Joe Lonsdale: American Optimist

As a former Principal at Founders Fund, Founding Partner at SciFi VC, and 8VC advisor, Eric Scott has invested in and helped build numerous technology leaders. He’s launching his new fund, Overlook Capital, where he sees missed opportunities in the market. How has venture investing evolved in recent years? Where does he see the dislocations? And how will AI change the game going forward?

After graduating from Claremont McKenna College, Eric emailed his way into Max Levchin’s network, becoming an early employee at HVF Labs where he learned to invest and build companies. He later spun out SciFi VC as its Founding Partner, before landing as a Principal at Founders Fund. He was an early investor in Anduril, Crusoe Energy, among others, and a senior advisor at 8VC where he helped us launch Harbor Health.

We begin our conversation with Eric’s journey — from persuading Max Levchin to hire him as a technical assistant to investing at HVF and launching SciFi VC. Next, we dive into the state of venture today. Learn why Eric believes that larger and larger fund sizes are concentrating capital into the hottest AI bets, creating real inefficiencies just below the top tier. He lays out the thesis behind his new firm and where he sees missed opportunities. Finally, Eric shares his optimistic vision for the years ahead and why he believes this is one of the best times in a generation to start and build important companies.

00:00 Episode intro

01:30 Meeting Max Levchin and learning to build

06:30 Launching SciFi VC & investment lessons

12:05 How VC is changing

13:40 Biggest missed opportunity in venture

16:15 Enormous dislocations in the market

21:30 How AI is changing the game

24:00 Overlook Capital

27:50 Optimism for the future

Jacob Helberg is leading the State Department's efforts to secure critical supply chains and win the global AI race. How is the U.S. shifting from dependency on China to building new partnerships around energy, minerals, and infrastructure? Which economies will grow fastest in the AI era? Who will be left behind? And how will this impact geopolitics? We discuss these timely topics with Jacob, Under Secretary of State for Economic Growth, Energy, and the Environment. A tech policy veteran who worked at Google and Palantir before serving on the U.S.-China Economic and Security Review Commission, Jacob was confirmed last fall to help execute the administration’s economic statecraft agenda. He's the author of "The Wires of War: Technology and the Global Struggle for Power."We begin our conversation with Jacob’s mission at the State Department and the launch of Pax Silica: a new US-led economic security coalition to secure supply chains and help America dominate in AI innovation. We dive into Jacob's recent deal in the Philippines to build an AI-native industrial hub, and explore the contrast with China’s Belt and Road Initiative. Next, Jacob makes the bull case for AI drawing on lessons from history: the PC revolution displaced 3.5 million jobs, he explains, but created 19 million more with the advent of the software industry! Finally, he explains why principled, positive-sum diplomacy is delivering results where old models failed, and how the AI revolution is transforming the global balance of power.

00:00 Episode intro

02:30 Historic deal with Philippines

05:25 Jacob's background

07:30 Why is Europe falling behind?

13:00 The asymmetric power of tech

15:35 Jacob responds to AI doomers & skeptics

19:15 Global Competition: China, AI, and Diverging Growth

21:45 What is Pax Silica?

23:45 New Global Order in AI age

29:30 Is China pushing back?

31:45 Optimism for the future

Shyam Sankar is one of my favorite American innovators. As CTO of Palantir, he's been a key leader for over 20 years and built much of what the company stands for. He's also a patriot, and recently commissioned as a Lieutenant Colonel in the U.S. Army Reserve. His new best-selling book "Mobilize" lays out the crisis of the American industrial base, how to revive what made us a global superpower, and what it will take to prevent the next great power conflict.

Shyam's father was raised in a mud hut in India. He and his family relocated to Nigeria but fled to the United States after armed robbers nearly murdered them. Shyam joined Palantir as the 13th employee, where he helped shape its unique culture, develop key business strategies, and scale Palantir into a $300+ billion global software giant. In 2025, he was commissioned as a lieutenant colonel in the Army Reserve's new Detachment 201: Executive Innovation Corps, and earlier this year, he released "Mobilize: How to Reboot the American Industrial Base and Stop World War III."

We begin our conversation with Shyam’s extraordinary journey to the U.S. and what this country means to him. Next, we reminisce about the early days at Palantir and what made the culture unique, from his famous Shyam-isms to living in the office for a month straight to earn free BBQ Fridays. Learn how Shyam coined the term "Forward Deployed Engineers" and proved that the best software is built shoulder-to-shoulder with the customer. Then we dive into his new book and the dangerous atrophy of America’s defense industrial base. Shyam reveals that the U.S. expended 10 years of production in 10 weeks of conflict, and explains how we can once again become the arsenal of democracy. We also discuss the culture at the Pentagon and why some heretics must be protected at all costs. Finally, we explore the clash between leading AI researchers and the Department of War, and how to bridge the gap between Silicon Valley and D.C. and secure the next great American century.

