early days, travel agent, that whole process was inefficient. And that's why we started the whole process of creating online booking. Just do it yourself. People will always question you in the beginning and then after it's done, they'll call you a genius. And the really question is how they put up with how things used to be in compared to how things are today. But you are right for all innovators along the way. People don't believe, right? You're the problem. Can I tell you a quick story about that? I can tell you a self-realization moment since you asked that. So of all places, we're at Epcot Center at Disney World. I'm with a bunch of friends. And we're in the 3D movie theater. And when you come out of the theater, it's hundreds of people. And when you come out of the theater, this is a moment I realize just accept who you are good or bad or I just be you. But we come out of the theater and down at the end of a long haul because it's hundreds of people are four glass doors. Three are closed and one is open. So all the people are in a line on the right to the open door. And it's like a hundred people in line. There's several hundred in the theater. My friends just get in the back of the line. And everybody's standing there all waiting to file through the one door because the other three are closed. And I step out of the line. I start walking. My friends said, where are you going? And I said to see if the other doors are open and they said Jeff, if the other doors were opened, you think 100 people would be standing here. And I said, yeah, because they all think like that. Well, that irritated all the people. Some guy goes asshole. I can hear them talking on the side. And they're like, where are you going? It's obviously locked or everyone wouldn't be here. I said, it's not obviously locked. And I'm going to find out. And people in the line were like, go to the back of the line. Every 100 people were watching me in the line. And I'm going towards this door. And I'm thinking because everybody assumes when they come out that because a few people got in the right, it must be locked. No one's checked it. So I'm going, my friends are yelling at me. People in the line are calling me names. And people are saying things like, when he comes back, don't let him in. Make him go all the way to the end again. Right? It's like, oh, hey, here is told you out. As I started getting there, I did really brave slash stupid thing. I accelerated. And I'm thinking, okay, there's two ways this ends. Either the door opens and it's a burst of glory into the sunlight, the Florida sun, or it's shattered glass and an ambulance. So I'm going out big. Either to pile a glass. And when I got to the end, I was going at full speed. And I put my hand out and I kind of almost closed my eyes. I was like, I'm either going through this glass or I'm right. And I pushed on that door and it flung open. It was never locked. Wow. And you could hear a hundred people groan. And then all of them poured off all the doors were open. Now one person tried the door because when they came out, they saw everybody else in line. When I came out, my friends were shaking their head and, you know, laughing kind of, but they were like, what is wrong with you? Right? And I was thinking, it's a good question. I don't know. Wrong wasn't the word I was hoping for. Right? But I was just sitting there thinking about the way people process stuff, right? People just assume. And I realized then there's going to be some times where I'm going to, I'm going to be hauled off in an ambulance in a, in a, a giant pile of shattered glass. But I'm still going to go straight for the door. That door opening moment was symbolic of the entrepreneurial tendencies that lives within you. I think so. And in fact, yesterday here in Jeddah, the talk I gave was the theme was that, uh, never lose your childlike curiosity. Yeah. One of the things I noticed studying, I, I've been blessed enough to become friends with my business heroes over the years. So I got a chance to dig deeper, right? To try to find out what makes them tick. And I noticed this common element that the world's most innovative creative people have never lost that inner child. Children, think about five year olds. That was my talk was about five year olds question everything, getting the car. Why? Cause we have to go to the store. Why? Cause we need food. Why? Cause if we don't eat, we'll die. Why? No matter what you say, a five year old is not satisfied. Cause they're trying to get all the way to the root of understanding. They're curious about everything, right? And when I started getting to spend time with, you know, some of the world's most successful business people, I was like, they're all, they allow their five year old curiosity room to roam. And everybody else doesn't. It's the pick up shiny objects thing, which everyone else thinks is irresponsible. But those people never stopped doing it. The difference is that they schedule time to do it. They're not distracted by everything all day. In fact, yesterday, I shared that I kind of have a technique for that now, which is the first 20 minutes of every day and habits, right? The first 20 minutes of every day, I don't work for my company. I don't work in my industry. I literally just allow my curiosity to roam. I call it info sponging is my word. Every morning, I just, wherever my curiosity points me, I spend the first 20 minutes learning about something I don't need to know, right? Something caught my eye. I'm going to go read that article. If someone said to me, if you said, Jeff, why are you reading that? There's nothing to do with anything you do. I would say right now, I have no idea why I'm reading it. But ask me again later this year because that knowledge might come back to help in something so childlike curiosity is so important. Yeah, and we lose that over time, don't we? It's funny how everyone's born with the tendency to ask questions. All five rules, right? And then over time, we ask less. It's almost like, I don't know, life gets in the way and we get tired and less inquisitive. It's absolutely that's what happens. And that's that's the problem. That's the they're in lies. The missed opportunity. Because people start wondered, stop wondering about the world. But again, what I noticed when I made it a formal study was the super innovative people never stopped wondering and then ever stopped questioning stuff. Everybody else kind of does because like you said, you get you get in your bubble and in your lane and now I'm an accountant and I run an accounting firm and that's what I do. So why do I care really what's going on in the picket industry, right? Agriculture, any other industry, it's not my industry. But innovators tend to go schedule time to go look to see what everyone else is doing, to see if they can find good ideas outside of their lane. And that's what I've been trying to emulate since I noticed that. I like your info, sponge 20 minutes every day to learn something that you have, you know, very little information on because into the day, knowledge is power. And you don't know when you might pick up something that could spark an idea that can carry a conversation that can open a door because that person found out that you knew something about rocket science, for example. Exactly. And then booking came along. How dissimilar was that venture to price line? Well, the thing was that it wasn't mature yet, right? So when you take a company and