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

Episode Date: August 17, 2021

Randall Kaplan is joined by Brad Keywell to discuss what it takes to achieve excellence at the highest level as an entrepreneur.  In this episode, Brad shares with listeners how to out-work and out-h...ustle the competition, why he channels his entrepreneurial drive into disrupting industries, how he grew Groupon from 124 employees to 5,100 employees in a single calendar year, and much more. Topics Include:Brad’s five keys to success.  Brad’s early business ventures, including a greeting card business he started at age six.  The power of preparation.  Brad’s mentorship under Sam Zell.  The lasting influence of loving, supportive parents.  Tangible versus intangible skills.  Fundamental truths about parenting.  Working with the energy of fear.  Choosing business ventures as an entrepreneur.  Overcoming early failures.  Focusing on what you can control.  Balancing individual needs and collective needs.  Mental health, self-care, philanthropy, and other topics.Brad Keywell is an incredible entrepreneur who has co-founded a variety of companies including Echo Global Logistics, Enterprise Transportation, Uptake, and most famously Groupon.  He is currently the CEO at Uptake, which reached the $2 billion valuation faster than any other tech company in history - and was a Co-Founder of Groupon, which at the time reached the $1 billion valuation faster than any other company in history.  In 2019, Brad received the Ernst & Young World Entrepreneur of the Year Award, becoming one of only three American winners in the award’s 21-year history.  He is the co-founder of Lightbank, a venture capital firm with $360 million under management that specializes in making venture capital investments in "disruptive" technology companies in the United States.  Brad is also the founder of Chicago Ideas Week, a week-long conference bringing together thought leaders and innovators from around the world to speak on a variety of topics - and he has also signed The Giving Pledge, promising to give away at least half of his wealth to charitable causes.Sponsors:Sandee | Bliss: BeachesWant to Connect? Reach out to us online!Website | Instagram | LinkedIn

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Starting point is 00:00:00 To me, someone who is an entrepreneur, period, is oriented around there being no other choice, but keep trying. Like, what else are you going to do? An artist is not going to stop making art because their art wasn't perceived as being attractive. They're going to make art. That's what they do.
Starting point is 00:00:20 Welcome to my podcast, In Search of Excellence. 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.
Starting point is 00:00:43 We all have different routes on 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 and 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 Starbelly, an online promotional products company that they started when he was 30, which was acquired for $240 million. Media Bank and Advertising, a media company which was acquired for $720 million. Drive-in, a car
Starting point is 00:01:26 data analytics company that was acquired for $43 million. And LightBank, a venture capital firm with $360 million under management, which has had several billion-dollar exits. And Uptake, which we're going to talk about later, where he is currently the CEO and 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 Ernst & Young World Entrepreneur of the Year Award, becoming only the third winner from the United States in the 21-year history of that award. He's also the founder of Chicago Ideas Week, a week-long conference where thought leaders and innovators
Starting point is 00:02:10 from around the world speak on a variety of topics, from leadership to life's lessons. Brad 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. I'm honored to have him as my guest today. I've met thousands of entrepreneurs over the years, and Brad is the most talented of all of them. Brad, welcome to In Search of Excellence. It's a pleasure to be here, Randy. Let's start with our family, which helped shape our personality, our values, and the preparation for our future. Your mom was a school teacher. 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
Starting point is 00:02:57 in you? 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 had the great fortune of loving parents, which I appreciate is not always the case. 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. But I also believe that his tenacity
Starting point is 00:03:46 to improve his lot in life, if you will, or he was the first person 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 family. It was not really, it was the ethos, I suppose, in my family. It was hard work versus it was not at all that we're fancy or privileged. It's a privilege to work hard. That's, I think, at the core of
Starting point is 00:04:16 my parents' influence on me. 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? And what did you do for fun? Popular is relative. So 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 athletically gifted, which is why I tended to veer towards individual sports that hard work was the payoff versus teamwork as the payoff, because I'm not sure I could be a reliable part of a team, given that I wasn't the best football, basketball,
Starting point is 00:05:03 baseball player. So I ran. I ran cross country and played a lot of tennis. But my leadership, I think, came through creativity. My earliest sources of validation or reward were all related to things that I did creatively. I played a lot of ping pong. So what did I do? I created a tournament and publicized it with little flyers in my school and things like that. So more resourceful. My first business was when I was really young. It was six or seven. Six years old. I created greeting cards because I had a book that taught me how to draw, and I made greeting cards, and I convinced the store to sell them.
Starting point is 00:05:46 I made boxes for them. So creativity or curiosity was, I suppose, how I found my identity. You called the company Key Creations. Did you come up with that name as well? And what was the inspiration for creating at six years old? I've never heard of a six-year-old creating their own company. I mean, creating boxes on top of it, going to stores door to door.
