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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Episodes
7 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: ...
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...
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...
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...
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...
Jim Armstrong: How VCs Really Think ($750M in returns)
Jim Armstrong, 4x Forbes Midas List venture capitalist with $750M in returns, reveals: The first meeting can NEVER end in a yes—and the strategies that actually close deals in 2026. Jim led PayPal's first institutional round, negotiated the Elo...
Eytan Elbaz: You Don't Have to Be The #1 Founder For A Huge Exit
Eytan Elbaz, legendary LA founder and 5x entrepreneur, reveals: You don't have to be the CEO or hold the most equity to achieve generational wealth.Eytan created Google AdSense—the advertising platform now generating $40-50 billion annua...