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Randall Kaplan 4:16

Well, the first thing that I think to think about is you have to create your own. All the interesting jobs I’ve had have come from not a job listing. I’ve went out and I found them but I started my career as a lawyer. I went to Northwestern law school, I did very well there. And I came out to Los Angeles to practice law and that was the beginning of a spectacularly horrible career in the practice of law. I lost my job five and a half weeks after moving here. I had not found out if I had passed the bar yet which I did. I had $3,000 in the bank, and I was looking at waiting tables and unfortunately it was a bad legal climate, which is why I was laid off so it was hard to find a job I got a job in Orange County and as naive as it sounds. I had Never heard of Orange County before. So I commuted from Westwood 53 and a half miles to work every day took me three hours round trip, if there was a traffic jam, could take up to four hours. I leave my apartment at 530 in the morning, get there at seven and barely came home before midnight. After six months of that I went to the managing partner downtown Los Angeles, I said I’d like to move down there. He said, No, we want you to move down there or leave the firm. So I was now looking for my third job my first year out of school, which is definitely not the way to go. So I ended up getting a great job at a Los Angeles based law firm. At first Chicago based law firm and their Los Angeles office, they had about 90 lawyers there. And I had a great boss there to two people, I took a tax job. I had no interest in tax law, but I thought people would think I’m smarter than I am because tax law is a very arcane thing to grasp and comprehend. So surely after starting there, I always wanted to be in business. I always had the gene to start my own business at a T shirt, business and college, but I went to law school as a means to an end. So I started plotting my way out of being a lawyer. Without going to business school I was making at the time, big law firms all paid the same wage I was making $70,000 a year in 1993. Today the wage is I think 165,000 for the Big Four, that was a lot of money back then. I thought I was rich making that much money. 100% Yeah, it was good money. So essentially, what I did is I thought I had to do something unique and different than what other people do. I wasn’t just going to write letters, to CEOs to meet with me or to companies or look for job ads. I wanted to be the right hand man, to someone successful, the right hand person to someone successful. And I had an idea I was going to write letters to all of the CEOs in Los Angeles, starting with the studios, because there are people a guy named Strauss Zelnick was running Fox at age 30. I wrote him a letter, by the way, and we’re still good friends today. And he was a guest on my podcast as well. And I thought that looked like a business where meritocracy rule the day. So I started there. And I started focusing on people who had been a lawyer and in transition into a successful business career, who were then the CEOs of large companies. And so I branched out my search to not only the entertainment companies, but large companies like SunAmerica, like Kaufman and broad. And I wrote 300 letters. And when I started this process, I told a few friends. And everybody said, These people are never going to meet with you ever a cold letter to someone running a $20 billion public company never going to happen. But I had an idea I had an idea to be different. Sometimes I think a little differently than people. People will say, okay, that’s interesting. I’ve never heard of that before. They mean it as a criticism, and I take it as a cop. So and and when people tell me that something can’t be done, and I think it can be done, then I want to prove them wrong. But I really want to prove myself, right. I want to trust my gut. And I’m very persistent when I want to do things. So in this case, the idea was I was going to write letters

that requested informational meetings, not jobs. And what I did that was unique as I went on LexisNexis there were no Google. There was no Google back then. So yeah, I had to use a paid subscription. With a law firm, I charged it to marketing. And I did all this research, I printed out every piece of press written on these people for last 20 years. So then I highlighted them my two bedroom apartment was a letter writing factory, the second bedroom where I had, I compiled the list, I had stacks of information, five inches thick on all these printouts with names on top Sumner, redstone, etc, etc. And then I compiled the facts from that research and I integrated them into a very unique, different kind of a letter. It was spiral bound with the self and cover. It was tabbed. I had certain things in there that were unique. I put my transcript from Michigan I was Phi Beta Kappa my junior year, only one of 10 students graduated and Northwestern did very well they’re also and was involved in some other things in my life, too. So it was very unique was very different. And it was something that they had never seen before. So I tracked all this on Excel. I tracked the date I sent the letter the phone calls the follow up. I was very persistent. Steve Bollenbach was the CEO of Marriott back then he was On my hit list, and I sent him a letter, I called his office once a week for 27 weeks in a row. his secretary was a woman named Ophelia Reese. I still remember this 20 something years later. And she was my my friend, you know, she was rooting for me. For me to take the meeting one day, she called me in my office at the law firm and said, Are you in your office? Yes, hang on, he’s gonna call you in the next 10 minutes. And he finally called in and persistence paid, the meeting went nowhere. But you never know where it’s gonna take you. And if you do your research, and you’re persistent, people will meet with you the end of the story there is I wrote 300 letters I got 80 meetings, Sumner Redstone, the CEO of Disney,