decide to go international, go to Asia and go to Europe. And the decision at that point was to acquire somebody that already had an office of license, all the everything you need to hire employees, starting from scratch versus buying a business, it's already a business in that country that's already set up to operate. Plus to fact, so price line acquired what was booking.com. But it was over time, it's the price line technology and marketing and everything else that rolled out underneath all of those things. But under a much better name, booking.com is a way better name than priceline.com. Yeah, for say price line was, by the way, that name is the investor thesis, really, because the thesis is that prior to the internet, you cannot see demand below the price line. And I'll just explain that really fast. If I sell shoes, I sell blue shoes for $80 in my store and 10 people come in. And two people buy blue shoes for $80 and eight don't. The only thing I know is that two people bought blue, this is pre internet is that two people bought blue shoes for $80 in my store. The other people wandered around and left. But with the internet, what I can see is that seven people would have bought green shoes for $70 if I had them because they're searching for it, right? So what we realized was that whatever in the in the retail of the physical world, whatever line you set the price at, you have no idea what the demand is below that. But in the internet, people were clicking looking for yellow and looking for $70. So if I had known that seven people would buy green shoes at $70, I would be selling green shoes for $70, not blue shoes for $80. So the thesis was, let's use the internet to harvest consumer demand. And find out all the people that were willing to buy something, they're just willing to spend something below the line, the price line. That's what the name came for. It's data that was never available to us. Correct. I would argue that travel today versus travel pre internet in 1998 has to be a few times over because through sites like price line or booking or our local version, which is al-Musafid, for example, you are able to set up an itinerary at a one-stop shop website and explore something in a country that you'd know nothing about. So I think it just made the world a lot more interconnected. And when someone recently told me that Qatar put 600 flights a day out of Doha and ember it's not too far off, I'm like 600 and we'll fact check this. 600 flights a day and they're all long hauled. Has that changed? Has the internet changed the volume of travel in the last 24? It has. One of the good ways it has changed and it's important to me because I fundamentally believe that if more, because there's a Mark Twain quote that has inspired me in my whole life, Mark Twain said that travel is the fatal enemy of prejudice. And Mark Twain's theory at the time I was a kid and I asked my mom to explain it because I could feel that in my soul. And what my mom said was, Mark Twain is saying that if more people got out of their bubble and spent more time getting to know people that don't look like them, we'd have less hate, we'd have less conflict, we'd have less, I fundamentally believe that. That he was right. So if more people could travel, it'd be a more tolerant world because instead of judging someone from afar that you like in America, when I hear something anti-Muslim. And I said, you actually know, I don't know your friend's Muslim know. Do you know any Muslim families know? And I said, so your comment came from what? Right? And the answer is nothing. They don't actually know people at all. It's whatever some media version. So the point was, what if you flew to a Muslim country and made friends there and met families and got to know people? Right? Only then should you be able to have an opinion because you've never even met anybody. And so part of our role for me is was a personal thing was if we could make travel cheaper, more people could access travel and hopefully it'd be a better world. So our little secret thing for me was maybe we can leave the world a little better by allowing more people to travel to more places. That actually mattered to me, which is why I got into travel in the first place. But yeah, it's changed a lot and it's still changing. I love the cause. An absolutely incredible cause. Tolerance really is the operative. Tolerance was really the more you I'm going to quiz you on something and my source is Chad GPT. Okay. Price line says it has saved users more than ex billion dollars. Fill in the gap overall. It's a staggering figure. It's funny. I've never looked that up. You never did, huh? No. So it's cited on Chad GPT, but something that price line released? Care to take a stab? No clue. $10 billion. Not too far off. 15. Okay. That's just trying to think of our total volume. Insane amount. When you said, when you said, you know, we wanted to make travel more affordable so people can travel more and be more tolerant of cultures and making it more of a marginous globe, if you will. That, I mean, the proof is in the pudding. You saved people 15 billion dollars. Yeah. That was definitely an important goal. In the end, right? For all of us, you know, legacy should matter. Right? There's a point in your life where you should stop and say, when it's all over, what footprint did I leave? What difference did I make? And of course, family's number one. Right? There are the private, you know, the private part of your legacy, your family and those things. But if you're going to be an entrepreneur, a business person, a career out here, did you make an impact along the way? Did you make a difference somewhere? And that was the hope, right? When it was all said and done, I'd like to have known that we actually made a difference and help some people. And that tolerance is the metric. You know, do you think about legacy a lot these days? I do. It's definitely obviously happens when you get older. But, you know, for me, it was really interesting because even though I speak all over the world, I'm not a public speaker. I'm an engineer, right? The fact that I can speak in semi-understandable English as an engineer is already an accomplishment. I've never had speaker training and I never set out to do speaking, but I was giving it, this was the first time. I was giving a talk. So in addition to a product, you build, right, the business, I get these. People will take a selfie in the airport next to a check-in kiosk. They'll be running to the airport. They'll stop and get the boarding pass. They'll take a selfie with the kiosk and just send it to me and say, thanks. Okay, that's nice, right? But that's not the legacy I was shooting for. We did a business that helps people. But, I was giving a talk one day on stage about, it almost was about bursting through the door, right? About just get up and go, right? Either way, you'll have a story to tell. It might be from the hospital, but you'll have a story to tell while everyone else is just standing there. And I was giving a talk and I got an email, but a letter from a woman. And she said, we've never met and she said, but I was in that audience. I was out there that night. And she said, you literally changed my life. And I was like, that's a thing. I didn't know that was an option, right? And she said, the words you said hit me so hard that I went home and basically rebooted my life. And here's what my life looks now. She said, if you hadn't said those words