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Brad Keywell: The Mindset of a World-Class Entrepreneur | E04 · In Search Of Excellence

• 1:14
  Randall Kaplan: Welcome to my podcast In Search of Excellence.
• 1:17
  Randall Kaplan: It's about our quest for greatness. To be the very best we can be to learn, educate and motivate ourselves to live up to our highest potential. It's about planning for excellence, which requires incredibly hard work, dedication and perseverance. Achieving Excellence is our goal. It's never easy to do. We all have different backgrounds, personalities, and surroundings.
• 1:35
  Randall Kaplan: We all have different routes and how we hope and want to get there. Today, my guest is my great friend Brad Keywell. Brad is the co founder of two public companies echo global logistics an enterprise transportation company with a market cap of$800 million. Groupon, which everybody knows in which at one point was the fastest growing company ever, and which has a current market value of $1.2 billion. He was also the co founder of star belly and online promotional products company.
• 2:07
  Randall Kaplan: They started which when he was 30, which was acquired for $240 million, media bank and advertising and media company which was acquired for $720 million drive in a car data analytics company that was acquired for $43 million and light bank, a venture capital firm with $360 million under management, and which has had several billion dollar exits in 2000, and uptake, which we're going to talk about later where he is currently the CEO in which has a reported last valuation of$2.6 billion and which reached the $2 billion valuation faster than any other tech company in history. In 2019, Brad received the Entrepreneur of the Year award for that, cut that up to and 2019, Brad received the Ernst and Young World Entrepreneur of the Year Award, becoming only the third winner from the United States and the 21 year history of that award.
• 3:06
  Randall Kaplan: He's also the founder of Chicago ideas Week, a week long conference where thought leaders and innovators from around the world speak on a variety of topics, from leadership to life's lessons. Bran is extremely philanthropic and he signed the giving pledge, which means he's going to give at least half of his wealth away to charity. Brad and I have been friends for 32 years when we were in college at the University of Michigan. So long time. I'm honored to have him as my guest today. I've met 1000s of entrepreneurs over the years and Brad is the most talented of all of them. Brad Welcome to a Search of Excellence
• 3:48
  Brad Keywell: it's a pleasure to be here Randy
• 3:50
  Randall Kaplan: So let's start with our family which helps shave our let's start with our family which which helped shape.
• 4:42
  Randall Kaplan: Let's start with our family which helped shape our personality, our values and the preparation for our future. Your mom was a schoolteacher, your dad is a corporate lawyer. You grew up in Bloomfield Hills, the third wealthiest suburb in the United States. Can you tell us about your parents and What they were like and what kind of values they instilled in you?
• 5:05
  Brad Keywell: Well, I grew up in West Bloomfield, which is not exactly the opposite side of the tracks, but it's also not Bloomfield. So, I, I had the great fortune of loving parents, which I appreciate is not always the case. And, and their love showed up in lots of ways. Even primarily, in terms of how it shaped me, they valued intellect, and they valued curiosity. They didn't say it explicitly like that, but that was part of who they were. And they valued hard work. And so my father, being a lawyer, worked hard as a lawyer, he happened to love the law, which I think is more of a rarity now than ever.
• 6:02
  Brad Keywell: But I also believe that his tenacity to to improve his his lot in life, if you will, or, you know, he worked hard. He he was the first person to go to go to college in his family. And then he worked his ass off and got into Harvard Law School. The old fashioned way, just worked hard. And so that was the ethos, I suppose in my, in my family, it was not really, it was hard work versus it was not at all like that were fancy or, or privileged. It was really, it's a privilege to work hard.
• 6:40
  Brad Keywell: That's, that's, I think, at the core of my parents influence on me.
• 6:48
  Randall Kaplan: So we'll talk about your childhood next. And I think everyone wants to know, What kind of kid you were, were you popular? Were you a leader?
• 6:55
  Randall Kaplan: And what did you do for fun?
• 7:02
  Brad Keywell: Popular is relative. I don't know. So I was not particularly popular. I wasn't unpopular either. I was, I don't know, I found my niche, I suppose of friends. I was a leader. from a creative standpoint, I'm not the most at most athletically gifted, which is why I tended to veer towards individual sports that hard work was the payoff versus teamwork as the payoff is I'm not sure I could be a reliable part of a team. Given that I wasn't the best football basketball baseball player. So I ran, I ran across country and played a lot of tennis. But my leadership, I think, came through creativity.
• 7:52
  Brad Keywell: My earliest sources of validation or reward was, were all related to things that I did creatively, like, I played a lot of ping pong. So what did I do, I created a tournament and it was and publicized it with little flyers, and my school and things like that. So more resourceful. My first business was when I was really young, it was
• 8:21
  Randall Kaplan: six years and six years old.
• 8:23
  Brad Keywell: I did it I created greeting cards because I I had a book that taught me how to draw and I make greeting cards and I convinced the store to sell them I made boxes for them and so So creativity or curiosity was I suppose how I found my identity
• 8:44
  Randall Kaplan: you call the company key creations did you come up with that name, as well?
• 8:46
  Randall Kaplan: And and what was the inspiration for creating it six years old?
• 8:50
  Randall Kaplan: I've never heard of a six year old creating their own company.
• 8:54
  Randall Kaplan: I mean, creating boxes on top of it going to stores door to door I mean, the stores must have looked at you who's this kid
• 9:08
  Brad Keywell: I think it was simply, you know, I don't know.
• 9:10
  Brad Keywell: I think we all find our family mosaics and try to find within those mosaics a way to stand out. So I think that the passion I had around earning money, I suppose or even more than money is earning recognition. I found a lane and I found a lane and I used to do odd jobs around the neighborhood and and then ultimately, I got some paper and a pen or some pens and I realized I can make reading cards. And then I bagged there was a small i don't know like an office supply or gift store called Li specialty. Yeah, I remember and I can I know the owner to give me space Based on the checkout counter for, for boxes of key creation cards.
• 10:07
  Randall Kaplan: Do you remember how much money that venture made? And did you continue to pursue it as you grew past the right page six years old.
• 10:17
  Brad Keywell: I don't remember details, but I do remember that we got reorders. That's good.
• 10:20
  Brad Keywell: And then I also remember, I mean, once I got into high school, then I started to branch on other other businesses while I was in high school. So that was not the core that was that was simply an early venture wasn't the foundation of the of the high school empire. I say that facetiously.
• 10:42
  Randall Kaplan: So you have a lot of positive reinforcement at a young age, which gives you a lot of confidence. And what other kinds of businesses did you start in high school, we're gonna get to college a little bit later. But tell us about high school and the importance of positive reinforcement. When you have a little success at something and you move on, you want to try something else.
• 11:07
  Brad Keywell: I suppose I didn't have the fear gene as the predominant gene ever. So the positive reinforcement that then gets built upon was what just happened organically because I suppose there was, what else? Or what else is possible orientation that I had. But the next business, there was a series of of businesses. I tried to create a valet parking business, which was a thing that people did. Back then I made T shirts, which was a thing that people did back then. And I tried the two that stuck. One was, I look back and I can't believe I mean, it's a it's a statement of the times, but the business was called home watch services, it watched your home when you were out of town. That was what I did. And I put fliers all over town. And I remember the first customer, I can tell you their name, even though I won't but and they were out of town for two weeks. And I picked I shoveled their driveway and picked up the paper and stuff.
• 13:14
  Brad Keywell: And then when they got home, like bought stuff for the refrigerator. And then the one that worked that was really fun was Sunday morning bagel delivery business. So these were all small things. But I guess I just felt there was no shame or judgment or glory. For that matter. I was just continuing to try ideas that could, I suppose distinguish me but more, I valued money. But the money part was part of the overall experience of putting myself out there.
• 13:50
  Randall Kaplan: You mentioned you didn't have the failure worried or you weren't afraid of failure? I think that failure and fear of failure is one of the greatest motivators to most entrepreneurs. I know it's one of it's one of mine. Did at some point, we're gonna talk about some of the challenges you've had in some of your businesses a little bit later as well. But at some point, did that change a little bit? As you started more and more companies? Does that creep into your mindset, I am afraid of failure. And that may help me prepare a little differently or motivate me a little harder.