00:00 Episode intro

01:45 Mud hut in India to life in America

05:25 Employee #13 at Palantir

09:45 How Shyam created Forward Deployed Engineers

13:05 What are Shyam-isms?

14:55 Business discipline & learning to say no

19:20 The crisis of the American industrial base

24:00 Some heretics must be protected

29:00 The factory is the weapon

34:00 Magical AI weapons

43:00 Optimism for America's future

Ben Black is the CEO of the U.S. International Development Finance Corporation (DFC). Backed by a $205 billion budget, his mandate is to invest in U.S. strategic interests, build new markets, and deliver real returns for taxpayers. What projects is the DFC prioritizing? How is he countering China's trillion-dollar Belt and Road Initiative? And how is the Trump administration shifting from a paternalistic view of foreign aid toward investing with accountability and an expectation of returns?

A history major at the University of Pennsylvania, Ben began his career in finance at Goldman Sachs before earning a JD and MBA at Harvard. He worked in private equity at Apollo Global Management before founding the investment firm Fortinbras. Last fall, he was confirmed by the U.S. Senate as CEO of the DFC. His drive to serve was shaped by his grandfather, a WWII tail gunner in the Aleutians, and by watching his father build Apollo into a global powerhouse.

We begin our conversation with Ben’s entrepreneurial journey before diving into the history of U.S. foreign aid. Learn how the U.S. regressed from the Marshall Plan, which rebuilt Europe and fostered investment in America, to promoting a culture of waste and dependency in foreign aid — and how the Trump administration is reversing course (check out our essay from January 2025 on these issues). Next, Ben lays out the flaws in China's extractive Belt and Road model and explains how the DFC is developing trusted partners, promoting free-market principles, and investing strategically. From maritime insurance in the Strait of Hormuz to rare earth mining, Ben reveals some of the DFC's recent wins and where he sees new long-term partnerships in South America and Asia. Instead of showering NGOs with taxpayer dollars and creating charity cases abroad, the Trump administration is restoring discipline and accountability — and Ben is a key leader in executing this vision and generating returns for the American people.

00:00 Episode intro

01:25 Ben’s path to DFC

08:30 $205 billion to invest abroad

10:00 Rethinking foreign aid

13:00 From Marshall Plan to waste and fraud

18:50 The Trump administration’s new approach

21:50 Countering China’s Belt & Road Initiative

28:00 Post-WWII order is changing / new opportunities

33:10 Maritime insurance and Strait of Hormuz

37:00 Optimism for America’s future

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

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?

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

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

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

Jake Paul is a social media influencer-turned-entrepreneur and boxer. He’s not only one of the most popular figures on the planet among Gen Z, but also an outspoken patriot, capitalist, and builder. Together, he and Geoff Woo founded Anti Fund and have backed OpenAI, Anduril, Ramp, among others. Why did Jake decide to speak out on politics? How do we win over the next generation? And how is AI changing the culture, from new social media platforms to prediction markets and the revival of in-person events?

We recorded this conversation the day after Jake appeared with President Trump at a Kentucky rally. He explains why he’s speaking out on politics, even if it costs him financially, and why authenticity is key to cultural influence. Next, we explore the origins of Anti Fund, and how Jake and Geoff had the conviction to back Anduril before defense tech was in vogue. They also invested in OpenAI and were instrumental in rolling out Sora; learn about the strategy behind the launch and the challenges around AI slop and identity authentication. Additionally, Jake is the co-founder of Betr, and we discuss its recent partnership with Polymarket, what’s next for prediction markets, and how to build guardrails for customers. Finally, we explore Jake’s success in pioneering the creator economy and building consumer brands. In the 1960s and 70s, most kids aspired to become astronauts. Today, they want to be content creators, in part because of Jake’s influence. We conclude with Jake’s advice for young people in the AI era, and how we can persuade the next generation to love their country and embrace a builder mindset.

00:00 Episode intro

02:20 On stage with President Trump

06:00 Attention is the most valuable currency

08:00 The origins of Anti Fund and backing OpenAI, Anduril, Ramp, and others

09:10 Betr + Polymarket and the future of prediction markets

14:58 Launching Sora with OpenAI

16:14 Are you worried about AI slop?

19:10 How AI is changing culture; revival of in-person events

21:20 Who should become a creator?

24:30 Fighters as cultural icons

31:30 How to win the culture