Randall Kaplan | Akamai Technologies and Early Investments in Google, Lyft, and Postini

Randall Kaplan 15:07

yeah. Strauss Zelnick, who has become a good friend and I have many, many good friends that have come from these cold calls. I mean, 20 something years later, Strauss would become a good friend. He’s someone that I looked up to before I met him. He was CEO of Fox at age 30. CEO when he was 32, CEO of BMG when he was 40. And has gone on to do some incredible things he bought two interactive, when I think for $14 million, it has a $18 billion market cap today. He’s chairman of CBS. I looked up to him, I wrote him a letter. First I went to a conference, an investment banker named Mikey Ageia, a man who has an MD at Bear Stearns back in the time when I wrote him a call letter. And I said at the end of my meeting, I said, Who else should I meet? Who else can you make an introduction to and he said, You should come to our media and entertainment conference, and Laguna, so I took off the day’s work. And again, it’s very nice of him. And he said to me before, they said, if you want to hunt, moose go where the moose are. And there were a lot of moose at this meeting. So Strauss’s there, that’s where I sat down with on the redstone and some others, and I met him there. And when someone is a speaker there, you know, the crowd, you get the circle when they’re done speaking, walking out there, free people deep. Yeah. Strauss is walking out and I wait for my turn. And you could tell I was waiting for the crowd to thin out and I finally said, Hey, I’m Randy. I wrote us a letter. He said, Oh, yeah, yeah, I said, I’m catching a plane back to New York. Call me and I’ll be back and we’ll set up a meeting. Each meeting that I had, I made sure I got there one hour before I showed up in a lobby one hour before, but I want to make sure I live in LA traffic, you plan for things. Never be late for a meeting ever, ever, ever, ever, ever. So I would go out 15 minutes before. And I think that’s a good sign. I think it’s good luck. You show up before you’re supposed to start. People recognize that the office manager who I still remember, Liz Ramirez, comes out, says Strauss will be out in 15 minutes. I thought that was interesting. She called him Straus, not Mr. Zelnick. And that was I took note of that. Strauss is running four minutes late. It comes out himself. He’s on the phone with one of those things. And he says, I’m really sorry

John Corcoran 17:44

to be right there.

Randall Kaplan 17:45

And I thought I’m looking around. I mean, I had a lot of meetings, people keep you waiting. They don’t care. And I’m the least important thing on the agenda that day. And Strauss by the way, was to have a phone call with Clive Davis, who’s probably the most important person and one of the most important people in the history of the music business. And we became good friends. That was a lesson that I learned. I learned a couple things. First name basis. I hate when people call me, Mister, I’m not a Mr. I’ve never been a Mr. I’m Randy. And people know to call me Randy. And you always want to treat people well. You never want to make somebody wait. things do happen. I have an important phone call. But I do the same thing. If I’m running late, and I’m on the phone and someone’s waiting for me. I’m going to go out there and say I’m really sorry. I’ll be right there. So that was a great one and another. There were some great ones. And there were some other ones. One you learn on the positive side. How do you want to be treated when someone treats you? Well, I always say okay, something good happens to me. I’m gonna borrow from that because I learned something. And I like how that made me feel. I was at another meeting with the head of a major studio, one of the biggest producers of all time, and he had me come to his house. There I was, I thought to this huge Beverly Hills mansion up on the hill. And there was in front of me a woman, a very pretty woman wearing a bikini top and a Mercedes convertible who pulls in first when she brings the gate. She goes in. I kind of wait, I wait and I go into the driveway, she goes left toward the pool. I’m thinking okay, this is how I would I don’t know what to expect. I get in the house. The butler shows me into the kitchen and I’m waiting outside of his office. I could see he’s on the phone. I’m sitting around. He has pictures in this part of the kitchen with every president of the United States for the past 40 years. So I’m thinking okay, whatever. I went into his office. Finally he’s running about a half a minute late. We shake , he says behind this big wood desk. I’m in front of his chairs and he pops up his shoes. on the desk sort of in front of my face. I still remember the Ferragamo. You know cursive on the bottom of the Ferragamo shoes. And I said, Okay, well that’s something that I’m never going to do. And the footnote to the story is I have to think about how to protect the identity of him. But my kids went to a very good private school in West Los Angeles where we live and one, one day we got called to the headmaster’s house. And it was not an invitation. It was your coming here, and I got there. As my wife and three other couples, including the chairman of the board of the school, I’m looking around, they were raising money for their school, they were building a big building, I’m new to the school. I’ve been there a month. I’m sitting there thinking, Okay, whatever. And this guy’s there. I’m thinking, Okay, it’s just a thing. Nice to meet you. And I said, Oh, we met a long time ago back in 1995. It said, Oh, where you know, I didn’t give them the details. But we ended up becoming friends with him. My wife and I went to dinner with him and his friends. And he’s more wise and he

John Corcoran 21:11

you’re in a different stature at that point?