that night. And while I was sitting there, she said, I don't know what my life would have been. So I read that thing and I thought I didn't know I had the opportunity to be able to impact somebody's life in a positive way. That was the night I started thinking about legacy, right? What do you want your impact to be in the end? And what difference do you want have made? So I kind of switched to when I fit. I was a CEO since I was 24. And when I finally stopped the last CEO of public, we did another public company was you bid.com that we also took public. And when I said, I'm done with the CEO thing. And now I want to spend the second half of my life giving back. But that's part of what inspired me to think. It didn't occur to me that I could positively impact people that way. And when I found out I could I thought, maybe that's literally my purpose. Maybe I should spend more time figuring out if there's ways I can positively influence people. Because if I can do that, then that's probably what I was putting here for. Do you ever pause to reflect on how you measure success outside of money valuation? Yeah. So for me, there's let me tell you two parts of that. And one of them is a very personal story. So the first part is success for you personally, right? And kind of the more popular definition of what success means. Because we were all raised to believe that success is typically a combination of these couple things, money and fame. If if you somebody drives by and they're Bentley and they're rich, people will say, well, he made it, right? And yet I literally have billionaire friends who are miserable. And then fame, you know, if you see somebody you knew that now famous actress on TV, people will say, look, she made it. And yet I have very famous friends who are miserable. But my best friend, Michael, and Michael came to work for me at one of my companies. And it worked out. I was unsure about hiring my best friend to work. And Michael had this habit, this hobby. And his hobby was climbing cliffs. And he found out one day what the world record was for climbing a cliff with no safety equipment. Normally you hammer yourself in, you tie the rope, you pull yourself up, you're wearing a harness, Michael decided to see if he could climb with no equipment. In fact, if you look this guy up, they call him the Michael Jordan of climbing. And so he started this climbing. And I pulled him aside one day and said, dude, seriously, you got to stop. I said, you're going to fall and you're going to kill yourself. And this is my best friend in the world, right? And I said, I wish you would stop the climbing. And Michael said, I understand that that my hobby is dangerous. But he said, can I tell you something? And I said, what? And this was the kind of soul, you know, impacting statement. Michael said to me, I know that my lifestyle, you know, might end my life prematurely. And he said, but Jeff, he said, I'd take 40 years of living life the way I live it versus 90 years of whatever one else is doing. Well, Michael died at 42. And standing there at his funeral, his parents wanted me to give the eulogy. And I just couldn't get words out, right? That was the worst speech I've ever given. Because I had to acknowledge that my best friend was gone. By the way, he never fell off a mountain. He drowned in an accident in the Irish sea. And so standing there, but at 42. And so I'm standing there. And all I'm thinking is, did this dude know he was only gonna have 40 years? Because he said, I will take 40 years of living life this way versus the 90 that everyone else is doing. So I'm standing at that funeral. And I'm thinking, why did he believe that? Because he did. And the answer is because Michael was living the life he actually planned to live. Everybody else is making excuses. Well, when I was young, I was going to do this, but now I have a family. And earlier, these were my dreams, but now I have a mortgage. And I started questioning people and everybody had the life they plan to live. And then the life they were living. And I said, what happened to that plan? And they're like, Oh, dude, you got to grow up at some point. And I was like, are you growing up? Are you giving up? Because you had a really cool plan for an epic life. And now you're accepting, that doesn't mean this life's not good. But if I asked your definition of an epic life, it's not the one you're living. Michael's was in every way. So here's my new definition of success. It's anybody's what I learned from him. Anybody that can stop at any moment, look back at your life, including all the mistakes you've made. And if you can nod and say, this is a pretty good ride. If you can nod and say, I am spending the time I was given in this life. Well, that's it. You might be rich. You might be, you might not. You might be famous. You might not. But the question is, do you love your life? Would you trade it in anyone else's? And that was Michael's thing. He's like, dude, don't touch my life because I like it. And I was like, how many people can honestly say that? So that changed for me. The definition of success wasn't about money or fame, but it was about and I hope our listeners will ask themselves, ask yourself this question. What life would you have to live that you'll look back one day and say that was time well spent? And are you actually living that because I was not? I was doing a lot of things that grown up stew that I never dreamed of doing. And so that's the moment I said, why don't I see if I can turn the things I dreamed of doing, which was traveling the world into my job so that I'm actually living the life? And you know the way I summarize it, I wrote down one day, your, your business, your career, your job, your business, your business should be the vehicle that takes you to the life you want to live, not the obstacle preventing you from living it. And it changed my whole life. So that's my success for me is I just want to live a life that I look back and say, I made a lot of mistakes, but I wouldn't change it. It's a pretty good ride. And I didn't think of it that way before. I was judging myself by society standards. And yet I had the money and that crap. And then I had friends who were just miserable, yeah, even though they had all the money. So yeah, I know that was long answer. No, I absolutely love that story. I never ends well for anyone who lives a life for society or for what people want. And the old saying may be a little pleasier, but it's not the number of years in your life, but the number of life in your years. Well, Michael, Michael definitely taught me that. And then I think the second part, I was, it's something that I would challenge people listening to us think about as well. So I'm sitting at Michael's funeral. How long ago is this? Now it's, uh, Uji's, I don't remember how many years it's been a while. Decade or yeah, yeah, more now. Sort of here about this. Um, yeah, I miss him every day still. I was an amazing human being. Um, I'm sitting at the funeral and I'm listening to people talk about Michael. And some of them, I'm like, no, no, no, you didn't, you didn't get him at all. He would not want to hear that. And then I did something again. I'm going to challenge everyone to do. I went and sat aside. We were, we were waiting to get started. And I grabbed a sheet of paper and I did this exercise. If today was your funeral, what do you honestly think people would be saying? And so I started thinking about that, right? And I