Starting point is 00:06:09 I mean, the stores must have looked at you. Who's this kid? I think it was simply, I don't know. 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, just earning a recognition, I found a lane. And I used to do odd jobs around the neighborhood,
Starting point is 00:06:36 and then ultimately I got some paper and a pen or some pens, and then I realized I could make greeting cards. And then I realized I could make greeting cards. And then I begged. There was a small, like an office supply or gift store called Lee's Specialty. And I convinced the owner to give me space on the checkout counter for boxes of key creation cards. Do you remember how much money that venture made and did you continue to pursue it
Starting point is 00:07:03 as you grew past the right page six years old? I don't remember details, but I do remember that we got reorders. That's good. And then I also remember, I mean, once I got into high school, then I started to branch out into other businesses while I was in high school. So that was not the core. That was simply an early venture. It wasn't the foundation of the high school empire. I say that facetiously. So you have a lot of positive reinforcement at a young age, which gives you a lot of confidence. And what other kind of businesses did you start in high school? We're going to 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, but tell us about high school and the importance of positive reinforcement when
Starting point is 00:07:46 you have a little success at something and you move on, you want to try something else. I suppose I didn't have the fear gene as the predominant gene ever. So the positive reinforcement that then gets built upon was, it just happened organically. Because I suppose there was what else or what else is possible orientation that I had. The next business, there was a series 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. 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,
Starting point is 00:08:33 I mean, 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 the flyers all over town. And I remember the first customer, I can tell you their name, even though I won't. And they were out of town for two weeks. And I shoveled their driveway and picked up the paper and stuff.
Starting point is 00:08:55 And then when they got home, bought stuff for the refrigerator. And then the one that worked that was really fun was a 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. 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 mine. Did at some point, we're going to talk about some of the challenges you've had
Starting point is 00:09:42 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. I'm not proposing I'm not afraid of failure. I mean, failure has energy. There's energy around failure. And the energy, if harnessed appropriately, is extremely positive. It keeps you on your toes and it makes you more capable of calibrating risk. I think that the fear that I don't think I had, nor do I choose to have, is a fear of trying. And failure is, let's say, that the idea, just try, is the opening door.
Starting point is 00:10:31 When you get in the room, the possibility or fear of failure fills the room. But many people, or most people, I believe, are stuck at the door. And that door is, just try. put yourself out there in the arena. But in terms of failure, failure is what entrepreneurs are in the business of failure. And their daily job is to mitigate risk and maximize reward. But failure is everywhere if you're not clear about that daily activity of risk mitigation and reward optimization. You mentioned hard work a couple of times already. You mentioned it, you saw it growing up with your dad, and you said that, this isn't exactly what you said, but you said
Starting point is 00:11:19 something similar to this, that hard work leads to better results. And I want to know, at what age did you really make a conscious effort to be the best at 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? Probably not as consciously as I understand today about the concept of hard work, but sorry, I probably did it reflexively or just it framed what I was doing. But when I think about it now, the idea is 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 has always been an idea that I believe is within
Starting point is 00:12:13 control. So when somebody who has a responsibility shows up, meaning in a room, in an opportunity, when they have a responsibility and they show up unprepared, that's unacceptable to me. But it's the preparation around understanding, calibrating, strategizing, whatever you want to call it, that 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. I've always been attracted to, there's a handful of quotes 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.
Starting point is 00:13:00 And the wait part is we all wait around for things, but what are we 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. 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.
Starting point is 00:13:26 We can watch them, learn from them, get advice and get coaching from them. Is that something you try to do? And what's your advice to people about this, playing with people who are better and more knowledgeable and just observing? Well, you think about the analogy of tennis. I played competitive tennis when I was young and had a chance to spend some time at the Boletari Tennis Academy when I was 15. And what you learn there and you learn through tennis is you only get better if you play with those
Starting point is 00:13:57 that are better than you or at least very similar 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. 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 49ers. He's in the Hall of Fame. We became friends when I was 24, and he was still playing in the NFL. But personally, he's now just a dear friend,
Starting point is 00:14:40 almost like an uncle to my kids. But when I met Ronnie, we started what's become like a 30, let's see, I'm a 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 the idea of coaching in athletics is relevant to life and business. And we did it. We did two of these events, both in Pebble Beach. And it was just extraordinary, whether the names from Bill Walsh,
Starting point is 00:15:35 Billy Bean, Chuck Daly, and even Bill Lambert, who at the time was the only person who had coached a worst to first situation. He coached a WNBA team that was one year the worst in the league. Next year, they won the championship. And then we have players like Joe Montana and Jerry Rice, who I'm still friends with to 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
Starting point is 00:16:25 mentors who can reflect and then I can absorb their lessons. Just a side note on Bill Lambert, you and I were both Pistons fans. We were both bad boy fans. You were at 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're never going to win anything. But I bought at a charity auction in LA a two-on-two with Rick Mahorn, who was part of the bad boys, Bill Ambeer's roommate. And a side note about Bill, which you probably know, he grew up in Palos Verdes, and I think he was the only player in the league whose dad made more money than he did. But Bill was not a well-liked guy in the NBA,
Starting point is 00:17:09 but Rick got sick the day before. Bill was out here for a game, and he came over to play two on two. And of course, I had friends from country day, my high school, they flew out, and I played three on three with Bill. He couldn't have been nicer. That's so cool. The problem is I had to guard him. He's like 6'11 and was not in playing shape at that point, by the way. Did you get an elbow? I mean, I'm almost 6'3 and it was like, I mean, I was shooting from 30 feet away because it was just no way things are going to go in. But that was super fun.