Jeremy Weisz 10:45

the great percentage, Randy

Randall Kaplan 10:47

it was a very high percentage. This went from a guarantee that people said it would be zero. And everybody I met with said, These people are said they had never taken a letter from a cold meeting before. And when I got these meetings, I did research, you’re doing research for the podcast, I do research for my podcast, I spent about 15 hours of my own time preparing for my podcast, and I have someone on my team do the research. So each podcast takes about 30 hours each, which is intensive, but I want to make sure I’m the most prepared. And I went into these job interviews. And this is what I tell the many people that I mentor, my goal was to be the single most prepared person to walk into that office ever. And just the kind of prep that I did for the SunAmerica. Meeting with a meal I brode was it was a public company. I read the 10k, the 10 Q. I studied for like a final exam. And that’s my advice, you’re going to spend more time at work than at home with your family. You should spend more than one hour looking over a website and some people have come to my office, and not even known the names of our portfolio companies, which means they spent no time and they’re all on our website. So I outlined the 10k. For the annual report. I memorize that I studied for it. I memorize 20 questions, including notes from the financial statements of things I didn’t really know, because I wanted to take these off. And in that meeting, the long of it was the meeting. The long short of it was the meeting went very, very well. And we spent 90 minutes together. I ended up working there for three years. I never had a 90 minute meeting with him again, one on one. And the meeting went well. He was started talking about something he told me about this job. He had the assistant to the chairman job and I said I know about the job. Five people have had it. I gave him the names, what years they had it and what they were doing with their life today. And Eli was scribbling furiously in I was nodding, nodding, nodding. So he was taking notes, which was which was a good thing. I left the office and he said, I no promises. I said I love that job, no promises. I want you to take one business class to UCLA, go get a catalog and then send it back to me and I’ll pick one for you. So at that point, I left this office, drove to UCLA, got a class catalog parked brand around campus, it was 90 degrees that day, I’m running around with my suit and tie. I’m soaking wet with sweat. I parked I found one. I got a ticket on the car on my car, drove back to my apartment, type the thank you letter, had it back, get his receptionist within the hour. And there’s a lot to the story. As you think about what I did. It’s making first impressions making first impressions really count. I could have waited a day I could have gone to UCLA the next day. The follow up would have been fine. But it was different. It showed what I made of it showed my personality. It showed how badly I wanted the job. And there’s a lot of lessons to be learned. So his assistant called me back two weeks later said Mr. Broad would like you to take one of two classes. I said I’ll take them both. And long story short, I got a job offer there on my 27th birthday. And I ended up working for him for three years. incredible opportunity. That was my big break. But the story of how does a 27 year old horribly unsuccessful lawyer end up as the assistant to the chairman for someone who started two fortune 500 companies. And that’s there are a lot more details there. But those are the broad strokes of how that happened. I was very lucky I think you create your own luck. And that was my that was my big break.

Jeremy Weisz 15:05

you do create your own luck. And people can tell the research to Randy and I want to hear some of the lessons you learn from him. But you know, one of the things that sticks out is you are the ultimate direct response copywriter. I mean with all those waters, but it comes down to I went on a stint of interviewing some of the top direct response copywriters, marketers on the planet. And it comes down to research, right, knowing the customer or the person on their side is really what it comes down to. And, and that’s really what he went deep on for all of these. He is a 300 letter as in at responding and getting meetings. I mean, there’s responding and not getting meetings, too. So that was that’s pretty amazing.

Randall Kaplan 15:47

There’s a there’s one other footnote to that, that I that I want to say. So I wrote letters to these people. And I one of the letters I wrote to is a guy named David Hermelin, who lived in Detroit. I grew up in Detroit, and he was an icon in the business community very philanthropic. So I wrote him a letter, I’m going to Detroit the next day. Or once we set up a meeting, I flew there, he wanted me to meet him at 7am at a deli, which is for ami time. And I said and I take in the red eye, so it didn’t leave me a lot, a lot of time him shirt from the airport, and I get there, and there’s a line of people waiting to see him. And I thought, Okay, this is interesting. So I got my turn in the booth. And he said, Okay, got your letter. That’s great. What do you want to do? I told him what I wanted to do. And I told him, I had a bunch of meetings so far. And he said, Well, what do you do during the meetings? Do you request and say that I want a job? I said, No. He asked, why not? And I said, you know, they’ve done so much for me. They’re taking the meeting, I sort of feel bad about it. And he said, that’s a huge mistake. Ask for the order when you’re there. He sold life insurance. That’s how he made his fortune. You don’t wake up one morning, say I need life insurance. I’m super excited. But you got to buy it from somebody. So he rang the bell. But he also told me that I’m going to get one shot at these people. And sometimes you take the advice of people, even successful people, you say, Okay, I hear what he’s saying. us for the order. But I said, I’m gonna have a lot of shots. I want to develop relationships with these people. And so I ended up not having a lot of shots with these people. I mean, you have one shot to make a good first impression. And I’ve got a podcast coming out with a bunch of lessons on how to do that. But I also was able to develop relationships with people like Strauss Zelnick, who I met through a cold letter where we’re friends many years later, he’s co invested with me and some of our companies. So so you never know where are these relationships will come from?