was like, well, people are going to say he built businesses, right? He was financially successful. Somebody might say he had a really cool house. And that's all a fail. But I was being honest, what would people say about me? They would talk about my business accomplishments. And I was like, that is not what I wanted. So underneath that, I wrote the second part. What do you wish? If you're a funeral, if you could write the script, what would people be walking by saying about you? And I knew what I wanted. I wanted people to walk by and say that dude made my life better. Not he had a big house or he had three exits from startups or whatever. I want someone to say my life was a little better because Jeff was in it. And then I did the third thing at turn the page over. And I said, I'm going to write down, what are you actually doing to make that happen? And I realized I wasn't. I was just doing business and making deals. And so in the end, I don't want to be judged by the number of dollars. And they want to be judged by the number of other people's lives. I made better. And so that changed my focus. If that's what you're trying to do, then go make somebody's life better, right? You can do another deal, have another exit, build a build another vacation home in some other country. Or you can take your time and money and go make somebody else's life better. That that's that was the change point for me. And Michael's passing reframe the way you approach. Absolutely. Which is great. You hear a lot about people saying don't let that person's death go in vain, learn something from from their passing. And and even his passing has allowed you to flourish or take a second take off in your life, which is pretty. Yes, for sure. Yep. In your experience. And you have a lot of it. I want to ask you, what do you feel separates entrepreneurs who build small businesses from those who build global, you know, categorical leadership? Yeah. So I think it's it's a process that starts way before you launch the business, which is really the way they do the problem assessment. So opportunity assessment. There are people that are looking at in a much narrower view. They're like, hey, I could make some money if I built this thing, right? That's the person that builds a small business. Then there are people. Now it's kind of nice because I get I meet with entrepreneurs all day long, right? Here at this entrepreneur's organization event here in Jeddah. I've been spending all my time with entrepreneurs are building businesses. And there are the people that say, I see this opportunity. Well, if I could build these, right? I could sell a bunch of coffee cups and make a bunch of money. And then there's the person that looks at it and says, how does the entire coffee industry work? I wonder if I could, if I could disrupt the industry and if there's a better way to get coffee into the cup before I ever even need a cup. What's the process? So when you talk to people, there are people that think with a much wider funnel at the beginning. They're like, I'm going to try to figure out how this industry works. And if there's a way to do it better. And then there's other people that say in this industry, they need cups. So I'm just going to make cups and sell them and make some money. You can tell pretty quick when you ask people, I always ask people, they always start by telling me what they're doing their business. And I'm like, no, back up and tell me why? What was the moment you, why did you decide to even get in this business? And that's when I can usually answer the question you asked because they'll be like, well, you know, I can make money selling cups or they'll be like, well, I think it's time to disrupt and redesign the coffee distribution, making up a dumb example, but you get it. You know, your, your, your disruptive demeanor is very, very refreshing. I love people that feel always feel that something can be better. Is there a belief about entrepreneurship that you hold dearly to yourself that perhaps other people would disagree with you on? Yeah, big time. And that's that it was never about you. And what I mean by that is that people rock, well, here's the most famous one. Steve Jobs, Steve Jobs used to famously stand up there and hold the iPhone and pretty much say, look what I did right and take all the credit. And then he famously said things like, uh, we never asked customers what we want. We tell them, okay, he didn't, but 600 other people at Apple did, right? So while Steve Jobs was brilliant and a marketing genius, there's no Apple without those 600, whatever the rest of the people. So the belief is the rock star leader, the Elon Musk, whatever, the innovator. Those people are really important, but nothing significant has ever been done without a good team. And so I see a lot of focus. That's why you said what other people believe that I don't. I see a lot of focus sometimes on these kind of celebrity CEOs, which are great to get attention. But in the end, if you don't have a team that executes and executes efficiently. So that's what I think it is is, is be less, be less fascinated by, you know, the sort of celebrity CEO and be way more interested in the depth of the entire execution team. Because if they can't build the amazing idea that that person had anyway, it's, it's never going to go anywhere. Mm-hmm. So people tend to focus on their fascinated by those people. And my question is, what team they have around them? Because that's a really cool vision. But can anybody in this building build that vision in business? There's a come down to timing or talent. Both. However, timing accelerates talent is the way I'll say it, timing without talent is just a missed opportunity. Talent ultimately finds a way to win, but talent with timing is an accelerant. That's what I think we, I've been through that many times where timing absolutely favored me. We were lucky. We were the right time in the right place. But I think the talent might have figured it out anyway. And if the timing had happened and I had no talent around me, it had just been missed. Yeah. It reminds me of the other algorithm that, that I sought to be true, which is success equals when opportunity meets readiness. If you put your reps in and you get the opportunity, you'll most likely be successful. Completely agree. And if luck comes, like I said, luck's just throwing gas in the fire. It accelerates the process, but the process started for those reasons. I agree with that. When you meet young entrepreneurs, do you pick up on something that they may have that would tell you whether they will be successful or not? Absolutely. They're sparking their eye. You see absolutely. And and you know what it is. Mostly people always taught the famous answer is passion, right? People say if they're passionate, that's not the one for me. The one for me believe it or not is humility, meaning are they capable of learning and listening because nobody gets it right at the beginning, everybody pivots, everybody makes mistakes along the way. So the thing that I'm looking for is, is this person thirsty for learning? Are they open to talking to people have been there to done that when they make a mistake, can they accept criticism? So all those things are, I think, functions of humility. And a lot of times I'll run into people that already know, sometimes I'll say, why'd you call me already know everything, right? You seem to already know the answers. That person isn't