Two decades ago, Aydin Senkut was a first-time fund manager with a thin track record to show prospective backers. LPs didn’t believe a solo GP, especially one without experience at a legacy firm, could build a lasting franchise. They were wrong. Today, Felicis is a Silicon Valley mainstay on its 10th fund, a $900M vehicle. Across its history, Felicis has backed a slew of winners, including Shopify, Canva, Crusoe, and dozens of other billion-dollar outcomes. Rather than specialize over time, Aydin has remained a true generalist, investing across markets and cycles. In this conversation, we dig into the frameworks, stories, and philosophies that shaped Felicis into what it is — and where Aydin believes the next decade of technology is heading.

We explore:

• How growing up in Turkey with entrepreneur parents shaped Aydin’s approach to risk and investing
• Lessons from working alongside Larry Page and Sergey Brin during Google’s early days
• Why Felicis deliberately chose a generalist strategy when most VCs were specializing
• How international experience became a competitive advantage in finding global winners
• The mathematical case for portfolio diversification (50-70 companies per fund)
• Why valuation concerns are often overblown when revenue growth is exponential
• Felicis’s aggressive AI investment strategy and what other investors are missing
• The future of robotics and physical AI through companies like Skild AI
• Why learning and adapting rapidly is Felicis’s constitutional principle

—

Thank you to our sponsor, Guru: The AI source of truth for work.

—

Transcript: https://www.generalist.com/p/why-being-a-generalist-vc-is-a-competitive-advantage

—

Timestamps

(00:00) Introduction

(03:09) How Aydin made his way to Silicon Valley

(06:15) What he learned from his entrepreneurial parents

(08:55) Learnings from the early days at Google

(15:05) The childhood roots of his investing philosophy

(16:31) Why rejection became a catalyst for his venture career

(19:28) Strategy behind Felicis's first $41M fund

(25:44) How his international background became an investing edge

(28:17) How Aydin approaches diversification at scale

(32:08) How he sizes investments based on conviction

(33:15) Generalist vs. specialist investing

(38:23) Why founders are the foundation

(42:48) Why success may look different than expected

(43:46) The Felicis journey

(48:18) Why Felicis is going all in on AI

(54:54) Why entry point matters less than potential

(57:33) How the AI bubble debate misses the point

(59:47) What makes Skild AI a standout company

(01:04:58) The AI bets Felicis missed

(01:07:55) How missing Airbnb and Uber led to backing Adyen

(01:11:20) Final meditations

—

Follow Aydin Senkut

LinkedIn: https://www.linkedin.com/in/aydins

X: https://x.com/asenkut

—

Resources and episode mentions

—Books—

• Antifragile: Things That Gain from Disorder: https://www.amazon.com/Antifragile-Things-That-Disorder-Incerto-ebook/dp/B0083DJWGO
• Clear Thinking: Turning Ordinary Moments into Extraordinary Results: https://www.amazon.com/Clear-Thinking-Turning-Ordinary-Extraordinary/dp/0593086112

—People—

• Larry Page: https://en.wikipedia.org/wiki/Larry_Page
• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin
• Eric Schmidt: https://en.wikipedia.org/wiki/Eric_Schmidt
• Brian Chesky on X: https://x.com/bchesky
• Shane Parrish’s blog: https://fs.blog

—Other resources—

• Felicis: https://www.felicis.com
• Mastering Portfolio Construction: https://www.generalist.com/p/mastering-portfolio-construction
• Steve Jobs’s quote on focus: https://www.goodreads.com/quotes/629613-people-think-focus-means-saying-yes-to-the-thing-you-ve
• Angry Birds: https://www.angrybirds.com
• Rovio: https://www.rovio.com
• Adyen: https://www.adyen.com
• Canva: https://www.canva.com

...Resources continued at: https://www.generalist.com/p/why-being-a-generalist-vc-is-a-competitive-advantage⁠

—

Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

Prediction markets are no longer a fringe curiosity. They are becoming one of the most revealing instruments in modern finance. Platforms like Polymarket, once a niche corner of crypto, now regularly clear billions in monthly volume as traders speculate on everything from political outcomes to sports to cultural events. Few people saw this future as early, or as clearly, as Joey Krug.

