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Invest Like the Best

Author: Patrick O'Shaughnessy

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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 InvestorFieldGuide.com
195 Episodes
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My guest this week is Charlie Songhurst, the former head of strategy at Microsoft and a prolific investor, having personally invested in nearly 500 companies throughout his career. I met Charlie at an event hosted in New York and you can tell within one minute of meeting him that his mind is sparkling with ideas and curiosity. Its no wonder he’s been among the most commonly requested guests when I asked several top investors and CEOs who I should have on the show. We discuss the lessons he’s learned about business, investing, and people from such a large sample size of companies. I won’t reveal any more here, I highly recommend you just listen to Charlie and learn. Let’s dive in. 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 (1:25) – (First question) –  Stack ranking the vices of power, money and fame (2:41) – Memorable response to the stack ranking question (3:13) – Best scenario to explore this stack ranking concept (3:55) – Other ways to rank founders (4:44) – Quick look at this career (5:16) – Time at Microsoft (6:03) – Features he looks for in startups (10:55) – Managing the declining curve of productivity (14:55) – Why founders are often unique people             (14:57) – Jeff Gramm Podcast Episode             (15:04) – Aliens, Jedi & Cults (19;43) – How early entrepreneurs need to make recruitment a serious part of their work (23:06) – How successful founders win the best candidates (25:27) – The East Coast vs. West Coast investment strategies (30:40) – When it’s time to bring in quantitative factors into early stage investing (34:36) – The markers that pop up in companies that hit (37:22) – Boring but successful investments (39:28) – Investor aesthetics (41:29) – Characteristics of investors that he believes are important to success (42:57) – Impacts of Covid and some of the permanent changes that have happened as a result (47:49) – Investing opportunities in the local community (49:13) – His take on cryptocurrencies (53:47) – Most mis valued asset in the world (55:16) – Investing opportunities in Europe (57:34) – Make up of his 483 investments             (57:58) – Matt Clifford Podcast Episode (59:17) – Curation as a skill (1:01:54) – Timing and startup success (1:05:11) – Kindest thing anyone has done for him   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
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  
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 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 (2:32) – (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
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
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
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
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 by Koyfin.   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
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. He has spent his career as a practicing business strategist: advising companies, investing based on strategic insights and teaching strategy.  In the last three decades, he has also utilized his strategy concepts as a public equity investor. In this conversation we cover all seven business powers, from counter-positioning to scale economies, and how companies earn and keep those powers. Any investor or businessperson should understand these concepts, and 7 Powers is the best work I’ve seen that explains them in depth. 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 (1:31) – (First question)  - What power means to him (5:05) – Benefits being more common than barriers in the power equation (6:28) – How early-stage companies develop their barriers (11:23) – The power of counter positioning and how he’s seen it applied (14:47) – The product side of counter positioning             (16:39) – Daniel Ek Podcast episode (17:27) – Applying the idea of counter positioning to yourself (20:40) – A cornered resource (23:49) – A look at google as a cornered resource (27:12) – Unique power of network economies (31:18) – What subtleties disqualify network effects (32:54) – Nuances of scale economies (35:56) – Learning economies and who can scale it better (37:07) – Building a switching cost and barrier into your business (40:10) – Branding as power (44:27) – Defining process power and how it differs from scale economies (46:40) – The notion of the time lag and cash flow (50:42) – Why is so much power concentrated in technology businesses (52:07) – What does power mean for customers (53:43) – Developing power as an art vs science, and the best power artists (55:08) – The 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
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
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 by Koyfin. 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
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 by Koyfin. 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
My guest today is Josh Kopelman, the founder of famed venture capital firm First Round Capital. Prior to starting First Round, which has invested at the earliest stages in companies like Square, Uber, and Roblox, Josh was a three-time entrepreneur, so our conversation spans early-stage investing, business building, and entrepreneurship. I’ll not sure forget his analogy distinguishing between navigators and cartographers, nor the rest of the interesting ideas he shared after seeing and investing in so many great businesses. We also discuss how First Round has bucked the trend to build what I’d call a platform adjacent to the core investing business which does a lot for their entrepreneurs and is a model for other professional investing firms, both in venture and elsewhere. Please enjoy my conversation with Josh Kopelman.  This episode is brought to by Koyfin. 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 (2:05) – (First question) – How pandemic has impacted their investing strategies (3:54) – How this stressful environment impacts founders (6:23) – His early career as a founder and how startup culture has changed (10:15) – Most important lessons from his entrepreneurial career and building from just an idea (11:50) – How to analyze a founder (14:05) – Common disagreements when it comes to deciding on an investment (15:33) – How many opportunities they evaluate in a meeting (16:16) – The curvy road to their investment in Roadblox (17:52) – Whether the concept for a platform is overused (19:36) – Founders asking what google search they should build on (20:46) – Solving existing or forecasted problems (25:39) – How the startup scene is impacted by the huge legacy tech companies (30:28) – What makes a great early stage investor (32:19) – Do they focus on founders or themes (33:19) – Where will valuations and returns come back to after the pandemic (36:30) – How are business models evolving in technology entrepreneurship             (36:31) – Matt Clifford Podcast Episode (39:40) – The Dorm Room Fund (43:02) – Whether investment funds should have their own platform (47:31) – Product mistakes in software building (51:52) – What he’s most excited about for the future (54:05) – The 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
