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

Connect with Joubin:

X: @Joubinmir

LinkedIn: Joubin Mirzadegan
Email: grit@kleinerperkins.com

kleinerperkins.com

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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• X
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• X
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• Email: grit@kleinerperkins.com

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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
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• Email: grit@kleinerperkins.com

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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 leading one of the most well-known names in modern financial technology—building a platform trusted by startups and enterprises alike.

In this episode, Pedro shares what it took to launch “Brex 3.0,” why he moved to a single-CEO model, and how tough structural changes set the stage for leaner, faster growth.

Chapters:
00:00 Trailer
00:46 Introduction
01:45 Startup roller coaster
05:21 Founders know how to have fun
07:12 Belief barrier evolution
12:00 Early state of life in Brazil
13:23 Controlling variables
15:32 Screen time
19:23 Making small decisions
23:27 Learning raises the bar
26:15 People manager
38:49 Getting underwater
42:05 Growth accelerated
47:51 Vision from the top down
52:13 Leadership organization
54:01 AI software engineering physics
54:43 People complain about change
59:42 Believers and non-believers
1:04:09 Equity and bonus controversy
1:08:40 Big swings and going public
1:14:15 Control in unpredictability
1:18:04 Living in a pixel

1:19:52 Meditate, sleep, diet, exercise

1:24:36 Mental health and stress
1:33:12 Who Brex is hiring
1:33:49 What "grit" means to Pedro
1:34:39 Outro

Mentioned in this episode: Silicon Valley, Facebook, Meta Platforms, Inc., Mark Zuckerberg, Mastercard, Rio de Janeiro, iPhone, Bill Gates, Tim Urban, Jony Ive, Apple Inc., LinkedIn, Salesforce, Brian Chesky, Airbnb, Anthropic Claude, Cursor, Codeium Windsurf, Cognition Labs Devin, Vercel, Retool AI, Amplitude, Spenser Skates, Elon Musk, Tesla, Inc.

Links:

Connect with Pedro:

• X
• LinkedIn

Connect with Joubin:

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

This episode was produced by Kleiner Perkins and edited by IQvideo.

The trailer and distribution for this episode were handled by Atomik Growth.

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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 radical idea: secure the internet in the cloud.

Born in a Himalayan village with no electricity, he built Zscaler into one of the world’s top cybersecurity giants.

In this episode, Jay breaks down why 50% of the Fortune 500 trusts Zscaler, why he still interviews candidates, and how he’s incubating the company’s next big AI bet.

Chapters:
00:00 Trailer
00:42 Introduction
01:21 His fifth company
04:26 Entrepreneurs’ existential fear
10:53 Customer engagement and new innovations
12:46 No private jets, no business class
19:34 “I never used money”
23:38 Born and raised in India
26:17 Hiring legends
30:35 Walking on water
35:09 “Dolphining”
39:55 Areas of weakness
42:11 Passionate even on the weekends
44:56 Work during roller coasters
47:35 The weight of the world is on your shoulders
49:21 Leveraging AI
56:20 Outro

Mentioned in this episode: Elon Musk, Microsoft, Bill Gates, BlackBerry, Steve Ballmer, Satya Nadella, Hewlett-Packard (HP), IBM, John Fellows Akers, Steve Jobs, NeXT, Inc., Linux, Cisco, United Airlines, San Francisco International Airport, Sundar Pichai, Ravi Mhatre, Lightspeed Venture Partners, Six Flags, AI (artificial intelligence), security

Links:

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• X
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• Email: grit@kleinerperkins.com

Learn more about Kleiner Perkins

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 Enterprises bought the company for $1.8 billion — but as far as Zac is concerned, “we’re just getting started.”

“ I left the vast majority of my net worth in the company,” he says. “So I'm a believer. I'm all in.”

The mission of powering “more effective and accountable government” has been stable since OpenGov’s earliest days, and that mission has informed everything from hiring to M&A to the decision to sell.

“These people buy and don't sell,” Zac said of Cox. “They're all in on the mission. And they're all in on taking care of employees. So I see a triple win: A win for employees, win for the investors, win for the customers, maybe a quadruple win for me and the management.”

Chapters:

• (01:46) - OpenGov’s mission
• (04:34) - Shrinking the product-market fit
• (07:34) - Super misson driven
• (08:59) - Why OpenGov almost shut down
• (13:08) - Zac’s early career
• (16:16) - Picking (and losing) a CTO
• (22:50) - Growing upside-down
• (25:29) - The SPAC backstabber
• (31:26) - Why Zac didn’t get fired
• (33:24) - Selling in 2024
• (37:04) - Growth by acquisition
• (42:31) - John Chambers and PMF
• (49:32) - Zac’s cross-country bike ride
• (56:25) - Expectations vs. reality
• (58:57) - The coup attempt
• (01:01:59) - Tiring work
• (01:05:47) - Going to the White House
• (01:09:40) - DOGE & disrespect
• (01:12:54) - “We’re just getting started”
• (01:14:18) - Who OpenGov is hiring (and where)
• (01:15:13) - What “grit” means to Zac

