Podcast Episodes

From White House to Wall Street: David Rubenstein

Episode 240

David Rubenstein helped pioneer modern private equity—building The Carlyle Group into a $400B global investment firm from a modest D.C. office and a relentless fundraising streak. But beyond PE, his …

Published on 4 months, 2 weeks ago

No Reset Button: Reinventing Amplitude in a Post-AI World (Spenser Skates)

Episode 239

Amplitude helped define the modern analytics stack, powering digital products with deep behavioral insights. But in a world shifting toward agentic interfaces and vertically integrated AI, even a cat…

Published on 4 months, 3 weeks ago

Flexport’s Third Act: Winning in a Broken Global Trade System

Episode 238

Flexport was a breakout success—reimagining global trade with tech at its core. But when the freight market cooled and efficiency overtook service, things started to unravel. Founder Ryan Petersen st…

Published on 5 months ago

Brex 3.0: Inside the Radical Turnaround with Pedro Franceschi

Episode 237

Guest: Pedro Franceschi

Pedro Franceschi is the co-founder and CEO of Brex, a fintech company reshaping how businesses manage their finances.

Originally from Brazil, Pedro went from teenage hacker to l…

Published on 5 months, 1 week ago

From India to Silicon Valley: The Jay Chaudhry & Zscaler Story

Episode 236

Before Zscaler was a $32B cloud security giant, it was just 10 engineers—half in Bangalore, half in a borrowed U.S. office.

As founder and CEO of Zscaler, Jay Chaudhry bet $50M of his own money on one…

Published on 5 months, 2 weeks ago

The Unlikely Path to Building a Billion-Dollar Gov Tech Company | Zac Bookman

Episode 235

Guest: Zac Bookman, CEO and Co-Founder of OpenGov

Thirteen years after co-founding the government transparency startup OpenGov, Zac Bookman is still finding ways to surprise people. In 2024, Cox Enter…

Published on 5 months, 3 weeks ago

Bootstrapped to $12B: Mailchimp’s Ben Chestnut on Life After the Exit

Episode 234

Guest: Ben Chestnut, Former CEO and Co-Founder of Mailchimp

If you find yourself selling your startup, then Mailchimp co-founder Ben Chestnut has some important advice for you: Get a dog. 

When Intuit …

Published on 5 months, 4 weeks ago

Meet the Man Who’s Making Supersonic Flight Possible Again | Blake Scholl

Episode 233

Guest: Blake Scholl, Founder & CEO of Boom Supersonic

“Passion and drive trumps knowledge and experience,” says Boom Supersonic CEO Blake Scholl. Long before he was running Boom — which earlier this y…

Published on 6 months ago

#232 CEO NetApp, George Kurian: New Chapters

Episode 232

Guest: George Kurian, CEO of NetApp

For almost 10 years, George Kurian has been CEO of the data infrastructure firm NetApp, overseeing its pivot to cloud services. After he  took the job — a surprise …

Published on 6 months, 1 week ago

#231 CEO & Co-Founder Harvey, Winston Weinberg w/ Ilya Fushman: Worthy Sacrifices

Episode 231

Guests: Winston Weinberg, CEO & co-founder of Harvey; and Ilya Fushman, partner at Kleiner Perkins

“If you think about pretty much any job out there in the world, we will have some sort of [AI] copilo…

Published on 6 months, 3 weeks ago