Invest Like the Best with Patrick O'Shaughnessy
Colossus
61 episodes
Martin Casado on Frontier Model Economics, AI's Slowdown, and the Cursor Deal - [Invest Like the Best, EP.498]
4 Nov · 1 h 5 min
- Martin Casado argues that frontier models capture over 80% of market dollars while enterprise penetration sits at roughly 1% or less, leaving the market exposed to a slowdown.
- Casado warns that an AI model's useful life is only three to six months, so a stumble of a few months could lose a market.
Cliff Sosin - Owning the Complements to Intelligence - [Invest Like the Best, EP.497]
27 Oct · 1 h 3 min
- Cliff Sosin argues cheap intelligence will not destroy the complements that matter most, naming data, attention, physical proximity, scale and regulatory capture, with Meta as his main example.
- Sosin says a frontier lab with better models that nobody can copy would have a great business, but expects good-enough intelligence to commoditise quickly.
Christina Cacioppo - Building an Enduring Software Company in the Age of AI - [Invest Like the Best, EP.496]
20 Oct · 57 min
- Christina Cacioppo says an 80% growth business with 80% margins will beat a 160% growth business with 30% margins over time, despite the latter's higher valuation multiple.
- Vanta's agent now generates interface on demand and asks permission before acting, with 25% of customers in that flow and a goal of 75%.
David Vélez - Building Nubank and the Future of Global Banking - [Invest Like the Best, EP.495]
13 Oct · 1 h 12 min
- Vélez argues financial services is still early in its shift to digital banks, with about 90% of the roughly $10tn global consumer market still run by incumbents and branches.
- Nubank has fully surpassed Brazil's biggest incumbent bank, serving close to 120m customers, with about 60% using it as their primary account.
Andrew Huberman - The Frontier of Neurotechnology - [Invest Like the Best, EP.494]
6 Oct · 1 h 12 min
- Huberman predicts Meta, OpenAI, Anthropic and Elon Musk's companies will become biotech firms focused on reading and writing the brain, calling it the real AI arms race.
- Huberman says he needs about seven hours of sleep, and that nicotine's focus benefits require avoiding chronic use because it is addictive and raises blood pressure.
Noah Shinn - Building Instinct: The Personal Agent - [Invest Like the Best, EP.493]
28 Sept · 1 h 12 min
- Noah Shinn says Instinct, a personal assistant reached by text, call, or email, is growing about 10% day over day with no marketing spend so far.
- Shinn says travel makes up 50% of transaction volume and the platform is approaching $1bn a year, while he rejects advertiser-driven influence and expects a blanket transaction take rate.
Gabe Stengel - Building Investing Superintelligence - [Invest Like the Best, EP.492]
22 Sept · 1 h 4 min
- Gabe Stengel, CEO of Rogo, says the best investors will spend the next two to five years reinventing their firms around AI, comparing the effort to Jane Street's fifteen-year build.
- Stengel says models became capable of basically anything a junior banker or investment professional did by late 2025, which turned Rogo's early 60-call system into a simpler product embedded in firm systems.
Michael Moritz - Lessons From 40 Years of Investing and Writing - [Invest Like the Best, EP.491]
16 Sept · 1 h 12 min
- Michael Moritz says writing his memoir revealed why he became who he is, and that parental imprints absorbed before age 12 to 14 last a lifetime.
- Moritz says his parents never discussed their Jewish refugee past from Nazi Germany, so he learned their stories only while writing the book.
Walter Russell Mead - How America Keeps Winning - [Invest Like the Best, EP.490]
8 Sept · 1 h 18 min
- Walter Russell Mead argues the postwar order is crumbling while American power itself is not in crisis, crediting the information revolution and rising productivity for continued dynamism.
- Mead says Trump has turned fame and drama into power, leaving him free of reputational constraints and accelerating the breakdown of postwar and post-Cold War structures.
Sarah Guo - Funding the Frontier - [Invest Like the Best, EP.489]
1 Sept · 1 h 0 min
- Sarah Guo says the central investor dilemma in AI is whether to miss the opportunity or repeat the mistakes of past tech booms and busts.