Randall Kaplan 21:13

Yeah. I mean, I told him generically about the meeting, I left out the shoe part of the meeting. I mean, he wanted to know what I was doing back then. And what we’re talking about, I said, I was a very unsuccessful lawyer, my career was going terrible. And I contacted you. And he said, Well, what are you up to now? And he said, Wow, that’s really great. It’s a good thing. You didn’t take that job. I mean, it’s there was no job there to be had anyway,

John Corcoran 21:40

Did anything happen with a woman in the bikini top walking around to the pool? Or is that just

Randall Kaplan 21:44

a great question? I was gonna mention that they got married and have several kids really? Oh, yeah. When when we went to dinner with them. I told him the story of the approach. And I said that was really cool about the presidents. But I left the office, the shoe was running late, and his wife said, that was me. Funny. That’s right. Yeah. So that’s the footnote there.

John Corcoran 22:10

Yeah. Any, any other crazy stories from that time before we move on to something else?

Randall Kaplan 22:16

Um, none really come to mind or that would be appropriate to mention on the show. So I think we’ll leave it afterwards over a drink or something.

John Corcoran 22:25

The funny thing is, I did something similar in Los Angeles. Also, when I graduated from college, I sent out I think about 100 letters, so not 300. And I did not do as much research as you did. And I was working to break into the entertainment industries before I went back and worked at the White House. But when I was working to break into the entertainment industry, and sending out to like different producers and stuff like that, and didn’t have as much success as you did, so I probably should have copied your style.

Randall Kaplan 22:49

Right. Let me let me. Okay, let me share one more with you. Okay. When I graduated from the University of Michigan in 1990, Larry Kasdan was the graduation speaker. Larry was a Michigan graduate, obviously, he produced and directed the Big Chill, which is about seven Michigan grads out actually was Kevin Costner’s first role. He played the dead person in the coffin. But Larry, in a non speaking role, obviously, Larry gave an amazing speech. And I said, you know, that’d be a great guy to meet someday. I was looking at possibly going into the entertainment business, I said, he’d be a really good guy to know. So I sent him a letter, sent it to the office, and I said, Okay, you know what? I’m gonna, that’s 17 at home, I think, but, uh, just drop it off at the front porch of his home, which I did. And so through LexisNexis, you can find out where people live. And I went by and I dropped off. The letter on his porch is my packet. It was the spiral bound thing, whatever, never heard from him. After our company went public, he had an event at his house where certain Michigan grads live in Los Angeles, so we’re sitting there, and his dad and two of us are talking and I said, Yeah, you were my graduation speaker as well. You know, so motivation I love you know, you love the movie, love, love your what you’ve done. And he said, okay, you know, what do you do? And I said, well, so I think I’m just gonna let it loose here. I think I’m gonna let it rip. And I want to tell him what I did. And I tell him the story. He said, I remember that letter. He said, You know what to make of it. He says, a little creepy. someone, someone left my house. But he said, and he’s looking at me and he said, what do you do again? And, you know, I mean, he knew I was at that point on the board of Michigan. And you know, the fact I was there was I had some credit that I wasn’t a crazy guy at that point.

John Corcoran 24:57

That’s funny. That’s funny. Well, anyone listening to this This highly encourage you to follow Randy strategy, not mine, put the effort put the extra energy into it, it pays off. So you connected with Eli Brode. Through this process as well. Yeah, so explain who he like brode is unfortunately just sadly passed away. Yes. But explain who he is. For those who don’t know.