Starting point is 00:17:51 I also believe in the value of coaching and mentorship, and that's what you've done there is great. We're 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? There's a fine line with this. Some parents push their kids a little too hard. The kids rebel. What's your advice on that whole package? My kids are 21 and 22. And I believe any parent can appreciate the cycles,
Starting point is 00:18:30 the chapters of parenting wisdom. Early chapter is, I don't know anything. 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. And there's more chapters that I've forgotten. At some point, there's becomes a wisdom chapter. And then the question is, who cares about your wisdom? Because there's so much wisdom out there that's hard to apply? 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.
Starting point is 00:19:13 And one of my fundamental truths are expressing belief in your kids is more enduring and powerful than love. Now, I'm not saying that the expression of love is not also enduring and powerful than love. Now, I'm not saying 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 creates more of a superpower in your kids, a superpower being their self-acceptance. So 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
Starting point is 00:20:00 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. The thing I believe most for sure is that belief in kids is a superpower. 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
Starting point is 00:20:42 told me the four most important words in the human language are, I believe in you. Wow. I think that's true. I say that to my kids and I say it to a lot of my mentees as well. 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. Thank you. So like you said, 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. And the seeking and then the doing are part of what makes you so special.
Starting point is 00:21:32 So 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. Randy Kaplan is someone who really demonstrates what it's like to find and embrace the guidance of mentors, which is not a skill, of course, that our kids are ever taught. Nobody taught you or me how to find a mentor, be a mentor, what a good mentee is. These are all concepts that are so, to this day, esoteric. I have a lot of admiration for those who get that. Well, thank you. Coming from you, 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
Starting point is 00:22:19 in across the country. I spend 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 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 can speak publicly. You're articulate. You're a team player. People like you. You smile. You have a good attitude when you walk in. You don't complain. And my goal, one of my main goals in life is to
Starting point is 00:23:11 make a difference. And I appreciate the kind words. And 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 cool. I'll tell you, you have 36 interns, you said, this summer? Yeah. Yeah, we get about 750 applications. Wow.
Starting point is 00:23:36 And we have a guest speaker each week. People like you, my friends, they're senior people. If you want to do it this summer, it's only 45 minutes. But really, my goal is to inspire and motivate. People love listening to successful people like you. That's why I did the podcast. I want to make a difference in people's lives. I want to inspire like you.
Starting point is 00:23:58 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 dump failure. You can fail. You can fail again. We all fail. We've all been down in the dumps. I love it. I mean, I love it.
Starting point is 00:24:10 And that's the impetus for the podcast. 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.
Starting point is 00:24:38 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, 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,
Starting point is 00:25:15 as opposed to it's me versus you. One of us is better, the other's worse. So the soft skills become pretty hard and foundational over time. Just a footnote on the intern front, I'm going to bring back something from a long time ago. One of my former interns was your first employee there, Uptake. And at one point, he was the COO of Uptake, John. Yep. And he was also one of my TAs when I taught a class at University of Chicago. Yep. Such a small world. It's a small world. And we talk about the interns and the mentorship.
Starting point is 00:25:53 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 out to me. He was working at a studio that summer. Then he was working at Mozilla. And he wanted to come work with me. 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. 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-liked, confident, great intangible skills, had gone to similar schools as me. And right before, he wasn't
Starting point is 00:26:55 super psyched about moving down to Los Angeles. And right before he was coming, he said, 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, 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 and I mentioned our very close friendship. And he said, will you make the... Well, first he said, no, 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 got to meet this kid. You and the other two co-founders met with him. You liked him. I think
Starting point is 00:27:43 he beat out 100 people. And as I remember correctly, it's something like this. He was the first non-tech employee at Groupon, and he did very well. And 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 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 and recommending somebody. 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.