• 14:28
  Brad Keywell: I'm not I'm not proposing I'm not afraid of failure. I mean, failure is a has energy, there's energy around failure. And the energy of harnessed appropriately is extremely positive, keeps you on your toes and it makes you more capable of calibrating risk. I think that my the fear that I don't think I had nor do I choose to have is a fear of trying. And, and failure is let's say that the idea just try is the door is the opening door when you get in the room, the possibility or fear of failure fills the room. But many people are most people I believe, are stuck at the door. And that door is just try put yourself out there in the arena. But but but in terms of failure, that failure is what entrepreneurs are in the business of failure.
• 15:33
  Brad Keywell: And their daily job is to is to mitigate risk and and maximize reward. But failure is is everywhere. If you're not clear about that daily activity of risk mitigation and reward optimization
• 15:53
  Randall Kaplan: You mentioned hard work a couple of times already. You mentioned that you saw growing up with your dad.
• 15:59
  Randall Kaplan: And you said that this isn't exactly what you said. But you said something similar to this, that hard work leads to better results. And I want to know what age did you really make a conscious effort to be the best that whatever you did? And how did you go about it? Was it the hard work? Or did you make a plan to do it? Or did you have set certain milestones at a young age?
• 16:31
  Brad Keywell: Probably not as consciously as, as I understand today about the concept of hard work, but so I probably did reflexively, or just it, it framed what I was doing. But when I think about it, now, the ideas is what can you what's in your control? And are you exercising control over what you are able to control? And the idea of being the most prepared or the best equipped or the most knowledgeable? It's always been an idea that I believe is, is within control. So when somebody who has a responsibility, shows up, shows up meaning in a room and in an opportunity, when they have a responsibility, and they show up unprepared? That's unacceptable to me. Right? But it's the preparation around understanding calibrating strategizing, whatever you want to call it, that I'm I just early on, realized, I can be good at that. I can be extremely well prepared, when opportunity arises, I can be the one who hustles while he waits, you know, I've always been attracted to there's a handful of quotes or or ideas that have been attractive to me for 40 years, one of which is those who are he or she who hustles while they wait, generally wins. And the wait part is, we all wait around for things. But what we're doing when we're waiting, are we wasting time? Or are we investing time. So preparing for possibility has been a frame of I suppose a lot of what I've chosen to do with my time over the years.
• 18:30
  Randall Kaplan: When we're trying to improve and get better. I think one way to do that is to work with people better than we are we can watch them, learn from them get advice and get coaching from them. Is that something you tried to do?
• 18:44
  Randall Kaplan: And what's your advice to people about this playing with people who are better and more knowledgeable and just observing?
• 18:55
  Brad Keywell: When you think about the analogy of tennis, I I played competitive tennis when I was young and had a chance to spend some time at the voluntary tennis academy when I was 15.
• 19:08
  Brad Keywell: And what you learn there and you learn through tennis is you only get better if you play with those that are better than you or at least very similar in your in your zone. And it's not even fun to play with somebody who's not as good. In fact, your game deteriorates. And there's lots of sports analogies that relate to business all over the place.
• 19:28
  Brad Keywell: That one actually is, I think more relevant than most. That's one two is coaches matter. Sort of tangentially in 2003. So long story, but I became friends with one of the great NFL players of all time, a guy named Ronnie Lott played for the 40 Niners in the Hall of Fame. We became friends when I was 24. And he was still playing in the NFL, but personally, you know, he's now just a dear friend almost like an uncle to my kids. But when I met Ronnie, we started with become like a 30. Let's see on the 40 year 30 year relationship 30 year conversation about leadership and about greatness. And he exposed me to how important coaches are or had been to him in the NFL. And so in the early 2000s, as I said, 2003 We both were in an organization called YPO. And we had an idea that came from my questions to him about his coaches. And the idea was we should create an event that brings together coaches and business people specifically to discuss how coach how the idea of coaching In athletics, is relevant to life and business.
• 20:54
  Brad Keywell: And we did it. We did two of these events both in Pebble Beach. And it was just extraordinary weather. The names from Bill Walsh, Billy Beane, Chuck Daly, who, and even Bill Bill lambier, who, at the time was the only person who had coached a worst to first situation he coached the WNBA team. That was one year the worst and league next year, they won the championship. And then we have players like Joe Montana and Jerry Rice from I'm still friends with this day, and all these different people, all of which we were there to explore the idea of coaching as something that mattered. That idea of finding elders, mentors, coaches, who have an opportunity to pay it forward to pay their genius forward through those that are committed to pursuing excellence, like Ronnie Lott or whoever, that's always been a very attractive idea to me. And I found it to be incredibly valuable to find coaches and mentors who can reflect and then I can absorb their lessons.
• 22:10
  Randall Kaplan: Just a side note on Bill and bear, you and I were both pistons fans, we were both bad boys fan, bad boy fans.
• 22:18
  Randall Kaplan: You're Michigan the same year that I was there. When Michigan won the national championship in basketball, the Red Wings won the NHL. Of course, the lions won nothing. And they'll never go to win anything. But I bought at a charity auction in LA, a two on two with Rick Warren, who was part of the bad boys bill and bears roommate. And a side note about Bill which you probably know, he grew up in pals verdades. And I think he was the only player in the league whose dad made more money than he did. But But Bill was not a well liked guy in the NBA.
• 22:56
  Randall Kaplan: But Rick got sick the day before Bill was out here for a game.
• 23:02
  Randall Kaplan: And he came over to play to on to and of course, I had friends from Country Day, my high school, they flew out. And I played three on three with Bill and he couldn't have been nicer.
• 23:14
  Randall Kaplan: That's the problem is I had to guard on, like 611 and was not in playing shape at that point.
• 23:20
  Randall Kaplan: Either way, so
• 23:24
  Brad Keywell: you get an elbow.
• 23:25
  Randall Kaplan: I mean, it was like it was I mean, I'm almost six, three. And it was like, I mean, I was shooting from 30 feet away, because it was just no way things are gonna go in and. But that was super fun. I also believe in the value of coaching and mentorship. And that's what you've done. There is is great. We were talking about kids before you have two amazing kids. Both are young adults. A lot of people listening today and watching who have kids. What's your best advice to the parents on how to motivate their kids and to live up to their potential and there's, there's a fine line with this. Some parents push their kids a little too hard the kids rebel. So what what's the what's your advice on that whole package?
• 24:18
  Brad Keywell: Well, my my kids are 21 and 22. I and I believe any parent can appreciate the cycles, the chapters of parenting wisdom. Early chapter is I don't know anything I want to know every I want to know, whatever I can know. The next chapter is I know everything. I don't need any advice. There's probably another chapter of back to I don't know anything, I'm scared or confused. Then there's a chapter of appreciation that kids got through what they did and seemed to be on solid paths.
• 24:56
  Brad Keywell: It's and there's more chapters I've forgotten. At some point, there's becomes a wisdom chapter. And then the question is who wants to hook who's who, who cares about your wisdom because there's so much wisdom out there. That's hard to apply.
• 25:10
  Brad Keywell: All of that is to say, I don't think there's any great formula of parenting. Although I do think there's some fundamental truths. And one of my fundamental truths are IX expressing belief in your kids is more enduring and powerful than love. Now, I'm not saying that love, that the expression of love is not also enduring and powerful. But I believe that expressing that I believe in you as a concept is on a relative basis a little bit even more powerful or or or creates more of a superpower in your in your kids superpower being their self acceptance. So that's the best advice I have. Because ultimately, now more than ever, people have a lot of space in America to be, quote unquote, themselves. And at the same time, there's more pressure than ever on that same person who has space to be themselves more pressure than ever, to not be themselves, but to be like others. And everybody has their own journey to understand who they are, which is a philosophical concept. And ultimately, what they really want to be is just accepted and liked for who they are, once they figure that out, all of which can be supported, I believe, at least a little bit by a parent who says, I believe in you, not you, if you or you when you are you. Based upon what you did. It's just you.
• 26:54
  Brad Keywell: That's my, that's probably the the thing I believe, most for sure. Is that belief in kids is a superpower.
• 27:06
  Randall Kaplan: I agree with that. Someone told me when I was a young adult, I think I was working at Sun America, I was getting some coaching like you, I always sought out people that I respected. And someone told me the four most important words in the human language are I believe in you. And I think that's true.
• 27:25
  Randall Kaplan: I say that to my kids. And I say to a lot of my mentees as well.
• 27:31
  Brad Keywell: Speaking of, I think, in the zone of people who understand the value of mentors and coaches, I'm not sure I've met many as articulate and committed as Randy Kaplan. And so, the, like you said, and I've known you now, since we were maybe 10, or 11 years old, so I've known you for 40 years. And you were always one of a kind in terms of seeking out those that inspired you versus reading about those who inspired you.