Jeremy Weisz 18:05

You know, Randy, I’m going to have you talk about the book Bliss, but but I’m going to make a case for your next book on this. Yes. Okay. Okay. And so out of the 300 letters. Yeah, you get 80 responses. How many meetings Do you think you got? Do you remember? Around 6565? Yeah, I would love a book that has a lesson and maybe it’s not all 65 but maybe 6060. I want to hear all the lessons from each of those meetings, even if it was a lead to nothing right? Because there’s less than that. What? What were you say out of those meetings? Do you remember like your top that was one like huge lesson is like just ask for the order from him. What were some other lessons that people instilled on you in those meetings? Well,

Randall Kaplan 18:52

I’ve had a lot of funny stories to tell, but I’ll tell you a lesson first, and I keep coming back to him. Strauss Zelnick is someone I admire immensely. He’s brilliant Harvard, a JD MBA running Fox at 30 running BMG at 40. He was chairman of CBS. He runs held like media they managed $25 billion CEO and chairman of take to a publicly traded gaming company, I think, with an $18 billion market cap when I met him the first time I went to a conference, someone told me if you want to go if you want to hunt, moose, go where the moose are. So there’s this big conference, one of the bankers who is a senior banker than it. Bear Stearns, I wrote him a call letter. At the end of the meeting, I said, you know, who else should I made? He said, Come to my conference. So I took a day off of work. I went to his conference. I met him as he was leaving, he was in New York, and I said, Hey, Strauss ian you speak and then you have the entourage and the circle following you out. He was flying back to New York. He said call I call him he set up a meeting in Los Angeles in big office here. And I studied for these meeting people ran late. So I had a cheat sheet, because I had memorized all of my questions. So I kept it in my suit pocket, and I read it. And then I put it away. I wanted to memorize my questions before I got in there. And he’s running a minute and a half late. I was looking on why he walks out into the lobby, he’s on the phone. And he puppies on. I’m super Sorry, I’m running a few minutes late. I’ll come get you. It wasn’t his assistant. It wasn’t the office manager. But that’s an amazing lesson of who he is how he treats people. When I got there, I got that I would get there one hour before my meetings. Why? Because I live in LA I plan ahead there’s traffic jams, the hour would give me some way to to get there. And that happened. Never show up late to a meeting. And when I when I got there, I would walk in 15 minutes before the meeting. And I remember her name Liz Ramirez was the office manager. She was sitting there and she’s like best friends with all these

Jeremy Weisz 21:11

people because you talk to them once a week probably forever.

Randall Kaplan 21:15

Well, Liz was awesome. And she said Strauss will be out soon. Strauss not Mr. Zelnick. And again, you you take these lessons, you’re 27 years old, or sorry, I was 26 years old. And you hear these lessons and you start thinking God, I really want to learn something from this people. Then you have something on the flip side in the world is a small world. Okay, I was a lawyer begging for a job. I wanted to work at Alvernia Myers, which is one of the best firms I the legal market picked up at callbacks there downtown and other Central City Office. No offer I was devastated. But sometimes the biggest disappointments turn into the best opportunities. I couldn’t have gotten the SunAmerica job if the malvani thing happened, because that was a law firm we use at SunAmerica and the ironic part of all this, I get to SunAmerica. I’m not practicing law. And I’m now working with some of the partners who I had met with when he got a job offer from so the world is a very round world. And in my job search, I met with one of the most successful producers of all time. Someone who ran a studio I met him he wanted me to come to his house. I bought his mansion in Beverly Hills, the gates the home is up on the hill. And there’s a woman in front of me in a bikini top. She’s very pretty Mercedes convertible. We drive in, she goes left by the pool. I could see her parked I pull up to this massive house, someone comes to greet me. He’s running late. I’m sitting basically in this kitchen on a on a counter and there’s pictures of him and every president of the United States in the last 30 years. So he calls me into his office, and he puts his feet up on the desk, I could see the imprint of the Ferragamo shoes or the Ferragamo shoes. And we talked about the movie business. They said, you know, do you love the movie business? I said, I didn’t grow up wanting to be in movies or in the movie business. But I like the meritocracy. I work hard. I think I’m bright. And he said, This is not for you. I started in the mailroom, you got to have a passion for it. It was a very good meeting. He was very nice, very blunt, which is great. But I remember the shoe in my face. So several years later, I go to a party in Malibu, this is the post occupy and he’s there. And he’s there with a beautiful woman. And we start talking I didn’t raise this with with him, by the way there. But he ended up being a parent of my kids school. And I went out to dinner with he and his wife and my wife, Madison. And I said to him, you know, we’ll call them we’ll call him Joe. But as I said, you know, Joe, we met a long time ago back at night, either Remember, you know, and he’s back with, you know, tons of people. And I told them a story. And I left out the shoe in the face part. Hi, I didn’t think that there was nothing to be gained from that. But I remembered it vividly and then I told him the story and he obviously knew about all the things that I had done and he said all that so great. It’s a good thing. You didn’t go into the movie business then and then the footnote is his wife is there. He says that was me in the bikini pulling in.