- Guo rejects the idea that one or two frontier labs will define the future, arguing high-agency people and entrepreneurs can change outcomes.
Neil Movva - Making AI 10x Cheaper - [Invest Like the Best, EP.488]
25 Aug · 1 h 18 min
- Neil Movva's Sail is betting that background agents will shift inference demand from roughly fifty-fifty with real-time work toward ninety-ten in favor of background workloads, making cost per token the metric that matters.
- Movva says Sail will buy cheap, interruptible capacity like small one-megawatt data centers at 95 percent uptime, because background agents tolerate interruptions and Sail does not sell low latency.
Ben Thompson on Big Tech, China, and the AI Boom Running Out of Money - [Invest Like the Best, EP.487]
18 Aug · 1 h 16 min
- Ben Thompson argues a decisive American AI and military lead would be dangerous because China's best response could be attempting to blow up TSMC.
- Thompson warns AI return on investment may not generate enough revenue to fund spending, comparing it to the 1870s railroads that ran out of money despite lasting value.
Eric Vishria - A Decade of Lessons Investing in Software & Hardware - [Invest Like the Best, EP.486]
11 Aug · 1 h 6 min
- Eric Vishria of Benchmark says AI will produce an oligopoly of winners, not one company consuming everything, citing the big three clouds' roughly forty, thirty and twenty percent split.
- Vishria says CEOs hitting their plans may be destroying equity value as public SaaS multiples fell from about thirty times revenue in 2021 to about six times.
Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485]
4 Aug · 1 h 5 min
- Gavin Baker argues AI fundamentals are improving even as AI stocks fall roughly 40 to 60 percent, citing rising compute rental prices up 50 to 60 percent in six or seven months.
- Baker says hyperscaler gigawatts are modeled to monetize at Ampere-era rates, which he considers unlikely, so a stronger monetization outlook would cut the roughly 700bn dollars of credit demand he sees in the models.
Sam Altman - How to Make an Abundant Future - [Invest Like the Best, EP.484]
28 Jul · 54 min
- Altman says OpenAI spread itself too thin last year, then made hard calls to refocus on the best, most cost-effective intelligence.
- Altman says OpenAI underbought early compute, betting that demand at a low price was basically uncapped and that Microsoft was the first to say yes.
Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483]
21 Jul · 57 min
- Matthew Smith argues the US faces a historic natural gas shortfall from 2028, as AI data centers and LNG exports draw more gas than production and pipelines can deliver.
- Smith says working gas storage could be exhausted by 2030, making upside price risk unbounded and convex, with electricity prices hit hardest in 2028 through 2030.
John Kim - How to Raise a Few Billion Dollars - [Invest Like the Best, EP.482]
14 Jul · 50 min
- John Kim argues that belief is not trust, so a founder can be logically right and still fail to get a yes.
- Kim says friends and family are high-trust investors, and borrowing from friends is the most expensive money because it strains the friendship if unpaid.
Jeremy Giffon - The Billion Dollar PDF - [Invest Like the Best, EP.481]
7 Jul · 1 h 15 min
- Jeremy Giffon argues that in long-term private markets, funds are judged on storytelling because realized cash returns take a decade, so a single crystallized narrative attracts capital.
- Giffon says institutions must become timeline native and reactive, since X functions as a global newspaper where everyone sees the same content and posting rewards prolificness.
Etched - Building AI Hardware to Make Inference Faster and Cheaper - [Invest Like the Best, EP.480]
30 Jun · 1 h 27 min
- Etched, founded by Gavin Uberti and Rob Wachen, sells a full inference rack including power delivery, boards and interconnects, not just a chip.
- Rob Wachen argues chip design tools default to freezing temperatures while AI data centers never run below about eight degrees Celsius, exposing general-purpose assumptions in the industry.
Vlad Barbalat - Investing $120 Billion in Permanent Capital - [Invest Like the Best, EP.479]
23 Jun · 1 h 10 min
- Vlad Barbalat says Liberty Mutual Investments, a roughly $120bn platform, invests insurer reserves and surplus without shareholders demanding dividends and buybacks, letting it play the long game.
