Joe Lonsdale: American Optimist

Michael Milken revolutionized American finance and democratized access to capital for thousands of companies that Wall Street had previously written off. Yet he was unjustly attacked in the 1980s in one of the most controversial prosecutions in U.S. history. As one of Michael’s key defense lawyers, Richard Sandler sets the record straight in his new book: Witness to a Prosecution: The Myth of Michael Milken. How did Michael transform capital markets through high-yield bonds? Why was he unfairly targeted? Why did he ultimately agree to a plea deal? And what are the lessons about government power that everyone should learn?
We dive into these topics in this week’s episode with Richard Sandler, Partner at the law firm of Maron & Sandler and Executive Vice President and Trustee of the Milken Family Foundation. Richard and Lowell Milken, Michael’s younger brother, met in first grade while growing up in Los Angeles. After practicing law with his father, Richard joined Michael and Lowell’s firm -- Drexel Burnham Lambert -- to help the high-yield bond team. He saw firsthand the entire saga: the explosive rise and fall of Drexel, the unprecedented investigation, and ultimately, President Trump’s pardon of Michael in 2020.
We begin with Michael’s breakthrough in high-yield bonds. Learn how he almost single-handedly transformed the “junk bond” market from $70 billion to $700 billion in a decade, and helped finance the growth of great American entrepreneurs and companies — Ted Turner, Steve Wynn, MCI Communications, among others. Next, Richard walks us through the investigation: the unprecedented use of RICO against Drexel, the targeting of Lowell as a “hostage,” and the novel charges Michael ultimately pled to (none of which had been prosecuted before or since). Finally, we explore the deeper lessons about prosecutorial power, media narratives, and Michael’s extraordinary resilience. He has pushed forward medicine, science, and education in myriad ways, while inspiring many of our great leaders today.
00:00 Episode intro
01:35 Richard’s career & Michael Milken’s legacy
06:25 Why write this book?
08:00 How Michael Milken transformed finance
14:00 Why did they go after Drexel & Michael?
19:30 Using RICO to bring down Drexel
22:30 Prosecutorial abuse & the power of government
26:30 Why did Michael agree to a plea deal?
33:25 Trump grants Michael a full pardon
35:00 Lessons on government power, media influence & Michael’s resilience


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John Melas-Kyriazi is the co-founder and CEO of Standard Metrics, which powers portfolio management for more than 150 venture capital firms and 10,000 companies. He runs a high-growth SaaS company at the leading edge of the AI wave. How is AI transforming how investors source and diligence deals? How are agents parsing pitch decks, prepping board meetings, and building powerful new workflows? And as competitive advantages shift, what are the new moats for SaaS companies in the AI age?
We discuss these and other timely topics with John. At an early age, he fell in love with science fiction and built vacuum-tube amplifiers in his parents' basement, before studying physics and materials science at Stanford. There he became a research scientist until pivoting to investing, first at StartX and later Spark Capital. Born out of firsthand experience, he co-founded Standard Metrics alongside the 8VC Build team to create a better solution for portfolio management software.
We begin our conversation with John’s path from academia to investor and founder. Next, we explore how Standard Metrics centralizes data, improves portfolio intelligence, and powers smarter investment decisions. Then we dive into the new possibilities with AI, from technical diligence copilots and investment stress-testing to new workflows and internal AI analysts. In an era of new agentic tools and shifting competitive advantages, we discuss new moats for existing software companies built around network effects, data, and more. The world of finance is changing quickly; John offers a unique perspective on the AI wave and how top investors are leveraging new workflows to get ahead.
00:00 Episode intro
02:10 Academia to investor and founder
08:00 The pain point that led to building Standard Metrics
12:10 How AI is transforming venture capital
14:20 AI as a technical copilot
17:10 AI Analyst vs human in the loop
19:20 Parsing pitch decks and new AI tools
23:10 How AI search is changing marketing
28:30 New capabilities and workflows
33:47 How quickly is everything changing?


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit blog.joelonsdale.com

In the coming years, over two million small businesses will change hands or close their doors as Baby Boomers retire. Will Fry, Founder and CEO of American Operator, is on a mission to save Main Street and seize this opportunity for the next generation of local owners and operators. How does the operate-to-own model work? Should talented young people think twice about traditional careers and pursue ownership opportunities instead? And why is Will especially bullish on small business in the AI age?
Raised in a small town in North Carolina, Will developed an early love for building, starting with electronic kits and later unique apps. After studying at Penn and Wharton, a trip home revealed the looming crisis: millions of local businesses that lack succession plans. This sparked the creation of American Operator, which pairs retiring owners with high-agency operators, along with the capital and know-how to build a thriving business.
We begin with Will’s entrepreneurial journey and the coming “Silver Tsunami.” Will explains why only 48% of small business owners have succession plans and what this means for the next generation of owner-operators. He highlights stories like Greenway Painting in Jackson, Wyoming, and how American Operator is helping create millionaires on Main Street while keeping local business local. Next, we explore the historical and cultural importance of small business in America, dating back to John Hancock’s import-export firm and Ben Franklin’s printing shop. Looking ahead, we examine AI’s impact on small businesses. Learn why Will believes SMBs are a great AI hedge, while also having unique upside as new AI tools make small cohorts of people dramatically more productive. Finally, Will explains the operate-to-own model and how American Operator aligns incentives so that original owners become valuable advisors, new operators can earn their way into majority ownership, and American Operator remains a committed partner over the long run.
00:00 Episode intro
01:25 Will’s entrepreneurial journey
04:15 The small business succession crisis
06:40 American Operator’s approach vs. private equity
11:55 Does AI mean boom or bust for small business?
15:55 Forget law school? Buy a small business instead?
21:20 AI use cases for small business
23:00 Why many business owners shut down instead of sell
26:00 How the operate-to-own model works
33:50 Optimism for Main Street America


