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 legacy spans presidential libraries, historic American artifacts, and a lifelong obsession with civic contribution.

In this episode, David shares how he raised billions without a background in finance, why owning a baseball team was more than just a trophy purchase—and what building true generational success really means beyond wealth alone.

Chapters:
00:00 Trailer
00:53 Introduction
01:40 Family, wealth, class
14:40 Happiness disparity and longevity
19:25 I need more to give away more
25:04 The relentless fundraiser
33:53 Kids and travel
36:06 No track record, the great white buffalo
38:59 Business and politics
43:53 Fired from Washington
45:52 Fundraising, presidents, podcast guests
48:04 Private equity and sports
53:44 Expenses — no charges
55:49 Waking up with energy
57:26 Preserving copies
1:02:05 Organizational architecture
1:03:41 Bury me in my plane
1:08:11 Not a big luxury spender
1:10:32 What “grit” means to David
1:10:50 Outro

Mentioned in this episode: Andrew Rubenstein, Stanford University, Bill Gates, Melinda Gates, Warren Buffett, Morgan Guaranty Trust Company, International Business Machines Corporation (IBM), Procter & Gamble Company, Forbes 400, Duke University, University of Chicago, Harvard Corporation, Johns Hopkins University, California Public Employees' Retirement System (CalPERS), President of the United States of America, Donald J. Trump, Jimmy Carter, John F. Kennedy Center for the Performing Arts, Smithsonian Institution, National Gallery of Art, George W. Bush, Barack Obama, Joe Biden, Arianna Huffington, Xi Jinping, Hank Greenberg, Stephen A. Schwarzman, Tim Cook, Jeff Bezos, Baltimore Orioles, Fred Trammell Crow, Harlan Crow, National Basketball Association (NBA), National Football League (NFL), Arctos Partners LP, Anthropic, Magna Carta Libertatum, Declaration of Independence, Emancipation Proclamation, Abraham Lincoln, US Constitution, National Archives, Lincoln Memorial, Thomas Jefferson Memorial, Mount Vernon, Monticello, Montpelier, Mark Cuban, Paul McCartney

Connect with David:
X: @DM_Rubenstein

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X: @Joubinmir

LinkedIn: Joubin Mirzadegan
Email: grit@kleinerperkins.com

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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 category leader has to evolve.

In this episode, CEO Spenser Skates shares how he’s rethinking AI within the constraints of a 13-year-old codebase, why analytics remains Amplitude’s competitive edge—and why taking the company public early was a risk worth taking.

Chapters:
00:00 Trailer
00:43 Introduction
01:26 AI is still very early
05:48 The urgency of building from the ground up
08:49 Bringing in new blood
11:23 Higher valuations and going public
15:00 Who’s leading who
18:39 Markets being open and closed
21:14 Being the incumbent in AI
24:40 Slow innovation
31:43 The ultimate founder
37:06 Things willing to relinquish
44:04 Being the person I want to be
46:41 Between family and work
50:08 Becoming the person you hate
55:16 Chief general, chief justice, chief priest
1:02:56 Tired founders
1:04:32 Missing out
1:14:51 Who Amplitude is hiring
1:15:41 What Spenser means to Spenser
1:16:54 Outro

Mentioned in this episode: OpenAI ChatGPT, Command AI, Oracle Corporation, Anthropic Claude, Jeff Bezos, Steve Jobs, Bill Gates, Larry Ellison, Rippling, Stripe, Meta Platforms, Inc., Mark Zuckerberg, Figma, Canva, Peter Thiel, Anne Lee Skates, Ruth Bader Ginsburg, Michael Jordan

Links:

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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 stepped aside, handing the CEO role to former Amazon exec Dave Clark. Months later, he was back at the helm.

In this episode, Ryan explains what went wrong, how he’s rebuilding Flexport—cutting $300M in costs, restoring customer focus—and why promoting from within beats chasing outside stars. He also weighs in on Trump’s proposed tariffs and what they could mean for the future of global trade.

Chapters:
00:00 Trailer
00:31 Introduction
02:07 Meeting smart people, seeing the world
03:40 Eroded margins
09:52 Charismatic and overconfident
15:32 Not an overnight decision
20:08 The founder has returned
23:10 Redoing the hiring
26:38 No substitute for passion
31:00 Working for and with my brother
37:28 Working with forwarders
42:14 Being a founder can be lonely
47:49 Life’s work
54:06 The right person for the job
1:00:55 19 countries
1:04:57 Blowing people up
1:07:24 Work and being a good dad
1:08:34 Not doing it for money and loving money
1:17:52 Import and export tariffs
1:22:57 De minimis
1:25:54 Panama and the Suez Canal
1:36:50 Going public
1:42:24 Who Flexport is Hiring
1:42:42 What "grit" means to Ryan
1:43:06 Outro

Mentioned in this episode: Founders Fund, Amazon, Toyota Motor Corporation, Slack, Brex, Pedro Franceschi, Henrique Dubugras, United States Customs and Border Protection, ImportGenius, Michael Kanko, Y Combinator, Paul Graham, Intel Corporation, Shopify, Geely Holding (Zhejiang Geely Holding Group Co., Ltd.), The Volvo Group, Intuit TurboTax, David Petersen, BuildZoom, TechCrunch, Google, Figma, Barack Obama, Donald Trump, Jimmy Carter, Panama Canal Authority, United States Navy, Coinbase, Uber, Airbnb

Links:

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• Twitter
• LinkedIn
• Email: grit@kleinerperkins.com

Learn more about Kleiner Perkins