• 28:12
  Brad Keywell: And the seeking and then the doing are part of what makes you so special. So I, those who are listening or who are engaged with you in the world. I'm sure they all realize this, but I'll just add my two cents that, you know, in Randy Kaplan is someone who, who really demonstrates what it's like to, to find and, and, and embrace the guidance of mentors, which is not a skill, of course that our kids are ever taught. Like nobody taught you or me how to find a mentor or be a mentor. What a good men tea is, these are all concepts that are so to this day esoteric and I, I have a lot veneration for those who get that.
• 29:02
  Randall Kaplan: Well, thank you coming from you that that means a lot. It's very important to me. As you know, I have a summer intern program. We have 36 kids this summer from 19 different schools they fly in. Across the country. I spent one hour per day with them. We give them a lesson we're building a hypothetical company. Now it begins with the idea, the name, the competitors, and I give a lot of intangible coaching as well. And I know you and I have talked about the value of intangibles over the years are many times more important than the tangibles. Can you do a model? Sure you can do a model did you go to Harvard? Did you go to you know, Southeast Tennessee State. I mean, I'm making it up. But it's the intangibles that rule the day and help those who are equally intelligent and capable. But you can get along with others you.
• 29:57
  Randall Kaplan: You can speak publicly, you're articulate, you're a team player, people like you, you smile, you have a good attitude.
• 30:04
  Randall Kaplan: When you walk in, you don't complain. And my goal, one of my main goals in life is to make a difference in the lives of people, and I appreciate the kind words and I think I think I've been able to do that with the summer program. And then some of the other people I've been able to coach throughout the years. I just love it. It's one of the things I'm super passionate about. It's really
• 30:31
  Brad Keywell: cool. It's, I'd say you've 36 interns you said the summer Yeah,
• 30:36
  Randall Kaplan: yeah, we got about 750 applications. It's now a thing. I mean, if you go on Glassdoor, I think we have something like a 4.7 review rating, which is very high. I think it's not a 5.0 I mean, you're you're free not to like A program that's fine. A couple of people have left us ones, but we've had to terminate them for things that they shouldn't be doing severe things. But yeah, we have 36. And we have a guest speaker each week. People like you, my friends, they're their senior people. If you want to do it this summer, it's only 45 minutes. But it really my goal is to inspire and motivate people love listening to successful people like you.
• 31:25
  Randall Kaplan: That's why I did the podcast, I want to make a difference in people's lives, I want to inspire like you get up off your chair, don't be afraid of failure, you can fail, you can fail again. We all fail. We've all been down in the dumps. But I love it. I mean, I love I love it. And that's the impetus for the podcast,
• 31:47
  Brad Keywell: what I was going to share is at uptake. For the first four years, I had breakfast, once or twice a week, with 10 randomly selected people. And one of these breakfasts a half of the people at the table did not graduate college. And they were senior data scientists or senior engineers at uptake. And it led to this long exploration. First with them, we ended up then I asked if they would be comfortable spending more time with me, helping me understand their journeys in life. Because they did something right. Even though dot dot dot, you know, they didn't fit into the college track that we have, that our society saw defined as being right. And it's just interesting, all the paths to greatness to your point of this podcast. And also, at the same time, the skills that do matter, like collaborating with others and having a sense of we're all better if we're all better, versus me, or, you know, as opposed to, it's me versus you one of us is better than the others worse. So the soft skills become pretty hard and, and foundational over time.
• 33:15
  Randall Kaplan: Just a footnote on the intern front, I'm gonna bring back something from a long time ago, one of my former interns was your first employee there at uptake. And at one point he was the CEO of uptake.
• 33:25
  Randall Kaplan: John,
• 33:30
  Brad Keywell: yep. And he was also one of my TAs when I taught a class at University of Chicago. Yep. It's such a small world.
• 33:39
  Randall Kaplan: It's a small world. And we talk about the interns and the mentorship. I had another mentee who I spoke at Northwestern University, I was a keynote at something. And you get the crowd afterward. I know, you get a zoo afterward. I had Around 10 people and this kid comes up to me, we're not going to mention him. But he moved out to LA he reached reach out to me working at a studio that summer, then he's working at Mozilla. And he wants to come work with me. And and I say work with me. I never say work for me. I really hated and felt demeaned. When I had a boss, who said I work, you know, Randy works for me. There's no need for that. That's ego driven.
• 34:32
  Randall Kaplan: Just a little tidbit for me. But this person wanted to come work with me. And we had nothing going on. He was smart, very well, light, confident, great intangible skills, had gone to similar schools as me. And right before he wasn't super psyched about moving down to Los Angeles. And right before he was coming. He said, what other because we really did have nothing going on. I was doing my own thing, the investing. But I was thinking about creating new companies. I said, come here.
• 35:12
  Randall Kaplan: We'll figure out something for you to do. We can create something together. Then he says to me, Well, what other companies do you know of doing great things I mentioned Groupon and I mentioned you I mentioned our very close friendship. And he said, Well, you make the well, first he said no, I'm not moving to Chicago. And then he did some poking around. And he said, Yeah, would you make the intro so I call you up. I said, You gotta meet this kid. You and the other two co founders met with him. You like them? I think he'd beat out 100 people and as I remember correctly, it's something like this. He was the first non tech employee at I grew up on, and he did very well. And it's, it's a source of pride for me. And I know for you as well to empower people like that to make the intros for people, I mean, it's one of one of the benefits of people who have been out in the working world who are senior who can make a difference in people's lives by just picking up the phone or recommending somebody,
• 36:15
  Brad Keywell: you know, he he's part of the fun of doing what you and I both do is we get to engage with extraordinarily talented people, that's part of the fun of this, quote, unquote, new economy, the newer part of the evolving economy. And there's an example of somebody who's just a joy to work with.
• 36:41
  Brad Keywell: He wasn't the first non tech employee, but he was an early employee who made a difference for sure. And I do reflect on how often good things happen in all directions, 360 degrees in my life, when we all win, when I make a phone call, or, or, or suggest something to someone, or something suggested, to me, the most informal kind of activity creates such extraordinary opportunity for people and then often extraordinary results. And I feel blessed to be like, you and I both have skills that happened to be oriented around technology, we couldn't just easily have skills around Mechanical Engineering on a factory line. And that might have or we just as well could be poets. But what we what we've chosen to focus on is, is creating businesses that happened to have a lot of technology orientation, that happens to be this kinetic exciting part of our economy.
• 37:49
  Brad Keywell: And it has emotion to it, it has a fluidity to it, that people are off freight people are created in terms of, of greatness of experience, or capacity. And then great people are motivated in the space that we're in. And then there's movement, there's action. And so being part of an active component of our economy. Is is exciting. And I appreciate that deeply. Because I began my career post law school in an extraordinarily unexciting part of our economy. And I do know what it's like to be at a trade show where people are sleeping, right? Whereas we go to trade shows, if you will, in the world of technology. And it's just intoxicating. So appreciating that I find it's hard to, I don't often appreciate it. But when I'm reflecting like this, it's pretty amazing to think about how fun it is to be doing business. In the world of technology in 2021.
• 39:00
  Randall Kaplan: Let's go back a few years to 1991 your freshman.
• 39:04
  Randall Kaplan: 18 years old, the greatest school on Earth, the University of Michigan. Back then there was no internet freshman in 87. Oh, sorry. Yeah, sorry, not didn't right. I was 1986. My bad. No cell phones. So we had the yellow pages, the big thick book with a bowl people who paid more for the bowl, which meant we walked a lot when we wanted to do something a bit, went door to door sounds like you had done that before. And you're walking in off the street, you're introducing yourself, it's a cold call, you're trying to convince someone much older than you you're 18 years old, and they're probably thinking what is this kid doing? It was 10 times harder, maybe 100 times harder back then to start a company. You started in college selling guidebooks and posters.
• 39:55
  Randall Kaplan: So what what was that about?
• 39:59
  Randall Kaplan: Where did it come from? Did you plan to do that? Talk to us about
• 40:05
  Brad Keywell: that. I got to Ann Arbor and something about me quickly understood. This entrepreneurially is Woodstock.