Starting point is 00:28:27 And there's an example of somebody who's just a joy to work with. 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 I make a phone call or suggest something to someone or something suggested to me, the most informal connectivity creates such extraordinary opportunity for people
Starting point is 00:28:59 and then often extraordinary results. And I feel blessed to be, look, you and I both have skills that happen to be oriented around technology. We could just as easily have skills around mechanical engineering on a factory line, or we just as well could be poets. We've chosen to focus on is creating businesses
Starting point is 00:29:23 that happen to have a lot of technology orientation. It happens to be this kinetic, exciting part of our economy, and it has emotion to it. It has a fluidity to it that people are off. Great people are created in terms 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.
Starting point is 00:29:50 And so being part of an active component of our economy 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. 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.
Starting point is 00:30:33 Let's go back a few years to 1991. You're a freshman, 18 years old, the greatest school on earth, the University of Michigan. I was a freshman in 87. Yeah, sorry. Right, I was a freshman in 87. Yeah, sorry. Right, I was 1986. My bad, 1987. No cell phones. So we had the yellow pages, the big thick book with the bold, people who paid more for
Starting point is 00:30:55 the bold, which meant we walked a lot when we wanted to do something in business. Went to 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 you'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. What was that about? Where did it come
Starting point is 00:31:26 from? Did you have a plan to do that? Talk to us about that. I got to Ann Arbor and something about me quickly understood this entrepreneurially is Woodstock. 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 help it. I was so excited about all the opportunity. And my reaction to opportunity is to create. And the poster business that I created was sort of a riff off of the modern art posters that I saw in people's dorm rooms. And my reaction to that was, that's amazing.
Starting point is 00:32:12 There should be a modern art version of the Michigan logo, the Block M, and modern art versions of other schools' logos. And why pay somebody to do it professionally? Let's have a contest for students to enter. And that worked. And then there should be a cultural handbook when you get to your dorm and get on campus every semester. And that worked. And so I just started to try things.
Starting point is 00:32:34 And those were days when I, or nights, more accurately, in the midst of being in a fraternity and doing all the things that, thankfully, I did 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. If you go back, this was a long time ago, there were a very small number of us creating companies in college. It was you, Jeff Blau, Happy Walters, Andy Stensler, Eric Lefkowski, 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.
Starting point is 00:33:21 Happy's gone on to start multiple business. Stensler's started multiple business. I have, you have, and we've all done pretty well for ourselves. What's the message here? We all knew each other. We were all friendly. What's the message here? The message is stay in touch with people that are doing stuff, because you'll probably be doing similar stuff sometime in the future. I see Jeff and we, we, you know, Jeff and I were fraternity brothers and, and the year, the, not just the year, but like the, I don't know, the month, but probably when I somewhat randomly met Sam Zell is the, is the same Jeff met, met Steven Ross, who has had this profound influence on Jeff's incredible
Starting point is 00:34:07 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 it's if you love what you do in my case and Jeff's case in case, what we love is being engaged in the arena of business. It's pretty fun as time goes by to have those relationships of long duration because you have brothers and sisters who've been in it with you and you can reflect. And that to me is part of the joy of life is sharing experiences together and saying, can you believe what we were doing? And can you believe how naive or maybe not naive? You just feel like, what was going on that we both were so interested in meeting these icons who came to campus? It's so interesting. Well, just backing up for a second, you're at Michigan, you hear
Starting point is 00:35:04 about an entrepreneurship class. You're really not allowed to take it. You go to the professor 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, 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. And it was my junior year. I wanted to do it. So I go see him.
Starting point is 00:35:35 Professor, 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 would love to do this. And he wouldn't let me do it. But you get in a class. So you did not get in? Did not get in. He would not let me in. I mean, there were like 300 people in the class. He
Starting point is 00:35:57 wouldn't take 301. He would not let me in. So my kids make fun of me all the time. You know nothing about US history. I said, yeah, it's Sidney Fiennes' fault. It's not my fault. I don't like reading. When I read for fun right now, I love to read fiction and business books. So I guess at some point, I need to go back and educate myself. The class that I talked my way into in 1988, and that was a class for MBA students. I was a freshman, and I somehow got in with all these 20, I was like 18, all these 21-year-olds. So I still talk to that professor
Starting point is 00:36:36 to this day. How many years is that? 80, 90, 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 inspirational at some level to them. And that they, I just offer the possibility of staying
Starting point is 00:37:06 in touch, which I think is less cool, if you will. 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 helps you. They care about you, is my story. Let's move on to Sam. For those of you who don't know, the short one-liner is he's the founder and chairman of five public companies in the 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 him and it led to an amazing relationship that has lasted for decades. He comes to speak. 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,
Starting point is 00:38:01 I'm Brad Keywell. Nice to meet you, Mr. Zell. What happened? Tell us about it. And then what happened to that relationship in the next few years? Sam, in my book, is now globally. In 2021, 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 so I knew enough to do my homework, and there wasn't really the internet back then. But part of my knowledge about Sam was his iconoclastic core, which included his
Starting point is 00:38:48 belief that you can wear whatever you want to wear and still be okay. And so he was advocating before it was even a possibility that one can wear jeans to the office, 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, something about me went to that, hear him talk. Something about me went after he finished talking to talk to him. And then I've recently, I see him a lot. 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.