A decade before prediction markets went mainstream, Joey dropped out of college to co-found Augur, the first decentralized prediction market protocol. He later became one of the most influential investors in the category by backing Polymarket at Founders Fund. In this conversation, Joey shares why the moment for prediction markets has finally arrived, what has changed, and how these markets are reshaping information flows across society.

We explore:

• The experimental mindset that led Joey from horse-racing predictions to mining bitcoin in high school
• Why Augur was the right idea at the wrong moment, and what it taught Joey about timing and infrastructure
• The product, liquidity, and founder-market fit signals that persuaded Founders Fund to back Polymarket
• Why resolution is the hardest problem in prediction markets, and how Polymarket approaches it
• How crypto treasury companies are emerging as a major force and where ETFs fit in
• Why mimetic behavior drives entire sectors and how savvy investors read those waves
• The rise and fall of Operation Choke Point and its impact on crypto
• How Founders Fund reframed Joey’s approach to evaluating founders, markets, and structural shifts

—

Thank you to the partners who make this possible

Guru: The AI source of truth for work.

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Transcript: https://www.generalist.com/p/joey-krug-on-prediction-markets

—

Timestamps

(00:00) Intro

(04:10) How Joey began making predictions with horse racing

(08:00) Why Joey began coding with Applesoft BASIC

(09:32) How Joey first discovered crypto

(11:06) Why Joey dropped out of school to pursue crypto

(12:52) The origins of Joey’s interest in medical school

(16:15) How Joey spends nights and weekends splitting time between biotech and trading

(17:18) The early influences behind Augur’s creation

(19:40) Why prediction markets captivated early crypto thinkers

(23:26) The unlock crypto created for prediction markets

(29:22) How Polymarket began and why Joey decided to back it

(32:11) What made Polymarket the right team

(35:25) The FBI raid and how Shane responded

(38:20) Why Joey expected Polymarket’s volume to hold after the election

(40:20) The trend toward duopolies in financial markets

(42:37) What sets Polymarket’s product design apart

(45:25) How to keep prediction markets clear and unambiguous

(48:31) The rise of crypto treasury companies and FF’s work with BitMine

(51:26) The value of crypto treasuries and the role of ETFs

(54:33) The mimetic rise of crypto treasury companies

(57:03) Joey’s take on where the crypto market stands now

(1:00:23) Why Founders Fund is bullish on ETH

(1:03:03) Operation Choke Point, regulatory whiplash, and the end of the crypto crackdown

(1:06:04) Where the Clarity Act falls short

(1:08:56) How Joey’s thinking has evolved since joining Founders Fund

(1:13:21) Final meditations

—

Follow Joey Krug

LinkedIn: https://www.linkedin.com/in/joeykrug

—

Resources and episode mentions: https://www.generalist.com/p/joey-krug-on-prediction-markets⁠

—

Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

In the summer of 2022, Parth Garg woke up in Bangalore to discover that his co-founder had fled the country and emailed their investors to tell them their company was dead. Just over three years later, Aspora is one of fintech’s fastest-growing startups. The company, which makes it faster and cheaper for India’s diaspora to send money home and access banking services, now processes close to half a billion dollars in volume every month and has earned a $500 million valuation with backing from elite investors like Hummingbird Ventures, Sequoia, and Greylock.

In this conversation, Parth shares his journey from physics prodigy to fintech founder, offering insights into what it really takes to build resilience as a founder and how to create a culture where feedback flows freely, even without a co-founder to provide checks and balances.

—

We explore:

• The moment when Parth discovered his co-founder had left the country and told investors the company was shutting down

• How Parth’s childhood moving between cities in India and later to the UAE shaped his adaptability and entrepreneurial mindset

• His journey from physics prodigy to startup founder, including early ventures before Aspora

• The process of discovering product-market fit through structured experimentation after the initial business model failed

• Why the Indian diaspora represents a massive, underserved financial opportunity (1% of the population contributing 30% of deposits)

• How stablecoins dramatically reduced Aspora’s working capital requirements and transformed their business model

• The regulatory landscape for fintech and crypto in India and the impact of the GENIUS Act in the US

• Aspora’s vision to become a comprehensive cross-border bank serving multiple diaspora communities globally

—

Thank you to the partners who make this possible

GoFundMe Giving Funds: One Account. Zero Hassle.