Jeremy Weisz 24:46

I thought you were gonna say she went left to the pool and then you went left and skip me.

Randall Kaplan 24:52

No One No One No one asked me to do the pool like bigger. It looks fine. But no, I was very prepared ready to roll when I pulled up to his front door?

Jeremy Weisz 25:03

Randy, I’m wondering what’s going on inside your head with these meetings, you know, it can be intimidating. And there could be self talk going on for people. Does that going on for you?

Randall Kaplan 25:14

tons. You know, one of the great motivations of all time is the fear of failure. I felt that then as a lawyer, I mean, I had failed badly, I’d never failed in my life. Before I was the top of my class wherever I went, I was a nerdy kid. But I sort of came into my own became less nerdy in college, my kids still think I’m very nerdy. But I had I had always done well, I could control the outcome. Through my hard work, I think hard work is the greatest determinant of our success. And I knew almost always going into all the tests, I had that I was going to get an A, I got one B plus that mission, Michigan first term, I was very disappointed in myself. But I think you can control the outcome. But you start going into these meetings. And so then I had a very unsuccessful legal career. And then I start going out and thinking, gosh, I’m hearing all these voices, these people are never gonna meet with me. And I said, I’m an entrepreneur. I know I think a little differently. And that’s okay. Successful people have been told no, a million times how stupid something is how something is not going to happen. And you trust your gut by when I’m in these meetings, Jim, I’m sitting there thinking, gosh, I mean, I was so nervous. Am I gonna blow this? Are they gonna like me, my goal was go in there, show my research and impress them, good things will happen. And they did. But I was, I was extremely nervous, you know, going on in my head, what are they thinking? You try to gauge the audience and see how they’re reacting to you. Some people don’t know how to do that, right? They just keep talking. Keep talking. Part of a good conversation is being a good listener. So as the interviewer as the interviewee, sometimes it’s good to flip the switch, the interview becomes the interviewer. And it allows for a more healthy discussion. And it also makes a good first impression as well. It shows that you want to know what they’re doing. And they want to know about the experience. But yeah, I mean, what was going on in my mind is, you know, don’t mess this up. You got one shot, and your future could be standing right in front of you.

Jeremy Weisz 27:32

No pressure, no pressure.

Randall Kaplan 27:34

You know, I feel pressure from every day today. I have a number of businesses, what if they fail? What if I make mistakes, I make a lot of mistakes. By the way, I’m in the venture capital business. So we have a 20% batting average, which is normal for a venture capital firm. So you look stupid, and lose 100% of your money. Eight times out of 10 roughly, sometimes it’s a little better, sometimes a lot more. You’ll hope that the winners make up for the losers, but fear of failure. I think that’s one of our great motivators on a daily basis. It’s still one of mine. today. Yeah,

Jeremy Weisz 28:13

it’s like Hall of Fame. Baseball players, right. I mean, you’re in the Hall of Fame, if you bet 300. Right, you That’s right, you know, get out 70% of the time and seems the same for that. I want to have you mentioned the book to Bliss. But I you know, talking about what you just said, I do want to hear after you talk about the book. Maybe one of the investments you made that maybe look like it was dead. A big surprise for you, but talk about Bliss for a second.

Randall Kaplan 28:40

Sure. Want to talk about bliss, we have to talk about Sandee first. Go ahead. So I’m a beach lover. The beach is my happy place. I went with my wife Madison to Greece. When we started dating in 2013. We went to the concierge of our hotel, we went to black sand beach, he whipped out a paper map. She unfolded it for two parshah with a sharpie. I think there’s one over here. Very little fiat convertible. Well we drive out there for two hours. no food, no bathroom. Nothing. The road wasn’t marked. We went through what looked like a road. weeds taller than our feet. I’m thinking the movie taken back like can I be? Yeah, yeah, I mean, yeah, this well to do person staying at a nice hotel. Someone’s following us and no one would have found me no one would have found our bodies. And we get to this expanse. We are the only ones there. black sand beach Cliff said yeah, there’s got to be a better way and seven years later, and 100,000 hours of research later, we’ve cataloged 94 categories of data for more than 50,000 pages in 212 countries. So we build the world’s best beach database. Sandee is basically a yelp for beaches and it’s the only resource though where you can find detailed information about beaches and all these countries now Do we have the data and nobody else has, you can filter through the data. So we’ve built something for a very small niche in the world, the global tourism businesses $9 trillion a year and the beach tourism business is $5 trillion of that. But yet, there’s no beach resource. So we have this little niche. And we’re excited for people to find out about us more than a billion people, you’re going to the beach, and the most important determinant of where they go as a quality or beach, or beaches within that location. So you can find that simply on on one website, we have all the data, most people consult 32 different websites before they book a trip. And that’s what we’ve done. And we built and one of the pain points we have is we need photos of all 50,000 beaches, people want to see in addition to the data, a picture of each beach, what it looks like before they go there. So I started looking through these photos, and doing a lot of homework and the due diligence, we have about 30 photos now on our database, we catalog them, we rank them, etc, etc, licensed and they’re all licensed free, etc, etc. And I started seeing all of these drone photos. I’ve been a hobbyist photographer, really since I was 13. I’m the dad that goes on vacation and takes 1000 to 3000 pictures each time. And my kids hate it. But I make them a birthday book each year for the appreciate it

