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Where Brad Gerstner Is Investing Billions May 29, 2026

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This is our full conversation with Brad Gerstner, recorded live on TBPN.

We discuss why he believes the AI boom is still in its early innings, how companies like Anthropic, Nvidia, and Snowflake are benefiting from the AI infrastructure buildout, why America must continue investing in data centers and compute capacity to stay ahead of China, and his vision for Trump Accounts, a new initiative designed to give every child a stake in the American economy through long-term stock ownership.

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Blue Origin Explosion, Enterprise AI Hits Spending Limits, Dinosaur Market Booms | John Gruber, Ronak Malde, Zane Mountcastle, Jamie Cuffe, Kyle Kuzma, Brad Gerstner May 29, 2026

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(00:43) - Blue Origin Explosion
(07:38) - Enterprise AI Hits Spending Limits
(21:48) - Dinosaur Market Booms
(29:13) - John Gruber, a prominent technology writer and podcaster, discusses the Ferrari Luce's design, expressing that its appearance deviates from traditional Ferrari aesthetics, making it hard to identify as a Ferrari without its nameplate. He also reflects on Apple's design philosophy, emphasizing their commitment to creating products that prioritize functionality and user experience over following market trends. Additionally, Gruber highlights the challenges Apple faces in integrating AI technologies, noting the importance of balancing innovation with maintaining the company's core values and user trust.
(01:11:16) - Ronak Malde, formerly an AI researcher at Windsurf and Google DeepMind, co-founded Trajectory, a startup focused on building a platform for continual learning in AI systems. In the conversation, he discusses raising $15 million from Conviction and partnering with companies like Harvey, Decagon, Clay, Rogo, and Mercor to develop agents that learn from real-world user interactions, enabling AI products to improve daily. Malde emphasizes the importance of creating AI agents with practical experience that understand business-specific rewards, allowing for efficient post-training and continual enhancement of AI capabilities.
(01:19:18) - Zane Mountcastle, co-founder and CEO of Picogrid, discusses the company's recent $45 million Series A funding led by Bessemer Venture Partners, aimed at expanding their team and scaling production to meet increasing demand. He explains that Picogrid develops technology to integrate mission-critical systems like sensors, drones, and weapon systems, primarily for military applications, by building open infrastructure that enables these systems to work together. Mountcastle also highlights the company's active contracts with the Pentagon, NATO, and allied partners, emphasizing their focus on serving military needs while acknowledging potential future commercial applications.
(01:25:10) - Jamie Cuffe, CEO of Pace, announced the company's $46 million Series B funding co-led by Thrive Capital and Sequoia, with participation from Emergence and Pruven. He discussed how Pace's AI agents are automating back-office operations for major insurers like Prudential and Convex, achieving over 99.9% accuracy and enabling clients to autonomously complete hundreds of thousands of tasks daily. Cuffe emphasized that this automation is helping insurers close the $9 trillion protection gap by making insurance more accessible and efficient.
(01:32:57) - Kyle Kuzma, an American professional basketball player for the Milwaukee Bucks, discusses his journey into investing, inspired by mentors like Kobe Bryant, and emphasizes the importance of focusing on basketball while exploring ventures in the tech and private investment sectors. He highlights the significance of leveraging his unique position as an athlete to access investment opportunities and stresses the value of surrounding himself with knowledgeable individuals to navigate the complexities of the investment landscape. Kuzma also touches on the evolving role of AI in basketball, expressing a cautious perspective on its influence on the game.
(01:50:08) - Brad Gerstner is the founder and CEO of Altimeter Capital, a technology-focused investment firm that invests across public and private markets. Known for his high-conviction bets on companies such as Snowflake, Meta, and Uber, he is a frequent commentator on technology, AI, capital markets, and long-term investing.

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Reactions: Ferrari’s First EV, The Enhanced Games | Diet TBPN May 26, 2026

Show notes

Diet TBPN delivers the best of today’s TBPN episode in 30 minutes. TBPN is a live tech talk show hosted by John Coogan and Jordi Hays, streaming weekdays 11–2 PT on X and YouTube, with each episode posted to podcast platforms right after.