Guru: The AI source of truth for work.

Persona: Trusted identity verification for any use case.

—

Timestamps

(00:00) Intro

(03:53) How Parth felt when his co-founder fled the country

(07:04) Parth’s early days in India and the UAE

(09:37) Parth’s love of physics and competitiveness

(12:15) The not-so-straightforward path from studying physics at Stanford to entrepreneurship

(14:13) Parth’s physics heroes

(16:24) The gap year that sparked Parth’s entrepreneurship journey

(18:36) Parth’s first startup: selling near-expired groceries

(21:58) Moving back to the United States and founding Vance

(28:00) Joining YC and finding early backers

(31:14) How Parth realized Vance needed to pivot

(35:22) How Parth moved forward after his co-founder fled

(37:37) Building psychological safety and open debate at Aspora

(40:15) How conversations with immigrants inspired Aspora’s idea

(45:13) How stablecoins solved Aspora’s biggest operational challenges

(46:57) Aspora’s current scale and why India was the perfect starting point

(51:34) How Aspora builds loyalty in a low-switching-cost market

(52:42) The GENIUS Act and the real opportunity in stablecoins

(55:52) The evolution of crypto and stablecoins in India

(56:50) The importance of partnerships for scaling Aspora in India

(58:18) The next phases of Aspora’s growth

(01:00:04) The role of Aspora’s new bets team

(1:01:20) Final meditations

—

Follow Parth Garg

LinkedIn: https://www.linkedin.com/in/parth29

—

Resources and episode mentions: https://www.generalist.com/p/banking-the-diaspora-parth-garg

—

Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

What if you could redesign the rules of society? Not tweak the margins, but start over entirely. That’s the question driving Erick Brimen, founder and CEO of Próspera, a private charter city in Roatán, Honduras. Próspera is a radical experiment in governance: a platform that lets governments and entrepreneurs build cities with new legal systems, regulatory frameworks, and institutions from the ground up. Brimen believes that governance itself can be innovated upon. That cities, like software, can be upgraded. His goal isn’t just to build one new jurisdiction, but to create an operating system for hundreds of prosperous, self-governing communities around the world. In this conversation, Erick and I explore what it really takes to build a modern Singapore from scratch — and why better governance might be humanity’s most powerful lever for progress.

Together we explore:

• How Brimen’s childhood in Venezuela shaped his understanding of governance and poverty

• The historical precedents for charter cities like Dubai, Singapore, and Hong Kong

• Why common law, trusted dispute resolution, and dynamic governance are essential foundations

• How Próspera’s Governance-as-a-Service model aligns incentives between governments, operators, and residents

• The current state of Próspera in Honduras, including its three hubs and economic impact

• The political challenges Próspera has faced and how international arbitration has protected the project

• Why regulatory innovation enables industries like biotech, crypto, and advanced manufacturing to flourish

• How the model could be applied to “catch-up growth,” industry diversification, and accelerating growth in developed nations

• The vision for a modern Hanseatic League of charter cities operating on shared governance principles

—

Thank you to the partners who make this possible

GoFundMe Giving Funds: One Account. Zero Hassle.

Guru: The AI source of truth for work

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—

Transcript: https://www.generalist.com/p/the-170m-experiment-to-build-a-private-city

—

Timestamps

(00:00) Intro

(04:10) An overview of Próspera and charter cities

(06:43) City of Próspera vs. the platform

(08:06) How growing up in Venezuela shaped Erick’s entrepreneurial vision

(12:36) The limits of seasteading and why Erick took a different path

(15:20) The opposing philosophies that shaped Erick’s path

(16:16) The moment that reshaped Erick’s understanding of poverty

(19:57) The limits of learning from Dubai, Singapore, and Hong Kong

(23:01) Building on the DIFC blueprint

(25:12) From Arizona to Honduras: how Próspera built its first city

(30:36) Why Honduras won

(32:12) Inside the ZEDE framework

(36:56) Próspera’s business model

(43:45) Conditions on the ground in Honduras

(47:14) A quick summary of how it works

(48:24) Quick stats on Próspera’s scale and financing

(50:47) What years of preparation made possible

(52:44) The scale and purpose of Próspera’s three hubs

(58:12) Próspera’s 10-year vision

(1:01:12) The people Próspera was built to serve

(1:04:10) Why less regulation unlocks more innovation

(1:05:58) Próspera’s political headwinds

(1:12:36) Why Erick remains optimistic that things will work out in Honduras

(1:14:44) Addressing criticism of ZEDEs and Próspera

(1:18:08) What’s next, and why the U.S. may be the greatest opportunity

(1:22:30) Final meditations

—

Follow Erick Brimen

LinkedIn: https://www.linkedin.com/in/erickbrimen

Website: https://www.erickbrimen.com

—

Resources and episode mentions: https://www.generalist.com/p/the-170m-experiment-to-build-a-private-city