Jeremy Weisz 31:33


Randall Kaplan 31:34

Yeah, they love the birthday book. But I started looking at drones I bought my first drone five years ago, I’ve think I’m on my ninth or 10th drone, they upgrade. And I started taking these pictures. And my the quality of my pictures have improved. I never leave home without two drones. And it’s something that I really like to do. And people people like my photos. So you start looking around and you look and see from a business perspective. I love coffee table books, I love photography books, there’s only one successful drone beach photographer in the world. And he really doesn’t even use a drone. He shoots from a helicopter, his name is Gray Malin. And he’s the only one so I started thinking about, okay, well, there has to be room for a second one. And you try to find another beach photography book online, you can’t. And again, the art coffee table photography market is, is big. So I looked and see where is who is this publisher, send a cold email to the CEO. I’m sure you’re good at writing those by now. The latter was good. He just because of some of the things that I’ve done, I have 100% rate on my emails that I send out. It’s it works 100% of the time. So he wrote back. Some of the photos are up on my website, So I really like your photos too similar to his. So most people would end it that okay, man, see. Thank you. I said I’d love to get on a phone call on Monday with you love to know how the book business works. I know most people wouldn’t do that. But he did. We spent one hour on the phone together. I wanted to learn about the book publishing business is something I wanted to do. And at the end of it, I said, you can’t do it. But who should I contact? You gave me two names. I said, will you make the intro for me and link us on a email? He said no. But you can mention my name. So I send out the first guy we met a time he called my photos interesting. And then the second guy was someone named Chris Gruner. At Cameron and Company. It’s a 70 year old book publisher high quality imprint. And long story short, we signed a book contract, I think three months later. And my book is called bliss. It’s a compilation of my drone beach photography photos from around the world. And I’m super excited for it comes out June 15. It’s a great Father’s Day gift. And it’s been very well received. so far. We just had a very nice write up in Frommer’s this week, when it was released for preorder. It was a bestseller on Amazon and for different photography categories. So I’m excited by the book, you know, this is a labor of love. And again, I I took a labor of love. I took my passion for travel, for beaches for photography, and then I thought about a business. And I said I’m gonna apply some of my business lessons to myself I cold called the CEO of the book company. And by the way, A Funny Thing Happened on Abrams I was bought Cameron and company six months later so now I’m back to Abrams I mean cameras my imprint but I’m Abrams owns a company and there’s a Salesforce is responsible for selling my book. But once again the author’s writing letters to CEOs of publishing companies is not a good strategy and is a very low probability outcome.

Jeremy Weisz 35:29

You don’t want if you do your research like you, Randy.

Randall Kaplan 35:32

Well, it wasn’t I mean, this was a qualitative judgment. You got like the photos or you don’t like the photo, so he likes my photos, people like the photos. But the point is, if you don’t ask you don’t get the SunAmerica job writing to the CEO of a book company. I mean, you got to try got to get up to the plate to get a hit.

Jeremy Weisz 35:55

That’s chapter three of your next book, which is back to the 65 letters that led me to success, which was ask for the sale.

Randall Kaplan 36:03

Right. 6065 meetings, in person meetings. 15 phone calls, 300 total letters.

Jeremy Weisz 36:11

It’s got to be your next book. I want to read it. So I’m skipping over the for a second. The Akamai Akamai by, right, um, I’m skipping over Akamai for a second to go to surprises in your portfolio for a second. Yeah. Because I would love to hear what which deal you gave up for dead than what happened.