Starting point is 00:39:29 He was hungry. And it's rare that people, anybody has a core intellectual and I think like an entrepreneurial hunger. That's all I know. Cause I can't, like I say, the fact that he responded to my enthusiasm by saying, come see me in Chicago. My response was, what does my enthusiasm by saying, come see me in Chicago.
Starting point is 00:39:46 My response was, what does that mean? Like, come see you in Chicago. He's like, call so-and-so and come see me. So I found myself in Chicago a week later with Sanzel in his office. And he said, come work with me this summer. What are you thinking about for the summer? And I said, I've got an offer with Arthur Anderson. And he said, why would you do that?
Starting point is 00:40:04 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 who I hoped I would be versus for where I was. It's an extraordinary feeling when somebody that you really, really admire and respect treats you like an adult, when in your mind, you're still sort of figuring out what it's all about. I saw a video of the first time you interviewed him. It was at your conference and you mentioned to him that you had two real mentors in your life, your dad and him. And I could swear I saw his eyes
Starting point is 00:40:47 water a little bit. Great moment, by the way. Great moment for him, for you, for me, knowing the 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. Yeah. We have a lot to cover yet, so I want to zip through some of this. 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 what you did and what happened there. And then I want to talk about Starbelly. And you and I talked about that a month or two ago. You told me some things there that I didn't know.
Starting point is 00:41:39 But I think it's important in our quest for excellence to really keep coming back. A lot of people want to go home. You failed. You lost a ton of money and a ton of time. It's embarrassing, especially when you get sued. Can you walk us through those businesses briefly and then how you picked yourself back up and how you motivated yourself to get back up? Sure.
Starting point is 00:42:03 I'll frame the answer to 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 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 every time I would say, 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, et cetera. And most people raise their hands. And then I said, how many people are interviewing
Starting point is 00:42:45 for a job right now in the process? Everyone raised their 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?
Starting point is 00:43:02 Maybe, but the job is just so I can do art. The idea of balancing, should I work for McKinsey or should I be an entrepreneur? Probably means you're brought up working for McKinsey, which brings me back to the answer to your question. To me, someone who is an entrepreneur, period, is oriented around there being no other choice but keep trying. What else are you going to do? An artist is not going to stop making art because their art wasn't perceived as being attractive. They're going to make art. That's what they do. 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 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
Starting point is 00:43:53 to choose, which is clothing, apparel. And we bought a company that was doing $3 or $4 million in revenue. We grew it fast, in our opinion. In my opinion, 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 are many. You've got to make the stuff. It's got to be the right size and color and got to be sold by, we sold to everybody from Neiman Marcus all the way down to Walmart, blah, blah, blah. 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 is in your control in terms of the things that must happen in order
Starting point is 00:44:41 for it to be successful. And then out of that came the idea for Starbelly, which was an idea around using technology to facilitate the transaction 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. And I was, if you will, put out there, 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
Starting point is 00:45:32 fun, I would assume, from the outside or pretty glamorous, let's say. Materially, there's a lot of glamour or a lot of excitement about that experience. But emotionally and personally, that was about as confused and challenging a situation as I've had in my professional life. And then when the buyer that bought our company went bankrupt, my net worth, if that's a measure 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 the entrepreneur is ultimately tested. What's next?
Starting point is 00:46:12 Well, if you're an entrepreneur, the next is keep trying. Well, you did keep trying and things got a whole lot better. Echo Logistics, you started in 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 a little over $700 million. You're feeling good about your future.
Starting point is 00:46:40 And then comes Groupon. So tell us about Andrew Mace and what he was doing when he approached you with this idea. And then tell us about thepoint.com. The story that I suppose is less than rich is the story of everything that I'd been a part of up until then was me and my business partner had started it. This was the first time that we were involved with something where a third person was involved. Three people is harder than two. And it's not just one third harder or it's exponentially harder for three people to agree than two people. Another lesson is this business started as thepoint.com.
