In this talk, Randall Kaplan recounts his transition from a high‑earning, senior‑track role at Sun America to becoming a technology entrepreneur. He describes his early years learning on a senior team, the internal conflict about leaving, and his decision to be honest with his boss, Eli, who offered support. Kaplan then details two pivotal opportunities: working with former investment banker Gary Winnick on a groundbreaking undersea fiber‑optic cable venture, and joining two MIT researchers developing novel web‑information algorithms. With $400,000 in personal savings, he invested $100,000 as a founder, negotiated to stay on the West Coast, and helped secure venture capital and a CEO for the startup. He narrates the personal sacrifices of commuting between Los Angeles and Boston, the loss of $2 million in Sun America stock after its sale to AIG, and the moment Apple’s Eddy Cue invested $25 million at a $250 million valuation. Kaplan reflects on the trade‑offs of risk versus security, the importance of self‑belief, and concludes with direct advice to aspiring entrepreneurs: trust yourself, ignore naysayers, and act now.
Chapters
But I put my head down and I learned, and after 2 years, I thought, you know, I want to be an entrepreneur. I want this same job for somebody else, or I want to leave. And I thought about, do I go to him and be straightforward, or do I go behind his back and look for a job? And honesty is always the best policy. 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. At any rate, I spent my first year on a very senior team as the junior person doing research and learning how to model. And I was so happy to be this junior person with all these senior brilliant people just A sponge. I was working 80 to 100 hours a week. I was making good money. I got stock options for the first time. And that job had historically been one year and out. You get promoted from that job into one of 6 corporate-level VP jobs. Our vice chairman and COO, Jay Winthrop, who's now the CEO at Oaktree, which is the largest private equity firm in Los Angeles— I think they manage around $120 billion. He was a 37-year-old COO and vice chairman when I got there. Fortunately or unfortunately, Sun America stock had appreciated 6,000% the previous 5 years before I got there, so no one's going anywhere. You had all these junior talented managers who are worth $10 million or more, and they're getting more options and more options. I knew I was there to put my head down. After my first year, I told Eli I needed more to do, and he said, be patient. You're my first round a draft pick. And I'm not a patient guy, but I put my head down and I learned. And after 2 years, I thought, I want to be an entrepreneur. I want this same job for somebody else, or I want to leave. And I thought about, do I go to him and be straightforward, or do I go behind his back and look for a job? And honesty is always the best policy. I went to him. I was afraid I was going to get fired. I was afraid he's going to say, you're ungrateful. I took a chance on you. But he was gracious, and he said, I appreciate you coming to me. And he said, you're making a mistake. But if you're going to leave, let me know if I can help you get meetings, even though I know you probably won't need it. And he allowed me to stay that third year. I still worked my tail off. Eventually, I looked into doing a bunch of things. The 2 things that were most interesting to me is I had found an opportunity to work with someone named Gary Winnick, who had been a very, very successful investment banker at a firm called Drexel Burnham, which was run by Mike Milken, probably the most successful investment bank of all time. Mike Milken is the most important financier probably in the last 200 years. Gary had retired, had a private equity firm. I had heard he was doing some interesting things, and he did something novel. He was going to raise $450 million in a bond, in debt, and he was going to lay fiber optic cable along the ocean floor to carry traffic, internet data, video traffic. No one had done that before. Then they raised $650 million instead of $450 million. I had an opportunity to be assistant to the chairman there. And I had also met these 2 guys from MIT. My girlfriend at the time, whose brother— my girlfriend's brother's best friend was getting his PhD there. He was working for a professor, and they had invented some algorithms. And I didn't know what those were, that was going to change the way that information was sent on the web. And I thought, this is great. I want to go in technology. I want to learn something. This could be fun. And originally, I thought I was just going to help write a business plan, and I would try to get a board seat, and I want to put a little bit of money. I had saved at that point $400,000 through savings and options from Sun America, and my annual nut was $40,000 per year. So I thought, I've got 10 years to make something of myself. And that was the bet. I wanted to finally bet on myself. The problem with this opportunity, it was in Boston. And we didn't have funding, and I was leaving a prestigious job, and it was hard to jump off. Some of you are going to get great jobs. You're going to have golden handcuffs working for Apple, Cisco, Google. They're going to throw a lot of money at you. You're going to get married, buy a house, whatever, and it's hard to leave and take a risk. Well, I wanted to bet on myself, and ultimately, I chose this opportunity to work in Boston, to commute every week. Leave on Sunday, get in at 12:30, get to my hotel at 1:15 if things went on time, work till midnight every night, work 12-15 hour days while I was there, and then to fly home on Thursday night to ballroom dancing lessons. Didn't know how to dance, still don't know how to dance. And I was home on Friday, and I'd have to leave again on Sunday. And I did this with all no salary, no CEO did not know who was going to be leading the team. And did this for a while. We finally got funding. And I did something also interesting that I have never seen someone else do. We, as founders, got founder shares. And not being a wealthy, successful person, in addition to what I got as a founder, I invested $100,000 of the $400,000 that I've saved. I was an investor. That was my first investment in a tech company. I thought, I really believe in what we're doing. I believe in what I am going to be able to contribute, and especially what my partners were going to be able to contribute. They were absolutely brilliant people, and what we were doing was very, very novel. They didn't have any experience in business, and I had a little bit working for Eli, but I had never run anything, and it was really We really needed to get VC funding and hire a CEO who was very, very good. The one condition that I had in taking this job, which I had turned down many times, was that I wouldn't have to move. I liked LA, my fiancée was from there, I wanted to make that my home. I grew up in Detroit, I didn't like the climate, and I knew no one in Boston. So as founders, we all have the same deal. My difference was I wouldn't have to move. And sure enough, we got some VC funding. We hired a CEO 6 months later who I'd never met. We had lunch his first day. He said, I want you to move. I said, I'm not moving. And he said, if you don't want to move, you can be the head of West Coast sales. I said, I'm not going to do that either. I helped hire the sales guy. And I faced a choice. By the way, something else happened. 6 weeks after I left Sun America, Eli sold the company. to AIG. This was a real company. We did $18 billion in revenue. We had an $18 billion market cap, and we did $1 billion in net income, GAAP net income that year. And so that was a full vesting event for everyone. So I lost over $2 million over the course of 6 weeks, which was depressing. Paying for our own wedding, and that was a huge thing. So I meet with the CEO. He says, you gotta move. I said, I'm not sure I'm going to. I called my old boss at Sun America. What would you do? He said, how much of this thing do you own? I told him. He said, what's it worth? The company then was worth, I think, $250 million. And when I started the company, I thought, what's the trade-off where this is going to be worth it? I thought, I'm going to learn something, and I want to make money. where's the fulcrum point there, and what I would need to make? And we really thought about, if the company's worth $200 million, I would make a premium over what I would've made at Sun America, and that was the goal. But at this point, a few months after, 3 and a half months after we started, 4 and a half months, Steve Jobs found out what we were doing. He sent Eddy Cue to Boston. And tried to buy the company, said no, and they invested $25 million at a $250 million valuation, and that's right around the time I was leaving, and Jay Winthrop said, why are we having this conversation? So I left the company, and that gave me a lot of opportunities to do a whole bunch of other things. 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.
