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Invest Like the Best

Patrick O'Shaughnessy

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1.4K
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Invest Like the Best

Invest Like the Best

Patrick O'Shaughnessy

394
Followers
1.4K
Plays
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About Us

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 InvestorFieldGuide.com

Latest Episodes

Blake Robbins – Investing in Gaming

My guest today is Blake Robbins, a partner at Ludlow Ventures. We talk about all things video games, including the major companies in the industry, how games monetize, how in-game economies work, how e-sports has evolved, and much more. This is a fast-growing segment of consumer attention and interest, I believe we are in the very early days of gaming going mainstream. I also have a favor to ask. My team and I have built a small survey for Invest Like the Best listeners and if you’ve enjoyed the podcast, I’d deeply appreciate it if you took 5 minutes to fill it out at investorfieldguide.com/survey. It will help shape the future direction of the show, which I intend to keep improving in the years to come. Thank you, and now please enjoy my conversation with Blake Robbins. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:35) – (First question) – Overview of the gaming industry and how folks may get involved as an investor (3:46) – Some of the biggest players in the space (5:30) – The monetization methods of these gams (9:22) – How do these games respond to real currencies (14:49) – The landscape of e-sports/e-gaming as a whole (19:57) – His involvement with 100 Thieves (25:52) – The media landscape and the role of influencers (29:05) – When he invests and what the opportunities are out there (33:07) – The engines behind a lot of this; Unity and Unreal (34:58) – Other investors that get this trend (37:43) – Other interesting areas of investment for him, including the creator economy (41:25) – Opportunities to build out and invest in the infrastructure of the creator economy (45:37) – Infrastructure opportunities that need to be built (48:08) – Advice for younger professionals (49:04) – Investment allocation he is most proud of (50:08) – A unique skill he couldn’t teach or train in others (52:27) – Something in gaming he doesn’t understand or wants to learn more about (54:08) – The kindest thing anyone has done for Blake Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

56 MIN4 d ago
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Blake Robbins – Investing in Gaming

Brad Gerstner – Public and Private Investing

My guest today is Brad Gerstner, the founder and CIO of Altimeter Capital, a multi-billion dollar technology-focused investment firm. Brad and his team are known for a deep expertise in internet-enabled businesses, including Expedia, Facebook, Uber, and many more. We discuss the evolution of opportunity in this style of investing, including the important shift to private investing, where so much of the value creation now happens. I won’t soon forget our discussion of consumer intent on the internet and how it has shifted, the role that essentialism plays in Brad’s business and life, and the rise of the Chinese internet giants like Bytedance. Please enjoy this great conversation with Brad Gerstner. This episode is brought to you by theMIT investment management company (MITIMCO) Reach out or learn more: Email:partner@mitimco.org Website:https://mitimco.org/partner/ MITIMCo 10 year Letter:https://mitimco.org/wp-content/uploads/2017/03/MITIMCo-Alumni-Letter.pdf MITIMCo brochure:https://mitimco.org/wp-content/uploads/2019/01/MITIMCo-Brochure_web_2018-12-05.pdf For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:32) – (First question) – Overall investment philosophy at Altimeter (5:12) – Most interesting thing in the landscape today (11:16) – Disrupting the tech giants moving forward (13:56) – The investing opportunity in the backend of the internet (16:42) – His take on old line businesses and how technology could shift his view on them (18:56) – Lessons from company founders whose platforms rely on consumer discovery (21:32) – Running his business on essentialism (21:40) – Essentialism: The Disciplined Pursuit of Less (26:11) – Tactical applications of essentialism (29:46) – Applying essentialism outside of business (31:16) – What travel has taught him about business (33:43) – What we should know about the Chinese internet market (37:11) – The emergence of bite sized transactions across the web (39:22) – Bite sized work (42:43) – How early on can you figure out what company would win a vertical (45:36) – What problem space would he tackle today (48:49) – Collaborating in the private markets (57:27) – Pricing businesses as a key component of his investment choices (1:02:47) – Fascination with life sciences and software (1:04:12) – What about the future excites him (1:06:48) – Kindest thing anyone has done for Brad Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

