Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.colossus.com
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Ramtin Naimi - The State of Venture - [Invest Like the Best, EP.499]
Episode 499
Friday, November 6, 2026 • Duration 46:24
My guest today is Ramtin Naimi, the founder of Abstract Ventures, back for our second conversation. Few people see as many companies as Ramtin and his firm, so this time we zoom in on what they’re seeing right now.
The question he keeps coming back to is whether this is 2019 or 2021: early in a run, or at the top of one. Hot rounds now come with a second, pricier tranche for the firms that lost the deal, and he’s seen more term sheets pulled or renegotiated in recent weeks than at any time since 2021.
We also get into the neolabs, one of which plans to spend $1 billion on a single training run, how the goalposts for a best-case outcome moved from $10 billion to a trillion dollars, and the biggest mistake he’s made building Abstract.
Please enjoy my conversation with Ramtin Naimi.
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.
-----
Editing and post-production work for this episode was provided by The Podcast Consultant.
Timestamps:
(00:00:00) The Speed of Today's Deal Market
(00:05:43) How Today Compares to 2021
(00:08:25) Mega Funds and LP Liquidity
(00:13:43) New Ways to Pay for Compute
(00:17:13) GPU Scarcity and the Neolab Boom
(00:20:42) Why Proactive Seed Bets Win
(00:27:42) Is Late Stage the Safe Bet?
(00:31:58) Data Companies and New Angels
(00:34:46) How Abstract Is Evolving
(00:38:17) Rating the Market's Froth
Martin Casado on Frontier Model Economics, AI's Slowdown, and the Cursor Deal - [Invest Like the Best, EP.498]
Episode 498
Wednesday, November 4, 2026 • Duration 01:05:13
My guest today is Martin Casado, General Partner at Andreessen Horowitz.
Martin has spent three decades building and investing in technology infrastructure. We discuss why traditional approaches to investing often fail to capture disruptive technologies, how AI is reshaping the economics of software, and why the ability to turn capital directly into technological progress may be the most important change of all. Martin also shares lessons from some of his biggest investments and acquisitions.
Please enjoy this conversation with Martin Casado.
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.
-----
Editing and post-production work for this episode was provided by The Podcast Consultant.
Timestamps:
(00:00:00) The Four Types of Investors
(00:04:58) Why Moats Rarely Matter
(00:14:45) The State of AI Infrastructure
(00:19:21) Frontier Model Economics
(00:24:12) What AI Makes Possible Now
(00:29:14) AI and Cybersecurity
(00:30:52) Why Money Can Finally Scale Engineering
(00:37:21) Neo Clouds, Neo Labs, and Data Centers in Space
(00:40:52) Why Private Markets Are Efficient
(00:47:23) Lessons From Strategic M&A
(00:54:17) How the Role of the Investor Is Changing
(00:58:49) Why This Is an Industrial Revolution
Cliff Sosin - Owning the Complements to Intelligence - [Invest Like the Best, EP.497]
Episode 497
Tuesday, October 27, 2026 • Duration 01:00:49
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.
-----
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.
-----
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
Christina Cacioppo - Building an Enduring Software Company in the Age of AI - [Invest Like the Best, EP.496]
Episode 496
Tuesday, October 20, 2026 • Duration 57:29
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.
-----
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.
-----
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 - Building Nubank and the Future of Global Banking - [Invest Like the Best, EP.495]
Episode 495
Tuesday, October 13, 2026 • Duration 01:11:40
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.
-----
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 - The Frontier of Neurotechnology - [Invest Like the Best, EP.494]
Episode 494
Tuesday, October 6, 2026 • Duration 01:12:28
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.
-----
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
Noah Shinn - Building Instinct: The Personal Agent - [Invest Like the Best, EP.493]
Episode 493
Monday, September 28, 2026 • Duration 01:11:30
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.
-----
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
Gabe Stengel - Building Investing Superintelligence - [Invest Like the Best, EP.492]
Episode 492
Tuesday, September 22, 2026 • Duration 01:04:24
Gabe Stengel is the co-founder and CEO of Rogo, the AI platform for finance. He believes the best investors will spend the next several years reinventing their firms around AI, and Rogo is trying to build the infrastructure that allows them to do it.
We discuss how Rogo evolved alongside the frontier models, why the last mile and the harness around the models matter so much, what happens when every portfolio manager can deploy thousands of agents against a problem, and how AI could transform the way capital is raised, assets are priced, and deals get done.
We also cover which investing skills become more valuable as AI improves, the move from seat-based to outcome-based pricing, Rogo’s internal company brain called Shrek, the 40 investor rejections Gabe received before his Series A, why building in applied AI requires extraordinary aggression, and what it takes to become a black hole for talent and capital.
Please enjoy my conversation with Gabe Stengel.
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.
-----
Editing and post-production work for this episode was provided by The Podcast Consultant.