—

Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

Often called the godfather of NYC tech, Kevin Ryan is one of America’s most influential entrepreneurs and investors. He co-founded MongoDB, Business Insider, Gilt Groupe, Zola, and Transcend Therapeutics, and continues to build and back new companies each year through AlleyCorp. Earlier in his career, he led DoubleClick from a 20-person startup to a global leader, taking it public before its acquisition by Google.

In this episode, Kevin shares his insights on two surprising pockets of the future that he’s betting on: psychedelics for mental health and AI-powered materials science. He unpacks how psychedelics are showing remarkable success in treating depression and PTSD, and why AI may discover revolutionary new materials, from helicopter blades to smartphone glass, that humans never imagined possible.

We explore:

• The promising results of psychedelics in treating depression, PTSD, and addiction

• How AI is accelerating materials discovery by exploring combinations humans wouldn’t try

• The challenges of building successful incubators and why most attempts fail

• How MongoDB lost $1 billion before turning a profit (and why it was worth it)

• Why e-commerce businesses like Gilt Groupe often struggle against physical retail

• How AlleyCorp plans for the future when shaping its investment strategy

• What it really costs society to imprison someone for a year

• The hard truth about Europe’s tech ecosystem and why it struggles to compete with the US

—

Thank you to the partners who make this possible

Enterpret: Transform feedback chaos into actionable customer intelligence.

Auth0: Secure access for everyone. But not just anyone.

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—

Transcript: https://www.generalist.com/p/why-psychedelics-might-be-the-breakthrough

—

Timestamps

(00:00) Intro

(04:30) How Kevin collaborated with Scott Adams

(07:11) The origins of AlleyCorp

(08:33) The challenge of incubation

(10:00) Why intellectual flexibility matters

(10:54) What made MongoDB a breakout success

(13:49) How shifting market dynamics hurt Gilt’s business

(16:22) What Kevin would do differently if he built Gilt again

(17:45) Juggling AlleyCorp’s long-term vision with day-to-day demands

(20:26) How to make boards more productive

(22:25) Why Kevin believes investors should also found companies

(24:18) Future spaces Kevin is excited to invest in

(25:52) Kevin’s interest in psychedelics and founding Transcend

(28:20) Psychedelics for mental health

(32:03) How psychedelic therapy is being conducted

(34:11) Transcend’s work and the path to approval for methylone

(37:47) The challenges of psychedelic research

(40:28) How the Trump administration aims to accelerate psychedelic research

(41:50) The size and growth of the psychedelic market

(44:28) Materials science: What it is, its design tradeoffs, and how AI speeds discovery

(49:02) Radical AI’s work creating new compounds

(50:34) The industries Radical AI is targeting

(52:50) The state of European tech and why it still lags behind

(58:26) Final meditations

—

Follow Kevin Ryan

LinkedIn: https://www.linkedin.com/in/kevinryan3/

X: https://x.com/alley_corp

—

Resources and episode mentions

—Books—

• How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence: https://www.amazon.com/Change-Your-Mind-Consciousness-Transcendence/dp/1594204225

• Breakneck: China’s Quest to Engineer the Future: https://www.amazon.com/Breakneck-Chinas-Quest-Engineer-Future/dp/1324106034

• Why We Sleep: Unlocking the Power of Sleep and Dreams: https://www.amazon.com/Why-We-Sleep-Unlocking-Dreams/dp/1501144324

—

Episode resources continued at: ⁠https://www.generalist.com/p/why-psychedelics-might-be-the-breakthrough⁠

—

Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

Navin Chaddha has spent three decades at the forefront of innovation—first as a founder, and now as managing partner at Mayfield, one of Silicon Valley’s oldest venture firms. A 17-time member of Forbes’ Midas List, Navin has guided generations of entrepreneurs through waves of technological change, from the dot-com boom to the AI era. At Mayfield, he champions a philosophy rooted in the firm’s founding ethos: investing in people, not markets. That approach has shaped his perspective on what it takes to build enduring companies. In this conversation, Navin shares why $1 trillion in infrastructure spending is fueling a new hardware renaissance, how stealth startups are going from zero to billions in a year, and what it means for the future of innovation.