Randall Kaplan 25:21

At that point in 1996, when he hired me, he was one of only three people to start two fortune 500 companies. The first was the Coffin and Brode home Corporation, which he started in the 1960s. It was a fortune 500 company, now renamed KB home. And then they started a company, SunAmerica, which is a insurance company that was bought by AIG for $18 billion in 1998. So I wrote him a letter. I did my research, I knew things about the CEOs and the companies that most people wouldn’t know, I knew he had a position, called the assistant to the Chairman. I knew the five people who had it, this was not a job that he put in the newspaper for it. And at the time, the 37 year old CEO and vice chairman Jay winch, Rob had been the assistant to the Chairman, I think a little less than 10 years before he was a former lawyer as well. And for the five people before me, they were also lawyers. So I wrote him a letter. And it was a public company. So again, research pays, and I read the 10k, the annual report, I outline both, and I went in there, and I prepared for the interviews like these were final exams, I see a lot of people phoning it in, they come into my office, now they haven’t looked at the website, or even glanced over, they spent 20 minutes, which is ridiculous, because you spend more time at work than you do at home with your family. And if you want to succeed and get a great job, you got to do your research, because I will, people will come in the first thing is what’s the name of my dog. And some people will spit it out right away. And some people will say, I don’t know. And the interviews over if they don’t know, it’s on my website. So for that meeting, I knew about the job, I knew I could change my life. And there were a few like this, as well. So I knew this was the most important meeting of my life from a business perspective at that point. And I studied for it, I outlined the annual report for the 10k. And I really didn’t know a lot about finance back then. I know a little bit more today. And I read through the financial statements, I would try to figure out what they meant. But I was gonna go in there and memorize 20 questions. And these aren’t softball questions. Why did you get into business? You know? What were you like when you were a kid? Those are not impressive questions. I noticed that you took a $346 million write off last year after purchasing this division of John Hancock. And I was wondering what if you bought the company? What the hit to the earnings would be and you worry about that when you think about growth for a public company? How would it impact the performance of the stock?

John Corcoran 28:29

Why not a small question? Yeah.

Randall Kaplan 28:31

You know, no, we’re not asking these questions, right. And I had to learn even while I looked at the footnote of the financial statements, to ask questions, and again, I memorized these. I was taking these off. And we had a lot of 90 minute meetings. We’ve worked there for three years. I never had a 90 minute one on one meeting with him for three years. But you can see him jotting things down as I went scribbling and the scribble is a good sign. Right of you sitting back near in his shirt. I I knew I was racking up some points. And then he started telling me about this job. You know, I have this job. Obviously the chairman said, Yeah, I know. I said, Here are the five people who have had that job. This is the year they had it this year they had at ease. He’s, you know, his head keeps going like this. And it’s really easy to find the animation. You can’t find it. I mean, it’s easy nowadays. It’s super easy these days, but it wasn’t back then. So we leave a meeting and he says, Well, he said to me, what do you know about finance? I said nothing. And he points to the stack of papers. It’s like a foot tall. He said, Could you go through that and tell me what that company is worth that we’re thinking of buying? I said no. And he said, because if you told me you could and you couldn’t. You wouldn’t last her one day and I said I couldn’t tell you. So he said I want you to take a business class at UCLA. And I get a catalog and I’ll pick one out for you. I said, Okay, no promises. So I left his office because he hasn’t offered me a job. He just says go, nothing does this class got we had a you know, get a catalog and whole pick one, no promises whatsoever. So I leave the office. And it was so hot that it was a 90 degree day, I left the office. My law firm was right across the street. So I ran out. I got in my car in the parking garage. I drove to UCLA. I didn’t know I’d never been on campus before I parked in a no parking zone. Thankfully, I didn’t get towed. But I did get a ticket. And I ran around campus. Where do I get a class catalog? I found one, I ran back to my car. I went home to my apartment, I typed a thank you letter. And I returned it to his office within an hour. And this is a lesson that I want people to know when I teach people that you have a meeting. You don’t wait till the end of the day to send a thank you meeting, you don’t wait till the next day impressions matter. First impressions matter. I showed I did a lot. I did a lot in 60 minutes. And he knew what I must have done in that amount of time. How did I get this back in an hour? I can, I’m sure the receptionist said, Mr. Bro, there’s a package for you here. And they bring it right to Sharon, his assistant and Sharon’s gonna show it to him. This is the guy who just met with Yeah, and that was huge. So his assistant calls back a week later. Mr. Brode is not in town, but he wanted me to tell you to take one of these two classes and recommend not not telling you and I said okay, Tom, I’m going to take both. And long story short, I was hired, I got a job offer on my 27th birthday. So I was just the chairman item Managing Director title as well. of Corp Dev, which is the m&a function within the firm. So we’re looking to buy different companies you’re asked about the outcome. I am introducing my girlfriend’s brother at the time my brother in law knew one of the co-founders who was getting his PhD at MIT. And they had Retton write they had invented some technology that was going to improve the way that information, video pictures were sent over the web. And it was very unique. And they wanted my Managing Director title for the business person on the business plan for the MIT 50k competition, which we lost. And that was the origin of how I became one of our founders at Akamai.

