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Invest Like the Best with Patrick O'Shaughnessy

Business & Economics Podcasts

Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at

Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at


United States


Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at




Karen Karniol-Tambour - All Things Macro - [Invest Like the Best, EP. 237]

My guest today is Karen Karniol-Tambour, Partner and Co-CIO for Sustainability at Bridgewater Associates. You will quickly understand why Ray Dalio described Karen as a “vacuum cleaner of learning” - our conversation covered a variety of market themes, and Karen goes deep on each of them. We touch on inflation, monetary policy, currencies, retail investors, ESG, and how each of these levers has become more important for investors to understand. Karen has a rare skill for making complex ideas...


Sebastian Mejia - Mastering On-Demand Convenience - [Founder’s Field Guide, EP. 44]

My guest today is Sebastian Mejia, co-founder and president of Rappi. Founded in Bogota, Colombia in 2015, Rappi set out to create an on-demand convenience store and has expanded into nine countries and over 200 cities. In our conversation, Sebastian and I discuss what differentiates Rappi from US-based delivery apps, how the company evolved early by understanding their customers’ behavior, and how the business balances growth vs. unit economics. I loved hearing Sebastian’s views of the...


Carl Kawaja - Wisdom from Decades of Investing - [Invest Like the Best, EP. 236]

Today’s conversation is one of my all-time favorites, with someone I’ve come to respect deeply in the field of investing. My guest is Carl Kawaja, who has served as a portfolio manager at Capital Group for decades. Capital Group is among the most respected shareholders in the world, with over $2T of assets, and listening to Carl, you’ll hear why. In our conversation, we cover Carl’s criteria for building conviction around long-term holdings, why he views uncertainty and ambiguity as...


Stewart Butterfield - We Don’t Sell Saddles Here - [Founder’s Field Guide, EP. 43]

My guest today is Stewart Butterfield, founder and CEO of Slack. Stewart’s 2014 essay “Why We Don’t Sell Saddles Here” had a massive impact on my own business journey, which made this discussion extra special. During our conversation, we discuss the concept of owner’s delusion, how to frame the boundaries between product and market, and the challenge of changing people’s mental models and behavior when introducing innovative products. I hope you enjoy my conversation with Stewart. Before...


Steve Mandel - Investing Behind Change - [Invest Like the Best, EP. 235]

My guest today is Steve Mandel, founder of Lone Pine Capital, one of the most successful hedge fund and investment firms of this generation. In our conversation, we discuss how the investing business has evolved since Steve’s start in the 1980s, why it’s so difficult to drive alpha by shorting stocks today versus 20 years ago, and why Steve still loves to get into the guts of a business. Steve shares his lessons through a variety of great stories, which made this such a fun experience....


Spenser Skates - Challenging Big Ideas - [Founder’s Field Guide, EP. 42]

My guest today is Spenser Skates, CEO and co-founder of Amplitude Analytics. Spenser founded Amplitude in 2012 with a thesis that building the best product requires, deep cross-functional understanding of customer behavior. During our conversation, we discuss Spenser’s long history in programming and how his early experiences tie into his work today. We also explore the nuances of equity compensation, how different VCs can play a role in the success of a startup, and Spenser’s desire to see...


David Sacks - How to Operate a SaaS Startup - [Invest Like the Best, EP. 234]

My guest today is David Sacks, General Partner at Craft Ventures and founding COO of PayPal. During our conversation, we explore what differentiates Enterprise SaaS from DTC subscriptions, what makes for a magical product launch event, and what key growth metrics David uses to measure success. David has written extensively on his idea of operating cadence, and we explore how that applies to the various functions within an organization. As time goes on, I am more and more impressed at the...


David Vélez - Building the Branchless Bank - [Founder’s Field Guide, EP. 41]

My guest today is David Vélez, founder and CEO of Nubank, the world’s largest digital bank with over 40 million customers. In our conversation, David talks about his venture capital background at Sequoia and how that led him down an entrepreneurial path in Latin America. We also talk about the pros and cons of building a digitally native business and what gets him most excited about innovation and technology in emerging markets. Before we start the episode, I would also like to highlight...


Balaji Srinivasan - Optimizing Your Inputs - [Invest Like the Best, EP. 233]

My guest today is Balaji Srinivasan, a serial entrepreneur and angel investor. Balaji is known to challenge conventional wisdom, and he lives up to his reputation in this conversation. We discuss a wide variety of topics, including advancements in health tracking, ways to evaluate your own information diet, and how technology is driving decentralization and what that could mean for countries, corporations, and individuals. Before we transition to the episode, if you enjoy this...


Michael Mayer - Business Boss Battles - [Founder’s Field Guide, EP. 40]

My guest today Michael Mayer, is the founder and CEO of Bottomless, a company that automatically replenishes your coffee supply where I am both an excited investor and customer. Today’s conversation is about tactical lessons Michael has learned while building the business. We talk about identifying an addressable problem, how to avoid solving for bottlenecks that don’t yet exist, and how to iterate through problems before scaling. As yet another example of a self-taught entrepreneur, it’s...


