Invest Like the Best with Patrick O'Shaughnessy
Colossus | Investing & Business Podcasts
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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
Afleveringen
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Christina Cacioppo - Building an Enduring Software Company in the Age of AI - [Invest Like the Best, EP.496]
20 oktober 2026 · 57 min
My guest today is Christina Cacioppo, founder and CEO of Vanta, which helps more than 16,000 companies manage security and compliance. Lees meer
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.
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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 …
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David Vélez - Building Nubank and the Future of Global Banking - [Invest Like the Best, EP.495]
13 oktober 2026 · 1 uur 12 min
David Vélez is the founder and CEO of Nubank, which serves 140 million customers across Latin America. Lees meer
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.
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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.
-----
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.
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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 ana…
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Andrew Huberman - The Frontier of Neurotechnology - [Invest Like the Best, EP.494]
6 oktober 2026 · 1 uur 12 min
Andrew Huberman is a neuroscientist and professor at Stanford, the host of the Huberman Lab podcast, and the author of Protocols. Lees meer
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.
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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.
-----
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.
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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 deliverabl…
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Noah Shinn - Building Instinct: The Personal Agent - [Invest Like the Best, EP.493]
28 september 2026 · 1 uur 12 min
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. Lees meer
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.
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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.
-----
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 of…
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Gabe Stengel - Building Investing Superintelligence - [Invest Like the Best, EP.492]
22 september 2026 · 1 uur 4 min
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. Lees meer
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.
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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.
-----
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 secu…
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Michael Moritz - Lessons From 40 Years of Investing and Writing - [Invest Like the Best, EP.491]
16 september 2026 · 1 uur 12 min
Michael Moritz led Sequoia Capital for nearly two decades and backed some of the defining companies of the internet era. Lees meer
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.
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Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how …
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Walter Russell Mead - How America Keeps Winning - [Invest Like the Best, EP.490]
8 september 2026 · 1 uur 18 min
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. Lees meer
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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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…
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Sarah Guo - Funding the Frontier - [Invest Like the Best, EP.489]
1 september 2026 · 1 uur
My guest today is Sarah Guo, founder and managing partner of Conviction, the venture firm she built to back AI-native companies from their earliest days. Lees meer
Sarah has become one of the most sought-after early-stage investors in AI, often the first check into the companies defining the frontier.
In this conversation, we go inside that frontier: what the small group of people actually building AI believe right now, why some of the field's best researchers are wrestling with their own sense of purpose, and how close we are to robots in the home and a genuine acceleration in scientific discovery.
At the center is Sarah's conviction that no single company will own the future of AI, and what that means for founders, investors, and anyone allocating their time and resources in a world moving this fast.
Our managing editor Dom Cooke wrote a profile of Sarah for Colossus, "Sarah's Wager," on how she built the firm closest to the AI frontier and why she's now betting against its biggest companies.
Please enjoy this conversation with Sarah Guo.
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-…
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Neil Movva - Making AI 10x Cheaper - [Invest Like the Best, EP.488]
25 augustus 2026 · 1 uur 18 min
My guest today is Neil Movva, founder of Sail. Sail is building what Neil calls a token factory, an inference company designed for a specific kind of future, one where AI agents run in the background for hours or days at a time rather than answering a human in real time. Lees meer
In that world, latency matters less and cost matters more, and Neil has built the whole company around driving the cost of a token as low as it can possibly go.
What makes this conversation special is that it is one of the most detailed tours I have ever done through the full stack of intelligence, the software, the chips, and the power, and how all three connect.
Along the way we cover the trade-off between speed and cost that lives inside every GPU, his scavenger strategy for buying the chips and power nobody else wants, his contrarian view on Nvidia, and why the premium the frontier labs charge for being three to six months ahead may not last.
Please enjoy my conversation with Neil Movva.
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…
-
Ben Thompson on Big Tech, China, and the AI Boom Running Out of Money - [Invest Like the Best, EP.487]
18 augustus 2026 · 1 uur 16 min
My guest today is Ben Thompson, the founder and author of Stratechery. Ben is one of my favorite business thinkers and I love talking to him about everything happening in markets and technology. Lees meer
We go through every important company, including OpenAI, Nvidia, Intel, Apple, Microsoft, Google, and Amazon. We also discuss why he thinks it would be dangerous for the United States to win the AI race outright, what container shipping and the railroads of the 1870s tell us about the buildout, and why the binding constraint on all of this may be capital rather than compute.
Please enjoy my conversation with Ben Thompson.
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, …
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- Categorieën
- Zakelijk , Technologie , Beleggen
- Verschijnt
- Elke week
- Lengte
- Meestal 1 uur 10 min
- Afleveringen
- 603
- Eerste aflevering
- 12 september 2016
- Taal
- Engels