69 MIN1 w ago
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Brad Gerstner – Public and Private Investing

John Collison – Growing the Internet Economy

My guest today is John Collison, the Co-Founder of the digital payments company Stripe. Stripe’s mission is to increase the GDP of the internet, a lofty and deeply interesting pursuit. John is clearly a voracious learner across business and investing, which you’ll hear instantly. He started Stripe with his brother Patrick when he was just 19 years old, and has grown it to, at last valuation, a $36B business. In our conversation, we discuss conglomerates, the internet economy, the power of writing, and why board members are like Pokémon characters, each with different powers. It’s a lively and wide-ranging conversation with one of the entrepreneurs I’ve most enjoyed speaking with. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:30) – (First question) – Interest in industrial conglomerates (9:10) – Their thinking on acquisitions vs starting new companies (11:42) – How the payment landscape looked when Stripe was started (15:55) – View on the internet economy (20:09) – Exciting possibilities for the future of the internet economy (22:11) – The forces of size vs speed among startups (26:53) – Driving reasons why employees choose Stripe starting with clear communication (28:55) – Tips for better internal communications (30:09) – The importance of rigor in Stripe’s corporate culture (32:15) – Investors and investing styles that are most intriguing to him (36:02) – Teaching vs experiencing business lessons (37:56) – Lessons from going to market with new ideas (50:58) – Allowing teams to explore new ideas at Stripe (44:11) – Best startup companies to study to understand the history of this space (44:52) – Softwar: An Intimate Portrait of Larry Ellison and Oracle (48:18) – Cable Cowboy: John Malone and the Rise of the Modern Cable Business (48:43) – Infrastructures of internet businesses that are missing (52:03) – Does general accounting practices need to change to capture the true value of a company like Stripe (1:01:53) – Shared playbooks in Silicon Valley (1:02:02) – The transition to the no code movement (1:08:22) – Other businesses that pique his interest outside of software (1:10:21) – Future trends that excite him (1:11:10) – First memory when he felt like he was participating in the tech economy (1:12:46 – The role of board members (1:15:48) – Kindest thing anyone has done for him (1:18:49) – Advice for young people Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

81 MIN2 w ago
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John Collison – Growing the Internet Economy

Jeremy Grantham – An Uncertain Crisis - [Invest Like the Best, EP.177]

My guest today is Jeremy Grantham. Jeremy is the co-founder and chief investment strategist of Grantham, Mayo, & van Otterloo (aka GMO). GMO, which manages more than $60B for clients, was a firm that helped educate me early in my investing career. They’ve long published thought-provoking research, most of which came from Grantham himself. He is regarded as a highly knowledgeable investor in various stock, bond, and commodity markets, but is particularly noted for his prediction of various bubbles. In this conversation we discuss the current crisis, which he calls the fourth major event of his long and storied career as an investor. As he says, this one is the most uncertain. We also discuss unique topics like commodity-based companies, and how opportunity often lies between fields of expertise. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:37) – (First question) – What keeps him going in investing (2:54) – Changing approaches to managing money over the decades (7:27) – Their investment forecast for major allocations and how that has evolved (10:06) – How to markets compete with FAANG stocks (16:06) – More opportunity for active investors and where (30:55) – How he talks to clients about major stock market events (34:09) – His interest in natural resources/commodities (47:07) – Long term argument for the three natural resources: oil, metals, and food (47:10) – An Investment Only A Mother Could Love: The Tactical Case (52:01) – Specific case for particular metals (56:46) – Areas in the future that excite him or that he wants to learn more about (1:03:42) – Advice for people interested in investing (1:05:15) – Kindest thing anyone has done for Jeremy Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

67 MIN3 w ago
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Jeremy Grantham – An Uncertain Crisis - [Invest Like the Best, EP.177]