listening, probably won't learn from their mistakes. And even if you bring in advisors that have been there, done that, they think they're smarter than them. So that's the part that I look for is that, is that humility that hunger to learn from other people, that willingness to accept that somebody might have a better idea than me, right? I add this in my own company one day. I just sit everybody down because our receptionist in a meeting, my VP of sales said, why is she even in the room? I said, because our meetings are open to anybody. And he rolled his eyes in the middle of the meeting. She raised her hand. This is an hourly employee. She answers the phones up front back then. And she said, can I make a suggestion? And I was looking at my VP and he's like, this is going to be a waste of time. And it was freaking brilliant. And he said, oh my God, where did you come up with that? And it was interesting. Because this is what her answer was, we have a call center, customers that are unhappy call the call center. But the customers that aren't happy and won't accept the call center try to reach me. So they call and ask for the CEO. So she's the one that deals with all the most difficult customers, not my call center. So she's been doing that for years. So she said, I'll tell you what, I've been handling the most difficult customers personally for years. And I got some ideas. And my VP of sales. was doing this thing. Right? And I was like, man, if you can't be open to the fact that a better idea than yours could come from anywhere, then, then, you know, then you're never going to get to that next level. So that's what I look for. Did you have a really listening? Did you have that at the age of 24 when you were CEO? Did you learn it throughout the years? I would say I learned it. I didn't, that wasn't automatic for me. But the more that I started surrounding myself with rockstar people, you know, one day it occurred to me, instead of trying to figure out how to do stuff, I need to hire people smarter than me. I'll tell you this story. I'm sitting with some other entrepreneurs. We're all having a lunch one day. And one of them is reading a paper. And I said, what is that? And he passed it over as a cash flow statement. And I just handed it back. And he said, you can't read that. I said, I looked at the bottom line. And he said, can you read cash flow statements? I said, well, enough. And he said, financial statements, do you understand them? I said, I'm a software engineer. Not a finance guy. And they're like, Jeff, you're the CEO and you own the company. You need to understand everything that goes on in the company. And all the other guys were like, yeah, you need to, you're the CEO. You need to know everything. So I went to Barnes and Noble. And I bought a book called Finance and Accounting for dummies basically, right? And I went home and I'm all excited. I'm going to learn finance and counting. And I opened the book to page one. I was like, oh my god, this is one of the stupidest things I've ever done. And you know, I'm going to do next. No, I'm going to go back and I'm going to buy a book called Be Your Own Dentist. And I'm just going to figure out, no, I'm never going to do that. I'm going to go to a dentist. So why am I going to pretend to be a finance guy? So that day, I decided even though everybody told me as a CEO, you need to understand everything. It's, it's a stupid idea. So that day, I said, I'm going to go, I'm only good at one thing marketing. I'm going to get the best finance person, the best HR person, the best operations person. And I'm going to surround myself with people smarter than me and just stay out of their way. I did not know that when I started. I was thinking, I got to figure everything out and I got to be the smart one. And sometimes you feel that way because it was your idea and you're the boss or whatever. But it was when I let go of that that I actually had growth. You're reminding me of a saying in Arabic, which goes, which translates to give each baker the specific bread that he is able to bake in the best way possible. So the sour dough would go to the best sour dough baker, you know, the white bread would go here. And yeah, you know, you don't need to be a one jack of all trades. You don't master. And you probably can't even though you think you can't. Yeah. So I learned that. I did not know. I did not know that. I learned it. Three months ago, four months ago, I was on, I was marketed on Instagram. It was a cool product that I saw. I think it was like a wallet or something. And then it said shop here. And I was like, oh, interesting. So I clicked it. And the next page, it took me to had my house address. And what? It had the Apple signs. So all I have to do is click twice. So it was two clicks. I'm on Instagram, shop here, click it. I clicked it once. It took me to a page where if I double clicked, that's coming to my house. But from a vendor, you didn't even know I didn't know. It marketed, it marketed me based on demographics. You right. It got me based on what it thinks I like. But what was amazing, Jeff, is that I didn't have to put my house number, house address, jedda, saturday, the postcode. I didn't have to do any of that. And there is a stat where if you have to have customers and I think you'd like this, if you have to have customers, put in those details, 70 or 80% of them will say I don't have time for this. But if they're details are already entered. Right. And it's just double click Apple pay. I was like, no, no, I don't like how easy that was. This is dangerous. Yeah. Yeah. This is stupid. Amazon has the one click that they added, right? It used to be you go through a checkout process. And then one day a button appeared that said one click purchase because they have all that in me. Yeah. What really got me was the Amazon supermarket in London, Amazon Whole Foods, Amazon All the Go whatever that is. That's a pretty crazy tech. It is walk out without. It's equally as efficient as it is scary. Yeah. I agree. I agree. I kind of want to deal with the human in that word. A lot of times I feel that way. So what predictions do you have over the next 10, 15 years or so? What do you think is something that we're putting up with today that in 10, 15 years, we probably won't be? I think there's a few, well, I'm going to take that little broader like the industries that still going to go through massive change, right? I still think education is the paradigms worldwide are so old and so inefficient that I think we put up with an educational system everywhere that is actually not doing the job. So I think there'll be another whole generation. And what I'm watching is you can't turn the battleship quickly. So the existing school and educational systems in a lot of countries are probably not going to adapt. What we're seeing is innovators just creating a brand new one from scratch. And I think, you know, you'll get some of both, but I think education is one that we put up with a really inefficient education system that misses a lot of what we need to educate people. I think that'll change. I think that what interesting is this may sound though, I think that work from home, right? The the digital nomad is brand new. And because of COVID, you know, the remote worker is brand new. And I will tell you even today, even this long after COVID, you know what CEOs tell me all the time like Jeff, I still have no idea how to optimize my remote workforce. I don't know, by the