Invest Like the Best with Patrick O'Shaughnessy

Cliff Sosin is the founder of CAS Investment Partners, which he started in 2012. Roughly 80% of his portfolio is in Carvana.

We discuss why Cliff thinks there are hard limits to what even the smartest AI can predict, which businesses benefit as intelligence gets cheap, and what that means for Meta and the frontier labs.

We also cover why he avoids investing in the AI build-out, how AI agents will push customers to the lowest-cost provider, and why he is comfortable with 80% of his portfolio in one stock.

Please enjoy my conversation with Cliff Sosin.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠.

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⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus.

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Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠.

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WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel.

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Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest.

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⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠.

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Editing and post-production work for this episode was provided by The Podcast Consultant.

Timestamps:

(00:00:00) Why Intelligence Has Limits

(00:02:34) Chaos Theory and the Butterfly Effect

(00:04:59) A 200 IQ Team in Every Pocket

(00:07:33) Meta as Personalized TV

(00:11:18) The Frontier Labs as Businesses

(00:14:59) Jevons Paradox and the Limits of Demand

(00:18:47) Automated Labs and the Speed Limits of Experiments

(00:20:39) Why He Stays Away from the AI Build-Out

(00:22:28) Why the Best Entrepreneurs Are Building Supply

(00:24:22) Lessons from Past Capital Cycles

(00:26:05) TSMC and Physical Moats

(00:27:03) AI Agents and the Low-Cost Producer

(00:29:44) Will AI Replace Investors?

(00:32:01) Price as a Signal Wrapped in an Incentive

(00:34:16) America’s Underrated Capital Markets

(00:37:05) Why America Dominates Risk-Taking

(00:38:36) What Higher Rates Are Telling Us

(00:39:24) The AI Speech He Gives His Companies

(00:41:45) The Best Time to Start a Company

(00:43:03) Corporate Margins and Vertical Stacks

(00:45:16) AI and the Income Distribution

(00:48:13) Letting AI Size the Portfolio

(00:50:56) Why He Holds So Much Carvana

(00:52:22) Educating Kids in the Age of AI

My guest today is Christina Cacioppo, founder and CEO of Vanta, which helps more than 16,000 companies manage security and compliance.

Five years after our first conversation, we discuss how Vanta became a category leader, what it takes to reinvent a successful software business in the age of AI, and why Christina is betting on agents to do the work rather than simply assist users.

We also explore the changing economics of software, the war for exceptional talent, AI's impact on cybersecurity, and what it takes to build an enduring company in Silicon Valley's rapidly changing environment.

Please enjoy my conversation with Christina Cacioppo.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠.

-----

⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus.

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Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠.

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WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel.

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Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest.

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⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠.

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Editing and post-production work for this episode was provided by The Podcast Consultant.

Timestamps:

(00:00:00) How Vanta Won a Crowded Category

(00:03:12) Living Through the Software Selloff

(00:05:41) Building an Agent-First Product

(00:07:39) Why Vanta Eats the Cost of AI

(00:10:35) The Search for Outcome Pricing

(00:14:31) Getting People to Actually Use AI

(00:17:46) Why Comp for Top People Is Up 10X

(00:22:13) Valuations, Tenders, and the Endgame

(00:24:20) What’s Overhyped and Underhyped

(00:27:54) The Problem With FDEs

(00:29:34) Why French Startups Use Chinese Models

(00:30:22) Vanta as a Security Company

(00:36:57) What Makes a Great Talk

(00:40:14) Where She Would Invest Today

(00:45:19) The Billboard War

(00:49:35) The AI Trust Crisis

(00:51:39) Security Five Years From Now

David Vélez is the founder and CEO of Nubank, which serves 140 million customers across Latin America.

David believes the industry is still in its Blockbuster era, with most of the world's banking still running through branches and incumbent banks, and that AI will make digital banks dramatically more efficient than the incumbents they compete with.

He explains how Nubank rebuilt its entire organization around AI after missing the moment the technology started working, and why he is now bringing Nubank to the US, a market he says is still dominated by big incumbent banks.

Please enjoy my conversation with David Vélez.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠.

-----

⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus.

-----

Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠.

-----

WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel.

-----

Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest.

-----

⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠.

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Editing and post-production work for this episode was provided by The Podcast Consultant.