Ben Thompson – Platforms, Ecosystems, and Aggregators

My guest today is Ben Thompson. Ben is the author of my favorite business strategy newsletter called Stratechery. He’s also the host of the exponent podcast, and now the Dithering, a podcast he recently launched with John Gruber. I think Ben is among the most interesting business analysts in the world, and I’ve learned from and directly applied many of his ideas. We cover many of the major concepts he’s introduced over the years, including his well know aggregation theory. I think that to understand how the internet has changed the business world for good, you must read Ben and follow his thinking. I’m excited to finally have him as a guest on the show. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (01:26) – (First question) – Companies that are built for the next disruption (1:32) – The End of the Beginning (9:58) – Aggregation Theory and the Smiling Curve (13:18) – Steps to creating an aggregator (19:46) – Pattern of successful aggregators or luck? (24:34) – How aggregators interact with suppliers and consumers (30:49) – Taking on other aggregators (34:09) – Platform vs aggregator in the scope of Shopify vs Amazon/Walmart (40:55) – The Moat Map (46:16) – Value chain thinking and profitable business models (51:58) – Future of media and independent content creator’s vs bundles (56:07) – Bundling independent creators (1:00:37) – The infrastructure layer of technology and software companies (1:02:35) – His thoughts on gaming platforms (1:06:13) – The atoms vs the bits in the tech world (1:12:18) – What he’s learned from covering Netflix (1:13:46) – Kindest thing anyone has done for Ben (1:15:56) – Stratechery Podcast Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

77 MINJUN 2
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Ben Thompson – Platforms, Ecosystems, and Aggregators

Shishir Mehrotra – The Art and Science of the Bundle

My guest today is Shishir Mehrotra and the topic of our conversation is the bundle: offering access to multiple products, services, or providers for a single bundled price. This topic is full of incorrect pre-conceived notions, and as it turns out, the bundle is one of the most powerful ideas in business. Properly harnessed it is good for everyone involved. Shishir explains the ins and outs of bundles in this conversation. Shishir ran product at YouTube for years and sits on the Spotify board of directors. He founded and now leads Coda (which is “A Doc” spelled backwards) in 2014, to bundle together productivity apps like docs, spreadsheets, databases, and applications. I love this wonky, detailed conversation which has me thinking differently about many businesses and business strategy. Please enjoy. This episode is brought to byKoyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:08) – (First question) – The arc of his career (3:32) – Why he has an interest in bundling (7:45) – The concepts of superfan, casualfan, and nonfan businesses (11:05) – Using Spotify as an example of bundles (13:24) – The first myth of bundling: Bundling is bad for consumers (17:53) – The second myth of bundling: 1st vs 3rd party providers and the bundlers (23:03) – Low usage but high Marginal Churn Contribution (MCC) business (24:26) – How insurance fits into these models (26:37) – Myth 3 of bundling: How this impacts consumers (32:12) – How marginal costs play into the thinking of bundling (34:54) – Myth 4: Bundling things that have nothing to do with each other (39:51) – How bundling companies can apply this into their product development (43:21) – Strategic advice to companies building bundles (49:01) – How price and pricing power play into advantages for certain bundlers (54:16) – How does bundling play into his investing thesis (56:47) – Most interesting bundles he’s observed (58:44) – Eigenquestions: The Art of Framing Problems (59:14) – What the future of this trend is (1:02:24) – What is an eigenquestion (1:06:29) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

71 MINMAY 26
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Shishir Mehrotra – The Art and Science of the Bundle

Hamilton Helmer – Power + Business

My guest today is Hamilton Helmer, the Co-Founder and Chief Investment Officer of Strategy Capital and the author of one of the best business books in history called 7 Powers, which is the topic of much of our conversation.

