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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


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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




Sam Englebardt and Richard Kim - Investing in Immersive Worlds - [Invest Like the Best, EP. 259]

Today, my guests are Sam Englebardt and Richard Kim, general partners at venture fund, Galaxy Interactive. Having come from the media and finance sectors, respectively, Sam and Richard joined forces in 2018 to invest in their shared thesis that immersive digital experiences would become the dominant way people engage with each other in the future. Our conversation centers around the evolution of art, finance, and gaming as they proliferate in Web3. Please enjoy my conversation with Sam...


Ricky Sandler - Building an Investment Compass - [Invest Like the Best, EP. 258]

My guest today is Ricky Sandler, founder of Eminence Capital. Ricky is a hedge fund veteran managing over $8bn of assets across Eminence's strategies. We cover Ricky's evolution as an active investor, why he thinks this is a stock-picker's environment, and what keeps him competitive after a long and successful career. Please enjoy my conversation with Ricky Sandler. For the full show notes, transcript, and links to the best content to learn more, check out the episode page ...


Orlando Bravo - The Art of Software Buyouts - [Invest Like the Best, EP. 257]

My guest today is Orlando Bravo, co-founder and Managing Partner of leading private equity firm, Thoma Bravo. Thoma Bravo manages over $90bn of assets and is best known for investing in software and technology businesses. It was Orlando who led the firm’s early entry into software buyouts some twenty years ago, and he has overseen more than 350 software acquisitions since. There are few, if any, people better placed to discuss private equity and software investing. Please enjoy this...


Nick Saltarelli - One Foot in Front of the Other - [Founder’s Field Guide, EP. 54]

My guest today is Nick Saltarelli, co-founder of the functional chocolate bar business, Mid-Day Squares. Nick started the company with his wife and brother-in-law a few years ago to build on a simple idea: if the big chocolate bar brands were to start today, what would they look like? In our conversation, we discuss the importance of Mid-Day Squares’ $100 million revenue target, what’s wrong with the CPG industry today, and how to keep a long-term mindset while making the most of every...


Jenny Johnson - Seven Decades of Investing Expertise - [Invest Like the Best, EP. 256]

My guest today is Jenny Johnson, President and CEO of one of the world’s largest asset managers, Franklin Templeton. Jenny joined the business in 1988 and has worked in the organization ever since. In early 2020 she became CEO of Franklin, which now manages some $1.5 trillion. I should, of course, note that I met Jenny as our two firms explored a partnership, which we cemented 3 months ago when we announced that Franklin Templeton would be acquiring O'Shaughnessy Asset Management. During...


Doug Colkitt - The Evolution of Markets - [Invest Like the Best, EP. 255]

My guest today is Doug Colkitt. Doug has spent his career searching for and trading inefficient markets, first at Citadel’s high-frequency trading group, then for himself, and then as an operator building CrocSwap - a decentralized exchange or DEX designed to bring modern functionality to crypto markets, which is closer to what large traders have come to expect from a modern electronic market like the NASDAQ. My interest in market infrastructure has continued to grow since my great...


Bill Gurley and Philip Rosedale - Back to the Future - [Invest Like the Best, EP. 254]

My guests today are Philip Rosedale and Bill Gurley. Philip created Second Life in the early 2000s and helped build it into the largest virtual 3D world ever created at the time. Frequent listeners will recognize Bill, who was an investor in Second Life via Benchmark Capital. During the conversation, we cover the fascinating story of Second Life and the billion-dollar economy that persists through to this day. Bill and Phillip share their key learnings from the experience, including the...


Francis Davidson - Design-led Hospitality - [Invest Like the Best, EP.253]

My guest today is Francis Davidson, founder and CEO of the hospitality brand Sonder. Francis launched Sonder in 2013 as an alternative to traditional hotels and rentals with a specific focus on technology and design. During our conversation, we discuss where Sonder fits into the hospitality ecosystem and why design is so key to their offering. We also touch on Francis’s unique views around customer-centric focus, the nuances of hiring a team, and how they approach decision-making. Please...


Niraj Shah - Developing Every Skill - [Invest Like the Best, EP. 252]

My guest today is Niraj Shah, the CEO and co-founder of Wayfair. Wayfair started life in 2002 as a collection of independent websites selling category-specific home furniture but became a one-stop-shop for the home category in 2011 when, at $500 million in sales, the team consolidated their 240 websites into Today, the business offers 22 million products from 16 thousand suppliers to more than 30 million customers. During our conversation, we discuss how the competitive...


Bored Ape Yacht Club - [Web3 Breakdowns, EP. 1]

Today, I am excited to share our newest show, Web3 Breakdowns. Similar to our Business Breakdowns series, Web3 will have it's own dedicated feed so make sure to hit this subscribe link or find it on your preferred podcast player. The first episode of Web3 Breakdowns covers Bored Ape Yacht Club. You will hear from guest, Eric Golden, who will also be coming back to host his own Web3 Breakdowns moving forward. We are sharing this first episode to make sure no one misses this...