John Corcoran 33:00

Got it. But let me take before we get into more about occupation, what else we focus primarily on what you did to get that job, which was amazing, with Eli Broad. But um, what did you learn from working for him for three years? What do you learn? What did he teach you?

Randall Kaplan 33:17

Well, to get a job like that is not simple. And to work with him was not simple. He worked a lot. I was so proud of myself when I got that job. And I mean, personally proud. I didn’t walk around, you know, you and my parents were proud. And my dad came to visit shortly after, and we were going to dinner. I said, and he said, Okay, see the office? That absolutely, you know, super pumped about it. We go by the office at 730 on a Saturday night. The opposite is spectacular, by the way. He’s a huge modern art. For those of you who haven’t been to Yes, Rob museum. Wow. Los Angeles. It’s spectacular. He must have had any all over the place. The office in Los Angeles was mostly up and coming California artists but there were some different kinds of pieces that were quite tacular there. Yeah.

John Corcoran 34:21

And by the way, given how hard it was to get a job working for him as appropriate, it was impossible to get into his museum for years.

Randall Kaplan 34:30

It’s become more impossible I mean, thankfully I know who is the curator of his collection and might need a museum like Nina if she’d been very nice to be your last minute you want I need to go there with friends or my awesome, that’s cool. But so we walk in, I mean, the doors open. I’m thinking the cleaning crew is going to be in there. So we walk in and oh, Look up. And there he is, in a suit in the middle of stacks of paper working and said, Oh, you know, this is my dad, and he was very nice. You know, you should be very proud of your son. My dad is super proud. And we walked out of there. And my dad shaking his head, and I’m shaking mine. Yeah. You know, I mean, you get it. People would say, Why is he still working that hard? He’s number this on the fourth for 100. And my response would be, if you ask the question, you don’t understand the answer.

John Corcoran 35:47

That’s how he got there, that that’s how

Randall Kaplan 35:49

he got there. And most of the workaholics I know are the super successful people I know. And I’ve been grateful to meet some of those people. They work like that, too. Yeah, we had nothing going on that weekend. I mean, I was privy to extremely confidential information. We were not buying a company. I mean, he was just working.

John Corcoran 36:09

I want to ask you. So you know, you’re a busy guy. And when you’re not, you know, wakeboarding you’re not planning to drop wake surfing, wake surfing, wake surfing, sorry. You’re not flying drones, doing photography or walking your mischievous dog karma. On the weekends. I wanted to ask you, you know, you’re big into mentorship, you, you have a lot of younger young people who come in and work for you. That’s important to you, you got five kids, what do you take away from that experience? You’ve already shared a bunch of lessons. But are there any other lessons from that experience of getting your first job in Los Angeles, working hard working for, you know, Uber, a successful entrepreneur? And how do you bring that to parenting or to mentoring?

Randall Kaplan 36:58

Well, there’s a lot to unpack in what you just said, and I don’t even know where to start. But I’ve learned a lot of lessons. As a professional, both an unsuccessful professional and a successful professional. I’m a big believer in that we learn more from our mistakes than we do from our successes, I believe it’s very important to look around and see how you’re treated. And think about whether you want to treat people the same way. And when people are mistreated. It doesn’t make you feel good. When someone treats you well, it makes you feel good. We have a team at my company, it’s very small, they work with me, they work a lot of hours. They get a lot out of it. But they don’t work. For me, they work with me. And I never liked being an employee of companies where so and so would say Randy works for me, I found that very egotistical, it didn’t make me feel good. And I took things like that saying, I’m not going to be that way. And I think it’s the right thing to do to just be very polite, and to be very humble. I’ve had an opportunity to meet a lot of very successful people who have a very large amount of money. Both those who were it’s family money, and those people who have made it themselves. I know a lot of people who are extremely humble, you would never know they have money. I know a lot of people who brag about money and how much they have because somehow they feel that they need to. I admire the humble people, and I teach my kids to be very humble. They grow up in a way that I did not grow up. We are going on a very nice vacation next week. My first real vacation since June of 2019.