58 MINMAY 19
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Hamilton Helmer – Power + Business

Tobi Lutke – Building a Modern Business

My guest today is Tobi Lutke, the co-founder, and CEO of Shopify. This is both a timely and evergreen conversation. Timely, as the world as moved aggressively digital in the past two months, and Shopify powers so much of digital commerce. Evergreen, because while we touch on Covid and the Shopify business, this is much more a conversation on business and personal principles, learning, design, and growth. Tobi is one of the CEO’s I look up to most for the type of company he is building and for the way he conducts himself. We discuss business focus, why video games help you learn the power of attention, what design means for products and organizations, and much more. Please enjoy my conversation with Tobi Lutke. This episode is brought to you by the MIT investment management company (MITIMCO) Reach out or learn more: Email:partner@mitimco.org Website:https://mitimco.org/partner/ MITIMCo 10 year Letter:https://mitimco.org/wp-content/uploads/2017/03/MITIMCo-Alumni-Letter.pdf MITIMCo brochure:https://mitimco.org/wp-content/uploads/2019/01/MITIMCo-Brochure_web_2018-12-05.pdf For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:35) – (First question) – The launch of the new Shopify shop app (2:44) – Deniel Ek Podcast Episode (2:45) – Jeff Lawson Podcast Episode (4:56) – Having the right focus and growing a good business (9:06) – Marketplace business model vs the merchant driven business model 9:16 – Bill Gurley Podcast Appearances - 162 | 144 | 137 (11:47) – His role as a decisionmaker as CEO of the company (14:07) – What does he mean when he talks about quality (18:28) – His thinking on design and quality (18:32) – Zen And The Art Of Motorcycle Maintenance (19:59) – The Design of Everyday Things (21:06) – Friction as a force in business and manufacturing (26:04) – His thoughts on systems and being free of process (26:08) – The Systems Bible (30:01) – The game of Factoria and how it relates to systems (32:16) – Transfer Learning (34:33) – What Real-Time Strategy games have taught Tobi (38:30) – Building context inside of a company and making it scale (41:17) – Personality typing (46:22) – The Tobi Blueprint (46:04) – Why he likes The Guide to the Good Life and stoicism (55:38) – Raising kids and the impact of Covid (1:03:16) – The kindest thing anyone has done for Tobi Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

65 MINMAY 12
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Tobi Lutke – Building a Modern Business

Ali Hamed – An Update on Private Credit

My guest today is popular past guest Ali Hamed, who joins us for an update on private credit. We discuss what has happened so far, what parts of the market are frozen, and where opportunities may lie. We also talk about how the world has shifted digitally since the beginning of the COVID pandemic. Please enjoy my conversation with my friend Ali Hamed. This episode is brought to byKoyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:41) – (First question) – World of private credit in the pandemic age (4:50) – Bag of uncertainty (6:27) – Important levers in private credit (9:15) – Scary scenarios and systemic risks in this world (13:21) – General trends in the credit data (15:30) – Are investors factoring government response properly (17:02) – Defining advanced rates (20:18) – Focus on quality vs rate of return now (22:26) – Pockets of opportunity as uncertainty declines (26:06) – Online ecommerce platforms, like the YouTube economy (29:40) – Non advertising driven ecommerce platforms (31:54) – How venture capital is responding (38:19) – How junior debt could be am opportunity (40:17) – Trends he’s thinking about; redefining small businesses (43:07) – Ali Hamed Podcast Episode Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

44 MINMAY 5
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Ali Hamed – An Update on Private Credit

Chris Bloomstran - An Update on Public Markets

My guest today for a flash update is Chris Bloomstran, the founder and CIO of Semper Augustus and a popular past guest on the show. We talk about his view on the state of the public equity market, why it will be hard for the market to deliver great returns for the next decade relative to the last, and where opportunities may lie. Please enjoy. This episode is brought to byKoyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:42) – (First question) – Adjustments to his portfolio in the age of a pandemic (6:41) – Chris Bloomstran Podcast Episode (9:36) – The Federal Reserve Act (12:32) – Surprising action in the markets during the crisis (13:08) – 2020 Investment Letter (15:02) – Why we won’t see the same performance in tech over the future as we’ve seen the last decade (21:00) – The carnage in energy sector and return potential (30:06) – Berkshires activity since the crisis started (35:48) – Where sectors are valued in the current market (41:12) – Expectation for deflation over inflation (48:54) – Characteristics to look for in businesses to own over the next 10 years (52:05) – Economic factors they are focusing on Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