way, how to cultureize them. I don't know if I'm engaging them because, right? And I don't know if I'm getting max productivity and CEO after CEO tells me I still don't feel on maximizing remote workers and virtual workers. So I think that's going to be the future of work is going to go through another whole revolution. And then for me, the third one is healthcare. We go physically to clinics and doctors for a lot of things we pay for that you'll be able to do at home, right? An example is I was asking the CEO of a huge medical clinic in the US. What one of his best revenue sources is and he gave me an example, an EKG. So your doctor says I want you to get an EKG. So you drive to the clinic and they put all those cables on you and they push your button and it takes a reading and then you leave because they send that to a doctor. So now I was at CES, the consumer electronics show. And there was like a kid, you didn't even have a booth yet a table and like an iPhone and some cables. And I was like, they have digital health now at CES. And I said, what are you doing? And he said, pick up the cables and touch start on the iPhone. And the iPhone told me put one ear, put one ear, put one ear, and then it said, push start. And he said, your data just went to your doctor. And what the CEO of the hospital told me is we get $200 every time you come in to use those cables. And now, if I just hook them up at home, he said, that's one of my biggest revenue streams is procedures you can't do at home. So I think a lot of healthcare is going to adapt to the technology and it's going to change the landscape. We'll do way more self-care than we ever have before. Very disruptive. I can just go to education for a second because it's something that's close to my heart. I complain about the system that hasn't changed in the last couple hundred years. It has not everything has changed except this. And I've been very vocal about it on the show. One day I was picking up my son from school and one of the senior teachers said, hey, Mo, can I just have a word with you for a second? I'm like, sure, like I saw your episode of two weeks ago and you were complaining about the education system. And by the way, I love your show. But can I ask, how do you think we can make it better? I didn't have a concrete answer for him. But what I did tell him is that the 20 to one system that has been around for all this time has not evolved. And whether it's five to one, whether it's children, kids not being institutionalized in school from such a young age, I know in Japan, they start at five or six, which allows them creativity to not be so indoctrinated with education that sometimes is just force, force fed down their throats. But I didn't have an answer, but I knew that change needed to happen. If I can just put that question to you, how do you envision a change for the better in the educational sector? Yes, so that's where I agree with you. That 20 to one thing that our kids are still in those classes. I think that's where AI is one of the exciting answers, right? Because I can't tell you how many companies have showed me their AI teacher, their avatar teacher. So you're going to have one on one. This is going to be a teacher that is designed for your child specifically and only teaches your child knows everything about your child tracks their learning, their education, knows what your desired goals are. So I've been seeing lately a lot of demos of the AI teacher avatar. And it's pretty impressive. But the goal of that is one on one personalized teacher just for your kid with access to way more information than a physical teacher has today, since they still use textbooks for the most part and things like that. So I think that's actually exciting. Do you think 22 years of schooling is too long? The way schooling is today, yes. Because the huge percentage of that really didn't do anything. I mean, I got out of school Jeff 2023 years of 23 years old and I didn't know what I want to do when I was out. So after all that, I studied for 23 years and I don't know what I want to do. I mean, I joined the family business because what else am I going to do? Kind of, I think. - Yep. - I knew I liked marketing the way, but I didn't really find my calling in life. - So I've been saying this, you know, when I talk about education for a long time that I think the answer to that is experiential learning. We don't have enough that. We depend too much on the teacher and the classroom. And meanwhile, right outside that door, we have the real world. So I think that more experiential learning where students are out of the classroom engaged in the real world, whether they're visiting companies or having more guest speakers come in that actually do those careers. But I think that wall, you know, it's funny today, an adult, you can't, for safety, obviously. You can't walk under a school campus, right? It's so isolated. But in fact, if we did more experiential and the kids had a literally more scheduled time in the world and outside of classes, however that needs to work, I think that would change it a lot. - I agree. - So 22, whatever you said, 22 years of sitting in a box, not helping. - It killed you with creativity. I was in school back in the day when I was in elementary school, it was from 7 a.m till 4 p.m. You know, you come back exhausted, you don't want to do anything. My son today at his school in judo, which is an international school, it's 9 to 3, and I still think that's long. I guarantee you in Japan, it's less, we'll fact check that. - That would be interesting to see, because I have a very different approach to it. It's interesting when I became a CEO, now I'm hiring people. So when I'm a student, I'm sitting in class, and I'm like, "Hey, Mo, question four." Can we talk about that? And the teachers like Jeffrey, you and Mo, stop talking, do your own work. But what's my first question when I start a company? I'm like, "Mo, how well do you work out as a team?" And your answer, we wouldn't really say this, we, I don't know, my whole life, I was not allowed to talk to the person next to me. The first thing we ask is your ability to work as a team, but a lot of schools are very focused on exactly the opposite of that. That's changed some. I see a lot more team things, but I'm just saying that the education doesn't reflect the product that you and I need out when we're building a business. - Yeah, and it teaches us to memorize, not to create and think. You want to create thinkers, not tell them what to think. - Yeah, you know, I was telling kids once, I said that even though I learned in school how to compute the square root of a number, I said, "I've never been in my office where a car came flying into the parking lot." Somebody came running in with a credit card and said, "I'd like to get the square root of a number." Like so, why did I learn that? I've never used it once, never sold one of those. What they should have told me was, we're teaching you structured thinking analytical problem solving. What students get is, I don't know why I need to know this, and so they have no interest in it. And really what I hope is that you're learning the, you're learning things like critical thinking and structured thinking and problem solving, but that's not what they tell you. They tell you the test is on square roots if you don't get them right, you're a failure. And no one mentions the whole real reason to learn that. - Yeah. I think the icing on cake is how