- Barbalat argues a fortress balance sheet lets the firm finance assets like data centers that a mutual insurer cannot fund because it cannot raise equity.
Kareem Amin - The Unusual Approach to Company Building - [Invest Like the Best, EP.478]
16 Jun · 57 min
- Clay co-founder and CEO Kareem Amin says the company's three core assumptions, including charging for usage rather than per seat, shape almost every other decision.
- Amin argues capitalism rewards risk above hard work or skill, defining real risk as not knowing what will happen with a high potential for shame.
Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]
9 Jun · 1 h 11 min
- Whale Rock Capital's highest conviction position is Anthropic, which Alex Sacerdote says emerged as a dark horse after the model race narrowed and coding proved the real unlock.
- Sacerdote says Whale Rock invested in Anthropic in August 2025 at about a $180bn valuation and calls the position a home run.
Dara Khosrowshahi - Uber's Bet on AVs, AI, and Building a Super-App - [Invest Like the Best, EP.476]
3 Jun · 1 h 7 min
- Dara Khosrowshahi says a headhunter's cold call while he ran Expedia led to his Uber CEO job, after an initial dismissal.
- Khosrowshahi says Uber is supply led, so winning autonomous vehicles means securing every driver, restaurant and courier, with over 30 AV partners including Waymo and Nvidia.
Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]
28 May · 1 h 3 min
- Dan Loeb says oil prices and AI spending now matter more to markets than growth, unemployment, inflation and rates.
- Third Point's hedge fund is about $9bn, roughly 30% credit, and in early 2026 held more credit than equity for the first time since 2009.
Darren Farber on Iran, China, and the Rise of Neoprimes - [Invest Like the Best, EP.474]
26 May · 46 min
- Darren Farber argues winning in Iran is politically defined, with the Strait of Hormuz reopening as the economic test for commerce to function.
- Farber says regime change is extremely hard under a martyrdom culture without an alternative power structure for defectors, even if most Iranians want change.
Gavin Baker - Watts and Wafers - [Invest Like the Best, EP.473]
20 May · 1 h 17 min
- Gavin Baker says Anthropic added $11bn of annual recurring revenue in March, which he argues equals the combined businesses of Palantir, Snowflake and Databricks in one month.
- Baker calls Anthropic's $900bn valuation on $50bn of ARR reasonable, citing a much lower cost per token and roughly 80% less cash burn than OpenAI.
Krishna Rao - Anthropic's CFO on Compute, Scaling to $30B ARR, and the Returns to Frontier Intelligence - [Invest Like the Best, EP.472]
13 May · 1 h 16 min
- Krishna Rao says compute is the lifeblood of Anthropic, and he spends 30 to 40 percent of his time on it.
- Anthropic says run-rate revenue grew from about $9bn at the start of 2026 to over $30bn by the end of Q1, with net dollar retention over 500 percent annualized.
Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.471]
5 May · 1 h 15 min
- Brian Chesky says no one is born a good CEO and that founders who over-delegate to professional managers become managed rather than managing.
- After the pandemic erased 80% of Airbnb's business in eight weeks, Chesky took full control and reviewed nearly every detail for two or three years.
Paul Tudor Jones - Lessons From 50 Years in Markets - [Invest Like the Best, EP.470]
28 Apr · 1 h 7 min
- Paul Tudor Jones says anyone who succeeds in investing is first a great risk manager, and argues AI development has zero risk management.
- Jones warns US stock market capitalisation at 252% of GDP versus 65% in 1929 signals a sovereign debt bubble, with a 30 to 35% decline possible.
Dylan Patel - The Infinite Demand for Tokens, Claude Mythos, and Supply Constraints - [Invest Like the Best, EP.469]
23 Apr · 45 min
- SemiAnalysis's Claude Code spend is about $7m a year against roughly $25m in salaries, and could pass 100 percent of salary by year-end, Dylan Patel says.