57 MINAPR 30
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Chris Bloomstran - An Update on Public Markets

Latest Episodes

Blake Robbins – Investing in Gaming

My guest today is Blake Robbins, a partner at Ludlow Ventures. We talk about all things video games, including the major companies in the industry, how games monetize, how in-game economies work, how e-sports has evolved, and much more. This is a fast-growing segment of consumer attention and interest, I believe we are in the very early days of gaming going mainstream. I also have a favor to ask. My team and I have built a small survey for Invest Like the Best listeners and if you’ve enjoyed the podcast, I’d deeply appreciate it if you took 5 minutes to fill it out at investorfieldguide.com/survey. It will help shape the future direction of the show, which I intend to keep improving in the years to come. Thank you, and now please enjoy my conversation with Blake Robbins. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:35) – (First question) – Overview of the gaming industry and how folks may get involved as an investor (3:46) – Some of the biggest players in the space (5:30) – The monetization methods of these gams (9:22) – How do these games respond to real currencies (14:49) – The landscape of e-sports/e-gaming as a whole (19:57) – His involvement with 100 Thieves (25:52) – The media landscape and the role of influencers (29:05) – When he invests and what the opportunities are out there (33:07) – The engines behind a lot of this; Unity and Unreal (34:58) – Other investors that get this trend (37:43) – Other interesting areas of investment for him, including the creator economy (41:25) – Opportunities to build out and invest in the infrastructure of the creator economy (45:37) – Infrastructure opportunities that need to be built (48:08) – Advice for younger professionals (49:04) – Investment allocation he is most proud of (50:08) – A unique skill he couldn’t teach or train in others (52:27) – Something in gaming he doesn’t understand or wants to learn more about (54:08) – The kindest thing anyone has done for Blake Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

56 MIN4 d ago
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Blake Robbins – Investing in Gaming

Brad Gerstner – Public and Private Investing

My guest today is Brad Gerstner, the founder and CIO of Altimeter Capital, a multi-billion dollar technology-focused investment firm. Brad and his team are known for a deep expertise in internet-enabled businesses, including Expedia, Facebook, Uber, and many more. We discuss the evolution of opportunity in this style of investing, including the important shift to private investing, where so much of the value creation now happens. I won’t soon forget our discussion of consumer intent on the internet and how it has shifted, the role that essentialism plays in Brad’s business and life, and the rise of the Chinese internet giants like Bytedance. Please enjoy this great conversation with Brad Gerstner. This episode is brought to you by theMIT investment management company (MITIMCO) Reach out or learn more: Email:partner@mitimco.org Website:https://mitimco.org/partner/ MITIMCo 10 year Letter:https://mitimco.org/wp-content/uploads/2017/03/MITIMCo-Alumni-Letter.pdf MITIMCo brochure:https://mitimco.org/wp-content/uploads/2019/01/MITIMCo-Brochure_web_2018-12-05.pdf For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:32) – (First question) – Overall investment philosophy at Altimeter (5:12) – Most interesting thing in the landscape today (11:16) – Disrupting the tech giants moving forward (13:56) – The investing opportunity in the backend of the internet (16:42) – His take on old line businesses and how technology could shift his view on them (18:56) – Lessons from company founders whose platforms rely on consumer discovery (21:32) – Running his business on essentialism (21:40) – Essentialism: The Disciplined Pursuit of Less (26:11) – Tactical applications of essentialism (29:46) – Applying essentialism outside of business (31:16) – What travel has taught him about business (33:43) – What we should know about the Chinese internet market (37:11) – The emergence of bite sized transactions across the web (39:22) – Bite sized work (42:43) – How early on can you figure out what company would win a vertical (45:36) – What problem space would he tackle today (48:49) – Collaborating in the private markets (57:27) – Pricing businesses as a key component of his investment choices (1:02:47) – Fascination with life sciences and software (1:04:12) – What about the future excites him (1:06:48) – Kindest thing anyone has done for Brad Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