a beach vacation I’ll have two drones with me. I never traveled without them. But every trip that we’ve ever taken with my kids from the minute they were young, even today, on the drive to the airport, what I tell them is, you know, we’re incredibly lucky the cost of this trip is more than 90% of the people in the world will make in their lifetime. And I didn’t grow up this way. And I want us to all appreciate the flight, the hotel, the cost of the meals, and I know they’re gonna take that with them. You know, they know dad, here comes the speech. I said the speech is never gonna go away. The other thing that I take from these trips is I’m taking away my girls, twin girls, they’re just finished their freshman year at college. It’s important for me to spend one on one time with My kids, it’s a tradition I’ve done. Since the kids were four years old, we have gone on one on one trips, it allows me to spend one on one time with them, it is something I want to do. And I have three kids, it’s something that I want to do now when I have five kids, and it’s my time to really not focus on work and to bond with my kids. And the older they get, the less time they want to spend with me, you know, they’re into their friends. And I think that’s cool. But I cherish these moments. And you look around and you see a lot of successful people who are Workaholics. And they really don’t spend a lot of time with your kids. And it’s important for me to connect with my kids and my kids now that even though they may not want to spend as much time with me, as I do with them, they know that I really want to spend that time with them. I mean, you learn so many things from watching different people. I’ve got a friend named Rick Rivera, who’s my parent, Guru, and I met him. I went on a date with my ex wife. This was our second date. I was 26 years old, I think. And she said, All my friends are going to Universal Studios with her four kids. So what? Yeah, do you want to go with them? And I really did not want to go with them. I couldn’t even imagine the thought of having kids at that time. Rick and Dana had a license plate. For under five, these were all young kids and went to Universal. I was a good sport, I had no interest in going there. And I went there. And they were a great family. And Rick and I became great friends. His kids are now older, I’m a mentor, and good friend to them. One of them got married at my house three months ago, and you don’t know what you’re doing as a parent the first time there, you talk to your friends. And he’s my guru. So you lean on people that you meet, you lean on your friends when you don’t know. And eventually you go through life. He’s an amazing father to his kids. And I’ve learned a lot from him. And I have a lot of other friends that I’ve learned things from as well. And I try to incorporate all the good things. And none of the bad things. Of course, no one’s perfect. I’ve done a lot of bad things. made mistakes as a parent that you learn from. Yeah, so lots of good lessons there.

John Corcoran 42:40

We went way longer than I expected. So I apologize for that. I got as much time as you. Okay, good. Yeah, I’ve got a couple more questions. I want to circle back to Akamai. And also in the context of some of the other investments that you’ve made. Because of an amazing track record or you know, you invested in Google and invested in left all these different companies. What did you see when you first connected with the other co-founders for Akamai? How did you see the potential? Did you see this is going to be a multi billion dollar company employing 1000s of people one day.

Randall Kaplan 43:18

So one of the expressions that I tell young entrepreneurs who come into my office, I probably met with several 1000. And you find some of them, and then you’re a mentor to some people. And there’s an old saying you don’t know what good is. They think that they’ve got this VP, he did this, she did that. And they don’t know what’s good to them may not look good to you. You’ve been doing it for longer. I had worked with an incredible team at SunAmerica, you got to be top top top to work with Eli. And I knew what greatness was. I’d prepare these very complex financial models. We were looking to buy companies, you have to merge the companies together. Very complex 100 page model. You go in there, and he presents it to you. I would look at it and find the mistake on page 34. And he was right. He had an innate sense that people there were very bright. So I had a good baseline for brilliant people. The Akamai founders, two of them, were brilliant. And I was around them and one of the questions that I said to them as we started talking, I got to know him better. How many people on earth today would understand the math behind the formulas, the algorithms that powered our technology? And one of the founders said, not many, I said, under 10, he said, probably under 10. And you look for certain criteria like that. So you want to work with very bright people. I mean, how had I studied and gone to school for 10 years, I don’t think I could have really comprehended the math that went into a lot of this after working there, I knew how it worked. I could explain it in plain English. But I liked the team. And I liked the opportunity. And when I, when I left America, I had in the money stock options, a company was the most successful performing stock on the New York Stock Exchange for the 135 and seven year periods. that preceded me, the stock had risen to 6,000% in five years. And I had options that were worth one and a half million dollars, which is what I gave up when I left there. Eli sold the company three months after I left for $18 billion full vesting for everybody there. So I have three years left on my grant. And if I had stayed three months, I would have collected $2 million. And you look at the opportunity cost. And you think about Okay, if I wait three years, these vast you assume this appreciation potential. And I said, geez, you know, here’s what I’m going to own this company. I said, Gosh, I hope we create a $200 million value company, because after factoring the risk and the loss, that’s kind of where I thought my math would be much, much better than that. If there’s a little bit better than that.

