Imagine starting a company to change the world of finance right before an epic stock market crash.

Elon Musk famously said that PayPal wasn’t a hard company to create. It was a hard company to keep alive.

In 1999, three future titans of technology—Max Levchin, Peter Thiel, and Elon Musk—charge straight into the blaze to bring payments and finance into the internet age. This is the story of how a handful of brilliant founders and their team navigate from crisis to crisis, face constant near-failure, and create the first successful internet payments solution. From the wreckage of the dot com bubble, they emerged refined—the founders, investors, and builders who would go on to shape the next two decades of Silicon Valley—and a lot of the world we live in today.

Chapters

(01:20) Mr. Buffett on the Stock Market

(02:17) The stock market in 1999

(05:21) Intro to Max and Peter

(09:49) Intro to Elon

(15:45) Why they choose to do startups this late in the cycle

(20:51) Insight of eBay as a perfect market for p2p payments

(22:51) Competition between Confinity and X

(26:55) Confinity and X merge

(34:09) Novel business model & technology innovation

(37:29) The stock market crash dynamics

(43:25) How PayPal navigates post-9/11 slump with an IPO

(48:42) The PayPal Mafia

(50:40) Nature vs. nurture

(54:02) Takeaways on market timing

(55:24) The internet delivered on its promise

References

The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley by Jimmy Soni (Link)

The PayPal Wars: Battles with Ebay, the Media, the Mafia, and the Rest of Planet Earth by Eric M. Jackson (Link)

PayPal S-1 Filing in 2002 (Link)

Mr. Buffett on the Stock Market, Nov. 22nd 1999 (Link)

Technology waves are easy to see in hindsight, but often hard to see before they arrive. It’s even harder to build enough conviction to take a risk, ride the wave, and build something great.

Jeff Bezos did just that. And while the Amazon story has been told many times, it’s fascinating to think about what he saw that gave him the confidence to leave his comfortable Wall Street job to start Amazon.

How did he see the wave before most people, and what gave him the conviction to go for it? We cover his key relationship with David Shaw, his market research, and his regret minimization framework.

Famously, Amazon focused on books and grew like a rocket ship. How did they navigate the hype cycle and the dot com mania? Was their approach to investing during the boom the right approach? What can we learn from how they navigated the crest at the height of the bubble?

Finally, we ask maybe the most important question of all—how did Amazon survive? What were the market conditions they had to navigate? Did they do anything specific to position themselves or did they just get lucky?

Chapters

(01:20) Increasing return games

(05:38) Jeff Bezos’s background

(10:27) Market backdrop in the late 1980s, early 1990s

(13:54) Jeff Bezos meets David Shaw

(16:47) How Jeff Bezos sees the wave and builds conviction

(32:22) How Amazon navigates the wave

(35:25) Joy Covey hired as CFO

(36:27) Amazon’s investment philosophy during the boom

(42:40) How Amazon survives the crash

(44:25) Amazon’s financings

(49:41) The market crash and Amazon’s reaction

(52:50) Why did Amazon survive?

(57:50) See the wave, ride the crest, survive the crash

References

The Everything Store: Jeff Bezos and the Age of Amazon by Brad Stone

Invent & Wander: The Collected Writings of Jeff Bezos

Amazon SEC filings & shareholder letters from 1996-2002

“Riding the Perilous Waters of Amazon.com” by Peter de Jonge, New York Times Magazine, published on March 14, 1999 (link)

Increasing Returns and the New World of Business by W. Brian Arthur (link)

2,300x web growth from ‘93-’94, John Quartermann, Matrix News, Vol. 4, No. 2 (link)

Acquired Episodes (History, Tom Alberg)

In the late 1990s, the internet grew exponentially to become an enormous engine for technological progress and economic disruption.

The existing telecommunications infrastructure was designed to carry voice and television signals—not data packets. The system needed billions of dollars in fiber and copper to support the tidal wave. Telecom entrepreneurs, incumbent executives and capital markets were eager to invest capital and ride the boom.

In this episode, we tell the parallel rise (and unraveling) of two giants who tried to wire the future from opposite ends of the network.

On one side: John Malone, the genius capital allocator behind TCI, stitching together last-mile cable systems and striking the blockbuster sale to AT&T in 1999 as the industry chased an “integrated provider” vision after the ’96 Telecom Act.

On the other: Bernie Ebbers of WorldCom, an acquisition machine that vaulted from discount long-distance reseller to national carrier—fueled by a once-accurate-later-obsolete statistic implying “internet traffic doubles every 100 days,” a meme born at UUNet and soon echoed by CEOs, analysts, and even the U.S. Commerce Department.

We follow the capex arms race, Williams’ ingenious move to pull fiber through abandoned pipelines, the strategic missteps at AT&T, and the line-cost KPIs that nudged WorldCom across the line from pressure to fraud.

