Exclusive: VC And Business Founder Randall Kaplan Talks Life, Relationships And Innovation

“When someone tells me something can’t be done, I think there’s always a will and a way.”

That’s according to Randall Kaplan, an American entrepreneur and venture capitalist working to fuel the next wave of disruptive innovation and inspire tomorrow’s leaders.

Known as “Mr. Beach,” Kaplan is known for early successes at SunAmerica, a financial services company acquired by American International Group Inc AIG, and Akamai Technologies Inc AKAM.

Today, Kaplan spends his time managing JUMP Investors, a venture capital firm and family office, as well as Sandee, a travel company, Thrive Properties and CollarCard, among other ventures.

In a conversation with Benzinga, Kaplan spoke about his origins and aspirations, as well as tips for building relationships and succeeding in today’s digitally disrupted business world.

Early Start, Standing Out: Born and raised in Detroit, Kaplan was academically driven during his youth.

After studying at the Detroit Country Day School, Kaplan then attended and graduated from the University of Michigan and Northwestern Pritzker School of Law.

During his studies, Kaplan sold clothes at local dormitories for spending money. In doing so, he said he developed an affinity for the concept of arbitrage and the challenge of selling.

After finishing school, Kaplan relocated to Los Angeles where he encountered mixed success in law. He worked at three law firms prior to looking for opportunities in business.

“I started looking for my way out of the law, at that point in time,” Kaplan said. “It wasn’t going well.”

In an initiative his peers deemed bound to fail, Kaplan wrote letters soliciting informational job interviews with the CEOs of Los Angeles-based companies.

“I came up with a list of 300 people and turned my two-bedroom apartment into a letter-writing factory,” he said. “Each letter was covered in cellophane and spiral-bound. I wanted it to be the best letter they ever received.”

As a result, Kaplan procured nearly 80 meetings with the likes of Michael Eisner at Walt Disney Co DIS and Stephen Bollenbach at Marriott International Inc MAR.

One of his pitches was sent to Eli Broad, founder at SunAmerica, a company that had one of the most successful performing stocks on the New York Stock Exchange.

“Their stock had risen 6,000% in five years, before the tech craze,” Kaplan said. “My research showed that [Broad] had a job called assistant to the chairman. I studied for that job interview like it was a final exam.”

One differentiator that helped Kaplan secure a position: he correctly identified individuals who previously held the same position and where they'd landed. 

“Long story short, I was hired as the managing director/assistant to the chairman,” he said. “People will hire great candidates, regardless of the economic climate. If you show promise — drive and an outgoing personality — people will hire you.”

Kaplan On Opportunity, Timeliness: “Do it now and don’t wait,” Kaplan said. 

Kaplan’s go-to mantra is one of the reasons he procured a job at SunAmerica, he said.

“At the end of my interview, [Broad] said ‘I want you to take a finance accounting class at UCLA. If you get some choices, give me a call, and I’ll help you pick one.’”

Kaplan left the office, drove to UCLA, found an extension catalog — and got a parking ticket in the process. 

"[I] came back to my apartment, typed a thank you note and dropped it off all within an hour.”

From there, Kaplan became a junior star on a senior team; he said he worked hard and had great fun.

Kaplan And Akamai Technologies: After two years, Kaplan began looking for new opportunities. He discovered a graduate student at the Massachusetts Institute of Technology.

“He and his professor invented some algorithms that were going to vastly improve the distribution of content on the internet and materially decrease the cost of serving data.”

In the late 1990s, the existing solutions for delivering content over the internet were easily overwhelmed during traffic surges.

“When Princess Diana died, for example, every news site went down,” Kaplan said.

“We had a complete solution to that. Also, if a farmer in Iowa cut a line, a quarter of the internet traffic could possibly go out. We had a 100% guaranteed uptime.”

Kaplan joined the MIT professor and two students, helping write the business plan that resulted in the company’s first licensing agreement and successful fundraiser.

Today, the publicly traded firm, Akamai Technologies, now employs nearly 10,000 workers, serves more than 25% of the world’s web traffic and earns more than $3 billion in revenue. The company works with organizations such as Microsoft Corporation MSFT and Netflix Inc NFLX, among others.

The decision to join Akamai meant that Kaplan lost out on nearly $2 million worth of in-the-money SunAmerica options after the company was sold to AIG for $18 billion, he told Benzinga. 

“I missed my goal to make $1 million by the time I was 30 by three months.”