We explore:

• How “vibe coding” is democratizing technology creation through conversational, collaborative, and cognitive interfaces
• Why Navin believes the “vibe economy” will transform how we work, live, and play
• How Mayfield’s 56-year focus on “backing the jockey, not the racetrack” shapes its investment approach
• The massive opportunity in AI hardware infrastructure
• How stealth AI hardware startups are going from zero to billions in under a year
• How India’s tech ecosystem has evolved and where the real opportunities are today
• How cricket taught Navin crucial lessons about company building

—

Thank you to the partners who make this possible

GoFundMe Giving Funds: One Account. Zero Hassle.

Auth0: Secure access for everyone. But not just anyone.

Tezi: The AI agent for recruiting high-quality candidates quickly

—

Transcript: https://www.generalist.com/p/the-trillion-dollar-ai-hardware-opportunity

—

Timestamps

(00:00) Intro

(04:52) Cricket and its parallels to venture capital

(08:13) Navin’s journey to Silicon Valley

(10:28) Growing up in an entrepreneurial family

(12:00) Early mentors and becoming an “accidental entrepreneur”

(13:46) Navin’s first company and unconventional fundraising approach

(17:35) How Navin moved from founder to venture capitalist

(20:11) What has worked in India’s tech market and what hasn’t yet taken off

(23:31) The future of outsourcing in the AI era

(27:14) How Navin landed at Mayfield

(30:36) How Mayfield’s people-first approach works in practice

(34:50) Why Navin sees AI and vibe coding as the next great wave of innovation

(38:13) Why Navin believes AI will push humans to level up their skills rather than lose them

(44:50) The hardware opportunities that excite Navin and where Mayfield is investing

(48:49) An overview of photonics and why it matters now

(50:06) How Mayfield balances market insight, big ideas, and the people behind them

(52:50) The surprising pace of growth in AI hardware

(54:54) The timeline from idea to product and scale in hardware startups

(56:26) Final meditations

—

Follow Navin Chaddha

LinkedIn: https://www.linkedin.com/in/navinchaddha/

X: https://x.com/navinchaddha

—

Resources and episode mentions: https://www.generalist.com/p/the-trillion-dollar-ai-hardware-opportunity

—

Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

From a child prodigy in a genetics lab to building a company that can pause life itself, Laura Deming has made a career out of chasing time. At just eight years old she became obsessed with aging. At eleven, she joined Cynthia Kenyon’s pioneering longevity lab. At seventeen, she launched The Longevity Fund—one of the first venture firms dedicated to extending human healthspan. Now, she’s tackling her boldest challenge yet: building a “pause button” for biology.

As the co-founder of Until, Laura is developing reversible cryopreservation: the ability to cool living tissue to ultra-low temperatures, hold it there, and then bring it back fully functional. By achieving vitrification (the process of turning tissue into glass instead of ice), Until aims to make organ preservation, and eventually medical hibernation, a reality.

We cover:

• Why longevity was once stigmatized, and what changed to make it one of the most credible fields in biotech today

• Why Until’s approach focuses on preserving the living, not the dead

• The physics and biological challenges of scaling reversible cryopreservation from embryos to human-sized organs

• How vitrification is making cryopreservation possible

• How this breakthrough could transform organ transplantation by eliminating time constraints (and eventually enable medical hibernation)

• The philosophical and social implications of being able to “pause” life and effectively time travel into the future

• How growing up homeschooled in New Zealand shaped Laura’s unconventional way of thinking

• The story of how legendary biologist Cynthia Kenyon invited 11-year-old Laura into her lab, sparking her lifelong obsession with aging

• How she learned to embrace her weirdness and trust it as her creative superpower

—

Thank you to the partners who make this possible

GoFundMe Giving Funds: One Account. Zero Hassle.

