In this talk, Randall Kaplan, co‑founder of Akamai and founding partner of Jump Investors, shares his multifaceted entrepreneurial life, describing his day‑to‑day roles across venture capital, real estate, philanthropy, and a new venture called Choose Your Beach. The story begins with a personal anecdote about a difficult trip to a black‑sand beach in Greece, which sparked the idea to create a comprehensive, searchable beach database. Kaplan explains the massive scope of the project—cataloguing 150,000 beaches across 52 countries, defining 94 data categories, and amassing 41,000 research hours over six years. He details the operational challenges of gathering public‑domain cover photos (8,755 to date) and the intensive summer internship program that powers the data collection, emphasizing the tedious, low‑skill nature of the work and the need for disciplined execution. Kaplan then outlines three core tenets he instills in his interns and team: hard work (first in, last out, punctuality), integrity (zero‑tolerance for ethical breaches), and attitude (positive, complaint‑free mindset). Throughout, he stresses leading by example, personally handling tasks like setting cover photos and COVID‑related updates. The talk concludes with practical advice for aspiring entrepreneurs: believe in yourself, ignore naysayers, and act immediately.
Chapters
And I have a day job too, right? I'm running Jump, I'm running Sandy, I have other companies, my real estate company, philanthropy, which I'm very involved in, and I'm setting the COVID photos every night late at night. And when they hear that, they think, wow, I wasn't expecting that, right? But, but as a leader, as the CEO of the firm, you gotta lead by example, and you have to do the same amount of work and motivate your team.
Hi, I'm Randy Kaplan.
I'm an entrepreneur and a venture capitalist. I am the co-founder of Akamai Technologies, and over the last 20 years, I have invested in more than 70 early and late-stage companies. To become an entrepreneur, please enroll at Draper University. I've invested in real estate over this time. I started a new company a year ago with a partner, and we are buying B- and C apartment buildings in Long Beach. We're fixing them up and creating value, re-renting them at higher rents. And then for the last 6 years, what I'm really excited about— who here loves the beach? Who here has had trouble finding their perfect beach? Who here has wasted a day or multiple days on vacation or locally going to a beach that they didn't know what was there and they were disappointed when they got there? Right. So I did too. And I was in Greece with my girlfriend. I'm remarried. I have 4 beautiful kids, by the way, 3 teenagers and a 2-and-a-half-year-old. I went on a trip with my girlfriend, now my wife, to Greece. We were staying in a nice hotel. We wanted a black sand beach. I asked the concierge. She whipped out a paper map, 32 parts, unfolded it, took out a Sharpie. I think there's one here. Don't know really what the road is. And we drove out there in a little Fiat convertible, got lost. We had no Wi-Fi, no cell service, didn't know if we should bring water. There was no food there. We drove through what looked like an old road with weeds taller than the car. I thought, this is like the movie Taken. I'm not really sure I wanna do this. I mean, I don't know the concierge. I don't know what she knows. And so my wife's a little younger, more adventurous. We're going through this thing. And we drove a mile through this thing. Rickety road opened up to this beautiful expanse of beach, black sand. We were the only ones there. We took phenomenal pictures. It was incredible. I thought, there's got to be a better way than this. This is crazy how hard this was. She should have known the beach. She should have had here the directions and here are some pictures. Well, I went back. We were in Greece. Did a Google search, .gr on Google, changed it to .us. Almost nothing. Local websites, nothing definitive. And I went back and I thought, God, did a lot more research. There's nothing out there. Try Googling how many beaches there are in the world. You will not find the answer. Try Googling how many beaches there are in California. You will not find the answer. Someone take a guess at how many beaches there are in Malibu.
20.
20? Another guess.
30.
Well, you know that the number is skewing high because I've implied that the number's higher. Take another guess. 47, right? I've talked to people in Malibu. Who tell me there's 10, and they're certain they know everything about every beach, right? They don't, I promise you. Malibu people are very knowledgeable about Malibu. They're certain they know everything. How many beaches within a 1-hour drive of downtown LA? There's 217.
Whoa.
