Randall Kaplan co-founded Akamai Technologies and went on to become an early investor in companies including Google and Lyft, building a career defined by spotting opportunity before the rest of the market caught on. He joined Sean Kelly on the Digital Social Hour to talk about the habits and choices behind that track record.
Their conversation moves from a simple $20 FedEx letter that helped Kaplan stand out early in his career into a broader debate about luck versus preparation, then into his intern program, his advocacy for AEDs, and his concern for homelessness in Los Angeles.
About Randall Kaplan
Randall Kaplan co-founded Akamai Technologies, one of the companies that helped build the infrastructure of the modern internet, before moving into venture capital as a founder of JUMP Investors. He was also an early investor in Google and Lyft, positioning him among a small group who backed those companies before they became household names.
Kaplan hosts the podcast In Search of Excellence and is a vocal advocate for wider access to AEDs, automated external defibrillators, a cause tied closely to his public persona. He has also built an intern program meant to give young professionals real-world experience and mentorship.
What Randall Kaplan and Sean Kelly Talked About
- Why a simple $20 FedEx thank-you letter can help a candidate stand out in any job search
- How he turned early career setbacks into momentum for building a billion-dollar company
- His perspective on the long-running debate between luck and preparation in a career
- Why first impressions form faster than most people realize, and how to manage them
- How his intern program is designed to give young professionals a real head start
- His perspective on tackling Los Angeles's homelessness crisis and why he stays involved
- Why he still champions the value of a college education in a changing job market
- Insights from his own podcast and book on preparation, mindset, and success
Why This Conversation Matters
Randall Kaplan's path from Akamai to early-stage investing gives him a rare view into what separates lasting success from a lucky break. Combined with his advocacy work, this conversation offers as much for anyone building a career as it does for aspiring founders and investors.
▶ Watch the full episode on YouTube
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About Sean Kelly & the Digital Social Hour
Sean Kelly is an entrepreneur and the host of the Digital Social Hour, one of the fastest-growing interview podcasts in the world, where he sits down with entrepreneurs, athletes, creators, and cultural voices for candid, long-form conversations. The show draws over 100 million views a month across platforms. Explore more guest features on SeanKelly.io.
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