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.

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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

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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.

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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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