Randall Kaplan 36:36

Yeah, well, that would be a company called Khalipa Networks, which was founded by the former chief evangelist, his son, the chief Java evangelist is Sun Microsystems, which was a huge company, one of the blue tech, one of the blue chip tech companies founded by Scott McNealy, who actually went to the rival high school where I grew up. I went to country day he went to Cranbrook. This is in Detroit, in Detroit. I didn’t know I might just do that’s an interesting factoid. So, Maiko, the CEO, he starts his company, I meet him through the chief of staff at Goldman Sachs, who was a partner there, and she was doing some tech investing, we’d become friends. So I put money into this company, I can’t remember what they did. But long story short, they ran out of money. And the company basically sold to another company. And and what that is, it’s a Aqua hire situation. So they want the team and you exchange stock into the new company, a company is basically left for dead. And it’s sort of a hope, and a prayer that something will happen with a new company that will have some kind of a positive result. In my experience, we’ve had 10 of those. And only two of work. This is the first one that works. So we gave the company for dead. They exchange khalipa for stock and Postini. And years later, I mean, we’ve written it off years later, you get the five inch Manila bound packet in the mail from a law firm. That’s that’s a good packet to get. So that packet said that Google was buying Postini for $650 million, plus another potential 100 million dollars and earn out. And we ended up making, I think, 10 times our money on a deal that we’ve given up for debt. And it just goes to show you you never know. And then the venture capital business or some companies where we said, okay, this is, you know, a definite This is for sure. Going to work. It’s the best thing I’ve ever seen. And many of those don’t work and sometimes the ones that shouldn’t have worked. And this one should not have worked for a lot of reasons which we found out once we got going, sometimes you get lucky. And and yeah, that was that was the best outcome on on that one on that front.

Jeremy Weisz 39:10

What do you look for Randy and investing in tech companies.

Randall Kaplan 39:15

So a lot of firms do it differently. They look at a variety of factors. Some VC firms won’t fund pre revenue, certain firms will do the seed stage, which is the first stage or series A or B or C, worst stage, agnostic most of ours had been seed stage. All the deals that we’ve done, have come from friends in the business, different VC firms, entrepreneurs that we funded. And the most important factor for me is the CEO and founder of the company or founders of the company. That’s always been, for me the most important ingredient of success and when I meet with them, we go through the salt All questions and I kind of warming up. And I saw the zingers in there. And you just want to find out what somebody is made of. I’m very driven. My friends who have known me my whole life have said, You’ve been very driven since since I met you. And I feel like I can judge that in different people as well. You look for that Killer Instinct, do you look for that drive. And the mentality that I want to find in which I had in myself was if I’m dropped off in the middle of the ocean, all find land now, I’m horribly afraid of sharks. So I don’t want to be dropped off in the middle of the ocean. But that’s the mentality that I had. And that’s, that’s the mentality of the people that that I want to fund

Jeremy Weisz 40:46

a relentless persistence,

Randall Kaplan 40:48

a relentless persistence. Someone once called me the first little piece that someone wrote about me called me indefatigable, and I had to look up what that means. I mean, I’m not coming back. You don’t give up you keep coming back for more. And very, very driven. And persistent.

Jeremy Weisz 41:11

I love it. I’m going to take a fourth stab at Akamai, Akamai, Akamai gees Randy, Akamai, Akamai. So how did that start?

Randall Kaplan 41:24

So when I was his son, America, my job was working with a very senior team, I was as a technical model on the corporate development group. One of my titles was managing director Corp def. And that job was an internal investment banking function, where we looked for different financial services companies to buy Tyler and how to model create these 100 page, complicated financial models. I did research and my primary job there was doing research. And I was sort of the research guru at the company. But I worked on a whole bunch of other things. But I was the very junior guy on a very successful senior team. There are only four people, five people, sometimes it came to these meetings. So it was it was a great group to work for. The Managing Director title was was key. I had meetings with the head bankers at Goldman and Morgan Stanley, and all the people, all the leaders in the financial services world from the investment banking perspective. But after a year, I went to Eli and I said, I need more to do. And I said, I’m I’m entrepreneur, I’m hungry, I want to make an impact. I want to make a measurable impact, so I could see what I was contributing. And he told me, you’re my first round draft choice, you’ll get more playing time this year. And at that point, I started a charity event called the Justice ball. from scratch. It was my idea. Long story of that is it was very successful. I got 1000 people to show up at the House of Blues. I had met with the CEO of the House of Blues, 12 phone calls to have lunch with him, told him what I wanted to do. People said 27 year old can create charity events. And you could never sell out the venue like this. So we sold out the venue, we raised a bunch of money and suddenly the SunAmerica bosses. That was important. I did it for the charity reasons and to give back. But it also showed them I had some other skills, leadership skills, organizational skills, clothing, closing skills, sales skills, you know, to raise all this money, bring the group together, I hand picked 20 people to be on the planning committee, one of those people was damn off. The second gentleman, but I’ve known forever. And people in SunAmerica took notice. So they know was extremely motivated. I got a little more playing time, the second year.

Jeremy Weisz 44:07

I mean, when I looked at it, by the way, Randy mean, you’ve had Billy Idol, the Bo, Sugar Ray, this, you know, the goat like so many. I think over 30,000 people ended up attending this, right?

