Jeffrey Chernick

High Five Energy Founders

Business EN ↓ 8 episodes

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.  Follow @H5Efounders

Author

Jeffrey Chernick

Category

Business

Podcast website

www.buzzsprout.com

Latest episode

Jun 30, 2026

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Episodes

From Bankruptcy to a $5.2 Billion Space IPO | Eric Salwan of Firefly 30.06.2026

Eric Salwan, co-founder and former Chief Revenue Officer of Firefly Aerospace, reveals: the company went bankrupt, laid off 160 people, and almost died in a fireball on the test stand — then became the first private company to land on the moon and IPO'd at a $6 billion valuation. THE REAL STORY: Before Firefly became one of only five private companies to ever reach orbit, Eric was sitting in...

The Drummer of Linkin Park Led Him to a $1B Company | Scott Dudelson, Swag Bucks 26.03.2026

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: Scott never wanted a boss. He lived in an attic he couldn't stand up in, organized benefit concerts, and turned down the MBA path. A serendipitous reconnectio...

He Timed 10 Exits for $500M. Here's the One Thing He'd Tell Every Founder. 13.03.2026

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 the internet, and the only thing founders should be focused on right now. Fred left Wall Street at 32 after trading bonds at Salomon Brothers with a billion-...

Jessica Jackley: $3 Billion in Loans that Changed The World (Kiva Co-Founder) 26.02.2026

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 stumbled into a lecture about microfinance, moved to East Africa with no plan, and spent months interviewing borrowers living on a few dollars a day. What she heard ch...

Darren Berkovitz: How to Build a $230M Company Nobody's Heard Of 12.02.2026

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 the planet — clients paying $2 million a month — Darren built a 12-year overnight success in the unsexy world of SMS security and two-factor authentication. T...

Raised $1.5B by Listening, Not Pitching (16x Founder) 12.02.2026

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 problems. From being named one of the Wall Street Journal's "Top 20 Money Losers in America" to fighting the DOJ, SEC, and NSA simultane...

Jim Armstrong: How VCs Really Think ($750M in returns) 28.01.2026

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 Elon Musk merger that created the PayPal we know today, and has backed companies from seed stage to billion-dollar exits. THE REAL STORY: Before his bigge...

Eytan Elbaz: You Don't Have to Be The #1 Founder For A Huge Exit 26.01.2026

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 annually—and co-founded Scopely, which sold for $4.9 billion. Named one of the Top 100 seed investors globally, he's generated billions in enterprise value....

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