I speak with legendary founders behind $200B+ in exits and IPOs, entrepreneurs who built Google AdSense, Scopely, Priceline, Dollar Shave Club, Tripadvisor, Natera, LegalZoom, and more. We talk about High Five Energy: the magnetic flow state where doors open, the right people show up, and opportunities align. Learn the pivots, failures, and mindset shifts that shaped the stories behind iconic companies.
Episodes released weekly
In 2005, Jessica and her co-founder spammed their friends and family to fund seven entrepreneurs in Uganda — $300 to $500 each. They weren't sure it was legal. Every loan got repaid. That $3,100 pilot became Kiva, the world's first peer-to-peer microlending platform, which has now facilitated nearly $3 billion in loans across the globe. A masterclass in starting before you're ready and seeing entrepreneurs where others saw charity cases.
Eric has founded 16 companies and raised over $1.5 billion — not by pitching harder, but by listening. The road wasn't straight. He lost it all during the dot-com crash, fought the DOJ, SEC, and NSA simultaneously, and came out the other side with his reputation intact and a clearer sense of what actually builds great companies. He shares the mindset shift that changed everything and what founders need to know about AGI arriving sooner than anyone expects.
Darren built a $230 million company that almost nobody has heard of — by solving boring problems nobody else wanted to touch. He breaks down why boring industries print money, why you should memorialize everything in writing, and what founders get catastrophically wrong about the VC game. His warning about FanDuel — where founders built a $500M company and walked away with almost nothing — is worth the listen alone.
Jim led PayPal's first institutional round and has been on the Midas List four times. He shares the one rule he has about first meetings that every founder needs to hear, why SaaS is dying and what comes next, and how to actually raise money in 2026 — including the story of how Elon Musk pitches, told firsthand.
Before AdSense became one of Google's most iconic products, Eytan spent 3.5 years building 8 failed products. An investor mocked their $250/month revenue: "We pay our gardener more than that." By product #8 they cracked the code — and Google came calling. Eytan reveals why you don't have to be the #1 founder to achieve a generational exit, what the acquisition dance with Google actually looked like, and the surrender principle that changed everything.