Along the way, we draw out lessons for investors and operators that resonate in today’s AI boom.

Chapters

(01:15) The meme that sparked the boom

(04:00) Market structure for telecom in the 1990s

(10:01) Huge capital expenses

(11:16) Opportunity space for entrepreneurs

(12:59) Introducing Bernie Ebbers and John Malone

(18:02) The invention of EBITDA

(20:18) Everything changes in ‘95 and ‘96

(26:50) LDDS becomes WorldCom—a top long-distance carrier

(31:20) TCI becomes a top cable company

(35:14) Prices down in long-distance telephone & last-mile assets become very valuable

(37:24) TCI acquired by AT&T

(39:10) Contrasting dot com vs telecom financing

(43:23) AT&T-TCI merger challenges & WorldCom earnings down

(52:02) Aftermath for John Malone and Bernie Ebbers

(55:53) Lessons learned and applications to today

References

Cable Cowboy: John Malone and the Rise of the Modern Cable Business (link)

Born to Be Wired: Lessons from a Lifetime Transforming Television, Wiring America for the Internet, and Growing Formula One, Discovery, Sirius XM, and the Atlanta Braves by John Malone (link)

Extraordinary Circumstances: The Journey of a Corporate Whistleblower by Cynthia Cooper (link)

Boom and Bust in Telecommunications by the Federal Reserve Bank of Richmond (link)

Description

Gold-rush energy meets browser wars.

In mid-1994 Silicon Graphics legend Jim Clark sits down with a 22-year-old programmer Marc Andreessen in the heart of Silicon Valley. Clark, a rebellious hardware icon trying to reinvent himself, and Andreessen, fresh off building the first web browser, bet that the browser will be the operating system to the open web.

Their new company races from zero to market share dominance, forcing Microsoft’s “tidal wave” pivot. They turn their IPO into a marketing weapon on August 5, 1995 when Netscape goes public without profits—and the stock soars—sending a blaring signal to founders, VCs, and retail investors that the internet era (and a historic boom) has begun.

Along the way, we unpack how Clark helped flip Silicon Valley’s power dynamics in favor of founders and engineers, and why Netscape’s triumph—and ultimate fate—should shape how we navigate today’s AI cycle.

Chapters

(00:18) Introduction

(01:13) The Tidal Wave Memo

(03:45) Microsoft’s Dominance in the 1990s

(06:40) The Origin Story of Netscape

(16:55) Who Was Jim Clark?

(18:34) The University of Utah as the Epicenter of Graphics Technology in the 1970s

(29:35) Jim Clark Changes the Game

(34:03) Netscape Shapes the Web

(36:31) Microsoft Responds

(38:20) The Mental Model of Dominating Operating Systems

(41:00) Why Was Netscape the Spark and Not Spyglass?

(42:17) Netscape’s IPO and the Macro Environment

(49:00) The Boom Starts

(50:25) Lessons from the Netscape Era

(52:24) Was Netscape Ultimately Successful?

References

The New New Thing by Michael Lewis (link)

Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages by Carlota Perez (link)

Marc Andreessen on Inventing The Internet Browser (link)

A run on the dollar, stagflation, and an election on the line—Part 3 wraps up the series with President Nixon’s shocking announcement to shut the gold window… a move that changed the monetary system forever and signaled the beginning of the end for the perception of gold as money. We meet John Connally, the swaggering Democratic governor of Texas who rode in the car with JFK when he was shot, and later became Nixon’s Treasury Secretary. He was the political closer tasked with averting a global monetary crisis and more importantly, securing Nixon’s re-election in 1972.

In the summer of 1971—with inflation rising, unemployment hovering near 6%, and foreign central banks suggesting they might convert dollars into gold—Connally, only months into the job, worked with Paul Volcker and others on a plan to fix the economy.

During an intense weekend at Camp David, Connally orchestrated consensus around a plan that included wage and price controls, a 10% universal tariff on imports, and most importantly, the suspension of dollar-gold conversion. These policies were sold as temporary and forced a global realignment.

At 8:00 p.m. ET on Sunday, August 15, 1971, Nixon announced the New Economic Policy to the world and kicked off a series of events that led to the monetary system we have today.

Chapters

(00:20) Connally’s 4 No’s Speech

(02:00) Gradualism & Stagflation

(04:26) Whispers of Global Monetary Crisis

(05:52) The Nixon Doctrine

(07:30) Introducing John Connally Jr.

(14:18) How Connally Gets on Nixon’s Radar

(15:47) Moving Away from Gradualism

(17:27) The Potential for a Run on the Dollar

(24:50) Camp David Economic Meetings Coordinated by Connally

(30:05) The British Allegedly Want to Redeem $3 Billion in Gold

(33:07) Policy Change Decisions at Camp David

(39:23) Nixon’s Speech Shutting Gold Window

(40:15) The Immediate Domestic Reaction of the Speech

(42:39) The Foreign Reaction to the Speech

(46:08) Smithsonian Agreement in December 1971

(47:56) By March of 1973 Bretton Woods Is Dead

(49:30) Why Did We Not Have Another Bretton Woods Agreement?