Brex: The banking solution for startups.

Persona: Trusted identity verification for any use case.

—

Transcript: https://www.generalist.com/p/biological-time-travel-laura-deming

—

Timestamps

(00:00) Intro

(04:55) How Laura became interested in longevity at such a young age

(07:40) The impact of homeschooling on Laura’s thinking

(09:29) The invitation from Cynthia Kenyon that set Laura on her path at age 11

(10:39) Why pursuing longevity once meant working in the shadows

(14:20) Why Laura shifted into VC at The Longevity Fund

(17:24) How longevity transformed from fringe science to a legitimate field

(19:40) Why Laura was driven to start Until

(21:08) A simple explanation of reversible cryopreservation

(23:10) Science fiction’s explorations of cryo

(25:38) What sparked Laura’s interest in reversible cryo

(27:35) How cryonics and reversible cryo differ, and the mechanisms behind each

(29:00) Until’s roadmap, beginning with cryopreserved organs for transplantation

(34:00) The biggest challenges in developing preservable organs

(35:53) How cryopreservation works

(38:30) Until’s building philosophy

(42:34) How Laura learned to trust her weirdness

(49:10) Finding the right co-founder in Hunter Davis

(51:17) Future applications beyond medical necessity

(53:00) Unanswered questions in cryopreservation

(55:05) What’s missing in Hollywood’s portrayal of genius

(56:21) Laura’s unique process for exploring ideas

(59:58) Personal longevity practices

(01:01:30) The positive impact of Bryan Johnson’s work

(01:02:38) Final meditations

—

Follow Laura Deming

LinkedIn: https://www.linkedin.com/in/laura-deming-b255362a/

X: https://x.com/laurademing

Website: https://www.ldeming.com/

—

Resources and episode mentions: https://www.generalist.com/p/biological-time-travel-laura-deming⁠

—

Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

Martin Casado has lived through multiple tech waves—first as a founder, now as a16z’s leading voice on AI and infrastructure. He helped pioneer software-defined networking, then moved from academia to entrepreneurship, and today backs founders building at the frontier of technology as a General Partner at Andreessen Horowitz. In this conversation, Martin shares his unique perspective on the AI boom, his market-first investment philosophy, and why he believes we’re still in the early days of AI’s impact.

We explore:

• Martin’s path from game engines and simulations to investing at Andreessen Horowitz

• Why Martin believes we’re only in “1996” of the AI boom cycle with years to run before any bubble

• Why Martin approaches investing “from markets in” rather than “from companies out”

• Why the AI coding market represents a potential $3 trillion opportunity

• The transformation of Andreessen Horowitz from a small generalist partnership to a specialized 600-person organization

• The concerning dominance of Chinese companies in open source AI models

• Why Martin thinks AGI discussions encourage “lazy thinking” and obscure meaningful conversations

• How World Labs is solving the 3D representation problem that could unlock robotics, VR, and more

—

Thank you to the partners who make this possible

Auth0: Secure access for everyone. But not just anyone.

Brex: The banking solution for startups.

Persona: Trusted identity verification for any use case.

—

Transcript: https://www.generalist.com/p/this-feels-like-1996-martin-casado

—

Timestamps

(00:00) Intro

(04:50) Martin’s early career

(08:35) Martin’s shift from academia to founding his own company during an economic downturn

(11:25) The story behind Martin joining Andreessen Horowitz

(17:55) Ben Horowitz’s most impactful advice

(19:49) How Andreessen Horowitz has transformed since 2016

(22:20) Why product experience matters more than technical prowess for infrastructure investing

(26:26) Martin’s market-first investment philosophy

(28:39) Andreessen Horowitz’s framework for assessing founders and startups

(33:14) Why Martin thinks Hock Tan may be the best CEO today

(35:18) The controversy around non-consensus investing in early stages

(38:42) Why today’s AI boom reminds Martin of the mid-’90s tech environment

(44:38) How today’s AI boom differs from 2021’s tech bubble

(47:10) Why the promise of AI in organizations remains largely unrealized

(50:29) How Martin uses AI for coding and as a reading thought partner

(52:56) Why Martin doesn’t use AI for writing

(53:24) Martin’s interest in Eisenhower and historical parallels to today

(55:33) Two equally important paths for AI’s future

(58:33) Why Cursor stood out as the leader in AI coding tools

(01:01:14) The lack of inherent defensibility in AI and how to build moats

(01:03:30) World Labs’ mission to transform 2D images into 3D environments

(01:06:42) 3D’s emerging use cases and why the VR market may expand

(01:11:50) Why Martin isn’t an “AGI guy” and how the term erodes conversation quality