Kaplan On Making An Impact: After a successful career at Akamai, Kaplan started JUMP Investors, an entrepreneur-focused venture capital firm and family office that invests in early to late-stage companies like Chime, real estate, public and private equity and hedge funds.

The reason for the JUMP’s diversification: the technology meltdown and high failure rate of venture investments.

“The model in the venture capital business is you invest in 10 companies. On average, seven or eight may go to zero, and one or two may break-even or make a little money, while one you expect to get a 10x-plus return.”

Alongside that venture, Kaplan has served as an adviser to more than 50 different companies, a board member to numerous companies and schools, as well as an active public speaker and mentor to students.

Kaplan's Philanthropic Efforts: Another one of Kaplan’s mantras is to never take no for an answer.

That’s the attitude that helped him, at the age of 27, start The Justice Ball, one of the largest charity events in the country.

It's hosted talents like Billy Idol, The B-52s, Nelly and The Go-Go’s, among others, at venues like the House of Blues, to raise over $7 million for Bet Tzedek Legal Services, a Los Angeles-based nonprofit that provides free legal services to poor, sick, elderly and homeless residents.

“[House of Blues CEO] Greg Trojan said it was never going to [succeed],” Kaplan said in reference to the event’s prospects at the outset. “We sold out every year. We later outgrew the House of Blues, and our biggest event was at the Museum of Flying, the night before they closed.”

From there, Kaplan founded The Imagine Ball, an event attended by the likes of Dave Chappelle, Chris Rock, Kendall Jenner, which raised over $1 million for Imagine LA, a nonprofit dedicated to ending family homelessness.

“I’ve also endowed a scholarship at the University of Michigan for a student in need,” he said.

The initiative — the Julia Eder Dean’s Scholarship — is in honor of Kaplan’s 102-year-old grandmother, a foster child whose biggest regret was not being able to go to college.

Kaplan's Current Projects: Kaplan told Benzinga there is no single destination or path to success. That’s one of the reasons why he looks to expose professionals in his family of companies to transformative experiences.

“I’ll bring in leaders, from various industries, and communities, and have them share their stories, and inspire interns,” Kaplan said in a discussion on hosting an event with the late Tony Hsieh, a co-founder at Amazon.com Inc-owned AMZN Zappos.com.

Kaplan’s personal interest in entrepreneurship is not yet over.

Kaplan is the founder and CEO of Sandee, a travel company focused on the promotion of beach tourism.

“Our research shows that 99.9% of people, in the world, love beaches. Yet, there is no definitive beach resource in the world.”

Sandee was the result of a make-it-or-break-it trip to Greece, during which Kaplan and his wife had difficulty finding a beautiful, hidden beach.

“We got out there, and we saw the most beautiful beach we’ve ever seen. We thought: 'there’s got to be a better way,’ and there wasn’t.'”

After doing some research, Kaplan said he found that beach tourism is a $1-trillion industry.

“75% of people around the world, taking a vacation, in the next year, will plan at least one beach vacation.”

The most important determinant for those beach-goers is beach quality, he said. 

Kaplan set out to create a list of all the beaches in the world and the categories beach-goers typically are interested in.

“We have 94 categories,” Kaplan said in reference to the brand’s trademark, "choose your beach."

“We have seven different sand types, and seven different sand colors,” for example.

After nearly 90,000 hours of work, Sandee did a soft launch and is in the middle of a fundraising campaign.

The company has two business models. The first is an advertising-driven model, or a Yelp for beaches. The second is based on licensing data to government agencies.

“We charge them a yearly license fee. The fee will include a white-labeled app that has all the beaches in their countries, regions, or states,” he said. The app will provide written and visual content that assists beach-goers in their pursuit of the perfect beach experience.

Another major focus for Kaplan is “In Search Of Excellence,” a podcast featuring top business leaders and actionable insights for success.

Notable participants include Strauss Zelnick of Take-Two Interactive Software Inc TTWO, former White House Communications Director Anthony Scaramucci, Ben Sherwood of Mojo, NHL All-Stars Jimmy Carson and Bobby Ryan and Dale Carnegie CEO Joe Hart.

“The podcast will launch sometime in April,” he added. “It’s really a quest to live up to our potential, and be the very best that we can be to inspire and motivate people.”

Kaplan is also an avid photographer; in developing content for Sandee, Kaplan procured a database of beautiful drone photography which he will now share in a hardcover beach photography book called "Bliss."