(52:10) Similarities and Differences to What’s Happening Today

References

Three Days at Camp David: How a Secret Meeting in 1971 Transformed the Global Economy by Jeffrey E. Garten (link)

Nixon's Economy: Booms, Busts, Dollars, and Votes by Allen J. Matusow (link)

https://wtfhappenedin1971.com/

On the journey towards President Nixon’s fateful decision on August 15th, 1971 to suspend dollar-gold convertibility—a decision that would forever change the global economy—we meet William McChesney Martin Jr, the longest-serving Fed chairman in history and arguably the most consequential economic US policy maker since Alexander Hamilton.

After negotiating Fed independence as an Assistant Treasury Secretary with the 1951 Fed-Treasury Accord, President Truman appointed Martin as chairman of the Fed. For two decades, Martin fought to establish Fed independence while pursuing the long-term interests of the US—fighting inflation, defending the dollar, and facing off against five presidents.

While he navigated the demands of a booming economy at home, Martin coordinated with US allies to stabilize exchange rates and grow world trade—all while balancing the needs of Cold War military spending, allied foreign aid, and private capital outflows.

We trace the mounting pressure from the late 1950s gold spike through Vietnam-era deficits as Martin tries to hold the line with rate hikes, diplomacy, and sheer credibility among global central bankers. It’s the story of a principled broker navigating guns-and-butter politics while the world loses faith in dollar-gold convertibility—and according to his own assessment, he was almost successful too… almost.

Chapters

(00:47) Introduction

(03:33) William McChesney Martin Jr.

(09:14) The 1951 Fed-Treasury Accord

(12:42) Truman Appoints Martin as Fed Chairman

(13:34) Eisenhower Presidency Reinforces Fed Independence

(17:00) Comparing Growth & Productivity during This Period to Today

(18:41) Gold Drain and Military Spending

(22:51) Price of Gold Breaks $35/oz

(26:52) The JFK Years: More Military Spending & Tensions with France

(34:12) Bretton Woods and Inflation

(36:36) Central Bank Swap Lines

(41:05) Confrontation at LBJ’s Ranch

(44:53) The Circularity of Dollar Strength and Military Spending

(56:40) Bill Martin’s Legacy and State of the Fed as Nixon Takes Office

References

Chairman of the Fed: William McChesney Martin Jr. and the Creation of the Modern American Financial System by Robert P. Bremner

Gold, Dollars, and Power: The Politics of International Monetary Relations, 1958-1971 by Francis J. Gavin

https://wtfhappenedin1971.com/

Gold, power, war, and spies—this series has it all. On August 15th 1971, President Nixon announced that he was suspending the dollar’s convertibility into gold. This announcement upended the Bretton Woods monetary system and set the world on a course towards floating exchange rates with the US dollar as a fiat reserve currency for world trade—a system that is under significant pressure today.

In the first episode of the series, we tell the story of how an ambitious, little-known American technocrat—Harry Dexter White—went toe-to-toe with the world-famous John Maynard Keynes to rewrite the rules of global finance.

Bretton Woods wasn’t just a conference. It put the US dollar at the center of a new monetary order, backed by roughly two-thirds of the world’s gold and America’s unrivaled economic power after World War II. Delegates representing 44 nations agreed to fixed exchange rates, created the IMF and World Bank, and made the dollar “as good as gold.”

We trace how global leaders were traumatized by the economic chaos following World War I—trade wars, currency collapses, and the Great Depression. Against this backdrop, we explore how White moves from the periphery of academic economics to play a central role in FDR’s Treasury. From there he outmaneuvers John Maynard Keynes and secures American primacy, despite also moonlighting as a Soviet spy.

This episode covers the genesis of a system every president from Truman to Nixon would struggle to defend—and the traces of which still shape the world economy today.

Chapters:

(00:18) Introduction

(03:47) Background on Harry Dexter White

(6:29) Economic Backdrop Leading to Bretton Woods

(12:58) Barter Trade vs. Free Trade

(15:22) Background on John Maynard Keynes

(18:06) Keynes and White Meet in London

(20:02) Harry Dexter White, from Periphery to Center

(24:13) White Gets to Work on New Monetary System

(32:24) US Leverage over the UK

(37:32) The Build Up to Bretton Woods

(41:54) Harry Dexter White’s Triumph at Bretton Woods

(46:59) The Aftermath for White and Keynes

(48:01) Reflections on White’s Soviet Espionage

(55:16) Questions for Today’s Global Trade & Monetary System

References:

The Battle of Bretton Woods: John Maynard Keynes, Harry Dexter White, and the Making of a New World Order by Benn Steil

https://wtfhappenedin1971.com/