- Anthropic's revenue has grown from about $9bn to an estimated $35 to $40bn annualized, with its revenue adding $10bn a month, which outpaces its compute.
Alex Karnal - The Trillion-Dollar Health Revolution - [Invest Like the Best, EP.468]
21 Apr · 1 h 32 min
- Alex Karnal, co-founder of Braidwell and former Deerfield Management investor, calls 2025 the most exciting year of his career because GLP-1 drugs show disease can be addressed at its root.
- Karnal argues GLP-1 sales will easily exceed $100bn a year, proving a trillion-dollar shift toward proactive public health.
Scott Nolan - SpaceX, Founders Fund, and Rebuilding American Uranium Enrichment - [Invest Like the Best, EP.467]
14 Apr · 1 h 16 min
- Scott Nolan says General Matter will start with HALEU for advanced reactors, then move to low enriched uranium, aiming to deliver before 2030.
- Nolan argues advanced reactors will fail mainly for lack of fuel, because enrichment is the missing step and a new private company must fill it.
Alan Waxman - Private Credit and the Modern Financial System - [Invest Like the Best, EP.466]
8 Apr · 1 h 2 min
- Alan Waxman traces today's private credit risks to Glass-Steagall's 1999 repeal, which unleashed mergers including JPMorgan Chase and pushed investment banks like Goldman Sachs to lever up.
- Waxman says the root cause of private credit stress is a behavior shift around 2018, when managers industrialized fundraising and deployment, lowering underwriting standards and accepting mismatched liabilities.
Sergey Levine - Building LLMs for the Physical World - [Invest Like the Best, EP.465]
31 Mar · 1 h 7 min
- Sergey Levine, co-founder of Physical Intelligence, says the company aims to build robotic foundation models that can control basically any embodied system to do any task.
- Levine argues general models may beat narrow ones in the long run, as language models did, and says real robot generalization means doing mundane tasks anywhere, not flashy demos in clean settings.
Mitchell Green - Lessons from Cold Calling 10,000 Companies - [Invest Like the Best, EP.464]
24 Mar · 54 min
- Lead Edge Capital's Mitchell Green says the firm's eight buying criteria narrow about 9,000 companies to roughly 900, with 5 to 7 deals made a year.
- Green says Lead Edge put about 12% of Fund 3 into Toast, selling $180m before the IPO and expecting $350 to $400m in total returns.
William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy - [Invest Like the Best, EP.463]
17 Mar · 1 h 11 min
- Column, a software company that owns a bank, makes over 90 percent of its money from software and charges per API call, passing bank economics to customers like Bilt, Wise, Ramp and Mercury.
- William Hockey argues founders should seek out non-consensus places, and says San Francisco's consensus culture is both a clutch and a founder's most valuable asset.
Shyam Sankar - Celebrating Heretics - [Invest Like the Best, EP.462]
10 Mar · 1 h 22 min
- Shyam Sankar argues heretics like Hyman Rickover are founder figures, citing Rickover's nuclear submarine built despite Navy hostility.
- Sankar says Europe has created no companies worth more than 100bn euro from scratch in fifty years, while the US rewards founders uniquely.
John Arnold - China, Energy Markets and Fixing America's Systems - [Invest Like the Best, EP.461]
4 Mar · 1 h 16 min
- John Arnold says China's industrial policy, with subsidised favoured firms and overcapacity, breeds better technology and supply chains the West cannot match.
- Arnold says he started his hedge fund after Enron's 2001 collapse, raising fees to 3 and 35 to fund better research and data.
Dan Sundheim - The Art of Public and Private Market Investing - [Invest Like the Best, EP.460]
24 Feb · 1 h 15 min
- Dan Sundheim says late-stage private companies now offer many interesting opportunities, since fewer investors scrutinize them than public stocks.
- D1 Capital originally invested in OpenAI's $125bn round when many doubted LLMs could work as a business, and Sundheim now puts the odds of an economic return at roughly 70-30.
Josh Kushner - Concentration and Conviction - [Invest Like the Best, EP.459]
18 Feb · 1 h 3 min
- Josh Kushner says Thrive's ambition has never been about asset scale, but about culture, process and the product it offers founders.