(01:14:59) How seeing AI as a continuum creates room for future products and investment

(01:16:28) The security and regulatory challenges of Chinese open-source AI models

(01:19:23) Final meditations

—

Follow Martin Casado

LinkedIn: https://www.linkedin.com/in/martincasado/

X: https://x.com/martin_casado

—

Resources and episode mentions

—Books—

• The Weirdest People in the World: https://www.amazon.com/WEIRDest-People-World-Psychologically-Particularly/dp/1250800072/

• The Beginning of Infinity: Explanations That Transform the World: https://www.amazon.com/Beginning-Infinity-Explanations-Transform-World/dp/0143121359

...References continued at: https://www.generalist.com/p/this-feels-like-1996-martin-casado⁠

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Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

Cate Hall is the CEO of Astera, a private foundation focused on AI risk and frontier technology. Before leading Astera, Cate’s unconventional career path took her from practicing law (including work on Supreme Court briefs) to becoming the world’s top-ranked female poker player in 2016. After overcoming personal struggles with addiction, she co-founded Alvea, a biotech company developing shelf-stable vaccines for pandemic response, before joining Astera. In this conversation, Cate shares insights on human psychology, agency as a learnable skill, and why she believes AI’s biggest risk may be a “soft takeover” in which humans gradually lose independence and meaning.

We explore:

• How Cate’s approach to poker focused on reading people rather than pure game theory, and why this contrarian strategy worked

• Why people who always try to “play” high status in conversations often have psychological issues

• The critical difference between ambition and agency, and why they’re often confused

• How LSD helped Cate break out of her career path and discover her own agency

• Why Cate believes we need a slowdown in AI development to develop the social technologies to manage it

• The challenge of maintaining meaning in human life as AI systems increasingly mediate our experiences

• How Astera is using investment as a philanthropic tool to help steer frontier technology development

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Thank you to the partners who make this possible

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Brex: The banking solution for startups.

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Transcript: https://www.generalist.com/p/how-to-be-agentic-in-the-age-of-ai-cate-hall

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Timestamps

(00:00) Introduction to Cate Hall

(03:56) Cate’s role as CEO of Astera

(04:52) Cate’s poker career and focus on live reading

(07:02) The intuitive ‘people radar’ Cate has in identifying exceptional talent

(11:16) Status dynamics in conversations

(16:13) The parallel between poker and startup evolution

(19:18) The German wave in poker and game theory

(24:22) Cate’s legal career and Supreme Court experience

(27:05) The difference between ambition and agency

(29:13) How LSD helped Cate discover her agency

(31:26) Leaving poker and dealing with mental health issues

(34:26) The founding story of Alvea

(38:14) The founding story of Astera

(43:15) Cate’s journey into AI risk

(45:50) The concept of a “soft takeover” and how AI might hollow out human experience

(49:46) The overwhelming challenge of addressing AI risk

(51:20) Astera’s approach to steering technology development

(53:15) Astera’s investment in Last Energy

(54:20) How philanthropy and investing work together at Astera

(57:22) Practical ways to increase personal agency

(1:07:20) Final meditations

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Follow Cate Hall

X: https://x.com/catehall

LinkedIn: https://www.linkedin.com/in/cate-hall-9a81a35/

Newsletter: https://usefulfictions.substack.com/

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Resources and episode mentions

—Books—

• Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296/

• Impro: https://www.amazon.com/Impro-Improvisation-Theatre-Keith-Johnstone/dp/0878301178

• Superintelligence: Paths, Dangers, Strategies: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/0198739834/

• The Righteous Mind: Why Good People Are Divided by Politics and Religion: https://www.amazon.com/Righteous-Mind-Divided-Politics-Religion/dp/0307455777/

—People—

• Jed McCaleb on LinkedIn: https://www.linkedin.com/in/jed-mccaleb-4052a4/

• Charlie Carrel on X: https://x.com/charlie_carrel

• Seemay Chou on X: https://x.com/seemaychou

• Ben Kuhn on X: https://x.com/benkuhn

Episode resources continued at: https://www.generalist.com/p/how-to-be-agentic-in-the-age-of-ai-cate-hall

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Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].