69 MIN1 w ago
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Brad Gerstner – Public and Private Investing

John Collison – Growing the Internet Economy

My guest today is John Collison, the Co-Founder of the digital payments company Stripe. Stripe’s mission is to increase the GDP of the internet, a lofty and deeply interesting pursuit. John is clearly a voracious learner across business and investing, which you’ll hear instantly. He started Stripe with his brother Patrick when he was just 19 years old, and has grown it to, at last valuation, a $36B business. In our conversation, we discuss conglomerates, the internet economy, the power of writing, and why board members are like Pokémon characters, each with different powers. It’s a lively and wide-ranging conversation with one of the entrepreneurs I’ve most enjoyed speaking with. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:30) – (First question) – Interest in industrial conglomerates (9:10) – Their thinking on acquisitions vs starting new companies (11:42) – How the payment landscape looked when Stripe was started (15:55) – View on the internet economy (20:09) – Exciting possibilities for the future of the internet economy (22:11) – The forces of size vs speed among startups (26:53) – Driving reasons why employees choose Stripe starting with clear communication (28:55) – Tips for better internal communications (30:09) – The importance of rigor in Stripe’s corporate culture (32:15) – Investors and investing styles that are most intriguing to him (36:02) – Teaching vs experiencing business lessons (37:56) – Lessons from going to market with new ideas (50:58) – Allowing teams to explore new ideas at Stripe (44:11) – Best startup companies to study to understand the history of this space (44:52) – Softwar: An Intimate Portrait of Larry Ellison and Oracle (48:18) – Cable Cowboy: John Malone and the Rise of the Modern Cable Business (48:43) – Infrastructures of internet businesses that are missing (52:03) – Does general accounting practices need to change to capture the true value of a company like Stripe (1:01:53) – Shared playbooks in Silicon Valley (1:02:02) – The transition to the no code movement (1:08:22) – Other businesses that pique his interest outside of software (1:10:21) – Future trends that excite him (1:11:10) – First memory when he felt like he was participating in the tech economy (1:12:46 – The role of board members (1:15:48) – Kindest thing anyone has done for him (1:18:49) – Advice for young people Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

81 MIN2 w ago
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John Collison – Growing the Internet Economy

Jeremy Grantham – An Uncertain Crisis - [Invest Like the Best, EP.177]

My guest today is Jeremy Grantham. Jeremy is the co-founder and chief investment strategist of Grantham, Mayo, & van Otterloo (aka GMO). GMO, which manages more than $60B for clients, was a firm that helped educate me early in my investing career. They’ve long published thought-provoking research, most of which came from Grantham himself. He is regarded as a highly knowledgeable investor in various stock, bond, and commodity markets, but is particularly noted for his prediction of various bubbles. In this conversation we discuss the current crisis, which he calls the fourth major event of his long and storied career as an investor. As he says, this one is the most uncertain. We also discuss unique topics like commodity-based companies, and how opportunity often lies between fields of expertise. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:37) – (First question) – What keeps him going in investing (2:54) – Changing approaches to managing money over the decades (7:27) – Their investment forecast for major allocations and how that has evolved (10:06) – How to markets compete with FAANG stocks (16:06) – More opportunity for active investors and where (30:55) – How he talks to clients about major stock market events (34:09) – His interest in natural resources/commodities (47:07) – Long term argument for the three natural resources: oil, metals, and food (47:10) – An Investment Only A Mother Could Love: The Tactical Case (52:01) – Specific case for particular metals (56:46) – Areas in the future that excite him or that he wants to learn more about (1:03:42) – Advice for people interested in investing (1:05:15) – Kindest thing anyone has done for Jeremy Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

67 MIN3 w ago
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Jeremy Grantham – An Uncertain Crisis - [Invest Like the Best, EP.177]