- Thrive led OpenAI's round at a $29bn valuation after Kushner approached Sam Altman in March 2022 and was struck by the ChatGPT preview.
Alex Behring and Daniel Schwartz - Inside 3G Capital - [Invest Like the Best, EP.458]
10 Feb · 1 h 36 min
- 3G Capital raises capital for one investment per fund, with partners committing their own money alongside outside investors, because truly great businesses are rare and seldom actionable.
- Alex Behring says 3G's downside case is capital preservation with a small return, and that technological disruption is now far more likely, so its investment process must be more detailed.
Ben Horowitz - Backing America’s Future - [Invest Like the Best, EP.457]
3 Feb · 56 min
- Ben Horowitz says AI will affect nearly every problem, from Autodesk to cancer, and land within 12 to 24 months because the internet already provides the infrastructure.
- Horowitz names government policy as the main risk, citing his father's warning that a bad government can destroy a strong country and criticizing the reversed Biden GPU export order.
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]
29 Jan · 1 h 16 min
- Gokul Rajaram says product managers now set the customer need and the why while engineers, designers and PMs build together in code, as long-running agents became reliable.
- Gokul Rajaram expects the designer and PM to engineer ratio to move from about 1:3 or 1:10 toward 1:20, and says PMs must own evaluations of non-deterministic software.
Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]
20 Jan · 2 h 7 min
- Patrick O'Shaughnessy says he has no goals, pointing to his 28-year-old essay The Growth Without Goals and his organising principle of championing untapped potential.
- He ties his investing and building philosophy to Bret Victor's talk Inventing on Principle, which he says he borrowed as the design principle of his previous software business.
Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]
13 Jan · 1 h 14 min
- Ladder, a fitness app Patrick O'Shaughnessy calls his first angel investment, is approaching $100m in annual recurring revenue with more than 300,000 paying members.
- Greg Stewart, who became CEO after Tom Digan proposed the change on the day after Christmas 2019, says Ladder survived deep debt by negotiating creditors down to around 20 cents on the dollar.
Reed Hastings - Building Netflix - [Invest Like the Best, EP.453]
6 Jan · 1 h 3 min
- Reed Hastings tells Patrick O'Shaughnessy that Netflix's Qwikster split failed because executives suppressed doubts after he had made 18 straight decisions, not because of the separation itself.
- Hastings argues a board member's job is an insurance layer ready to replace the CEO, not to add day-to-day value.
Nick Kokonas - Know What You Are Selling - [Invest Like The Best, REPLAY]
30 Dec 2025 · 1 h 18 min
- Nick Kokonas says he would rather be right 80% of the time, since a business that wins more than half its bets wins overall, like a casino.
- Kokonas says Alinea's no-shows and misstated party sizes cost over a million dollars a year, which led him to propose ticketing at Next.
Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS]
23 Dec 2025 · 1 h 25 min
- Ric Elias says Red Ventures' edge is operating improvement, claiming a company bought at 10 times can be worth about 4 times within two years.
- Red Ventures stayed bootstrapped for a decade, taking its first outside capital in 2010 from General Atlantic before Silver Lake followed about five years later.
Henry Ellenbogen - Man Versus Machine - [Invest Like the Best, EP.452]
16 Dec 2025 · 1 h 48 min
- Henry Ellenbogen says about 40 stocks in a rolling ten-year window compound at 20% a year, and about 80% start as small caps, so Durable hunts for them early.
- Ellenbogen argues that quantitative funds beat humans at repeat-actor problems on known data, while human judgment about people and change is the edge.
Gavin Baker - Nvidia v. Google, Scaling Laws, and the Economics of AI - [Invest Like the Best, EP.451]
9 Dec 2025 · 1 h 26 min
- Gavin Baker says Google's temporary edge as lowest-cost token producer let it drain the AI ecosystem with negative 30% margins while Blackwell deployments lagged.
- Gavin Baker says Gemini 3 confirms pre-training scaling laws are intact, though nobody can explain why.