Starting point is 00:47:27 Thepoint.com was an idea around, well, I'll make it easy. It was Kickstarter way before its time. And it was Kickstarter, but for social action. I will do something contingent upon 100 people agreeing to do it 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 it ultimately went live. And like most websites and most businesses, expectations were far undermet by reality. What was different about is that we collectively did not throw in the towel and stop the business. What we did is pretty quickly acknowledge
Starting point is 00:48:15 it was not working. The idea behind the point.com was not working. What might work with a similar technology-oriented approach? Well, one thing would be collective action around buying stuff. And Groupon was born reactively or iteratively versus miraculous conception. Groupon is a story, a fortuitous story, where the experience, be it of MediaBank, now renamed MediaOcean in modern 2021, it's called MediaOcean, but MediaBank, Echo, all these experiences we had had of growing businesses fortuitously or materially became core to
Starting point is 00:49:04 the operational execution of growth. Not that the growth of Groupon was without lots of flaws and sort of small failures, but being able to start a calendar year with 124 employees and that calendar year with 5,100 employees is, those are the facts. That's what happened 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, and execution behind the wheel. And so that's part of the Groupon story. There's a lot of stories 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 some of Jeff's board members from the early days and hearing those
Starting point is 00:50:05 stories. So I think all stories of this new breed in the last 30 years of companies that have been created, and then the reflection that those companies have nearly replaced those who 30 years ago dominated the Fortune 100, or Fortune 10 or 20 for that matter. This is a great age in which to learn. And so these stories of group bonds or sales forces or whatever are ripe with lessons. I remember you staying at my house right at the time this thing wasn't working. And you told me you just sold the first group coupon, group bond. You were days away from shutting down the company, returning the investors money, and then you made the shift. I think it's important for listeners and viewers to know
Starting point is 00:50:52 that don't be tunnel-focused. Listen to customers. Be open-minded to changing. And then I remember you also telling me, I think you said, this is 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. By the way, one of my favorite stories is the gut.
Starting point is 00:51:32 We had an email service provider, as it came to be known. And at the time it was, I forgot the name, and it couldn't handle the volume of our emails. And so I found a company called Exact Target. So we found them and the volume of our emails. And so I found a company called ExactTarget. So we found them and they started processing our emails. And there was a delay because we had so many members adding to our customer base. And they couldn't, ExactTarget couldn't process the volume of our emails. And I called a guy named Scott Dorsey, who I didn't know.
Starting point is 00:52:02 And I called him and I said, you need to focus on Groupon. We're going to be very important to you. How do we rank right now? How important are we? And he said, basically, you're not that big of an emailer. 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 a bigger consumer or user of email than American Airlines and others. And to this day, when I talk 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. You had a chance at some point, and there's all this
Starting point is 00:52:46 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 thousands of companies trying to copy you. And you had a chance to sell the company. It was reported for $5.75 billion, $6 billion in cash. You guys didn't take it. You went public. The first day you closed, the valuation was $12.7 billion. The value when you went public was $12.7 billion. And then I think it closed at $16 billion that day. The company's worth today, $1.25 billion. Was it a mistake at that point not to sell? Do you look back and think, I probably should have done that? And if so, are there lessons for people out there? Well, first of all, an enterprise value is the quote-unquote, what's a company worth,
Starting point is 00:53:40 is a relative term. And the enterprise value is greater than the number you just described. But also remember the value of liquidity. And this company has had a series of values, if you will, over time. But the lessons are many. One lesson is some stores 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 come from every aspect of growth, whether you're growing a $1 million company or whether you're growing a company that is valued at $6
Starting point is 00:54:34 billion. Everything you do is valuable if you learn from it or make it better. 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 in that I can now see patterns when they're emerging often before others might see them. Let's talk about career goals, which is incredibly important to everybody. And one of the questions that comes up when I'm mentoring people is, what's important to you? What do you want to do? For some people, and what I say to them is rank them, list them and rank them. Is it money, experience? Is it location? Is it passion for what you're doing,
Starting point is 00:55:29 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 and have a little bit of money now? You can buy as much free city sweatpants as you want. And where does money rank today? And 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 you have certain factors that you would rank and you would consider, or is this situational? I've been studying philosophy, literally studying philosophy with a professor for a pretty decent period of time at this point, purely independently with having lunch, talking on the phone,
Starting point is 00:56:17 getting reading assignments, reflecting on it. 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 even know what you're talking about. I don't even think about mattering in the world. That is where I generally start if it's a serious conversation about what
Starting point is 00:56:45 should I do. Now, 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 kind of questions or conversations, I'm their dad, so they can blow it off. But most kids in their 20s, when I'm talking about careers, I find myself starting with like, tell me about what a great day feels like. Tell me a little about 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. I'm much more clear about ideas like, if you tell me what you hate, then we can talk about what you might like or love.