Marc Andreessen - Making the Future - [Invest Like the Best, EP. 232]

My guest today is Silicon Valley icon, Marc Andreessen. Before co-founding the legendary venture capital firm, Andreessen Horowitz, Marc was an early pioneer of the internet. At age 22, he built Mosaic, the first widely adopted web browser and the technology that underpinned Netscape Communications. Marc was an early proponent of cloud computing, social networks, and the software business model. In each case, Marc seemed to be well ahead of the crowd. During our conversation, we explore how...


Will Ahmed - Optimizing Human Performance – [Founder’s Field Guide, EP. 39]

My guest today is Will Ahmed, founder of fitness wearable company WHOOP. What started as a business plan in 2011 has evolved into the 24/7 health-tracking device you’ll often see on athletes across professional sports. During our conversation, Will and I discuss how his own backstory ties into the founding of WHOOP, the key design decisions they made in the ultra-competitive wearables market, and how the company grew slowly before inflecting in recent years. Will shares awesome details on...


Howard Marks - Embracing the Psychology of Investing - [Invest Like the Best, EP. 231]

My guest today is Howard Marks, co-founder of Oaktree Capital, a leading investment manager, and one of the world’s largest distressed debt investors. In our conversation, we discuss takeaways from the market selloff and rapid recovery in 2020, the importance of assessing both quantitative and qualitative factors in markets, and the benefits Howard has realized from a career of writing. I hope you enjoy this great conversation with Howard Marks. For the full show notes, transcript, and...


Christina Cacioppo - Building the New Standard in Security – [Founder’s Field Guide, EP. 38]

My guest today is Christina Cacioppo, founder of Vanta, a security and compliance software business founded in 2017. In our conversation, Christina brings to life the idea of “finding a problem that exists and fixing it.” We dive into the experiences that led her to launch Vanta, the strategy she took to build, price, and distribute the product, and we touch on her lessons from running a growing organization. I always admire the drive that founders have when they set off to build something...


John Harris - Resilience and Imagination - [Invest Like the Best, EP. 230]

My guest today is John Harris, Managing Partner of Ruane, Cunniff & Goldfarb, where the flagship Sequoia Fund has an incredible 50-year track record running a highly concentrated portfolio of equities. In our conversation, we cover John’s approach to finding businesses that can be owned for the long-term, what goes into their diligence process, and the importance of resilience for investors. I think many of the stock pickers will enjoy many of the points on good management, good businesses,...


Florian Hagenbuch and Mate Pencz - Everything Will Be Bought Online – [Founder’s Field Guide, EP. 37]

My guests today are Florian Hagenbuch and Mate Pencz, co-founders of Loft. Based in Sao Paulo, Brazil, Loft is a digital platform designed to bring Latin American real estate into the e-commerce age. The 3-year-old startup scaled to over $150mm in annualized revenue in 2020 and is on track for multiples higher this year. We dive into the market opportunity in Brazilian real estate and how that differs from the US market, the value proposition for iBuying across the US and Latin America...


Gabriel Leydon - Designing Digital Economies - [Invest Like the Best, EP. 229]

My guest is Gabe Leydon, who is the co-founder and former CEO of MZ, also known as Machine Zone, the company behind huge games such as Mobile Strike and Game of War. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I have talked to in a long time. In our conversation, we cover why great design can be a bad sign that we’d run out of ways to innovate, the most important lessons from human psychology for building games and products, and why...


Assaf Wand - Innovation in Static Industries – [Founder’s Field Guide, EP. 36]

My guest today is Assaf Wand, CEO, and co-founder of Hippo, a homeowner insurance startup founded in 2015. In March 2021, Hippo announced a SPAC merger, valuing the business at over $5bn. In our discussion, we cover how Hippo approached innovation in the highly regulated insurance industry, unique strategies for building brand trust, and how direct relationships with homeowners has opened up Hippo's business model to a wide range of opportunities. I was excited to speak with Assaf, given his...


Dennis Lynch - Delivering Alpha in Adapting Markets - [Invest Like the Best, EP. 228]

My guest today is Dennis Lynch, Head of Counterpoint Global, where he oversees over $100bn in AUM and boasts one of the strongest track records of any public investor. In our conversation, we cover Dennis's unique approach to building a research team, how misclassification of companies often creates the highest upside opportunities, and how Dennis has adapted his investment process over the past 20 years. I think Dennis defines what it means to be intellectually honest, and you will hear...


Henrique Dubugras - Building the Financial Center of Gravity – [Founder’s Field Guide, EP. 35]

My guest today is Henrique Dubugras, co-founder and CEO of Brex, an all-in-one finance account for businesses. Brex recently raised funding at a valuation of over 7 billion dollars despite being founded only four years ago. In our conversation, we cover Brex’s transition from a credit card for start-ups to the central account for businesses, why building that central account was orders of magnitude more difficult than expected, and the difference between building a business in Brazil and the...