• 40:16
  Brad Keywell: You know this is this is like this is Woodstock in the in the 60s. You know, this is this is unbelievable. The freedom to be expressive entrepreneurially once I found myself independent, and in Ann Arbor, and I don't know why but I couldn't know. I was so excited about all the opportunity and and my reaction to opportunity is to create and the and the poster business that I created was sort of a riff off of the modern art or posters that I saw in people's dorm rooms and, and my reaction to that was, that's amazing I should do my maybe there should be a modern art version of, of the Michigan logo and you know, the black end and modern art versions of other schools logos.
• 41:08
  Brad Keywell: And why pay somebody to do it professionally, let's have a contest for students to enter.
• 41:11
  Brad Keywell: And and, and that worked. And then there should be a cultural handbook when you when you get to your dorm and get on campus every semester. And that worked.
• 41:24
  Brad Keywell: And so I just started to try things. And those were days when I are knights more accurately, in the midst of being in a fraternity and doing all the things that thankfully I did more that were sort of, you know, more cliche or core to the college experience. I chose a different path to complement those more traditional activities, called creating businesses. And it helped me figure out who I was.
• 41:55
  Randall Kaplan: If you go back, there's a long time ago, there were a very small number of us, creating companies in college.
• 42:03
  Randall Kaplan: It was you, Jeff plow, happy Walters. And he stands there.
• 42:09
  Randall Kaplan: I'm Eric with kowski, your partner who sold remnants of carpeting at Michigan and some other schools. Jeff is the CEO of the related companies, largest real estate developer in the world. Happy he's gone on to start multiple business standards gone up started multiple business I have you have we've all done pretty well for ourselves. What's the message here? We all knew each other. We were all friendly.
• 42:37
  Randall Kaplan: What's the message here?
• 42:40
  Brad Keywell: Message just stay in touch with people that are doing stuff. Because you'll probably be doing similar stuff sometime in the future. I don't know. I mean, I see Jeff. And we, you know, Jeff and I were fraternity brothers. And yeah, you're the not just the year but like the I don't know, the month probably when I read somewhat randomly met Sam Zell.
• 43:07
  Randall Kaplan: Well, we're getting there. We're getting to Sam in a minute. He,
• 43:11
  Brad Keywell: you know, Jeff Metz met Stephen Ross. Right, exactly, has had this profound influence on Jeff's incredible career. And around the same time I met Sam Zell who's had such an influence on my life, and I but I remember talking to Jeff, and about the person I'd met, and the person he'd met. And if anything, the message is it's if you love what you do, in my case, in Jeff's case, in your case, what we love is being engaged in the arena of business, it's pretty fun as time goes by, to have those relationships at have long duration, because you have brothers and sisters who've been in it with you, and you can reflect and that's, that, to me is part of the joy of life is is sharing, sharing experiences together and and saying can you believe what we were doing? And can you believe? How naive or maybe not naive, you know, you just do like what was going on that we both were so interested in, in meeting these icons who came to campus just so interesting.
• 44:21
  Randall Kaplan: Well, this backing off for a second, you're at Michigan, you hear about an entrepreneurship class, you're really not allowed to take it you go to the professor to enroll you convince yourself and he lets you in, by the way, if you remember a professor called Sidney fine, the history professor, which was the class everyone wanted to get into.
• 44:42
  Randall Kaplan: Yeah, and the class would fill up first. I mean, today you go online, and then it was tougher to get the classes that you wanted, so I couldn't get in.
• 44:49
  Randall Kaplan: And it was my junior year, I wanted to do it. So I go see him. You know, Professor, fine.
• 45:00
  Randall Kaplan: I'm Randy Kaplan. Here's my transcript. I had all A's I think you knew I was Phi Beta Kappa, my junior year. And I said, I'm would love to do this.
• 45:08
  Randall Kaplan: He and he wouldn't let me do it.
• 45:14
  Brad Keywell: But you get in a class, so you cannot get in. Did not
• 45:18
  Randall Kaplan: get anywhere. I mean, there were like 300 people in the class he wouldn't take three or one he would not you would not let me in. So you know, my kids make fun of me all the time. You know nothing about US history. I said yeah, it's Sydney finds fault. It's not my fault. I don't like reading you know, when I read for fun right now, I love to read fiction and business books. So I guess at some point, I need to come back and educate myself but but but now I want to talk about Sam. So for those people who don't know about
• 45:49
  Brad Keywell: real quick, those clashes I've talked my way into Back in 9919 88, and then a similar class that I also taught. And that was a class for MBA students, I was a freshman.
• 46:05
  Brad Keywell: And I somehow got in with all these 20. You know, I was like 1821 year olds, 22 year old. So I still talk to that professor to this day. How many years is that? Each night, that's like 30. And then the next year, there's another class that I was not allowed into that I somehow found a way to get into. I talked to that guy too. So I have a handful of professors that I've stayed in touch with, to this day. And that's pretty I say to my kids, my hope is that there's at least one or two professors they encounter, who are influential or, or inspirational at some level to them, and that they, I just offer the possibility of staying in touch, which I think is less cool, if you will, or it's, it's not the norm, I think of the new generation to stay in touch with professors. But I think I advocate there's value to that, because it's helps you just they care about you. As my story. I believe that.
• 47:05
  Randall Kaplan: Fast forward a couple of years. I'm at Northwestern law school, and I wanted to take some Kellogg classes, which I am not permitted to take. So I went into the register, Chris Jones, and I did get a two classes. The first time I was in there, JB Pritzker was my law school classmate, we're friends, those of you who know it comes from the Pritzker Family, the governor of Illinois today, but I did get two of the classes he did as well. But let's move on to Sam. So for those of you who don't know, the short one liner is he's the founder and chairman of five public companies in New York Stock Exchange. He's been a member of the Forbes 400, since the list came out in 1982. He's the inventor of the modern day REIT. So he comes to speak at the B school, you go up to them, and it led to an amazing relationship that has lasted for decades. We're going to talk about well, let's, let's stop there. So he comes to speak.
• 48:12
  Randall Kaplan: Were you waiting for him to speak? Did you plan it out? Did you dress up first? You prepared? I'm sure. So when you went off? I'm Brad Keywell. Nice to meet you. Mr. Zell. What happened? Tell us about it. And then what happened to that relationship for the next few years?
• 48:36
  Brad Keywell: The best I will, in terms of dressing up part of the SAM, in my book is now globally, in 2021. I believe Sam, I reflect on Sam Zell and his life. And I say he's one of the all time great entrepreneurs this world has ever seen ever. I agree. That being said, in 1988, he was not a household name. But I was very curious. And I and so I knew enough to do my homework.
• 49:15
  Brad Keywell: And there wasn't really the Internet back then. But I, part of my knowledge about Sam was his iconoclastic core, which included his belief that you can wear whatever you want to wear and still be okay. And so he was advocating before it was even I a possibility that one can wear jeans to the office, that which was at one point, radical, controversial. So in terms of getting dressed up, I don't think I got dressed up. And to this day, I'm not a big fan of getting dressed up. But that being said, I something about me went to that, hear him talk something about me went after he finished talking to talk to him.
• 49:58
  Brad Keywell: And then I've recently, you know, I see him a lot he, somebody asked, he and I together what he saw in me, and he said, it's very simple. I can picture it. You know, this is like 34 years ago, but he said, I can picture right now he was hungry. And it's rare that people, anybody has a core intellectual and I think an entrepreneurial hunger. That's all I know, because I can't like I say, I can't, you know, the fact that he responded to my enthusiasm by saying, come see me in Chicago. My response was, what does that mean? Like, comes in Chicago, he's like, call so and so and come see me. So I found myself in Chicago a week later with Sam Zell in his office and he said, come work with me this summer. You know, what are you thinking about for the summer and I said, I've got an offer with Arthur Andersen.
• 50:49
  Brad Keywell: Yep. And he said, Why would you do that? Come spend time with me. So there's so many things about the way he treated me that all I can do is be committed to paying forward to others, treating others the way he treated me because he saw me for who I who, who I hoped I would be, versus for where I was, like, he sort of saw me in the form of what I could be if I apply myself or it was, it's an extraordinary feeling when somebody that you really, really admire and respect, treat you like an adult, when in your mind, you're still sort of figuring out what it's all about.
• 51:35
  Randall Kaplan: I saw a video of the first time you interviewed him, it was at your conference.