Ben Thompson – Platforms, Ecosystems, and Aggregators

My guest today is Ben Thompson. Ben is the author of my favorite business strategy newsletter called Stratechery. He’s also the host of the exponent podcast, and now the Dithering, a podcast he recently launched with John Gruber. I think Ben is among the most interesting business analysts in the world, and I’ve learned from and directly applied many of his ideas. We cover many of the major concepts he’s introduced over the years, including his well know aggregation theory. I think that to understand how the internet has changed the business world for good, you must read Ben and follow his thinking. I’m excited to finally have him as a guest on the show. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (01:26) – (First question) – Companies that are built for the next disruption (1:32) – The End of the Beginning (9:58) – Aggregation Theory and the Smiling Curve (13:18) – Steps to creating an aggregator (19:46) – Pattern of successful aggregators or luck? (24:34) – How aggregators interact with suppliers and consumers (30:49) – Taking on other aggregators (34:09) – Platform vs aggregator in the scope of Shopify vs Amazon/Walmart (40:55) – The Moat Map (46:16) – Value chain thinking and profitable business models (51:58) – Future of media and independent content creator’s vs bundles (56:07) – Bundling independent creators (1:00:37) – The infrastructure layer of technology and software companies (1:02:35) – His thoughts on gaming platforms (1:06:13) – The atoms vs the bits in the tech world (1:12:18) – What he’s learned from covering Netflix (1:13:46) – Kindest thing anyone has done for Ben (1:15:56) – Stratechery Podcast Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

77 MINJUN 2
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Ben Thompson – Platforms, Ecosystems, and Aggregators

Shishir Mehrotra – The Art and Science of the Bundle

My guest today is Shishir Mehrotra and the topic of our conversation is the bundle: offering access to multiple products, services, or providers for a single bundled price. This topic is full of incorrect pre-conceived notions, and as it turns out, the bundle is one of the most powerful ideas in business. Properly harnessed it is good for everyone involved. Shishir explains the ins and outs of bundles in this conversation. Shishir ran product at YouTube for years and sits on the Spotify board of directors. He founded and now leads Coda (which is “A Doc” spelled backwards) in 2014, to bundle together productivity apps like docs, spreadsheets, databases, and applications. I love this wonky, detailed conversation which has me thinking differently about many businesses and business strategy. Please enjoy. This episode is brought to byKoyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:08) – (First question) – The arc of his career (3:32) – Why he has an interest in bundling (7:45) – The concepts of superfan, casualfan, and nonfan businesses (11:05) – Using Spotify as an example of bundles (13:24) – The first myth of bundling: Bundling is bad for consumers (17:53) – The second myth of bundling: 1st vs 3rd party providers and the bundlers (23:03) – Low usage but high Marginal Churn Contribution (MCC) business (24:26) – How insurance fits into these models (26:37) – Myth 3 of bundling: How this impacts consumers (32:12) – How marginal costs play into the thinking of bundling (34:54) – Myth 4: Bundling things that have nothing to do with each other (39:51) – How bundling companies can apply this into their product development (43:21) – Strategic advice to companies building bundles (49:01) – How price and pricing power play into advantages for certain bundlers (54:16) – How does bundling play into his investing thesis (56:47) – Most interesting bundles he’s observed (58:44) – Eigenquestions: The Art of Framing Problems (59:14) – What the future of this trend is (1:02:24) – What is an eigenquestion (1:06:29) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

71 MINMAY 26
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Shishir Mehrotra – The Art and Science of the Bundle

Hamilton Helmer – Power + Business

My guest today is Hamilton Helmer, the Co-Founder and Chief Investment Officer of Strategy Capital and the author of one of the best business books in history called 7 Powers, which is the topic of much of our conversation.