Randall Kaplan 44:20

Yeah, I think it’s in its 25th year now coming. It’s amazing. I ran it for 10. It’s probably it’s the thing I’m most proud of in my career, and we can talk about it in a few but I want to go back to the ACA my story. So there’s two ways to leave a job. You can quit and give your your two weeks. Notice I don’t think that’s that’s the right way to do it. A good leader finds his replacement or her replacement before they leave. And he had given me the opportunity of a lifetime and I didn’t want to go behind his back but you talk about fear. I knew I wanted to leave and I was terrified that he was going to say Get out of the, you know, leave, because I was being ungrateful. On the other hand, I was extremely good at my job. You’re sort of public and people are looking you within that job, what is, um, Eli Broad, like, tell me what he’s like, I hear you so tough. And I loved him and never set a negative word. And the loyalty that I showed to him was huge. And I went to him, and I told him what I want to do. And he said, You’re making a big mistake. But you can stay as long as you want. And use your office, we’re going to continue to pay you, you’re going to still work your tail off. And that’s what I did. At that point, I looked around, I had freedom to look at two different opportunities. I looked at a whole bunch of things, buying laundry mats, writing novels, which is on my bucket list, and found this opportunity through my van girlfriend who became my wife. Now she’s my ex wife, but her brother in law was best friends with one of with a graduate student at MIT, they had event a technology that was going to improve the efficiency of to deliver content to the World Wide Web. It was very complicated, sophisticated technology. I helped them write a business plan and essentially had a bunch of job opportunities. I took that one I commuted to Boston, four of us began a company, I left for no salary, no funding, no CEO, people again, felt I was absolutely out of my mind. What are you doing, you have a great career going, that’s a high profile job. And I wanted to be a entrepreneur like I want it to be since I sold t shirts in college, I always knew I was gonna go back to that. And we ended up raising some money. One thing happened, by the way, shortly after I left SunAmerica, Eli sold the company for $18 billion to AIG, full vesting event for everybody. $2 million vanish, just like that. So I thought, geez, we better make this thing work. And that’s how it began. They, they wanted me to be part of the team originally, because I had a managing director title. And we use that on the business plan that we use for the MIT 50k Business School competition. That was our first foray into the real world. Here’s what we’re doing. And that’s how it all began.

Jeremy Weisz 44:22

Amazing. So I have the title of your book, which I’m going to keep pitching to, for no apparent reason I get nothing out of it. Because out of my mind, you know, the 65, great book, The 65 lessons or meetings that lead to my career success or something like that. Because people tell

Randall Kaplan 48:07

me, I think I’m a, you know, maybe we can talk about you be my public listen.

Jeremy Weisz 48:15

You know, first of all, Randall thank you. I want to point everyone towards your podcast. I have one last question. Before we end, I want to point everyone to your podcast to check out more In Search of Excellence and check out all the episodes check out Bliss. The book we all go to beaches, including me and, and I agree, there’s nothing I’m like, I don’t know, we should just head to that one. So probably a resource to to know what we’re doing here. And people can check, you know, check out also, you know, JUMP Investors, where else should we point people towards online to check out just a term to check out some things about you know, yeah, what you’re working on? Yeah.

Randall Kaplan 48:54

Well, the podcast is really the big one, it’s going to launch May 19. And the podcast, In Search of Excellence is about our desire to be the best we can to achieve our potential to overcome obstacles, which we all face along the way. And to, to succeed, how to be the best we can be. And one of the constant themes in that podcast is believing in yourself. I believe in you are four of the most powerful words in the English language. And we’re going to reinforce that because so many people out there, they have ideas, they want to leave, they’re afraid to do things. And you have to give them the confidence and the ability to believe in themselves. Help them just give them a little push and the speakers that we have on there. You mentioned Sam Zell Sharon Stone, Kliff Kingsbury, the head coach of the Arizona Cardinals football team. We have a lot of other very good people. Great People coming on soon, so you’ll have to check in. But I’m very focused on that. I’m very focused on the promotion of our book. Sandee is my 70 hour a week job. The others are maybe 10 hours a week. I work very, very long hours. We’re raising money now for the first time. So that’s exciting. It’s, it’s going well, and then I have a couple of other things that I’m doing. Also, I have a company called Thrive, frat Thrive Properties, a real estate company. We’re buying apartment buildings. First, we are focusing a Long Beach. We bought four buildings there. It’s going very well. We fixed them up. And they’re beautiful buildings. And then we just bought six townhouses in Nashville. We’re super excited about that market. We love Nashville. Amazing things are happening there. So we’re, we’re going to grow that business this year. I started something fun. I like empowering people. A lot. We have a vacation home up in Cortland, Idaho. I met my gardener there six years ago, was my gardener. He’s come to me for financial advice, building business advice. And I loaned him money for a trucking business. He paid me back. And then we started last year, a car restoration business building old Ford Broncos. So I knew nothing. I know nothing about cars. I knew nothing about cars. I know a little something about old cars and rebuilding old cars. Now the Ford Bronco business is a huge business, these beautiful old Ford Broncos go for two to $300,000 each, and there’s no shortage of buyers for them. So we knew. Yeah, who knew? You see them you’re driving around town. I think they’re beautiful. And they’re beautiful. And they’re expensive. And there’s a good opportunity there. And it’s, it’s fun. So there’s really nothing online there. It’s called River City Restoration. I’ll be putting the first Ford Bronco, which should be finished at the end of May up online. Hopefully, I it’s quite beautiful, I think will sell very soon after it goes for sale.