• 51:39
  Randall Kaplan: And you mentioned to him that you had two real mentors in your life, your dad and him and I, I could swear, I saw his eyes water a little bit. That was a great moment, by the way, great, great moment for him for you, for me knowing the whole whole thing, and the influence that he's had on your life, personally and professionally. I mean, I think he was truly touched by the words that you said to him was
• 52:13
  Brad Keywell: like that, I found me the experience of creating an ideas Conference, which then became, has become a meaningful one. And then interviewing Sam on stage. Everything about it was so touching to me. That moment, and my family was backstage and yeah, we spend time together, which, yeah, it's it's, you know, we all with life happens, right. And so you meet somebody when you're 18. And that person becomes a part of your life. And life keeps happening. And it's and and if you're lucky and fortunate, that person continues to stay in your life, and it's a mutually positive relationship with which I have had with Sam. And, and it keeps going, the idea of stopping once in a while to appreciate each other, and having a chance to say to the mentor, right in his eyes, I appreciate you. It's pretty extraordinary thing.
• 53:25
  Randall Kaplan: You graduate with honors from the B School, undergraduate B school at Michigan van, your dad and you think even Sam pressured you to go to law school, you go to Michigan, you meet your partner, you look down in the row, Eric Lefkofsky was their love was in the air. And you guys are still partners today. But then he went to work for Sam. And it was ironic that Sam encouraged you to do this because he practiced law for four days, as you know, and that didn't go so well. But then Sam pulled you aside. And he gently in Fenway basically told you to leave. And you need to go do something on your own.
• 54:14
  Randall Kaplan: So
• 54:16
  Brad Keywell: well, not quite.
• 54:16
  Brad Keywell: So the story was, was that the story or not really? I mean, okay, working with Sam, there was there was never like a so what I did with Sam, I met Sam when I was a freshman or sophomore, undergrad. And, and what he gave me was opportunities to intern with him. Okay. And so I did that part of my summers, the other parts of my summers were doing my own businesses in Ann Arbor getting them oriented towards the the school year. So but then law school, I was not going to go to law school. I was I was I had, I had offers to go into investment banking, which was something that was a fancy thing, or I thought it was and and other ideas or what I might do. My dad and Sam, both were emphatic saying you got into Michigan Law School. It's the best at the time, it was ranked the best law school in the country. They're like you, you just have to go. And I still was not going to go in Sam said, I'll make you a deal. If you first year you're on your own.
• 55:23
  Brad Keywell: He said first year law school.
• 55:26
  Brad Keywell: It's like bootcamp. You're all in but the second year, it's possible to go to law school, basically, two days a week. And you can arrange your classes such that you're you're really in class for two, maybe two and a half days a week. And if you can pull that off, I'll fly you into Chicago and you can work on my m&a team. while you're taking classes, and he any and he's in he had a second apartment in Chicago, he said you can stay in my my place, which was just the most extraordinary kind, generous meant act of mentorship and love. I couldn't ever. I mean, it's just extraordinary and, and I said, Okay, deal. So I went to, it wasn't the reason.
• 56:19
  Brad Keywell: But it was an amazing opportunity which I took advantage of. So I said yes. And I, my second year of law school, I literally, my classes were Monday and Tuesday ish. And I was on a plane Tuesday night or Wednesday. And I was working on deals Thursday and Friday, and often Saturday and Sunday as well. It's pretty it was an amazing time. And then I Yeah, but then once I graduated law school, I went straight into business with Eric.
• 56:46
  Randall Kaplan: Right. So we have a lot to cover yet. So I want to zip through some of this. But we all talk about challenges. We've all had failures. We've all been depressed and feeling crappy about our failures. You sort of had two out of the gate you had Brandon apparel, I want you to talk about that a little bit and, and what you did and what happened there. And then I want to talk about Star belly. And you and I talked about that. A month or two ago. You told me some things here that I didn't know. But I think it's important in our quest for excellence to really keep coming back. A lot of people want to go home there, you know, you failed, you lost a ton of money and a ton of time.
• 57:37
  Randall Kaplan: It's embarrassing, especially when you get sued. Thankfully, I've never been sued. Well, that's not true. I've been sued once, for some bullshit claim, by the way. But but you're down on yourself, can you walk us through those businesses briefly? And then how you pick yourself back up? And how you motivated yourself to get back up?
• 58:09
  Brad Keywell: Sure, I'll frame the answer your question with this quick story. When I teach this class, or I taught a class for five years at University of Chicago, around entrepreneurship. And on the first day of class, I would ask people why they were there. And and the the sort of undercurrent was because I want to be an entrepreneur. And these were MBA students, I believe, first semester, second year MBA students. And so then I every time it's okay, raise show of hands, how many of you want to be entrepreneurs? Meaning start your own thing and be independent of quote, unquote, working for someone else, etc.
• 58:51
  Brad Keywell: And most people raise their hands. And then I said, How many people are interviewing for a job? Right now in reprocess?
• 58:58
  Brad Keywell: Everyone Raise your hands? And then I just offered the possibility that very similar to an artist, where you say to an artist, are you going to? Who are you? I'm an artist? Do you have a job? Maybe, but the job is just so I can do art? The idea of like balancing should I be? Should I work for McKinsey?
• 59:23
  Brad Keywell: Or should I be an entrepreneur?
• 59:28
  Brad Keywell: probably means you're better off working from McKinsey. Which brings me back to the answer to your question. You know, to me, someone who is a who is an entrepreneur period, who is oriented around there being no other choice, but keep trying.
• 59:44
  Brad Keywell: Like, what else are you going to do? You know, an artist is not going to stop making art because their art wasn't perceived as being attractive, they're going to make art, it's what they do.
• 59:54
  Brad Keywell: So an entrepreneur does what they do. In that spirit, the first thing I did after law school, that Eric and I, as partners were part of was, was buying a company, a very small company, in an industry that I had no idea but now appreciate is a very poor choice for industries to choose, which is clothing, apparel, and the lesson and so we bought a company was doing three or $4 million in revenue, we grew it fast in our opinion, in my opinion, you know, within two years, it was $20 million in revenue, not three or four. But that's a hard business because the number of things that have to go right. In order to make money or many, you've got to make this stuff. It's got to be the right size and color and it's got to be sold by we sold to everybody from like Neiman Marcus, all the way down to Walmart, blah, blah, blah. You know, it was It's very, there's so many moving parts in that business, any one of them goes wrong, it all goes wrong. The lesson there is choose businesses, where more of the more is in your control in terms of the things that must happen in order for it to be successful. And then out of that came the idea for Star belly, which was an idea around using technology to facilitate the transaction and, and supply chain of promotional branded products. And it was a very fast growth company. It was started in the perfect year 1998. And we raised $8 million. And we soon had an offer for $190 million to sell it, which was then raised to 240. And I found myself at age 29, the president of a New York Stock Exchange company. And little did I know that the company that bought us, a year later would be filing bankruptcy. So the lessons of, and I put my you know, I was I was, if you will put out there, you know, as the President, I was on earnings calls, when I was 29. I was the youngest president on the New York Stock Exchange, it looked pretty fun, I would assume from the outside are pretty glamorous, let's say it materially there's a lot of glamour, or a lot of excitement about that experience. But emotionally and personally, that was about the heart is about as confused and, and challenging situation as I've had in my professional life. And then when when when the buyer that bought our company went bankrupt, my net worth, if that's a measure of of, however you perceive the measure of a person's net worth, my net worth went from a lot to almost none. And that's when you know, the entrepreneur is is ultimately tested. What's next.
• 1:02:56
  Brad Keywell: Well, if you're an entrepreneur, the next is keep trying.
• 1:03:02
  Randall Kaplan: While you did keep trying, and things got a whole lot better echo logistics, who started 2005 and went public in 2009. It's worth nearly a billion dollars today media Bank, which merged with another company, VISTA equity, probably the best private equity firm in the world bought that company for little over $700 million.
• 1:03:22
  Randall Kaplan: You're feeling good about your future. And then comes Groupon.
• 1:03:26
  Randall Kaplan: So tell us about Andrew Mason, what he was doing when he approached you with this idea.
• 1:03:38
  Randall Kaplan: And then tell us about the point.com. And again, I just want to we're gonna try to condense this, I know you're, we have a hard stop in a little while. But this is a great story. And there's so many lessons from the story.
• 1:03:55
  Brad Keywell: Well, the story I that I suppose is, is less than rich, is a story of everything that I had been a part of, up until then, was me and my business partner had started.