58 MINMAY 19
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Hamilton Helmer – Power + Business

Tobi Lutke – Building a Modern Business

My guest today is Tobi Lutke, the co-founder, and CEO of Shopify. This is both a timely and evergreen conversation. Timely, as the world as moved aggressively digital in the past two months, and Shopify powers so much of digital commerce. Evergreen, because while we touch on Covid and the Shopify business, this is much more a conversation on business and personal principles, learning, design, and growth. Tobi is one of the CEO’s I look up to most for the type of company he is building and for the way he conducts himself. We discuss business focus, why video games help you learn the power of attention, what design means for products and organizations, and much more. Please enjoy my conversation with Tobi Lutke. This episode is brought to you by the MIT investment management company (MITIMCO) Reach out or learn more: Email:partner@mitimco.org Website:https://mitimco.org/partner/ MITIMCo 10 year Letter:https://mitimco.org/wp-content/uploads/2017/03/MITIMCo-Alumni-Letter.pdf MITIMCo brochure:https://mitimco.org/wp-content/uploads/2019/01/MITIMCo-Brochure_web_2018-12-05.pdf For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:35) – (First question) – The launch of the new Shopify shop app (2:44) – Deniel Ek Podcast Episode (2:45) – Jeff Lawson Podcast Episode (4:56) – Having the right focus and growing a good business (9:06) – Marketplace business model vs the merchant driven business model 9:16 – Bill Gurley Podcast Appearances - 162 | 144 | 137 (11:47) – His role as a decisionmaker as CEO of the company (14:07) – What does he mean when he talks about quality (18:28) – His thinking on design and quality (18:32) – Zen And The Art Of Motorcycle Maintenance (19:59) – The Design of Everyday Things (21:06) – Friction as a force in business and manufacturing (26:04) – His thoughts on systems and being free of process (26:08) – The Systems Bible (30:01) – The game of Factoria and how it relates to systems (32:16) – Transfer Learning (34:33) – What Real-Time Strategy games have taught Tobi (38:30) – Building context inside of a company and making it scale (41:17) – Personality typing (46:22) – The Tobi Blueprint (46:04) – Why he likes The Guide to the Good Life and stoicism (55:38) – Raising kids and the impact of Covid (1:03:16) – The kindest thing anyone has done for Tobi Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

65 MINMAY 12
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Tobi Lutke – Building a Modern Business

Ali Hamed – An Update on Private Credit

My guest today is popular past guest Ali Hamed, who joins us for an update on private credit. We discuss what has happened so far, what parts of the market are frozen, and where opportunities may lie. We also talk about how the world has shifted digitally since the beginning of the COVID pandemic. Please enjoy my conversation with my friend Ali Hamed. This episode is brought to byKoyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:41) – (First question) – World of private credit in the pandemic age (4:50) – Bag of uncertainty (6:27) – Important levers in private credit (9:15) – Scary scenarios and systemic risks in this world (13:21) – General trends in the credit data (15:30) – Are investors factoring government response properly (17:02) – Defining advanced rates (20:18) – Focus on quality vs rate of return now (22:26) – Pockets of opportunity as uncertainty declines (26:06) – Online ecommerce platforms, like the YouTube economy (29:40) – Non advertising driven ecommerce platforms (31:54) – How venture capital is responding (38:19) – How junior debt could be am opportunity (40:17) – Trends he’s thinking about; redefining small businesses (43:07) – Ali Hamed Podcast Episode Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

44 MINMAY 5
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Ali Hamed – An Update on Private Credit

Chris Bloomstran - An Update on Public Markets

My guest today for a flash update is Chris Bloomstran, the founder and CIO of Semper Augustus and a popular past guest on the show. We talk about his view on the state of the public equity market, why it will be hard for the market to deliver great returns for the next decade relative to the last, and where opportunities may lie. Please enjoy. This episode is brought to byKoyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:42) – (First question) – Adjustments to his portfolio in the age of a pandemic (6:41) – Chris Bloomstran Podcast Episode (9:36) – The Federal Reserve Act (12:32) – Surprising action in the markets during the crisis (13:08) – 2020 Investment Letter (15:02) – Why we won’t see the same performance in tech over the future as we’ve seen the last decade (21:00) – The carnage in energy sector and return potential (30:06) – Berkshires activity since the crisis started (35:48) – Where sectors are valued in the current market (41:12) – Expectation for deflation over inflation (48:54) – Characteristics to look for in businesses to own over the next 10 years (52:05) – Economic factors they are focusing on Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

57 MINAPR 30
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Chris Bloomstran - An Update on Public Markets

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