David George - Building a16z Growth, Investing Across the AI Stack, and Why Markets Misprice Growth - [Invest Like the Best, EP.450]
2 Dec 2025 · 1 h 7 min
- David George says the dominant AI product isn't found, and ChatGPT has 1B users but under 50M monetized.
- He is more skeptical than consensus on enterprise AI, calling white-collar labor capture hand-wavy.
Palmer Luckey - Inventing the Future of Defense - [Invest Like the Best, CLASSICS]
28 Nov 2025 · 1 h 15 min
- Palmer Luckey says synthetic hydrocarbon fuels at $1 a gallon would waste trillions spent on electric and hydrogen vehicles.
- Anduril only enters markets where the Pentagon cares, Congress cares, it can execute, and rivals are weak.
Martín Escobari - Inside General Atlantic - [Invest Like the Best, EP.449]
25 Nov 2025 · 1 h 10 min
- Escobari calls AI his fourth or fifth bubble and says Anthropic's $200m to $4bn growth in 12 months is unprecedented in B2B.
- General Atlantic has deployed AI across 200-plus portfolio companies and reports a 4% loss ratio versus 20-40% common.
Wolfgang Hammer - The Power of Story - [Invest Like the Best, EP.447]
11 Nov 2025 · 43 min
- Wolfgang Hammer's storytelling method requires three layers: what the company does, the founder's emotional why, and a philosophical layer.
- He argues originality is overrated, citing Raymond Loewy's 80/20 rule: about 20% new and 80% familiar.
Luca Ferrari - Building Bending Spoons - [Invest Like the Best, EP.446]
4 Nov 2025 · 1 h 21 min
- Luca Ferrari says Bending Spoons is 25% private equity and 75% technology company that buys businesses outright and keeps them forever, aiming to become an institution like Berkshire Hathaway.
- Bending Spoons raised $700m in equity at an $11bn valuation after using free cash flow, then commercial bank debt, for its first five years.
Kevin Kelly - Be Generous and Unique - [Invest Like the Best, CLASSICS]
31 Oct 2025 · 1 h 8 min
- Kevin Kelly says life's goal is to become fully yourself, which he has never seen anyone achieve.
- Kelly argues you cannot become unique alone and should prototype a life rather than follow a plan.
Ken Langone - The American Dream - [Invest Like the Best, REPLAY]
30 Oct 2025 · 50 min
- Ken Langone, Home Depot co-founder and former NYSE director, says people are 95% of his investment criteria.
- Langone won Ross Perot's underwriting deal by valuing the company at 100 times earnings, far above rivals' 30, and it priced at 115 times.
Karim Atiyeh - Building Ramp - [Invest Like the Best, EP.445]
21 Oct 2025 · 1 h 46 min
- Ramp has passed $1bn in revenue in just over five years as the fastest-growing finance automation platform.
- Cofounder and CTO Karim Atiyeh says Ramp's AI policy agents enforce expense policy 24/7 and check invoices for fraud, delivery and negotiated pricing.
Dan Wang - The US vs China In The 21st Century - [Invest Like the Best, EP.444]
16 Oct 2025 · 1 h 36 min
- Dan Wang calls China an "engineering state" that treats society as building material, explaining its capacity and brutality.
- Wang says US pluralism is an advantage, but manufacturing neglect since the 1980s makes scale-up harder than China's science catch-up.
Jesse Zhang - Building Decagon - [Invest Like the Best, EP.443]
6 Oct 2025 · 1 h 22 min
- Decagon found customer service was an order of magnitude ahead of other AI use cases, with budgets in the low-to-mid six figures.
- Oura Ring cut customers demanding a human from one in three to one in 20.
Micky Malka - Building Ribbit - [Invest Like the Best, EP.401]
10 Dec 2024 · 1 h 34 min
- Micky Malka, whose Ribbit Capital backs Coinbase, Robinhood and Nubank, declares fintech dead with a 2012-2023 cemetery slide.
- Malka expects only 50 compounders among 3,000 fintechs, with 1,500 failures, 500 profitable survivors and 200 acquisitions.