Described by The New York Times as “Silicon Valley’s newest obsession,” the show has recently featured Mark Zuckerberg, Sam Altman, Mark Cuban, and Satya Nadella.

The Lean Startup Author on What Ruins Good Companies May 26, 2026

Show notes

This is our full conversation with Eric Ries, recorded live on TBPN.

We discuss why successful companies drift away from the principles that made them great, how short-term incentives and quarterly reporting can damage long-term value creation, why companies like Costco and Patagonia have built mission-first cultures that resist outside pressure, and how governance structures like public benefit corporations and long-term trusts could reshape the future of capitalism.

Ferrari EV, Enhanced Games, Alcohol & Podcasting | Christopher Hale, Sean Henry, Eric Ries, Alex Atallah May 26, 2026

Show notes

(00:27) - Ferrari EV
(40:58) - Enhanced Games
(47:41) - Christopher Hale, a Catholic writer and former executive director of Catholics in Alliance for the Common Good, discusses Pope Leo XIV's recent encyclical on artificial intelligence, highlighting the Pope's emphasis on maintaining human dignity and responsibility in technological advancements. He notes the Pope's concern over delegating human decisions to machines, especially in contexts like warfare, and underscores the call for Silicon Valley to consider the ethical implications of AI development.
(01:10:48) - Alcohol & Podcasting
(01:17:21) - Sean Henry, co-founder and CEO of Stord, announced the company's recent $250 million funding round, elevating its valuation to $3 billion. He discussed Stord's decade-long development of a vertically integrated platform that leverages robotics and AI to enhance commerce, enabling faster deliveries and cost efficiencies. Henry also highlighted the launch of Stord Labs, dedicated to testing next-generation robotics and AI, and the company's international expansion into markets like Canada, Europe, China, and Australia.
(01:31:05) - Eric Ries is an entrepreneur and author best known for The Lean Startup, which helped popularize iterative product development and rapid experimentation in startups. He is also the author of The Startup Way and Incorruptible, where he explores institutional trust, governance, and how organizations can remain resilient and accountable at scale.
(02:09:45) - Alex Atallah, co-founder and CEO of OpenRouter, discusses the evolution of AI models and the importance of neurodiversity in AI agents selecting cost-effective tools for specific tasks. He highlights OpenRouter's recent $113 million funding round, led by Capital G with participation from existing investors and strategic partners like Nvidia, ServiceNow, and Databricks, emphasizing the company's commitment to fostering a diverse team. Atallah also addresses the trend of companies optimizing AI inference costs by utilizing multiple models tailored to specific tasks, leading to significant cost savings and improved performance.
(02:22:45) - 𝕏 Timeline Reactions

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IPO Giga Boom, World’s Fairs of the Past | Diet TBPN May 22, 2026

Show notes

Described by The New York Times as “Silicon Valley’s newest obsession,” the show has recently featured Mark Zuckerberg, Sam Altman, Mark Cuban, and Satya Nadella.

Starship Launch, World's Fair Retrospective, Sacks Spikes AI EO | Dan Shipper, James Rogers May 22, 2026

Show notes

(01:01) - Sacks Spikes AI EO
(07:56) - America's IPO Market Wakes Up
(17:47) - Starship Launch
(28:28) - World's Fair Retrospective
(45:46) - Dan Shipper, co-founder and CEO of Every, discusses the transformative impact of AI agents like Codex and Claude Code on knowledge work, highlighting how these tools have automated tasks in coding, writing, design, and customer service, leading to Every's growth from 4 to 30 employees since GPT-3. He emphasizes that while AI makes expert competence more accessible, it simultaneously increases the demand for human expertise to provide judgment and differentiation, as AI outputs often require human framing and evaluation to be truly valuable. Shipper also notes that AI enables small, generalist teams to accomplish tasks that previously required larger, specialized organizations, allowing for a more fulfilling and versatile work experience.
(01:09:01) - James Rogers is the founder and CEO of Apeel Sciences, a company developing plant-based coatings that extend the shelf life of fresh produce and reduce food waste. He launched the company out of research funded by the Bill & Melinda Gates Foundation, with a focus on improving global food distribution and sustainability through materials science.

