Joe Lonsdale: American Optimist

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


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Small Business Administrator Kelly Loeffler is playing a pivotal role in our nation on two fronts: supporting the next generation of small business owners, while exposing and combating billions of dollars in fraud. How is AI impacting small businesses? Could this be a golden age for Main Street America? What's the staggering scale of fraud she's uncovering? And how is she working with Palantir and other top talent to ensure it never happens again?
We discuss these timely topics and more with Administrator Loeffler. Growing up on a farm in rural Illinois, Kelly raised cattle and was exposed to the challenges of small business early on. She became the first in her family to graduate college and built a distinguished career in financial services at Intercontinental Exchange. In 2018, she became the founding CEO and first employee of the fintech startup, Bakkt, which brought institutional infrastructure to crypto. Kelly was appointed to serve in the U.S. Senate in 2020 and later confirmed as Administrator of the Small Business Administration in February 2025.
We begin our conversation with Kelly's entrepreneurial journey, before diving into her mission at the SBA. Her leadership comes at a pivotal juncture: a $10 trillion generational wealth transfer amid a technological revolution. As Baby Boomers retire and new AI tools emerge, Kelly believes young talent should think twice about traditional pathways and consider small business ownership instead. She lays out the administration's agenda, including expanding SBA loans for reindustrialization and bolstering the manufacturing jobs of the future. Next, we dive into her other core responsibility: exposing fraud. Learn how the SBA uncovered over $400 million of COVID-era fraud in Minnesota, $9 billion in California, and they're just getting started. She's also investigating 8(a) minority contracting — a program for disadvantaged communities hijacked by the Biden administration for race-based contracting and grift. The SBA is bringing in top talent and technology, including Palantir, to expose the fraud, revamp the programs, and protect taxpayers.
00:00 Episode intro
01:40 Farming to finance
04:46 Building Bakkt & institutional infrastructure for crypto
09:00 AI & the future of small business
13:58 How to supercharge manufacturing in America
16:15 Exposing billions in fraud
18:50 The scandal of minority contracting
20:25 Using Palantir to investigate fraud
27:15 The NGO grift scheme
29:50 Optimism for the future


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

As a teenager, Jared Isaacman built a billion-dollar payments company. He then pursued aviation, acquiring the world's largest private air force and creating “Top Gun as a service,” before commanding the first all-civilian spaceflight. Now, he's taking on his greatest challenge: returning NASA to greatness. Can we beat China back to the Moon? Will we reach Mars within a decade? And how close are we to making nuclear propulsion, space colonies, and other sci-fi futures a reality? We discuss all this and more with NASA Administrator Jared Isaacman. We begin with his upbringing and the origins of Shift4 Payments, which now processes more than $200 billion annually. A prolific pilot, he went on to build Draken International and acquire over 100 fighter jets for adversary training — at one point, he owned the 12th largest air force in the world! Next, we dive into his experience as a commercial astronaut and why he sought the helm of NASA. Jared outlines his bold vision to reform NASA, starting with his announcement to increase the Artemis launch cadence and ensure a return to the Moon by 2028. We discuss the challenges of building a permanent Moon presence, and why nuclear power and propulsion in space is a NASA-unique mission that will attract top talent and help the agency achieve greatness again. Finally, we explore the growing space economy and exciting sci-fi realities we will experience in the years ahead. NASA is a storied American institution; we are fortunate to have a talented leader like Jared who wants to see it not only thrive again, but reach even greater heights.
00:00 Episode intro
01:30 Top Gun as a service
07:40 Founding a billion-dollar payments company
09:30 Pioneering private spaceflight
12:00 What happened to NASA?
14:40 Getting back to the Moon by 2028
20:47 Jared announces new plans for Artemis
25:15 Future of the space economy
27:50 Nuclear power in space
29:00 Sci-fi futures becoming reality


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

JD Ross is one of my favorite entrepreneurs. I hired him out of college at Addepar where he quickly became Head of Product. He went on to co-found Opendoor with Keith Rabois and is now building WithCoverage — one of the fastest growing AI-first service companies. JD believes we're entering an "invention era" again. What are the new possibilities with AI? What does it mean for legacy software companies? And why is he especially excited for young talent entering the workforce today?We discuss all this and more, starting with JD's entrepreneurial journey, from founding a moving company in college (that still generates +$10M a year in sales!) to joining Addepar and later founding Opendoor. We discuss some of the breakthroughs and challenges at Opendoor, and why its meme stock moment is infusing new energy and ideas into the company. Next, we dive into WithCoverage and his mission to upend the insurance brokerage industry by combining new AI tools with human expertise — think Ramp for risk management. Initially backed by 8VC, WithCoverage already serves more than 700 enterprise customers and recently closed a $42 million round led by Sequoia and Khosla Ventures. Talented builders like JD are scaling and iterating on new products faster than anything we've seen before — learn what this means for the startup ecosystem, as well as existing SaaS companies looking over their shoulders. Finally, JD explains how AI is leveling the playing field and why he believes this is the best opportunity for new entrepreneurs in recent decades.
00:00 Episode intro
01:28 JD's entrepreneurial journey
05:18 Wins and challenges at Opendoor / meme stock moment
09:55 WithCoverage and upending insurance brokerage with AI
13:11 Mimetic frameworks for entrepreneurs
15:45 How AI is changing the way companies are built
20:21 The impact of AI on existing SaaS
26:50 How to stop AI spam and imposters
31:27 How should young people prepare for the AI era?
34:20 The new invention era / why AI levels the playing field


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

Advances in AI are occurring at a pace we haven’t seen before in Silicon Valley. How do we know what’s real versus hype? What does it mean for large software incumbents? And how are the top investors and builders thinking about the new possibilities? This week, we talk with two of my partners at 8VC, Alex Kolicich and Jack Moshkovich, who are on the ground working with the leading AI talent to get their perspective on what’s really happening.
Alex Kolicich is a Partner at 8VC, where he specializes in IT and Bio-IT investments. Prior, he was a Partner at Formation 8 and worked alongside Peter Thiel at Mithril Capital Management. Alex was also an engineer and early-product advisor at Clarium, Palantir, and Google. Jack Moshkovich began his career at 8VC and helps lead our investment practice alongside Alex out of San Francisco, where he focuses on enterprise software.
We begin with Silicon Valley’s most recent technological wave: smart enterprise. In 2013, we published our smart enterprise thesis, predicting the B2B software explosion that drove tremendous value creation over the past decade. Now, we’re entering the next landmark shift: the AI wave. Learn why AI is fundamentally disruptive (you can find our thesis here), and the enormous leap from data retrieval to automated decision making and from linear to non-linear problem solving. Next, we dive into the six layers of the AI investment stack, and why we are focused on level five: the application layer. We dissect the tremendous opportunities for AI-native upstarts, as well as the challenges — and upside — for smart enterprise pioneers that can reorient around AI. Finally, we discuss some of the key questions in the years ahead: When and where will we see massive productivity gains in the economy? Will LLMs become commodities, or is each frontier model sufficiently differentiated? And are we entering a bubble, or is the AI wave just getting started?
00:00 Episode intro
01:40 Smart enterprise thesis
04:00 Did enterprise software dramatically boost productivity?
08:30 Understanding the AI wave
11:45 Are LLMs becoming commodities?
17:10 OpenAI vs Anthropic vs Meta vs Grok
20:30 Frontier models vs enterprise incumbents
25:20 What did Palantir get right?
32:30 AI case studies/new possibilities
43:00 The most surprising aspect of the AI wave
46:10 Are we entering a bubble? Or just getting started?
52:40 Biggest concern with AI
58:00 Biggest reason for optimism


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