Right? Most people don't know that. Think about all the local use cases about where you'd go. Our trademark is Choose Your Beach. We've cataloged 94 categories of information for every beach in the world, 150,000 52 countries, right? The data set does not exist. As an entrepreneur, you want to do things that are very difficult. I know that several people have tried to do this before. They weren't able to do it because it takes an enormous amount of resources. We have 41,000 hours of research into this project in 6 years. I have 36 interns this summer from 19 different schools. It's a teaching internship. I spend an hour to 90 minutes per day with them. We have guest speakers each week. Right now, the focus on the interns is getting cover photos, license-free cover photos that we can use. We never take anyone's IP, ever, ever, ever. These are all public domain photos. That's very hard to do too. Good luck in going trying to do this on Flickr in a systematic way. It's very hard to do. A lot of the interns Come from great schools. We tell them when they come, before they come, it's going to be tedious work. It is below your intelligence level, everyone's, right? You're going to be finding and looking at cover photos, uploading them to our portal. It goes into a queue, and then they complain sometimes. And by the way, I'll go into in a minute the 3 tenets at Jump that are important to be successful here. But we tell them the work is tedious. Welcome to being an entrepreneur. It's sweat equity. If it was so glamorous and so great, everyone would do it. If it were that easy, everyone would do it. It's not easy. No one else has done this. We have better beach data than Google has, than TripAdvisor, then Expedia. So I tell all the interns, you know, they look at me, yeah, yeah, yeah. So someone has to set the COVID photos, right? We have 8,755 cover photos right now. We're uploading more each day. We don't release a beach online until we have cover photos. I tell the interns, guess who sets every single cover photo on the site? We have to move it. We have to get the right fit within a screen. I set every single one. I tell— and I have a day job too, right? I'm running Jump, I'm running Sandy, I have other companies, my real estate company, philanthropy, which I'm very involved in, and I'm setting the COVID photos every night late at night. And when they hear that, they think, wow, I wasn't expecting that, right? But as a leader, as the CEO of the firm, you gotta lead by example, and you have to do the same amount of work and motivate your team. So we're getting ready to launch. I'm very excited about this company. We have a great summer intern program for you or your friends. Please feel free to contact me afterward if you or someone would like to learn more about either the remainder of this summer or next summer. But what I tell all the interns when they come in, I kind of read them the riot act in a strict way. I said, number one, Hard work. Hard work is gonna be the greatest single determinant of your success at work. When you're new at a job, first one in, last one out. Never leave before the boss, ever. Be on time. I tell my interns, 8 to 6, do not show up at 8:01. You live in LA, plan for traffic. We had an intern 2 years ago driving from Santa Barbara, and you know what he did before he began? He did a test run on Sunday to find out how long it would take him to get there. You know how many times he was late? Zero. We had a Navy SEAL intern drive up from San Diego last term, a decorated Navy SEAL. How many times he was late? Zero. Right? I got the first intern a job. He wanted to go into real estate business. Called my friend who was the CEO of a company. I told him what this young man had done. He said, I want that And the Navy SEAL, I'm in the process of doing the same thing for him right now. So we've had— okay, so hard work. 2, integrity. We do not tolerate mistakes of integrity at any level. It is a termination event immediately. And what people don't realize, an error of omission is equal to an error of commission. So we tell people, if you see someone Doing something bad and you don't tell me or one of the lead interns or someone who works at our firm, you're equally as guilty. Okay, and the last one is attitude. I ask every new intern when they come, how's your day? You know, my day's fine. Really fine? Fine's like a B minus. That's a 2.7. Things are good. Okay, that's a B. You've got a 3.0. Do you wanna be a 3.0? No. Right? My day is fantastic. Fake it till you make it. Right? At work, no one wants to hear about your problems. Oh, things are okay. I had a rough night. Right? Complaining is a cancer. We allow no complaining in our firm whatsoever. Right? And just imagine how great it is to walk in. How was your day? It's fantastic. It's amazing. It's great. Couldn't be better. Verging on superb. Right? People will want to work with you. You'll be a better leader. You'll get along better with others, and you'll be more successful wherever you go. I promise you.
Okay. Thank you. Thank you. Thank you.
The best advice I have for any wannabe entrepreneur is to believe in yourself. Don't listen to anybody else and to just go do it right now.