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit blog.joelonsdale.com

Last year, JoeBen Bevirt joined the show to discuss the vision behind Joby Aviation and bringing air taxis to life. Now, he's back to talk execution and getting to market this year! What states will be first to offer Joby rides — and when? How is Joby ramping up manufacturing to meet the moment? And how is AI making Joby’s top scientists over 10X more productive and accelerating decades of advancement into the next few years?" As Founder and CEO of Joby Aviation, JoeBen has spent more than a decade building Joby into the leader in electric vertical takeoff and landing (eVTOL) aircraft, and we begin with its unique design: 100 times quieter than a helicopter and dramatically safer to operate with layered redundancy across six propulsion stations, dual motors, and dual battery packs. Next, we talk about the significance of Joby's partnership with Toyota, how they're ramping up manufacturing, and why they're massively expanding their Ohio facilities. Then, JoeBen lays out their regulatory progress, from achieving their first FAA-conforming aircraft to the White House's historic pilot program that will bring air taxis to 12 states starting this year, including Texas!Additionally, we explore the coming age of autonomy, why Joby is partnering with NVIDIA to build out its autonomous flight stack, and how AI is transforming everything from aerodynamics research to back-office tasks. You'll also learn about Joby's breakthrough hydrogen-electric program — unlocking long-range commercial and defense applications — and why staying ahead of China is critical for American leadership in this next age of flight. Finally, JoeBen shares his grand vision for an electric era of aviation and a future without traffic — something we can all get behind.
00:00 Episode Intro
01:50 What sets Joby aircraft apart
04:50 Key partnerships with Toyota & NVIDIA
06:50 Closing in on FAA Certification
08:00 Air Taxis coming to 12 states this year!
13:35 Autonomous flight is the future
20:00 Hydrogen aircraft for the Pentagon
24:10 Why AI is a game changer
28:15 Expansion in Ohio and Global Competition with China
34:40 Addressing critics / future vision
35:50 Making air travel ubiquitous


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit blog.joelonsdale.com

Scott Wu and Russell Kaplan, co-founders of Cognition, are leading one of the fastest-growing, talent-dense AI companies. Their mission: make expert software engineering ubiquitous. What does a world of software abundance look like? How is Cognition delivering massive productivity gains inside some of the largest companies and organizations? And can AI finally modernize the broken, $100 billion government IT systems?
We discuss these and other timely topics with Scott and Russell. Scott was a three-time gold medalist at the International Olympiad in Informatics and world champion at age 17. After high school, we hired him at Addepar, where he became a top software engineer. Russell began his career as a machine learning engineer on Tesla’s Autopilot team before selling his video data company, Helia, to Scale AI. In 2023, Scott and Russell co-founded Cognition, and a year later, they shocked the technology world with the release of Devin, the first AI software agent.
We begin our conversation by discussing the incredible collection of young talent at Cognition, and why the next generation has new advantages in the AI era. Next, we catch up on Cognition’s explosive growth: Devin usage in the first few months of 2026 already surpassed all of 2025. Scott reveals that Cognition engineers no longer write code and explains how they’re able to test and ship new products faster than ever before. Then, we dive into the new era of software abundance and what it means if everyone has access to high-quality engineering, from modernizing large legacy enterprises to supercharging small businesses. We also discuss Cognition’s recent foray into government services and its work to modernize complex outdated systems. Finally, we explore the talent flywheel that has drawn so many former founders to Cognition, and why Scott and Russell believe we’re moving from Minecraft “survival mode” to “creative mode” — where the only limit to building is imagination itself.
00:00 Episode intro
01:35 Why technical talent & execution matters in AI
06:10 Do young people have an edge in the AI era?
08:26 Cognition’s rapid growth
11:55 The new era of software abundance
14:30 Cognition engineers don’t type code anymore
19:20 “Never sleep while Devin is idling”
21:25 The case for AI disinflation
23:50 How Devin generates 12X productivity gains
28:25 Cognition for government / taking on complex, broken systems
36:40 The AI race / competition with Anthropic
39:00 Forward deployed engineers?
43:40 How fast are LLMs improving?
47:10 AI-led small business explosion


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit blog.joelonsdale.com