Will Marshall - Indexing the Earth - [Invest Like the Best, EP. 251]

My guest today is Will Marshall, the co-founder and CEO of Planet. Will founded Planet in 2010 with a small team of NASA scientists to build a constellation of satellites that would image the entire Earth every day. Since then, Planet has successfully built and deployed 450 satellites into space, which the company is using to create a time series of images for every place on Earth. Our conversation covers the untold space story. How space is going through an internet moment where cost...


Roelof Botha - Sequoia’s Crucible Moment - [Invest Like the Best, EP. 250]

My guest today is Roelof Botha, a partner at one of the world’s oldest and most successful venture firms, Sequoia Capital. A few days ago before I sat down with Roelof, he announced Sequoia’s boldest innovation since the firm was founded by Don Valentine in the early 1970s. Going forward, the firm will break from the traditional VC mould of fund cycles and instead restructure around a single, open-ended, permanent structure named The Sequoia Fund. In our conversation, we first discuss the...


Sarah Friar - Building the Local Graph - [Invest Like the Best, EP. 249]

My guest today is Sarah Friar, the CEO of Nextdoor, which connects people in local neighborhoods together. Sarah’s CV sparkles with impressive achievements at interesting businesses, and we spend a lot of time in this conversation thinking through what excellence looks like as a CEO, CFO, equity analyst, and board member. The rest of our discussion is focused on Nextdoor and how the soon-to-be public business is fostering connections between people and businesses in their local areas. I...


Universal Music Group: The Gatekeepers of Music - [Business Breakdowns, EP. 32]

Today, we are running a special episode of Business Breakdowns on our Invest Like the Best feed. When we launched Breakdowns, we hoped to cover industries and businesses that we were “well known but poorly understood.” This deep-dive on UMG and the music industry is just that - you will walk away with a whole new appreciation for artists, labels, and what streaming technology has done for a historic industry. If you enjoy this episode, please be sure to subscribe on your preferred podcast...


Alex Rampell - Investing in Operating Systems - [Invest Like the Best, EP. 248]

My guest today is Alex Rampell, General Partner at Andreessen Horowitz. Alex has a long history in fintech, having co-founded six companies in his career, including Affirm and TrialPay. During our conversation, we cover Alex’s framework for positive selection in investing, why the best investments are often operating systems or systems of record, and Alex’s views on the future of fintech. For those that have listened to our Business Breakdown on Visa with Alex - you know the intellectual...


Sam Bankman-Fried - Creating a Perfect Market - [Invest Like the Best, EP. 247]

My guest today is Sam Bankman-Fried, founder and CEO of leading cryptocurrency exchange, FTX. In a little over two years, FTX has registered 1.2 million users, grown to facilitate $10.9 billion of daily trading volume, and reached an $18 billion valuation. Prior to FTX, Sam worked at Jane Street Capital before founding a quant trading firm of his own, Alameda Research. At just 29, Sam has packed a lot into a short period of time, and as I’m sure you’ll hear, he has a special ability to...


Nick Neuman - Becoming Your Own Bank - [Invest Like the Best, EP. 246]

My guest today is Nick Neuman, CEO and co-founder of Casa. Casa helps bitcoin investors and owners keep their digital assets safe from loss or theft by providing managed self-custody services. In our discussion, we cover the history of asset custody from ancient temples to decentralized ledgers, look at the mechanics of how private keys work, and explore why people are better off holding the keys themselves. We then dive into the future of digital wallets as gateways into our virtual lives,...


Devin Finzer - An Everything Store for Digital Assets - [Founder’s Field Guide, EP. 53]

My guest today is Devin Finzer, co-founder and CEO of OpenSea, the world’s largest NFT marketplace. In a journey that started like many other founders in the space, Devin went deep down the crypto rabbit hole in 2017 and became particularly fascinated with the potential behind digital assets. During our conversation, we touch on the origin story of OpenSea, how Devin differentiates between the spectrum of NFTs in the market, and what he sees as the opportunity in the future for the...


Jenny Lefcourt - The Go-to-Market Motion - [Invest Like the Best, EP. 245]

My guest today is Jenny Lefcourt, an equal General Partner at seed-stage venture firm Freestyle Capital, where she manages $450 million in seed investments. Jenny has been engrained in the tech world since the early days of the internet. She dropped out of her Stanford MBA program to co-found online wedding registry startup with classmate, Jessica Herrin, which was subsequently acquired by The Knot. During our conversation, we cover Jenny's investment frameworks, why she...


Dave Girouard - Making Better Loans - [Founder’s Field Guide, EP. 52]

My guest today is Dave Girouard, co-founder and CEO of Upstart, a lending platform that leverages AI to make loans more accessible and affordable. Dave started in Silicon Valley as a Product Manager at Apple and later spent eight years at Google, where he built their suite of cloud apps. In our discussion, we cover the lessons Dave has learned about building speed into a habit, the intricacies of training an AI model to predict the future, and what it was like to start a fintech business as...