Mentioned in this episode: Joe Lonsdale, Cox Enterprises, OpenAI, the Department of Government Efficiency, Workday, H.R. McMaster, Stanford University, Formation 8, 8VC, the National Academy of Sciences, the Stanford Review, Kamala Harris, Marc Andreessen, Balaji Srinivasan, Coinbase, Earn, Ben Horowitz, Facebook, Steve Laughlin, Cisco, Laurene Powell Jobs, Glynn Capital, Acme, Allen & Company, Harry You, Joe Tucci, EMC, Bill Green, Accenture, Tyler Technologies, HP, Josh Kushner, GTY Technology Holdings, John Keker, Palantir, CKAN, Oracle, Kevin McCarthy, The American Technology Council Summit, Jeff Bezos, Tim Cook, Satya Nadella, Pat Gelsinger, Donald Trump, Jared Kushner, Elon Musk, Bill Clinton, and Al Gore.

Links:

Connect with Zac

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• Email: grit@kleinerperkins.com

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This episode was edited by Eric Johnson from LightningPod.fm

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 bought Mailchimp in 2021 for $12 billion, the company asked Ben if he wanted to stay on as CEO, but he chose to “walk off into the sunset” and let the new owners take over.

After that, he estimates it took 6 to 12 months before he stopped checking his email, social media, and calendar with the same level of stress a CEO might have. Adopting a dog, he discovered, forces you to “get OK with the voices in your head."

“After the acquisition, that's all I do, I walk the dog,” Ben says. “And the dog was good therapy ... No judgments from a dog.”

Mentioned in this episode: Intuit, Wolt, DoorDash, LinkedIn, Dan Kurzius, Salesforce, ExactTarget, Pardot, Constant Contact, Rackspace, Free by Chris Anderson, Wired Magazine, Charles Hudson, the Freemium Summit, Drew Houston, Dropbox, Evernote, Phil Libin, TechCrunch, Brian Kane, Catalyst Partners, Georgia Pacific, Scott Cook, Bing Gordon, Vinay Hiremath, Loom, Joe Thomas, Caltrain, Flickr, Saturday Night Live, Droga5, Cannes Film Festival, Strava, Twitter, LinkedIn, Nvidia, Glean, Rubrik, Amazon AWS, and Mechnical Turk.

Links:

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• Email: grit@kleinerperkins.com

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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 year successfully tested the world’s first privately-developed supersonic jet — he was enabling “the world’s most obnoxious spam cannon” at Groupon, or designing a barcode-scanning game for retail shoppers.

But eventually, Blake found the courage to be more audacious and do something closer to his lifelong love of aviation. He began educating himself about things he had never thought to learn, and tapping his LinkedIn network to get intros to the smartest people in the industry.

“If you imagine yourself on like the day of IPO, 99 percent of what you needed to know to get to that day, you didn't know on day one,” he says. “So, why not take 99 percent to 99.5 percent, and work on the thing you really want to exist, even if you don't know anything about it yet?”

Chapters:

• (01:07) - Blake on Boom’s beginnings
• (01:52) - Breaking the sound barrier
• (05:23) - Concorde’s legacy
• (09:36) - Navigating regulations
• (12:08) - Boomless supersonic flight
• (16:48) - The test flight
• (20:11) - Day-of nervousness
• (24:26) - Carrying passengers
• (26:55) - Cost & wi-fi
• (30:19) - “No middle seats”
• (32:35) - Hard tech
• (36:48) - What if Apple made a plane?
• (39:08) - Blake’s career journey
• (43:29) - The risk of failure
• (49:12) - Finding the courage
• (52:49) - Balancing life with Boom
• (56:42) - Learning how to build a jet
• (01:00:20) - The power of LinkedIn
• (01:02:38) - Y Combinator Demo Day
• (01:08:24) - Richard Branson
• (01:11:38) - Dividing yourself
• (01:14:19) - Being a focused dad
• (01:20:05) - Exuberance vs. fear
• (01:24:15) - Hiring slowly
• (01:27:17) - What “grit” means to Blake

Mentioned in this episode: Chuck Yeager, ChatGPT, the Apollo program, Elon Musk, SpaceX and Falcon 1, Boom Overture, Starlink, Boeing, Airbus, iPhone, Jony Ive, Uber, Airbnb, Anduril, United Airlines, American Airlines, Eclipse Aviation, Tesla, Scott Kirby, Mike Leskinen, Inktomi, Yahoo!, Amazon, Pelago, Google Ads, Kima Labs, Barcode Hero, Groupon, iPad, Eric Schmidt, Steve Jobs, Khan Academy, Sam Altman, Loopt, Virgin Atlantic, Paul Graham, Michael Seibel, Ashlee Vance, Bloomberg, Hacker News, Jared Friedman, Sen. Mark Kelly, SV Angel, Ron Conway, Virgin Galactic, Lockheed Martin, Gulfstream, Jeff Bezos, Jeff Holden, and How It’s Made.

Links:

Connect with Blake

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• Email: grit@kleinerperkins.com

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This episode was edited by Eric Johnson from LightningPod.fm