Timestamps:
(00:00:00) Welcome to Invest Like The Best
(00:01:24) The Model Eras of Rogo
(00:04:15) Why the Last Mile Mattered
(00:06:14) Who’s Using Rogo Right Now
(00:10:55) Which Investor Skills Still Matter
(00:12:23) Inside Rogo's Data Stack
(00:14:33) Competing With the Frontier Labs
(00:16:57) Why the Harness Matters Most
(00:18:05) What Makes a Vertical AI Winner
(00:22:00) How Firms Buy AI Software
(00:23:43) From Seats to Outcome Pricing
(00:31:19) Auditability Beats Accuracy
(00:32:55) Scaling Enterprise Sales Fast
(00:34:48) Meet Shrek, Rogo's Company Brain
(00:35:49) The Pitch to Great Talent
(00:39:37) What Chewing Glass Feels Like
(00:42:18) Forty Investor Rejections
(00:47:41) Finance's Innovator's Dilemma
(00:50:22) Questions Every Firm Should Ask
(00:53:09) What Remains Most Uncertain
(00:56:46) Becoming a Black Hole for Talent
(00:57:56) The Kindest Thing
Michael Moritz - Lessons From 40 Years of Investing and Writing - [Invest Like the Best, EP.491]
Episode 491
Wednesday, September 16, 2026 • Duration 01:12:28
Michael Moritz led Sequoia Capital for nearly two decades and backed some of the defining companies of the internet era.
In his new memoir, Ausländer, he turns his attention to his own family, Jewish refugees who fled Nazi Germany and rebuilt their lives in Wales.
We discuss the imprint his parents left on him, the method he used for decades of asking founders about their childhoods and the Time profile that ended his relationship with Steve Jobs.
We also also cover Lee Iacocca, why Don Valentine hired him, Alex Ferguson's approach to managing players, Elon Musk, and why Mike still struggles to feel proud of anything he has done.
Please enjoy my conversation with Michael Moritz.
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.
-----
Editing and post-production work for this episode was provided by The Podcast Consultant.
Timestamps:
(00:00:00) Welcome to Invest Like The Best
(00:02:16) Where Does One Person End?
(00:11:15) The State of the World Today
(00:15:08) The Unlived Life of Parents
(00:17:33) Lee Iacocca, Eternal Outsider
(00:21:03) His Most Revealing Question
(00:26:03) Resisters, the Silent, and Collabos
(00:33:30) The Profile of Steve Jobs
(00:38:04) Frank Auerbach's Total Obsession
(00:41:04) Why Don Valentine Hired Michael
(00:46:44) Building Sequoia
(00:49:49) What Michael Learned from Alex Ferguson
(00:52:57) The Great Man Theory
(01:00:36) Defining Extraordinary Writing
(01:03:40) Stepping Back From Sequoia
(01:06:54) A Philosophy of Parenting
(01:09:00) The Next Book: Iran
(01:11:44) The Kindest Thing
Walter Russell Mead - How America Keeps Winning - [Invest Like the Best, EP.490]
Episode 490
Tuesday, September 8, 2026 • Duration 01:18:08
My guest today is Walter Russell Mead. Walter is a columnist at the Wall Street Journal and the author of Special Providence and God and Gold, two of the best books written on American power.
He has spent decades studying how the United States came to dominate the world, and our conversation is about whether it can keep doing so.
Walter lays out the five step playbook that carried the Dutch, then the British, then America to global leadership, and why the same pattern keeps beating centralized continental powers.
We discuss how Trump turned fame into power, the four schools of American foreign policy and the rise of the tech Hamiltonians, what the drone war in Ukraine means for the Pentagon, and why the erosion of deterrence is the deeper story in the Middle East.
Please enjoy my conversation with Walter Russell Mead.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Editing and post-production work for this episode was provided by The Podcast Consultant.
Timestamps:
(00:00:00) Welcome to Invest Like the Best
(00:02:16) America and the World Today
(00:05:34) Trump’s Method of Power
(00:09:43) Why America Keeps Winning
(00:12:25) The Five-Point Plan for Global Dominance
(00:20:11) China and American Power
(00:22:10) The Risk of American Isolationism
(00:25:50) Technology and Global Power
(00:28:42) Riding the Technological Wild Horse
(00:34:29) Four Schools of American Foreign Policy
(00:40:22) The Rise of Tech Hamiltonians
(00:43:51) India and the Next Great Powers
(00:48:54) The Risks of the Information Revolution
(00:51:30) How Technology Is Changing War
(00:55:06) Taiwan
(00:57:20) The Future of American Society
(01:00:44) What It Means to Be American
(01:03:25) Iran and the Middle East
(01:06:28) The Erosion of Deterrence
(01:08:53) America’s Role in the Next 20 Years
(01:12:08) AI and Global Power
(01:14:26) Reasons for Optimism
(01:16:33) The Kindest Thing
Details about Invest Like the Best with Patrick O'Shaughnessy, a podcast by Colossus | Investing & Business Podcasts
