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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




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...


Jay Hoag - Calibrating Market Adoption - [Invest Like the Best, EP. 244]

My guest today is Jay Hoag, co-founder of TCV. If you look at Jay’s investment track record, it’s a “who’s who” of tech giants with Airbnb, Netflix, Peloton, Zillow, and a list that does not stop there. Needless to say, Jay has a Hall of Fame career. During our conversation, we talk about his own journey founding TCV, what advice he has for visionaries, and why he sees advantages for private to public crossover investors. Jay has such a wealth of experience that is on display throughout this...


Gina Bianchini - Helping Creators Build Communities - [Founder’s Field Guide, EP. 51]

My guest today is Gina Bianchini, founder and CEO of Mighty Networks, which gives creators a platform to start, grow and own their social communities. In our conversation, we cover the differences between leadership and management, the lessons Gina learned building a similar business in the 2000s with Marc Andreessen, and the elements that make up a thriving community. We talk about community design, finding ways to connect like-minded people, why it’s so important to create movement, and...


David Fialkow - Paint Outside the Lines - [Invest Like the Best, EP. 243]

My guest today is David Fialkow, co-founder of General Catalyst. If you are looking for a dose of fun, charismatic energy from a very unique investor then this is the conversation for you. David has a diverse background not only as an investor but also as a philanthropist and filmmaker. He won an Academy Award for his role as the producer of the 2018 documentary Icarus. During our conversation, David and I dive into what makes a great founder, the importance of storytelling, and the value of...


Justin Waldron - The Future of Social Gaming - [Founder’s Field Guide, EP. 50]

My guest today is Justin Waldron, co-founder and President of Playco. Justin is a pioneer of the social gaming industry after he co-founded Zynga at age 19, and he has continued to build games ever since. In our conversation, we cover how Justin sees the future of gaming as social platforms evolve, how gaming may be the next tool for content creation, and how Playco has approached aligning incentives for game creators and players. As talk of the metaverse becomes more mainstream, it’s...


Daniel Ek - Enabling Creators Everywhere - [Invest Like the Best, EP. 242]

Today is a special episode because it marks five years since I released the first episode of Invest Like the Best. Over those years, I’ve learned so much from so many investors and builders, but today’s guest may have taught me the most. Daniel Ek is the CEO and founder of Spotify, and I find him to be one of the most thoughtful business leaders in the world. Daniel is the perfect guest for this special occasion because he exemplifies the curiosity, humility, leadership, and dogged...


Gabby Dizon - Mapping the Metaverse Economy - [Founder’s Field Guide, EP. 49]

My guest today is Gabby Dizon, co-founder of Yield Guild Games or YGG. In 2020, Gabby and his co-founders built YGG around the growing “play-to-earn” economy within blockchain-based games. Based in the Philippines, YGG effectively backs players - who might not otherwise be able to afford to play - in exchange for a share of their profits. Today, YGG is paying out over a $1mn US dollars a week to players within its community - largely concentrated in their home country of the...


Scott Malpass - Building a Great Endowment - [Invest Like the Best, EP. 241]

My guest today is Scott Malpass. Scott was the CIO of Notre Dame's endowment for 32 years and has always been a pioneer at the forefront of the endowment investing world - leading Notre Dame's early investments into Sequoia as well as some of the premier fund managers in China decades ago. Scott built the endowment into a powerhouse, scaling it from $400 million to over $12 billion of assets under management across 175 managers. In our conversation, we talk about the qualities he looks for...