John Corcoran 46:57

So even your estimates were, I hope that it’s going to be much under what it actually ended up being. Yeah,

Randall Kaplan 47:05

I mean, something happened to Akamai, to us, that will never happen again, I think in history. We started a company in August of 1998. We went public on October 27 1999. My mom’s birthday, the anniversary date of my first firing. When I left law school, I was crying that day, and I was a little bit happier when we went public. And the stock, we had raised the offering price almost doubled from where we had filed it based on the demand of the stock. And the stock went public at $28 a share the first trade was closed that day at 144 as a foreigner and 58% return on that first first day. So I don’t think anyone expected that week. The shortness by which we lasted from when we started coming to when we went public will probably never happen again. And we only have $3.2 million in revenue, gap revenue through that period of time. Most of it for one company, APA. Wow. That’s amazing. So I laugh at these days, would you say it’s a really high bar for companies before their Oh, yeah, yeah, that would never happen. I mean, the average length, the average age of a company that goes public to the US or between 12 and 14 years. Hmm. So you left. Why did you leave? I left. I was commuting back and forth to Los Angeles. I mean, what I did again, people thought I was out of my mind. So I had this great job at SunAmerica things probably gonna go well for me there. I knew lots of people in LA from my letter writing campaign. And I went from this kid, this hungry kid that no one knew what to do with 2k. This guy worked for someone who’s successful. He now has a background and an eye. I had some opportunities to do some other things. I went to Eli after the first year. I said I need more to do. He says you’re my first round draft pick, you’ll get more playing time this year, a little bit more playing time that year. But at that point, I was reading about what people were doing in Silicon Valley. I thought technology was something I wanted to do. I didn’t want to go back to business school. So I had the option I was going to look behind his back for a job. Or I was going to tell him and I thought honesty was the best quality policy he had been given me. He gave me my big break. I was super grateful to him. Of course, I was worried he was gonna say you’re ungrateful. You’re out of here, but I told him and I told him what I wanted to do. And I told him why and he said I think you’re making a mistake, but you can stay as long as you want here. And I stayed that third year with the freedom to do and go find different opportunities. And I had 10. But I picked this one for a number of reasons. But I was commuting to Boston with no funding, no salary, no CEO, and again, everybody, everybody told me, I lost my mind. But I trusted my gut. And I did it. And ultimately, the one condition that I had to join the company, which I said no to more than a few times, was that I didn’t want to move, I was going to commute every week. But I just didn’t want to move. And I had helped raise a lot of the money in that first round. And I’d also put my own money into that round as well. And the commute was tough, I would head out Sunday on the four o’clock flight, I get in at 12 1230, I would get to my hotel. And at first it was a motel with the cord light sign blaring in the window I did not take. I was so glamorous I was not on the nonstop, you know, back then for some of the flights. But we finally hired a CEO. And he said, I want you to move and I said I don’t want to move. And that’s part of my deal. And he said if you don’t want to move, you can be the head of West Coast sales. And I didn’t want to do that either. I had some other things that I could have done, CEO type roles that I had turned down and I had helped hire the VP of sales. So that wasn’t, that wasn’t something I wanted to do. So I had the option to leave. Or I had the option to stay and take a job that I didn’t want that I didn’t think would be good for my career and is a very tough thing to do. We raised money.

I had, we had 10 beta customers. My name was on the contract for seven of them. I was our VP of biz dev. And I think we had maybe 30 to 50 people back then. And it was very tough. I didn’t know what to do. I told the CEO, I would get back to him. I called Jay when I was troppings at SunAmerica. But at that point, I think he’d been promoted to the CEO. And I view j as one of my mentors. And I said, Jay, here’s, here’s the deal. I told him, I’m conflicted. And he made it simple. He said, What’s this thing worth? I told him what our private company valuation was. He said, what percent of the saying you do on and I told him and if it was, you know, he said to me, why are we having this conversation? And the bell went? In other words, he knew the answer already. He made it clear what the answer would be. He had done all the calculus and the calculus was extremely simple. And it became simple for me. Yeah, so I left and I started my own venture capital firm. Now we do a bunch of different things. Yeah. But that’s

John Corcoran 53:06

Let me ask about that. So you invested in Google, invested in Lyft, Postini, all these different companies, what you mentioned, you know, an important factor for you is preparation, intelligence, smart team. What else goes into your evaluation of companies these days, when you’re considering investing?