expensive school has become over the years. It just keeps going up and up and up. - I just saw the annual price of my alma mater, my college this year, one that I went to Yale, and it's up to $100,000 a year. - A year? - $97,000 per year to go to Yale. - It's almost a half a million dollar investment for a college career. - For a college. - I get it, I mean, you're gonna come out like you and say, "I don't actually know what I wanna do," after all that. And back in your day, was it like 20 or 30 a year? - I can't, was it 100? - Remember, I went to school before there was currency, I'm kind of old, so I would imagine it was a quarter of that per year. - That's probably my guess. - Now it's probably right. - Not your first time in Saudi. How is your experience been every time you come here? - You know what, I love it. This is why I come here so much. Probably more. So our nonprofit, I'm the chairman of it, so I'm very involved in it. The Global Entrepreneurship Network, we're on the ground in 200 countries. And if you look at the last five years, I've been in the kingdom more than any other country. And there's a reason. - It's probably vision 2030 related. - So there is so much change going on, positive change happening so fast, you and I were talking about it earlier, that it's encouraging. So I'm here a lot because the commitment to adapting to today is so visible here. So it's been very progressive. There've been so many changes that I only wish the rest of the world really saw what I see. They don't come here, right? And so they really don't understand how much has changed for the positive in the kingdom in these last few years. But every time I come, it's better. There's more commitment, there's more tools, there's more resources, especially in my field for entrepreneurship. So yeah, I love coming here. - The foreigner footfall has exponentially grown. And I'm just talking about what I see in the malls, what I see on the road, a lot of people have, because I mean, for the longest time we've been closed. We've been closed for the better part of 25 years. And now I think there's 100 nationalities online where you can get a visa in no time. But I want you to experience the touristic parts of Saudi and not just the business end. Just up the road an hour is flight from Jeddah. There is an area called Red Sea Resorts, Red Sea Global, where the master plan is 50 hotels. And there's 12 open right now. They basically, we saw them. - We learned a little bit about that yesterday. - The people from Ministry of Culture came to the EO event and told us about that. - Okay. - It's a piece of mall devs. It's basically the mall devs model. - Ash, that's a good model. - It's a great model. Let's see if we can see that in one up it. And for the longest time. - I have to go visit that. - You really do, we didn't capitalize on our Red Sea shoreline, all my growing up years. We never had a five star resort on the water. And now there are dozens. - Okay. - And just the fact that Red Sea is one of the top diving sites. It's an, I love diving. And last night when we were at the museum here in Jeddah and we were at the, what is that museum called? - The Red Sea Museum, right? - Yeah, when we were at the Red Sea Museum. - How was that? - It was good, but they were showing us what the diving looked like, the reef. And I was like, why have I not been here? So I was really impressed. Definitely gonna come back to that. - There are a lot of spots for you to check out. Any closing message you'd like to give our young listeners, you know that Saudi Arabia's 55% of the country is under the age of 30 years old. So one of the widest population permits you can imagine. And the biggest demographic of our listeners is 18 to 25. - Okay. - Do you have a message for those looking to find their feet in the business world? - Yeah, absolutely. One of the things it's hard to see from the inside, right, if they born and raised here in Saudi, so they wouldn't see this. But there's some really good news for you. Like I said, we work in 200 countries and I literally travel to 120 of them for the most part. So I can comfortably tell you you have a moment in time where everything is going your direction to make you succeed. The government programs, the investment programs, the entrepreneurship organizations, if you're a young innovator and you wanna start your own business, the kingdom, the Gulf in general, but the kingdom specifically is a wonderful place. There's so many people and so many organizations and efforts going on that are all designed to help you succeed and the rest of the world doesn't have that. Every time I'm here, I hear about some new program that's helping businesses, helping startups, some other investment fund. It's a really exciting time and you have advantages that everybody else doesn't. So I think that's the important message is that, well, I think there's a second part of that. You're not gonna get an invitation, right, as an innovator. If you have ideas and you wanna launch this company, whether it's a business goal or it's a goal to try to make life better for people, make the world a better place, there's nothing to wait for, now is the time. The tools are there, the government is backing you, the population here and the businesses are backing you, there's a lot of reasons for you to succeed instead of the opposite. So this is your moment, you're not getting an invitation, just jump in. - Absolutely, I don't know if you know this. I don't think I've ever mentioned it on the show, but do you know that if you are a student with decent grades, so see and above, the government will fund your college career, there's a scholarship program that was established in King Abdullah's days that still is active today. - Well, it's fantastic. - That's phenomenal, if you have, I don't know, if it's C plus or B, but you need to have decent grades, the government will fund your college career, including housing, including monthly allowance. Name a country that does that. - Yeah, that's absolutely spectacular. - And I'm talking in the US, England, in other countries, if. - That's what every other country wants, and if you have that, people should absolutely find out about and take advantage of it. - Which is pretty cool as well, because you're getting exposure and tolerance to other cultures as we spoke about earlier. - Yes. - Which is something you'll definitely need in the business world, travel without a doubt, and the business world is just getting rapidly more global. And luckily, if you're here, right, outside of the Gulf, this is the country everybody wants to bring, business too. When I talk to businesses anywhere in the Gulf and even elsewhere in the world, they're all trying to break into this market. You're already in this market. So if you live here, you have an advantage, you know this market, you live in it, you have relationships, you should launch something right here. Yeah. Sometimes I just want people to appreciate and acknowledge something that is, you know, right under their nose. And often it's those who don't have it that strive for it and those who have it kind of push it away. So it's important to recognize and appreciate the opportunities we have. Thank you for bestowing your wisdom on us. Thanks for having me today. It was my pleasure. Enjoy the rest of your time in Saudi. And I'd love to pick up things with you again next time you're in town. I would love that. Thank you. Thank you, Jeff. Thank you.