Starting point is 00:57:27 But if the question is, what do you want to do? I guess because I've got kids that are in their 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 that's horrible, let's talk about what at least goodness is, if not greatness. That's exactly what I asked them on the flip side too. Name the five things you don't want to do,
Starting point is 00:57:57 name the five things you're best at, and name the five things you're worst at. And this should take you days, and then come back to me a week later when you really think about it. Can someone learn the entrepreneur gene? I think so. I mean, but that's, I believe that as people, we all desire to be our best. If that's not a desire that, if you believe that your best is important, then I believe you can learn or refine 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 in priority to societal best.
Starting point is 00:58:45 In other words, what's more true today for a young person? They want to work hard in a capitalist system such that they can make enough money to do fill in the blank? Or 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 creating a business or creating enterprise, even a not-for-profit. I just want to join something and stand up against those who are due or polluting or whatever.
Starting point is 00:59:18 Often these days, 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 society over individual hard work and judged as bad is hard work wanting to make money. Unfortunately, that is the case in a lot of campuses these days. One of the things I think of, and it's hard to think of when you're younger, is having fun. Sam likes to have fun in the office. You like to have fun. You do a lot of things for fun. You write,
Starting point is 01:00:00 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? 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.
Starting point is 01:00:27 I look at experience, going to concerts, seeing amazing bands in small venues is outrageous to me. That's the coolest thing. Doing crazy adventure experiences with friends, what could be better? So fun is really important. Art is pretty fun. Buying art is not so fun. So it's 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've been one of the people along my journey of art that's been important. And you've taught me a lot as you shared with me your journey of understanding, buying, selling, and appreciating art, Randy. And so that was part of my journey is learning from you.
Starting point is 01:01:17 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 thing. So Ed Ruscha, who's an LA artist, he's inspired me and I collected 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. You could copy an artist's work, but there's something about that artist doing that work, that original work, taking the risk of being counter, being provocative, and then being validated. It just feels so much like the role of or the activity of being an entrepreneur. And the other artist that has been a big part of my collection is Kusama,
Starting point is 01:02:01 Yayoi Kusama, who's 91. This woman was anything but accepted until she persisted for decades and finally was appreciated. That sounds like an entrepreneur to me too. And then now when I'm making art, I created a museum that's basically I'm the artist. 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
Starting point is 01:02:44 certain things that I see as inexplicably 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 art could step in to provoke people about how ridiculous certain things are. So to be continued on, I'm currently working on what is a full show, if you will, of my art. But it's very much about art as a way to provoke us to look at ourselves as a society and question what our values are. 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. Here we go. The most important thing in life is?
Starting point is 01:03:31 Finding your bliss. Just, I hate to plug myself, but I'm going to, by the way. The hero's journey. Is that what you're going to do? No, I'm going to talk about my book, Bliss, which came out this day. Oh, there you go. I mean, you said blissful a couple times, Brad, so come on, I got to hit that. I love that. Congratulations. Thank you. So next sentence,
Starting point is 01:03:54 the most exciting thing about the future is? Constant change. I think change is extraordinarily exciting and promising. The best way to give back is? One person at a time. 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? Curiosity is a core ingredient. Two is a relationship to and hopefully understanding of risk and reward is core to all, I believe, all success. Three is some philosophical clarity, some framework of why, so that it's not just about
Starting point is 01:04:55 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 four, success to me is also about joy and bliss 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 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, helping others. Speaking of helping others, each year, I look forward to getting something in the mail from you.
Starting point is 01:05:53 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. It's numbered, you know, please take a number, backside and front side.
Starting point is 01:06:12 And it says on top of the number, the time is now, exclamation point. Stop waiting, exclamation point. And I think this one came with a poem. I'm just going to read a few lines. I encourage you to stop waiting for your number to be called. 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.