Randall Kaplan 53:26

The first and most important factor for me is the quality and my evaluation of the founder or founders. And I always had that burning desire to succeed, I always had that Killer Instinct, where I want it to be successful. And I was gonna do whatever it took on the work ethic front, and on the intangible front, to try to reach my dreams. And the interviews that I have are focused around that and trying to bring out those qualities to see if I can evaluate those. Obviously, we look at the business, the moat, whether what the competition is, we look at all kinds of things, but it always comes back for me to tell the people that that’s the most important factor for me.

John Corcoran 54:19

Yeah. And of all the different founders that have come through that you’ve evaluated, maybe pick one or two that have just knocked your socks off. And wow.

Randall Kaplan 54:29

Yeah, one of my oldest and a very close friend, named Brad keywell. He’s founded public companies. Groupon was his fourth uptake and will be his fifth. He’s going to be a guest on my podcast. I’m super excited to have them. We’ve been friends since college. Brad is the best entrepreneur that I know. Hands down. He thinks differently. He’s brilliant. He’s creative. He’s easily the best. Brian Lee is just right there with Brad. He’s a superstar, co-founder of LegalZoom. As a CEO, co-founder of the Honest Company, which went public this week, runs BAM ventures, a venture capital firm. I’m very close with Brian, he’s one of my buddies, we can talk about very sensitive things that would be hard to have a conversation with people without the experiences that we had. And he is a great entrepreneur. He’s someone I admire a lot. He’s one of the nicest guys you’ll ever meet. He’s as humble as humble can be. And he’s a great thinker, too. We co invest a lot together. And I’ve learned a lot from him. And you know, the funny thing is that philanthropy is hugely important to me. And I started an event called The Justice Ball when I was 27 years old, it’s thick. We’re in year 25. Right now, I ran it for the first 10 years. It’s done, done very well.

John Corcoran 56:00

You’ve had some amazing musical acts at that.

Randall Kaplan 56:03

Yeah, yeah, we have the Go Go’s Billy Idol be 50 twos. But I was considering and thinking about what’s going to start a second charity event. I was looking for something in foster care for the homeless, my grandmother was raised in foster care, it’s a cause I’m most dedicated to, and I was cold calling to see CEOs of nonprofits. They all knew of The Justice Ball, they had heard of me. And they all ran in my office. Except for one. This guy wouldn’t show up one day, his cat was sick. And I have a lot of people who would like me to donate to their nonprofits, and they’re all great causes, you have to pick and choose which ones that you want to do. And I donate very quietly, often, anonymously, I think that’s the best form of giving. But this guy would not show up to my office. So I looked at the board and I said, Oh, you know, Brian, I know a Brian. And I could call them. I’m like, hey, Brian, my name is Randy Kaplan. I’m trying to meet with the executive director of your nonprofit. I’m interested in getting involved in giving money. And that’s how I became friends with Brian.

John Corcoran 57:23

Interesting. Yeah, that’s great. Well, we’re way over on time. So I want to wrap it up. And I, you mentioned a bunch of great names here. But I want to ask my gratitude question, which is, I’m a big fan of gratitude, which I can send you as well. And when you look around at your peers and contemporaries, however, you want to define that, you know, a lot of founder entrepreneur investor types you respect. Who do you admire?

Randall Kaplan 57:52

I mean, I’ve named a few of my contemporaries. I’ve named Brad, Brian. You have to give the credit where the credit is due. I mean, it begins with my grandmother, she was raised in foster care. She’s a breast cancer survivor. She volunteered for Children’s Hospital for 40 years. She had a very tough life. She’s the matriarch of my family. She’s my role model. She’s my hero. So I give her a lot of credit. And then I had some, you know it. What’s interesting is at some point, you become, you go from being the mentee to appearing. And there was someone named David Paige who I grew up with. He was the CEO of the best law firm in Detroit. m honigman. was the hardest job to get. I spent my second summer there, he wrote me my letter of recommendation for law school. He believed in me, I know when I was a young kid. He coached my brothers in my little league team. And he was Mr. Page. And Mr. Page was incredible. He was an icon in the Detroit community, the legal community. And when I went public, he said at one point, yeah, you can call me David. And he was David and during that summer, there were 10 of us in the summer program, and he put the fix in. We all had a mentor and his fix was my mentor David Fulton. And David was the head of the corporate group. He was David Page’s protege. And David was my mentor. So he’s 12 years older than I am. He’s married for the second time like I am. He has twins who have become really good friends with my kids. And he was the best man at my wedding. Very cool. So yeah, it’s funny how things work out. I have a number of mentees who are now my peers as well. And it’s great to see.