Podcast Summary

Key Points:

  1. Jeff Hoffman’s early ventures, like airport check-in kiosks, stemmed from personal frustration with inefficient processes and demonstrated his instinct to challenge the status quo.
  2. The launch of Priceline in 1998 was achieved in under two years, marking one of the first e-commerce successes and a key milestone in internet history.
  3. The core innovation behind Priceline—harvesting demand below the price line—was revolutionary, enabling businesses to discover unmet consumer demand through data.
  4. Hoffman emphasizes that true success is not measured by wealth or fame, but by the positive impact on others’ lives and personal fulfillment.
  5. A key entrepreneurial mindset is humility—being open to learning, listening to others, and recognizing that better ideas can come from anyone, not just the leader.
  6. Success is driven by the alignment of opportunity and readiness, with talent and timing both critical, but humility and team execution being more sustainable.
  7. Hoffman identifies major future shifts in education, remote work, and healthcare, all of which will be transformed by technology and experiential learning.
  8. He believes in radical curiosity and urges entrepreneurs to spend time each day exploring unrelated topics, as such "info-sponging" fuels innovation and personal growth.

Summary:

Jeff Hoffman reflects on his journey from founding airport check-in kiosks to launching Priceline, highlighting how personal frustration with inefficient systems sparked his entrepreneurial drive. The early days of e-commerce were marked by technological uncertainty and deep skepticism about trust in online transactions, yet Hoffman saw a market gap in consumer demand—leading to the revolutionary “price line” model that revealed what customers were willing to pay below the surface. He credits his success not to wealth or fame, but to meaningful impact on others’ lives, a realization forged through a personal moment at a funeral where his best friend’s life was transformed by a simple truth.

A central belief in his philosophy is humility—being open to learning, feedback, and ideas from anyone, even non-technical staff. He emphasizes that true innovation comes not from individual genius, but from strong team execution and a willingness to delegate. Looking ahead, Hoffman sees profound changes in education, remote work, and healthcare, driven by technology and experiential learning.

He argues that traditional schooling systems, with their rigid structures and long durations, fail to prepare students for real-world problem-solving. He also notes how the rise of AI and self-service technologies—like one-click shopping and home-based health monitoring—are redefining consumer experiences. Ultimately, Hoffman sees entrepreneurship not as a career, but as a lifestyle built on curiosity, humility, and a commitment to making a positive difference in the world.

His vision for legacy is deeply personal: to live a life one can look back on and say “this was time well spent,” regardless of financial success.

FAQs

The main challenges were the lack of internet expertise and the difficulty of convincing users to trust a fully online booking process without human interaction, as they were used to speaking with travel agents and verifying reservations in person.

It took less than two years—developed between 1996 and 1997, with the platform launching in 1998—making it one of the earliest successful e-commerce ventures.

He was frustrated waiting in long lines at airports to get boarding passes, realized the inefficiency, and imagined a kiosk system that would allow travelers to check in independently, just like using an ATM.

Yes, the technology was patented, and the company eventually sold it, which allowed for a successful acquisition and business transition.

The name reflects the idea that before the internet, businesses couldn’t see demand below their price line. The thesis was to use the internet to discover unmet consumer demand and offer lower prices, thus harvesting hidden demand.

His impatience with inefficient processes—like long airport lines—led him to challenge the status quo, and he believes this curiosity, combined with a childlike willingness to ask questions, is central to innovation.

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