High Five Energy Founders
Host Jeffrey Chernick, a serial entrepreneur and investor, sits down with the world's top founders to unpack how they build, scale, and think. Featuring legendary entrepreneurs behind $200B+ in exits and IPOs—from Google AdSense to Prodege, Kiva to Telesign. Each episode reveals the pivots, failures, and mindset shifts behind iconic companies. Discover High Five Energy: the magnetic flow state where doors open, the right people show up, and opportunities align. Tools and inspiration for entrepreneurs at every stage. New episodes weekly.
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Podcasting since 2026 • 7 episodes
High Five Energy Founders
Latest Episodes
The Drummer of Linkin Park Led Him to a $1B Company | Scott Dudelson, Swag Bucks
Scott Dudelson, co-founder of Prodege and Swag Bucks, reveals how a chance meeting with the drummer of Linkin Park at the Grammys led to a company he bootstrapped from his attic to a $1 billion exit — with zero VC money.THE REAL STORY: ...
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Season 1
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Episode 7
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40:12
He Timed 10 Exits for $500M. Here's the One Thing He'd Tell Every Founder.
Fred Krueger is one of the most prominent Bitcoin maximalists on the internet — and a Stanford PhD with 10 successful exits totaling over $500M. In this episode he says something that will surprise you — AI is bigger than Bitcoin, bigger than t...
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Season 1
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Episode 6
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55:30
Jessica Jackley: $3 Billion in Loans that Changed The World (Kiva Co-Founder)
Jessica Jackley, Co-Founder of Kiva, reveals: How a $3,100 pilot with 7 friends in Uganda became $3 billion in micro loans — and why she never set out to be an entrepreneur.THE REAL STORY: Jessica wasn't chasing a startup. She st...
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Season 1
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Episode 5
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44:19
Raised $1.5B by Listening, Not Pitching (16x Founder)
Eric Pulier, 16x founder who has raised over $1.5 billion, reveals: He didn't pitch his way to $1.5B — he listened. The most successful companies don't come from brilliant innovation. They come from conversations with people who have real probl...
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Season 1
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Episode 4
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47:26
Darren Berkovitz: How to Build a $230M Company Nobody's Heard Of
Darren Berkovitz, co-founder of TeleSign ($230M exit to BICS), reveals: The real money is in solving boring problems nobody wants to talk about. From living at home with zero external validation to protecting every major internet platform on th...
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Season 1
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Episode 3
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1:03:27