• 1:04:13
  Brad Keywell: This was the first time that we were involved with something where a third person was involved. And since group on a post group on it went back to almost everything I've I've done has been either just me or me and, and my business, my business partner. And that's been so three people, I guess one lessons, three people is harder than two. And it's not just 1/3 Harder, or, you know, it's exponentially harder for three people to agree than two people. Another lesson is this business started as the point.com. The point.com was an idea around well, I'll make it easy. It was Kickstarter way before its time. And it was Kickstarter, but for but for social action. I will do something contingent upon 100 people agreeing to do with me otherwise I won't do it. And it didn't work. We spent a lot of time building a website and theorizing about what would happen and then ultimately went live. And like most websites and most businesses, expectations were far under under met by reality. What was different about that is that we collectively did not throw in the towel and stop the business.
• 1:05:42
  Brad Keywell: What we did is pretty quickly acknowledge it was not working.
• 1:05:47
  Brad Keywell: The idea behind the point.com was not working Seeing what might work with a similar technology oriented approach?
• 1:05:56
  Brad Keywell: Well, one thing would be collective action around buying stuff. And group on was born reactively or iteratively, versus more miraculous conception of Groupon is a story of iteration. And it then became a story of fortuitous story where the experience, be it of media bank, you know, now renamed media ocean in modern, in the modern 2021. It's called Media ocean, but media bank, echo all these experiences we had had of growing businesses, fortuitously, or materially became core to the operational execution of, of growth, not that the growth of Groupon was without lots of flaws and, and sort of small failures. But being able to start a calendar year with 124 employees, and end that calendar year with 5100 employees is, those are the facts. That's what happened in two in 2010. Having that happen, and at the same time, having the train, stay on the rails and continue to chug forward is only possible, I believe, if there's some conception of growth metrics, discipline execution, behind the wheel. And so that's part of the group on story.
• 1:07:41
  Brad Keywell: There's a lot of stories of behind the Groupon story, we can go on for a long time. But that's the fun part about some of the whether it's Amazon, I find a lot of guidance from Jeff and, and, and some of Jeff's board members from the early days and hearing those stories, I think, all the stories of of this new breed in the last 30 years of companies that had been created. And then the reflection that those companies have nearly replaced. Those who 30 years ago dominated the fortune 100. You know, for Fortune 10, or 20, for that matter. This is a great age in which to learn. And so these stories of coupons or sales forces or whatever, are ripe with lessons.
• 1:08:32
  Randall Kaplan: I remember you stay at my house right at the time this thing wasn't working.
• 1:08:34
  Randall Kaplan: And you told me you're just sold the first group coupon group on your days away from shutting down the company returning the investors money, and then you made you made the shift. I think it's important for listeners and viewers to know that don't be tunnel focused, listen to customers be open minded to changing and then I remember you also tell him a thank you, you said this completely nuts. And you had famous venture capitalists showing up in your lobby without calling. And you telling me that one of the challenges you have it was growing so fast, fastest company in history to a billion dollar valuation that you couldn't find companies to process, couldn't find credit card companies to process the payments. You had a chance to sell Groupon.
• 1:09:35
  Brad Keywell: But then we went to a favorite stories is the gut. We had an email service provider as they became to be known. And at the time it was I forgot the name, and it couldn't handle the volume of our emails.
• 1:09:47
  Brad Keywell: And so I found a company called exact target. I don't know how I found them. And I called a guy named Scott Dorsey who I didn't know when I called him and and I said, this might sound crazy. I said how big of a knife, maybe we found them. We found them and they started pressing our emails. And there was a delay because we had so many members adding to our customer base. And they couldn't exact her couldn't process the volume of our emails. And I call them and I said you need to focus on Groupon. We're going to be very important to you. What how do we rank right now? Like how important are we? And he said, basically, you're not that big of an email or don't you know, I'm good. We can handle you. And I said, we're going to be your biggest customer soon. And literally like a year and a half later we were that we were we were we were a bigger consumer or user of email than American Airlines and others And to this day when I talked to Scott, who I'm good friends with, it's hilarious that that's part of the fun of business, you could be like, can you believe when I said to you, I'll be your biggest customer. And then we were so funny.
• 1:11:06
  Randall Kaplan: You had a chance at some point. And there's all this competition, which of course happens when you don't have a patent on what you're doing. And despite the competition, I mean, there were hundreds, probably 1000s of companies trying to copy you.
• 1:11:21
  Randall Kaplan: And I had a chance to sell the company, as reported for 5.7 5 billion, 6 billion in cash, you guys didn't take it. You went public, the first day you closed the valuation was 2.7 billion, or the value when you went public was 12. Point 7 billion.
• 1:11:38
  Randall Kaplan: And then I think it closed at$16 billion that day, the stock the company's worth today 1.2 5 billion, was it a mistake at that point not not to sell? Do you look back and think I probably should have done that?
• 1:11:55
  Randall Kaplan: And if so, are there lessons for people out there?
• 1:12:06
  Brad Keywell: There's first of all that an enterprise value is, you know, so the quote unquote, what's a company worth is a relative term and the enterprise value is greater than, than the number use describe but also remember that the the value of liquidity. And this company has had a series of value values, if you will, over time. But the lessons are many. One lesson is, some stories are not as simple as they might seem, from a headline. One of the considerations when Google was considering and made an offer to acquire Groupon is antitrust review. And there were contingencies in their offer regarding antitrust approval, that were material or that were relevant. But there's a lot of lessons that that come from every aspect of growth, whether you're growing a $1 million company or whether you've, you're growing a company that you know, is valued at $6 billion. Everything you do is valuable if you learn from it, or make it better, everything you do has the opportunity to offer valuable lessons, that's probably a better way to say it.
• 1:13:33
  Brad Keywell: And everything about Groupon, or many things about Groupon better yet have proven to be very valuable lessons because as a committed learner, I am committed to learning actively, and not making the same mistake twice. Not that there's any easy to describe mistake, they're pretty complicated mistakes regarding Groupon, but they have proven to be valuable mistakes and that I can now see patterns when they're emerging often before others might see them.
• 1:14:10
  Randall Kaplan: Let's talk about career goals, which is incredibly important to everybody. And one of the question that comes up when I mentoring people is what's what's important to you, what do you want to do for some people?
• 1:14:23
  Randall Kaplan: And what I say to them is rank them list them and rank them Is it money experience? Is it location is a passion for what you're doing the team around you? What's your advice to others when they're going through this exercise? And was money the primary motivation for your career when you started in a little bit of money now you can buy as much free city sweatpants as you want. And where does money rank today? And um, you know what I'm talking about on the free city point, don't you know of course, okay.
• 1:14:58
  Brad Keywell: I think is as good as my memory pal parallels yours? I have an eerie ability to remember ridiculously irrelevant facts like going shopping free city with some friends. Where does money rank?
• 1:15:13
  Brad Keywell: Or what's the lesson is your point?
• 1:15:19
  Randall Kaplan: What What? What would your advice be to people who are looking at a career change whether they're graduating or they're older in life? What factors do have certain factors that you would rank and you would consider or is this situational?
• 1:15:39
  Brad Keywell: I've arrived at a time right now who knows where I'll be years now, but I've been studying philosophy literally studying philosophy with a professor for a pretty decent period of time. At this point, purely independently, you know with in having lunch, talking on the phone, getting reading assignments, reflecting on it.
• 1:16:01
  Brad Keywell: I'm very curious when I give advice to people about their philosophy, do they even have a philosophy? Is there an idea of what a good life might look like? What does it look like or sound like if they were to describe the sense of mattering in the world? Or maybe they say, I don't, I don't even know what you're talking about. I don't, I don't even think about mattering in the world. That is where I generally start. If it's some, if it's a serious conversation about what should I do? Now, young, young people, if they're related to you are probably not going to engage in that conversation. That's my experience my kids when I ask them, or have these kinds of questions or conversations, you know, I'm their dad, so they can throw it off. But most kids in their 20s When that when I'm talking about careers, I find myself starting with like, tell me about what, what, what a great day feels like. Alright, tell me what, tell me who live by who you are and what you believe to be true. And from there, we start to discuss not what you want to do. But what you know, you don't want to do.
• 1:17:07
  Brad Keywell: I'm much more clear about ideas.
• 1:17:13
  Brad Keywell: Like, if you tell me what you hate, then we thought about what you what you might like, or love. But if the question is, what do you want to do? I guess, because I've got kids that are young 20s? I understand often the answer is I don't know. And my response is, that's totally fair. But what do you not want to do? What would look like a horrible life for you different than others, but for you, what's horrible, then you start to say, Okay, if you That's horrible.