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SpaceX S-1, Anthropic Revenue Booms, OpenAI Cracks Erdős Problem | Diet TBPN May 21, 2026

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Described by The New York Times as “Silicon Valley’s newest obsession,” the show has recently featured Mark Zuckerberg, Sam Altman, Mark Cuban, and Satya Nadella.

SpaceX IPO, The Erdős Problem, Spotify CEO Joins | Alex Tabarrok, Bill Clerico, Alex Norström, Jordan Schneider, Christina Lee Storm, Erik Bernhardsson May 21, 2026

Show notes

(01:25) - SpaceX IPO
(12:37) - Anthropic Revenue Surges
(17:31) - OpenAI Solves the Erdős Problem
(27:53) - Alex Tabarrok, a Canadian-American economist and professor at George Mason University, co-authors the Marginal Revolution blog and co-founded Marginal Revolution University. He discusses the Baumol effect, explaining how sectors with stagnant productivity, like education and healthcare, experience rising costs due to increasing wages in more productive industries. Tabarrok also explores the potential of AI to mitigate this effect by enhancing productivity in traditionally labor-intensive sectors.
(01:02:22) - Bill Clerico, founder and managing partner of Convective Capital, discusses the firm's recent $85 million fundraise, doubling their previous fund, to invest in disaster resilience technologies. He highlights the increasing frequency and severity of disasters due to aging infrastructure and climate change, emphasizing the need for private market solutions. Clerico also shares insights into the fire technology market, noting the challenges and opportunities in selling to utilities, insurance companies, and government agencies, and underscores the importance of technological innovation in enhancing disaster preparedness and response.
(01:15:12) - Alex Norström, Spotify's Co-Chief Executive Officer since January 2026, discusses the company's recent Investor Day, highlighting significant user growth and financial achievements over the past four years. He introduces four major future initiatives, including a new feature that reserves concert tickets for premium users, addressing challenges like ticket scarcity and scalping. Norström also emphasizes Spotify's advancements in AI, particularly in enhancing user experience and content personalization.
(01:36:38) - Jordan Schneider is the creator of the ChinaTalk podcast and newsletter, focusing on China, technology, and U.S.-China relations. In this conversation, he discusses the recent U.S.-China summit, highlighting the stalemate in relations and China's leverage over the U.S. through rare earths. He also touches on the absence of key AI leaders at the summit and the implications for future technological collaboration.
(02:02:17) - Christina Lee Storm, Head of Studio at Secret Level and co-founder of Playbook PLBK, discusses the evolving role of AI in film production, emphasizing its integration as a natural progression in storytelling rather than a disruptive force. She highlights the importance of embracing technology to enhance creativity and efficiency, while underscoring that compelling storytelling remains paramount. Storm also reflects on the potential for AI to democratize filmmaking, enabling independent creators to produce high-quality content, provided they maintain a strong focus on narrative depth.
(02:14:28) - Erik Bernhardsson, co-founder and CEO of Modal Labs, discusses the company's recent Series C funding round, raising $355 million at a $4.65 billion post-money valuation led by General Catalyst and Redpoint Ventures. He highlights the rapid growth of their Sandboxes product, which has been doubling in usage every month for the past six months, enabling safe execution of language model-generated code. Bernhardsson also addresses the challenges of demand planning in the AI infrastructure space, emphasizing the need to secure GPUs months in advance to accommodate their 30-40% monthly growth rate.
(02:25:14) - 𝕏 Timeline Reactions

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Google I/O: Day 1 Reactions, Goldman to Lead SpaceX IPO | Diet TBPN May 20, 2026

Show notes

Described by The New York Times as “Silicon Valley’s newest obsession,” the show has recently featured Mark Zuckerberg, Sam Altman, Mark Cuban, and Satya Nadella.

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