Timestamps:

(00:00:00) Banking Is Still In Its Blockbuster Era

(00:02:52) 140 Million Customers, 10,000 Employees

(00:04:53) What Banks Could Do in Five Years

(00:06:31) The $600 Billion Tax on Deposits

(00:08:06) A Private Banker for Everyone

(00:12:21) How a Startup Would Attack Nubank

(00:14:56) When Nubank Took AI Seriously

(00:17:08) Data as a Moat

(00:21:29) How Global Finance Will Change

(00:25:20) Stablecoins and the End of Cash

(00:28:45) Creating Creditworthiness

(00:32:35) Where Fintech Opportunities Remain

(00:34:19) Nubank Comes to the US

(00:41:11) Lessons From Disney and Amazon

(00:43:44) How to Sell AI to Nubank

(00:46:51) Agents as a Customer Segment

(00:48:39) How AI Changed Nubank

(01:01:33) What Motivates Him Now

(01:06:21) Founder Versus CEO

(01:14:01) What Latin America Needs

(01:15:40) The Bear Case for Nubank

(01:19:42) Finding the Right Mission

Andrew Huberman is a neuroscientist and professor at Stanford, the host of the Huberman Lab podcast, and the author of Protocols.

Most of our conversation is about where neuroscience goes next. For decades the field has focused on reading from the brain, and Andrew believes the next era is about writing to it with precise control over specific brain states.

He explains why he thinks the leading AI companies are really building toward this, and why understanding our waking brain states is the problem he most wants to see solved.

Please enjoy my conversation with Andrew Huberman.

For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.

-----

Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠.

-----

⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus.

-----

Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠.

-----

WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel.

-----

Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest.

-----

⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠.

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Editing and post-production work for this episode was provided by The Podcast Consultant.

Timestamps:

(00:00:00) Energy as the Bottleneck for Top Performers

(00:06:20) How to Downshift and Fall Asleep

(00:14:06) Neurotech for Sleep and Focus

(00:17:57) The State of Public Health Discourse

(00:22:07) The Biggest Problem in Neuroscience

(00:23:30) Why AI Companies Will Become Biotech Companies

(00:26:18) How We Read Brain Activity

(00:42:07) Crossing the Cyborg Line

(00:43:30) Measuring the Nervous System Directly

(00:57:34) The CRISPR Babies Story

(01:00:24) Embryo Screening and Genetic Engineering

(01:03:01) Understanding Waking Brain States

(01:06:12) Technologists Becoming Neuroscientists

(01:09:35) The Kindest Thing

My guest today is Noah Shinn. Noah is the founder of Instinct, a personal assistant that you text, call, or email the same way you would a person. It has its own phone and its own computer, and it can do almost anything on your behalf that you would do yourself online. Instinct is about a year old, still invite-only, and growing roughly 10% day over day without any marketing spend.

We discuss the surprising ways people are already using Instinct, the trusted network that lets two people's agents coordinate directly, and what Noah has learned about how long it takes users to trust an agent with their credit card, inbox, and calendar. He explains why he refuses to build an ad model and why he believes a personal agent should never influence users against their own interests.

We also cover the take rate model behind the more than $1 billion a year now flowing through the platform, how travel and food delivery businesses should prepare for a world of agents, why he spends 40% of his time thinking about compute, and why he believes all of software will eventually collapse into one simple interface.

Please enjoy my conversation with Noah Shinn.

For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.

-----

Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠.

-----

⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus.

-----

Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠.

-----

WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel.

-----

Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest.

-----

⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠.

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Timestamps:

(00:00:00) The Most Exciting Software Race Ever

(00:00:49) What Instinct Is

(00:04:11) The Wildest Things Users Have Done With Instinct

(00:07:15) The Instinct to Instinct Trusted Network

(00:13:24) How Agents Will Reorder the Internet

(00:14:44) Reinventing Restaurant Reservations

(00:17:23) Travel and $1 Billion in Transaction Volume

(00:21:00) How Users Learn to Trust an Agent

(00:23:25) Keeping Sensitive Data Safe

(00:26:08) Alignment and the Business Model

(00:31:07) Take Rates and the Payments Stack

(00:34:52) When Incumbents Push Back on Agents

(00:40:46) How Businesses Should Prepare for Agents

(00:44:43) Designing for Understandability

(00:48:15) Taste Versus Data

(00:50:03) Invite-Only Growth at 10% a Day

(00:54:46) How Far Ahead to Buy Compute

(00:56:58) The Cost to Serve Each User

(00:59:24) How Much Compute Proactive Agents Will Need

(01:02:30) Thoughts on Muse

(01:03:59) Mistakes and Staying Proactive

(01:05:34) The Future of Security

(01:08:32) Where the Interface Goes Next

(01:12:35) Agents That Pursue Goals

(01:14:35) Personality and the Movie Her

(01:16:27) Why It's Called Instinct

(01:17:34) Allies, Enemies, and Distribution Channels

(01:18:43) Raising Capital

(01:20:34) The Kindest Thing