David Krakauer is a leading complex systems researcher and the president of the Santa Fe Institute, a unique institution dedicated to studying complex systems across disciplines. In this episode, David challenges conventional wisdom about AI, arguing that large language models pose a more immediate threat to humanity than commonly discussed existential risks—not by destroying us directly, but by eroding our cognitive capabilities through addictive, low-quality information.

We explore:

• Why David believes LLMs aren't intelligent at all and how the AI community misunderstands emergence

• The three dimensions of intelligence: inference, representation, and strategy—and which one LLMs lack

• How AI acts as a "competitive" rather than "complementary" cognitive technology, atrophying our thinking abilities

• What makes great minds unique, from analogical reasoning to the cultivation of unconscious creativity

• How Cormac McCarthy's approach to knowledge and creativity offers lessons for the AI age

• Why David believes the greatest threat from AI isn't existential risk but cognitive atrophy

• How to protect your mind against AI's addictive pull and maintain cognitive autonomy

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Thank you to the partners who make this possible

Brex: The banking solution for startups.

Enterpret: Transform feedback chaos into actionable customer intelligence

Persona: Trusted identity verification for any use case

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Transcript: https://www.generalist.com/p/maintaining-human-intelligence-in-the-ai-era-david-krakauer

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Timestamps

(00:00) Intro

(04:39) The Santa Fe Institute’s approach to complex systems

(06:45) Murray Gell-Mann’s ‘Odysseus vs. Apollonian’

(10:35) How SFI was shaped by the legacy of Los Alamos

(12:45) Traits David looks for in great minds

(14:43) Cormac McCarthy on naivety and how thoughtful people treat knowledge

(19:24) A simple explanation of complexity science

(22:50) Why vantage point doesn’t matter when studying systems

(24:36) Aesthetic preferences among complexity scientists

(26:07) Films and directors with complexity science themes

(29:57) Why David argues LLMs are not intelligent

(32:10) What’s missing in the study of LLMs

(36:40) The three qualities of intelligence and how LLMs measure up

(42:19) Lessons from "The Glass Bead Game"

(44:00) David’s perspective on reinforcement learning

(45:38) The greatest threat of LLMs: overreliance and the decline of thinking

(47:40) Competitive vs. complementary cognitive artifacts

(51:55) Why exposing yourself to quality ideas matters

(54:00) How to derisk LLM use

(58:32) Cormac McCarthy’s legacy at SFI and beyond

(1:02:40) The Kekulé Problem: cultivating the unconscious

(1:05:01) Why David and McCarthy were inspired by Wittgenstein

(1:09:00) What Cormac McCarthy liked to talk about

(1:12:20) David’s questions to a higher being

(1:14:46) Final meditations

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Follow David Krakauer

Website: https://davidckrakauer.com/

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Resources and episode mentions

—Books—

• “The Hedgehog and the Fox”: https://www.amazon.com/Hedgehog-Fox-Tolstoys-History-Second/dp/069115600X

• The Birds and The Frogs: https://www.amazon.com/Aristophanes-Frogs-Birds/dp/B000QBPUTY

• The Glass Bead Game: https://www.amazon.com/Glass-Bead-Game-Magister-Novel/dp/0312278497

• Frankenstein: https://www.amazon.com/Frankenstein-Mary-Shelley/dp/0486282112

• Blood Meridian: Or the Evening Redness in the West: https://www.amazon.com/Blood-Meridian-Evening-Redness-West/dp/0679728759

• Stella Maris: https://www.amazon.com/Stella-Maris-Cormac-McCarthy/dp/0307269000

• The Passenger: https://www.amazon.com/Passenger-Cormac-McCarthy/dp/0307268993/

• Pale Fire: https://www.amazon.com/Pale-Fire-Vladimir-Nabokov/dp/0679723420

...Episode resources continued at: https://www.generalist.com/p/maintaining-human-intelligence-in-the-ai-era-david-krakauer

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Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].