• 1:17:41
  Brad Keywell: Let's talk about what, at least goodness is of not greatness.
• 1:17:49
  Randall Kaplan: That's exactly what I asked them on the flip side, to name the name, the five things you don't want to do, name the five things you're best at and name the five things you're your worst at. And this should take you days, and then come back to me a week later, when you really think about it.
• 1:18:08
  Randall Kaplan: Can someone learn the entrepreneur gene?
• 1:18:13
  Brad Keywell: I think so. I mean, but that's, I believe that as people, we all desire to be our best. But if that's not a desire, if you believe that your best is important, then I believe you can learn or refined your essence of entrepreneurial activity. But these days on campus, a lot of kids are being taught that personal best, should be relegated as second or third or fourth and priority to societal best. In other words, what's more true today for a young person? They want to work hard, and and a capitalist system such that they can make enough money to do fill in the blank. Or are they is that more important? Or is I want to work with others actively as activists, if you will, to make our planet better. I don't really care about making money, or, or creating a business or creating enterprise even a not for profit, I just want to join something and stand up against those who are doing or polluting or whatever. Often these days, there's, there's a lot of encouragement for the latter and not much encouragement for the former on campus. And I think it's hard to explore or lean into your entrepreneurial instincts. If what's being judged as good, is, you know, society over over, over, over individual hard work and judged as bad as hard work, wanting to make money. Unfortunately, that is the case in a lot of campuses these days.
• 1:20:03
  Randall Kaplan: One of the things I think of it as hard to think of when when you're younger is having fun. Sam likes to have fun in the office. You'd like to have fun. You do a lot of things for fun. You you write, you buy art, you make art. I know you collect art, who are some of your favorites and what kind of art do you make and what do you think about the importance of having fun? Well
• 1:20:35
  Brad Keywell: I think having fun is very important. I think fun comes in different forms. You know, I'm not I don't look at drinking and doing drugs, for example, as fun but a lot of people do. I look at learning as fun, like blissful fun. To look at experience, going to concerts, you know, seeing mazing bands and small venues is like, outrageous, to me, that's the coolest thing. Going with doing crazy adventure experiences with friends, what could be better so, so I love so fun is really important. Art is pretty fun, buying art is not so fun. So, you know, buying and selling of art, if you will, is not as fun as the understanding of the role of an artist in a society. So that I've been collecting art for, I guess, you know, for, you know, you've been, you've been one of the people along my journey of art that's been important and, and you've taught me a lot as I as you, you, you share with me your journey of understanding, buying, selling and appreciating art. Randy and so that was part of my journey is learning from you. What I've picked up around art is what it feels like to really identify with an artist, and how it's a self validating things. So Andrew che, who's an LA artists is one of my he's inspired me and I collect a lot of his work. But why does he inspire me because I've had a chance to dig into who this guy is, and why does he do what he does, and then it lets you appreciate, yeah, anybody you know, Pete, you could copy an artist's work. But there's something about that artists doing that work. That original work taking the risk of, of being counter, you know, being provocative, and then being validated, it just feels so much like the role of or the activity of being an entrepreneur. So there's something about the artist, and the other artists that that we've that has been a big part of my collection is Kusama Kusama, who's 91 This one was was anything but accepted.
• 1:22:52
  Brad Keywell: Until she persisted for decades, and finally was appreciated.
• 1:22:59
  Brad Keywell: That sounds like an entrepreneur to me too. And then now when I'm making art, I created a museum.
• 1:23:08
  Brad Keywell: That's basically I'm the artist.
• 1:23:08
  Brad Keywell: I'm creating art out of technology. And it's immersive, reactive, responsive art where people walk in rooms, and the room changes based upon what they do their motion, their heartbeats. And it's called wonder Museum, that's been extremely rewarding because I get to be the artist. And then beyond that, the things I'm working on now. I've gotten very frustrated about certain things that I see, as in explicably broken and you can write all the articles you want and all the op eds you want and I don't see things being fixed. That's where I believe maybe are could step in to provoke people about how ridiculous certain things are.
• 1:23:59
  Brad Keywell: So to be continued on. I'm currently working on what what is a full show, if you will, of my art. But it's very much about art as a as a way to provoke us to look at ourselves as a society in question what our values are.
• 1:24:20
  Randall Kaplan: And we both love Mark Bradford, of course. Yeah.
• 1:24:23
  Randall Kaplan: So you mentioned fill in the blank. I'm going to start three sentences. I want you to finish them in three seconds or less.
• 1:24:30
  Randall Kaplan: Be good on this. I'm good. Okay, here we go. The most important thing in life is
• 1:24:38
  Brad Keywell: finding your bliss.
• 1:24:43
  Randall Kaplan: Just I hate to plug myself but I'm going to by the way,
• 1:24:49
  Brad Keywell: the hero's journey, is that what you're gonna do?
• 1:24:51
  Randall Kaplan: I'm gonna talk about my book list, which, there you go. It's so I mean, you said bliss. So come on, I
• 1:25:01
  Brad Keywell: gotta hit.
• 1:25:01
  Brad Keywell: Congratulations.
• 1:25:03
  Randall Kaplan: Thank you. Thank you. I don't know if you got yours. Yes, but when you do if if you would share it on social media, that'd be great. Okay, so, next next sentence, the most important, the most exciting thing about the future is
• 1:25:18
  Brad Keywell: constant change. I think change is extraordinarily exciting and promising.
• 1:25:27
  Randall Kaplan: The best way to give back is
• 1:25:30
  Brad Keywell: one person at a time.
• 1:25:36
  Randall Kaplan: elements of success. We're off the fill in the blank. I think one of the guiding hopes of both my podcast and our talk today is to learn from others. through their journey, how they rank and qualify and think about their success. So what are the three to five ingredients to success and excellence in people's life, in your view?
• 1:26:10
  Brad Keywell: Curiosity is a core ingredient success. So one is curiosity two is a relationship to an hopefully understanding of risk and reward is core to all I believe all success. Three is some philosophical clarity, some, some framework of why. So that it's not just about the surface money, if you will, or status, but there's something deep about it that to me feels correlated to success in my definition of success. And then for success, to me is also about joy and bliss and, and the sheer wonder of being alive. And then the fifth to me part of success, part of the giving pledge letter I wrote was, I don't view philanthropy, or charity if you as a burden of success, but I do view it as a choice towards a good life towards a successful life, which is, to the extent that you experience material success. Part of the joy of achieving success is the correlative joy, of sharing that success, paying it forward.
• 1:27:36
  Brad Keywell: Helping others.
• 1:27:41
  Randall Kaplan: Speaking of helping others each year, I look forward to getting something in the mail from you. It started, I think, five or six years ago, maybe a little longer. And it comes in the mail. And I've got a few behind me, but I'm gonna talk about this one. So this came in the mail is numbered, you know, please take a number backside in front side. And it says on top of the number, the time is now exclamation point, stop waiting exclamation point.
• 1:28:19
  Randall Kaplan: And I think this one came with a poem. And I'm just gonna read a few lines.
• 1:28:37
  Randall Kaplan: I encourage you to stop waiting for your number to be called The time to act. This is the time to act to give your precious podcast to the world is now. I think you give back by encouraging people to get off their chairs, and go do what you want to do. I mean, these are brilliant, you have the napkin that you gave a pat on Afghans, you you put a a pen there, obviously, the ideas a lot of businesses are formed from writing down on a napkin. Tell us briefly about these things. I mean, they're, they're brilliant. You're brilliant guy.
• 1:29:23
  Randall Kaplan: The most creative guy I've ever met. And I said this well before the group on success. You know, I've been saying that for a long time. I mean, people love a winner, right? I mean, you and I have talked about this in private many, many times. But you just have this amazing mind.
• 1:29:38
  Randall Kaplan: But tell us about these amazing things that you're sending out.
• 1:29:48
  Brad Keywell: Well, look inspired by our friend Sam Zell, I love the idea of, of something creative as an as a holiday, you know, instead of a holiday card.