Starting point is 01:06:46 You have the napkin that you gave, a pad of napkins. You put a pen there. Obviously, the idea is a lot of businesses are formed from writing down on a napkin. Tell us briefly about these things. I mean, they're brilliant. You're a brilliant guy, the most creative guy I've ever met. And I said this well before the Groupon 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. Tell us about these amazing things that you're sending out. Well, inspired by our friend Sam Zell, the idea of something creative,
Starting point is 01:07:30 instead of a holiday card, the idea of something creative always struck me as, I always love that idea. And one year I had this idea that, 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, the idea of, I don't know how to make a book of
Starting point is 01:07:52 napkins, but I figured it out and I sent it out to 500 friends. And now I sent out a thousand New Year's gifts. And every year comes out of my mind. I get a chance to create something fun. And what I've learned, it's fun to give. I'm probably a better giver than receiver in terms of things. And I get to give whether anybody wants it or not is secondary. I choose to make something creative and send it out every year as a reminder that I'm here and I care about my friends. So it's been joyful to say the least. Thrilling in terms of hearing stories about once in a while, one of my gifts stays on, like that take a number, that was just like a play on those take a 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 dinner
Starting point is 01:08:51 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. It's fun to have a chance to do something creative that somebody might be affected positively by. 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? 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.
Starting point is 01:09:27 Other times 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? I'm just doing what I like to do or what I find joyful. The two things that have shown up recently, one is the outrageously high value of a nap. I am now a religious napper, 20 minutes maximum, middle of the day, but 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 me, 15, 20 minutes,
Starting point is 01:10:04 I don't want to sleep longer than that. So one is a nap. 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 didn't start it until about a year ago, but every day. Those are two new parts of my day that I find sincerely thrilling. I did not know about that cold plunge. I do not like cold water. As you know, we have a home up in Coeur d'Alene.
Starting point is 01:10:39 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 cussing for quite a while until my body got a little warm in that wetsuit. It's good for you. That's all I'm saying. There's something, imagine 47 and wearing a bathing suit after one minute. But I learned about this from, I started doing Wim Hof, the breathing technique. So I breathe for 25 minutes a day. That's my sort of meditative ritual in the morning, which is very deep breathing. And then after that, whether it's shortly after that or later in the day, I'll do a
Starting point is 01:11:16 cold plunge. So I didn't say this yet, but I started 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 I come out of the cold. So it's not random jumping into cold. There's a process around it. So it mitigates, if you will, the shock. But it's true. If you're not used to it and you go into cold water, that's why I was in Antarctica years ago with my family. And on New Year's Day, they said, we're going to do a polar plunge. And the doctor brought the EKG, literally, he brought the paddles on shore in case somebody had a heart attack. So if you're doing this without intention, there's risk, I believe. But there's risk crossing a street.
Starting point is 01:12:10 Does it get easier with the plunge? Yes, shockingly easier. It goes from painful to therapeutically joyful. I wish I meditated. People said meditation would be great for you, Randy, because I'm type A, wound tight. And I have so much to do. I mean, I work very long hours. Early, I'm up 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 wake up and meditate? And then do you ever feel the pressure?
Starting point is 01:12:45 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- It's a longer conversation.
Starting point is 01:13:01 But 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 incomplete if I don't do the Wim Hof breathing method, which is becoming more well known. But if I don't do the Wim Hof breathing method, which it's becoming more well known, but if I don't do the breathing, it's my form of meditation, 25 minutes, and then a cold plunge at some point, which is five minutes. It's not a complete day without that at this point. What time do you wake up? Is this the first thing you do when you get up in the morning? Pretty much. I mean, after I wake up
Starting point is 01:13:41 and I'll read a little bit maybe and maybe have some coffee, but then I'll do the breathing. Longer conversation, but I highly recommend it. Okay. The last question I have for you is what goals in life haven't you fulfilled that you want to fulfill? And is part of that your legacy in life? Legacy is not where I'm at right now. I'm just thinking about exploring ideas. So the answer of what goals in life have I not fulfilled?
Starting point is 01:14:13 Way more than I have fulfilled. And I feel like, as cliche as it might sound, I'm just getting started creatively. And the opportunity to create and see just and explore the possibility of some of the ideas that I think are compelling that I have is where I am right now. I mean, I'm just getting started. Thankfully, 51 is not as old as it used to be. So there's decades, multiple, many decades still of firepower in all 51-year-old lives. That's what I think. Is there anything you want to leave our viewers with today before we finish here? Any parting words of wisdom or advice? 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 and during COVID. I think my advice
Starting point is 01:15:12 is it's worth it to understand oneself, whether it's the idea of mental healthiness or mental agility through understanding in 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 as important and available now as ever. And I think that's the next horizon of human evolution is the demystification and also destigmatization of mental health so that we all can feel that understanding ourselves is positive versus shameful or embarrassing. So I'll leave you with that as a last note of provocation.
Starting point is 01:16:03 It's been tremendous. Brad, you're an awesome friend. I appreciate your friendship. I've told you this. Randy, as are you. 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 onto this platform. So congratulations for what you're doing. And I really admire it. Thank you. I appreciate you. Everyone, thanks for listening and watching today and
Starting point is 01:16:31 look forward to the next episode.

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