John Corcoran 59:56

Yeah, that’s great. That’s great. And that brings us full circle to your new podcasts. I’m totally, totally excited for you because you’re going to get to reconnect with all those different mentees who became peers, mentors, so you became a peer of. So In Search of Excellence, the name of it, you’ve got Sharon Stone already amazing. Talk about some of the different guests. You have Sam Zell and some really amazing guests already.

Randall Kaplan 1:00:21

We have Sharon, who’s awesome. Sam Zell, who’s awesome. Strauss Zelnick, I’ve mentioned Anthony Scaramucci. I had an incredible session yesterday with Tim Draper, one of the most successful venture capitalists of all time. Kliff, Kingsbury, the head coach of the Arizona Cardinals football team. We met on a boat and we almost drowned together. We went snorkeling in Vegas Bay. That was a phenomenal bonding moment seven years ago, you can check out the podcast to hear that funny story. And you can learn more about Tom Brady and what he said to me on that trip as well. One of the highlights of my career one of the highlights of my athletic career which with which wasn’t very much the podcast is about our desire

John Corcoran 1:01:09

really too bad you didn’t you know, if you drowned on a boat with temporary Brady at the same time. Tom was on El Cap was on the boat, because that probably would have been the headline, it would have been a shame. You know, there’s some other people on the boat too.

Randall Kaplan 1:01:23

Yeah, yeah. No one would have cared about me, you know, sorry, would have been about Tom. But yeah. So the podcast is about our quest and desire to maximize our potential and be the best we can be to, to live our dreams, to believe in ourselves, and overcome the challenges, trials and tribulations that we all have. No matter how successful Sam went through his Tim Draper went through his insurance stone has an amazing book that just came out the beauty of living twice. It’s Thing number four on the bestseller list. But there’s a common thread to people who have been successful, and you have to plan for if they keep coming back. They’re going to be all kinds of challenges and you really have to have a plan. And so my goal is that my podcast inspires and motivates people to achieve their dreams and maximize their potential on their way to excellent,

John Corcoran 1:02:23

That’s awesome. And then Sandee, of course, is also another portfolio company that you are focused on. Tell us what that is.

Randall Kaplan 1:02:30

Yeah, Sandee is my full time job. That’s the 70 hour a week job. And we’re creating the world’s largest beach database, it’s a Yelp for beaches. We’ve catalogued 94 categories of data for every beach in the world, more than 50,000 beaches in 212 countries and we have a yellow for beaches that’s the business events the consumer side and then we have a proprietary database that we’re licensing to government tours Boris throughout the world to help them increase tourism revenues. So super excited about that business. We have about 100,000 hours into that business over seven years. I’ve self-funded it we’re just raising our first round of outside capital but our future there is very bright. I’m super excited about that one.

John Corcoran 1:03:22

All right. If you are an investor and you are in the beach space or want to contact Randy. Alright, jumpinvestors.com, sandee.com is the website for Sandee, correct?

Randall Kaplan 1:03:34

John persistence pays so I first reached out to the woman who owned sandee.com seven years ago. Her name is Sandy Swanson. She lives in Aurora, Colorado. I have attempted to buy it I think more than 70 times and was successful three and a half weeks ago. I know so we know on the domain name you know persistence pays and that’s one of my lessons so nice. We bought it three weeks ago, so it’s now sandee.com. Thank you, Sandy. And Tom as well, Tom, her husband. 

John Corcoran 1:04:13

Very cool. All right, Randy. It’s such a pleasure. Jumpinvestors.com is the other website. Anywhere else people should go to connect with you or learn more about you?

Randall Kaplan 1:04:20

Sure, I want to mention one other thing. I want to give a big shout out to my book Bliss. It’s a coffee table book of a selection of my beach drone photo photographs from around the world. You can get it on sale. Pre Order right now on amazon.com. I promise it’ll make you happy and smile when you look at some of these photos and will inspire you to travel to new places. Alright, Randy, thank you so much, John, thanks for having me. I appreciate you.

Intro 1:04:47

Thank you for listening to the Smart Business Revolution Podcast with John Corcoran. Find out more at smartbusinessrevolution.com and while you’re there, sign up for our email list and join the revolution. And be listening for the next episode of the Smart Business Revolution Podcast.