• 1:29:58
  Brad Keywell: The idea of something creative always struck me as I always love that idea. And one year, I had this idea that, uh, what if, what if you got a book of napkins? And the idea is like, stop thinking start writing it down and doing something about it was the first idea that I just did it. I don't know. And the idea of I don't know how to make a book of napkins, but I figured it out and I sent it out to 500 friends and now I've got about there's I do 1000 I send out 1000 New Year's gifts and every year comes out of my mind I get a chance to create something fun and and what I've learned is it's fun to give. I'm probably a better giver. and receiver in terms of things, and I get to give, whether anybody wants it or not is secondary, I choose to make something creative comes out of my imagination and, and send it out every year as a reminder that I am here and I and I'm, and I care about my friends. So it's been joyful to say the least, you know, thrilling in terms of hearing stories about once in a while one of my gifts stays on like that, take a number that is just like a play on those ticket number things in the front of the store. And I'm like, let me just screw around with that idea. And now, it's not, I mean, I've had more than a few stories of people's kids. They read it at their, at their dinner table, or whatever the quotes that I put on that one. So there's something fun about speaking of what you mentioned earlier about making an impact or mattering.
• 1:31:48
  Brad Keywell: It's fun to have a chance to do something creative that somebody might be affected positively by.
• 1:31:57
  Randall Kaplan: Two more questions. We're near the end walk us through a day in the life of Brad Keywell. And what gets you up in the morning? What motivates you today, after all the things that you've accomplished in your life?
• 1:32:11
  Brad Keywell: I've got a lot more to do. That's one thing motivating factor. That's one two is I'm an entrepreneur, I can't help it. Sometimes it's fun to be an entrepreneur. Other times it's it's challenging, because some might say, why are you working so hard? Or why are you so driven? And my response is, what does that even mean?
• 1:32:29
  Brad Keywell: I'm just doing what I like to do or what I find joyful, but a day in my life. The two things I think are worth just offering is the two things that are that are have shown up recently. One is the outrageously high value of a nap. I am now a religious snapper 20 minutes maximum, middle the day. But it's it's I can't believe I spent so many years not taking a nap, I happen to be pretty good at falling asleep when I want to. And then to meet 1520 minutes. I don't want to sleep longer than that.
• 1:33:07
  Brad Keywell: So one is a nap. It's the it's like a drug in terms of what it does energetically. And the other one is I do a cold plunge every day for five minutes in 47 degree water. And that is another radically amazing thing I can't believe I hadn't started till about a year ago. But every day. Those are two new parts of my day that I find sincerely thrilling.
• 1:33:37
  Randall Kaplan: I did not know about that cold punch. I do not like cold water. As you know we have a home up in quarter lane.
• 1:33:45
  Randall Kaplan: When we went in the water three weeks ago, the water was 58 degrees. And I had a full wetsuit on including the booties and I was you know, cussing for quite a while until I feel my body got a little warm and that that wetsuit,
• 1:34:01
  Brad Keywell: it's good for you.
• 1:34:01
  Brad Keywell: That's all I'm saying. There's something imagine 47 And wearing a bathing suit.
• 1:34:08
  Randall Kaplan: does not suit does it? I mean, after we have a heart it can you have a heart attack doing that seriously. i The answer is I
• 1:34:17
  Brad Keywell: think, Well, geez, do I hope that I don't have a heart attack doing it one day.
• 1:34:22
  Brad Keywell: Now we look back on this. But I exactly learned about this from I started doing Wim Hof the breathing technique. So I breathe for 25 minutes a day.
• 1:34:35
  Brad Keywell: That's my sort of meditative ritual in the morning, which is very deep breathing. And so that's and then after that, whether it's shortly after that, or later in the day, I'll do a cold plunge. So remember, I started by taking cold or I didn't say this yet, but I start with cold showers. So I've eased my way into this. And now it's a deep there's a ritualistic aspect to it. I'm not just jumping in for no reason out of nowhere. I'm doing a breathing exercise before I go in the cold. I'm doing exercise after after come out of the cold so it's not random jumping into cold. It's it's it's there's there's a process around it so it mitigates if you will the shock but it's true if you just if you're not used to it and you go into cold water. That's why I was I was in Antarctica years ago with my family and a New Year's Day. They said we're gonna do a polar plunge and the doctor brought on the EKG literally he brought the brought the paddles on shore in case somebody had a heart attack. So if you're doing this untrained, you know without intention, there's risk I believe, but there's risk crossing the street I'm comfortable with with risk.
• 1:35:49
  Randall Kaplan: Does it get easier I with science, I mean sure.
• 1:35:52
  Brad Keywell: shockingly easier and it goes from painful to therapeutically joyful.
• 1:35:59
  Randall Kaplan: Most people, I mean, I wish I meditated people said, meditation would be great for you, Randy because I'm, I'm type a wound tight. And I have so much to do. I'm gonna work very long hours early, I'm very late on email, because you're in meetings all day long. And I have tried to really cut down on that so I can get more work done during the day. But do you do wake up and meditate? And then do you ever feel the pressure? I mean, you're running a huge company, and you got a ton of things going on, Brad. So how did you clear out the space where you said, I'm going to do this no matter what I mean, I don't care if I have a deadline, I'm selling a company, we have a board meeting. I mean, how do you
• 1:36:49
  Brad Keywell: have to separate it's a longer conversation, a longer conversation, the fact is, science would show do something for 30 days, and have a positive feeling about it. And there's a good chance you'll do it for a year or longer. I mean, I've been doing this now for a year and a half. And it's just the day feels off the day feels incomplete if I don't do the Wim Hof breathing method, which is becoming more well known. But if I don't do the breathing, it's my former meditation 25 minutes, and then a cold plunge at some point, which is five minutes.
• 1:37:28
  Brad Keywell: It's not a complete day without that at this point.
• 1:37:31
  Randall Kaplan: Do you wake up?
• 1:37:31
  Randall Kaplan: What time do you wake up? Is this the first thing you do when when you get up in the morning?
• 1:37:37
  Brad Keywell: Pretty much? I mean, after I wake up? And I'll read a little bit maybe and maybe have some coffee? But then I'll I'll do the breathing.
• 1:37:44
  Brad Keywell: Yeah, all right conversation, but
• 1:37:47
  Randall Kaplan: longer conversation. Okay, I like following you and many things you do. So we'll talk about that. In a separate conversation, the last question I have for you is, what goals in life Haven't you fulfill that you want to fulfill? And as part of that, your legacy? In life?
• 1:38:20
  Brad Keywell: I haven't yet even thought about? You know, I think once in a while. Legacy is not where I'm at right now. I'm just thinking about exploring ideas.
• 1:38:26
  Brad Keywell: So the answer of what goals in life have I not fulfilled way more than I have fulfilled, and there's so many interests, I just, I just, I feel like, as cliche as it might sound, I'm just getting started creatively.
• 1:38:48
  Brad Keywell: And the I opportunity to create, and, and, and see, just explore the possibility of some of the ideas that I think are, are compelling that I have is, is where I am right now. I'm just getting started. We're thankfully 51 is not as old as it used to be. So there's decades multiple, many decades still of firepower, in in all 51 year old lives. That's what I think.
• 1:39:24
  Randall Kaplan: Is there anything you want to leave our viewers with today? Before we finish here, any parting words of wisdom or advice?
• 1:39:42
  Brad Keywell: Yeah, I'll give my one piece of advice as I think about my reflecting on some of my interactions with my kids and their friends post COVID entering COVID I think my advice is it's worth it. To understand oneself. Whether it's, you know, the idea of mental healthiness or mental agility, through understanding and whatever form the understanding is, whether it's work you do yourself, whether it's with the therapist or the idea of mental health, coming out of the closet, and being something that we talk about, freely without judgment is as important and available now as ever. And I think that's the next horizon of human evolution is the is the is the demystification and also D stigmatization of mental health so that we all can feel, you know, that understanding ourselves is a is positive and versus shame fuller embarrassing. So that's, I'll leave you with that,
• 1:40:55
  Randall Kaplan: as this has been tremendous education. It's been tremendous Brad, you're an awesome friend. I appreciate your friendship. I've told you this.
• 1:41:05
  Brad Keywell: I've admired you for a long time. And now I admire that you've stepped into the arena to share your thoughts and to bring your friends and acquaintances on to this, this platform so congratulations for what you're doing and I really admire it.
• 1:41:20
  Randall Kaplan: Thank you. I appreciate you, everyone. Thanks for listening and watching today and look forward to the next episode. Okay, I'm turning it off here Brad. Trying to turn it off here. Recording Stop.
• 1:41:42
  Brad Keywell: All right, looking for stuff only because I have to leave Okay. I'm going to be out on the West Coast. I