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Randall Kaplan is the Founder and CEO of JUMP Investors, a venture capital firm. Since its formation in 1999, JUMP has invested in more than 60 early-to-late-stage technology companies, including Google, Seagate, Lyft, and Chime. They also invest in real estate and private equity.

Randall is also a Co-founder of Akamai Technologies. Akamai Technologies is a content delivery and security software company. They serve nearly 30% of the world’s web traffic, are a member of the S&P 500, employ almost 8,000 people with 64 offices in 28 countries, and have $3.2 billion in 2020 revenues.

Randall has several other ventures like Sandee, Thrive Properties, CollarCard, and hosts the podcast In Search of Excellence. He is also an accomplished drone photographer. His coffee table book, Bliss: Beaches, features his beach photos from around the world and will be released in June 2021. When he’s not working, Randall loves to wakeboard, toss the football, play the drums, fly his drones, and most importantly, spend time with family.

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Here’s a glimpse of what you’ll learn:

  • How Randall Kaplan hustled at the age of 27 and wrote 300 cold letters to meet with CEOs of big companies
  • Top lessons Randall learned from his meeting with 65 CEOs
  • What was Randall’s mindset going into those powerful meetings?
  • How Randall’s love for beaches led to creating his book, Bliss: Beaches
  • Randall shares the story of how a company he invested in — but left for dead — turned into a 10x deal
  • What Randall looks for when investing in a company
  • How Randall started Akamai Technologies and the Justice Ball
  • Randall’s ongoing projects and missions
  • Why Randall’s 102-year-old grandmother is his inspiration — and what he’s done in her honor

In this episode…

Ever wonder what makes a multimillion-dollar founder successful? Here’s a clue: the DNA of relentless persistence. That’s how Randall Kaplan, JUMP Investors’ Founder and Co-founder of Akamai Technologies, describes it. At the start of his entrepreneurial journey, Randall researched deeply into Fortune 500 CEOs and wanted to meet with them. He had to send 300 cold letters — and with persistent follow-ups, he landed 65 meetings, 15 callbacks, and a dream job at SunAmerica Inc.

Beyond the job, Randall came out of those meetings with lessons and insights that have shaped his rise to becoming a multimillion-dollar founder. Do you want to hear Randall tell these stories about the lessons he learned? Have you been looking for a way to connect with him and discover how to succeed as an entrepreneur?

Listen to this episode of the Inspired Insider Podcast with Dr. Jeremy Weisz featuring Randall Kaplan, Founder and CEO of JUMP Investors. They discuss how Randall quit a struggling law career to become a thriving serial entrepreneur and investor. He shares his hustle story, big unexpected wins, the mindset that helped him prosper, his love for drone photography, and lots more!

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Episode Transcript

Jeremy Weisz 0:19

Dr. Jeremy Weisz here, Founder of where I talk with inspirational entrepreneurs and leaders and I’m gonna introduce today’s guest Randall Kaplan in a second but Randall I always like to mention past guests of people to check out and some of the past guests that are must listen to the Founder of Paylocity Steve Sarowitz he started in a 600 square foot office grew to a billion dollar company that went public. The Founder of non Atari Nolan Bushnell was Steve Jobs his mentor he talked about in the interview, Randall you’ll get a kick out of this that Steve Jobs offer him 33% on Apple for $50,000 and he talked about why he said no to that and I know we’re going to talk about JUMP Investors and we’ll see if you’ve turned down any of those those type of deals in your you know, journey but um, anywhere from the stories of Founders RxBar quest nutrition many more you can check them out on Before I introduce Randall Kaplan. This episode is brought to you by Rise25 at Rise25 we help businesses give to and connect to their dream 100 relationships. We do that by helping you run your podcasts and we are easy button to do that. And you know, Randy, for me, the number one thing in my life is relationships. I’m always looking at ways to give to relationships. You’re the person who introduced us, Larry Benet is, is like the biggest giver, I know of relationships. And I love having people and companies on my podcast that I respect and admire and that’s why I asked you to come on. So if anyone has thought about launching and running a podcast, we are an easy button to go to and today’s guests again, like I said, big shout out to Larry Benet. He is a master he speaks to lots of organizations in the art of connecting check them out. But Randall Kaplan is a serial entrepreneur, venture capitalist, and he’s a Co-founder of Akamai Technologies. If you’ve never heard of it, Akamai. Akamai I got it. If you haven’t heard of like I hadn’t, but it basically powers 30% of the world’s web traffic practically. And it’s a member of s&p 500 employs nearly 8000 people with over 64 offices and add $3.2 billion in 2020 revenues. It gives you any idea of the size and capacity of it. And he’s also Founder and CEO of JUMP Investors. It’s a venture capital firm. Since its formation in 1999. They’ve invested in more than 60, early late stage technology companies some of you probably have heard of like Google, Lyft, Seagate and many more they also invest in real estate and other private equity in other genres. And there’s several other ventures you know, I don’t even know how you do it all. Randy, like Sandee Thrive Properties, CollarCard that makes patented men’s collar stays, he has a podcast, which you should check out. It’s called In Search of Excellence. He’s had people like Sam Zell, Sharon Stone, and many, many more. He has a book called Bliss. Randy, thanks for joining me.

Randall Kaplan 3:25

Thanks for having me. I appreciate being here. And Nolan is awesome. By the way, I met him two years ago at a function and we chatted for a long time. His son also has a really cool business as well. So the family definitely has a DNA.

Jeremy Weisz 3:40

You’re gonna have him on the podcast, or

Randall Kaplan 3:42

you’re gonna ask them yet, but he I should I appreciate the reminder. Yeah,

Jeremy Weisz 3:46

totally, totally, we’ll have to send them a quick message after this and get them on. Um, there’s so much you know, I did research on you, you, you have a really amazing career and is not just for profit, but non for profit, which I want to talk about too. But I want to kind of start at the beginning. And we were talking a little bit before we hit record is go back to your 27 year old self. And you’re presented with this opportunity and talk about how you got that opportunity and some of the lessons.