Jeremy Weisz 52:18

This is not my last question, Randy. But

Randall Kaplan 52:21

you can keep going by it some Feel free to keep going. I love your question. Great.

Jeremy Weisz 52:25

This is not my last question. But um, for people listening it you know a lot of people and you you’re gonna have a lot of interesting guests who out there maybe that you don’t know, that you do want to have on the podcast. If someone’s listening and they happen to know them. They can happen. introduce them to you who you who is on your list of gas that you don’t know.

Randall Kaplan 52:47

Sure. It’s a long list. Elon Musk, Bill Gates. There’s numerous Nobel laureates I love to have on my show, where I want leaders from different fields to talk about what they’re doing. It’s very important, by the way for me to have 50% of my guess as women. I work in a industry where women are traditionally underrepresented. And I’ve been working with many, many people with causes to try to improve that we do our share by trying to hire women in our field at our portfolio companies. We have a summer intern program where I tell the lead interns who do the hiring, I want 5050 and we can’t get 5050 we’ve been trying it for years. Last year we had around 40%. This year, we’re right around the same number, maybe a little less. I’m an advisor to a company called Beyond Board run by by awesome friend, Sarah Zapp shout out to shout out to Sarah. Its mission is to provide opportunities for women to be on private and public company boards. And these things are very important to me. And they’re things that that I’m focused on. So I want I want more women on my show. I want diversity on my show, particularly with all the the racial issues that are happening now that are that are first in form for at the forefront. Things that should have been addressed a long, long, long time ago, that thankfully they are being it today. And it’s meant to be educational, thought provoking. Have a broad group of people but those those are, those are some of the few because there’s actually a very long it There was over 300 people off that just listed on the episode show notes. So

Jeremy Weisz 55:04

yeah, if you allow we’ll put it in if you know one of these people recommend them to Randy introduced Randy to them. My last question, Randy is, you know, what’s been an inspiration for you? One of the things that I found in my research is your grandmother was a big inspiration for you and to talk about that inspiration and then what you did, because in honor of your grandmother,

Randall Kaplan 55:31

yeah, so my grandmother who’s 102 and a half years old, and she still lives alone in Michigan, she’s is really my inspiration. She’s had a very hard life. She was raised in foster care. Her mother left her when, shortly after birth, her dad dropped her and her sister off when she was six years old streets of downtown Los Angeles with a jacket on their back and nothing else, no money. And she was raised in foster care, foster care homes. often don’t don’t treat people well. And, you know, she had a very tough life. tough life. A lot of these foster families, treat you like you’re a housekeeper. You’re the hired help you have to eat separately. They sleep in the closet. And that still goes on today. By the way, one of the interns we hired this summer was raised in foster care. At the exact same background. I got a full ride to USC. I’m super pumped to have them this summer. But you know, my grandmother never graduated high school. She married my grandfather when she was 16 years old. She lied about her age. And we did a for her. I’m 85th birthday. Ah, I created a video biography for her. I’m of her life. I want to make sure we had it down. We hired a professional film crew. They flew to Detroit, she showed on the first house and all kinds of things and it was really cool. And in the interview, she said that one of her greatest regrets was not going to college, even though she had straight A’s in high school. And by the way, she later gave me her report cards from 1936, which I have in shock. She still had a Yeah, I mean a. So for her dumb 87th birthday, I created a foster care scholarship. I made her name at the University of Michigan and presented that to her the student got it. Her name is Cherish Thomas shout out to her. And she was in her car. In high school. We gave her a full ride. She’s she graduated, she’s a social worker, a public speaker, a motivational speaker, a mother, a homeowner and a wife. She’s a member of our family has been been one of the best things that I’ve done. I if I look back, and I think about all of the positive things I’ve done, these are the two I’m the most proud of what I did for my grandmother and cherish. And then what I’ve done with The Justice Ball, and then I have another function called the imagine ball which focuses on helping the homeless in Los Angeles, which is the homeless capital of the United States. But what I’ve done for my grandmother, cherish has been just one of the highlights of my life.

Jeremy Weisz 58:35

Randy, I want to be the first one to thank you. Thank you everyone, check out In Search of Excellence podcast, check out Jump Investors, check out the book Bliss and much more. Randy, thank you so much.

Randall Kaplan 58:48

Appreciate it. Thanks for having me.