My guest today is Manny Stotz, the founder of Kingsway Capital. Manny is one of the leading investors in Frontier Markets, investing in equities in countries like Egypt, Bangladesh, and Pakistan. We discuss the opportunity in these markets from all angles: demographics, valuations, sectors and beyond. It is important to note that we recorded this conversation before COVID, and these markets have fallen 30% without a similar rebound in prices that we’ve seen in the U.S. As you listen you’ll hear why this may be relevant for the companies Manny focuses on and may accentuate the opportunity in Frontier Markets even relative to the numbers quoted in this conversation. Listeners will know my interest in Frontier Markets runs deep, so I was excited to have one of the categories leading investors join me. Please enjoy my conversation with Manny Stotz. This episode is brought to by Koyfin. 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 2:07 – (First question) – How Kingsway was conceived, their focus on frontier emerging markets, and his career path 11:57 – What are the best company builders good at when it comes to fostering a brand 18:30 – How country-specific factors impact the tailwind 25:43 – How markets are faring in these special circumstances 32:09 – Building a book in many of the markets they trade-in 37:10 – Understanding your edge in frontier markets, showing up 39:59 – Importance of solid distribution for the companies he invests in 42:12 – Concentration in various markets 44:10 – Moving beyond consumer brands in these markets 47:14 – Some of the most interesting countries they are looking into and the country business model             47:42 – Guns, Germs, and Steel: The Fates of Human Societies             47:44 – Civilization: The West and the Rest             47:46 – Why Nations Fail: The Origins of Power, Prosperity, and Poverty 53:21 – New topics he’s excited to learn about that will impact his business over the next 10-20 years 55:37 – Best way for people to get involved and invest in these markets 58:17 – 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
My guest this week is Sarah Tavel, a general partner at Benchmark, working alongside past guests Bill Gurley and Chetan Puttagunta. Sarah has a long history as both an investor and as an operator.  She was an early product leader at Pinterest before joining Benchmark. Sarah has become one of my go-to resources for topics like networks, consumer technology, and marketplaces among many other topics. I’ve used her framework for how to think about client engagement, company data, and marketplace liquidity and quality over and over again in my business life. I’m so excited to finally have her 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 1:24 – (First question) - Lessons learned from watching the food delivery space 5:44 – Hip camp and how they are thinking about the space rental sector             5:45 - The a16z Marketplace 100 7:47 – Valuing private companies vs public companies 9:37 – Building marketplaces 14:24 – Tipping a market             14:30 – Bill Gurley Podcast Episode 18:09 – How to incorporate reputation scores into a network 19:55 – Search ranking as a tool for marketplaces 21:00 – Size of marketplaces vs their competitors 22:15 – Niching of marketplaces             22:21 - Chetan Puttagunta Podcast Episode 23:26 – State of the consumer social sector 27:50 – The LinkedIn problem and how she would build a social platform 30:42 – Things that are piquing her interest in the consumer space 32:20 – Lessons learned about scaling while working at Pinterest 38:42 – Pricing and the marketplace 41:25 – Identifying and optimizing a Core Action in a digital business 44:18 – Accruing benefits and mounting losses as part of the product design 47:48 – Her investment in Reci 52:18 – How should companies gather the best data from their business 56:03 – Lessons to SaaS investing 56:29 – Kindest thing anyone has done for Sarah 57:45 – Most interesting philosophy lesson             58:09 – Creating a Kingdom of Ends   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
In the midst of the worldwide quarantine, my friend Boyd Varty decided to begin an adventure he has been considering for a long time: a 40 day and 40 night stay in the African wilderness. I’m releasing this short conversation with Boyd to pique your interest in his daily dispatches. He will be taking short audio journal-like recordings and sharing them with the world as he goes. As of today they are several that you can listen to by subscribing to the Track Your Life podcast on Spotify or wherever you get your podcasts. Please enjoy this short chat with my good friend Boyd Varty. 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 (0:31) – The start of his 40-day trip (1:42) – Origin of the word quarantine and how it led to this journey (3:07) – History of this idea (6:14) – The logistics of this 40-day venture (9:59) – His experience doing this before and how it changed his psyche (12:07) – What is he most fearful of (13:22) – How he feels about sharing this experience when he returns (15:47) – The mental preparation to this journey             (15:48) – Priya Parker Podcast Episode             (15:49) – The Art of Gathering: How We Meet and Why It Matters (17:33) – How can outsiders make a connection to Boyd while he’s in this isolation (19:55) – How can people actually follow him on this journey             (20:23) – Track Your Life with Boyd Varty Podcast – Apple Podcasts | Spotify             (20:33) – Instagram - @boyd_varty             (20:36) – boydvarty.com             (20:43) – 40daysand40nights.com (21:05) – The story of the 17 lions 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
My guest today is with past guest Gavin Baker, the founder and CIO of Atreides Management, LP. We discuss investing during a bear market and the major ways in which the COVID19 outbreak has dramatically altered the investment landscape. Please enjoy my second conversation with Gavin Baker. This episode is brought to by Koyfin. 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 (1:40) – How he sees the markets right now (3:06) – How he handles information uncertainty and the value spreads (5:53) – Trading in today’s market and the volatility (9:45) – How the economic activity squares with the amount of stimulus being pumped into the market             (13:11) – Market Wizards: Interviews with Top Traders (13:56) – Asset tests for individual companies in this environment             (19:09) – This Time Is Different: Eight Centuries of Financial Folly (20:45) – His take on software companies during the crisis (28:57) – Fast pace of change during extreme times of duress (35:14) – Space as a service (39:52) – Attention and time inside digital universes and how investors can take advantage (46:17) – Why chaos is a ladder             (50:42) – It Was a Very Good Year: Extraordinary Moments in Stock Market History   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
My guest today is D.A. Wallach, one of the more interesting investors I’ve come across. He is the former lead singer of the group Chester French and the former artist-in-residence at Spotify, where he was also an early investor. While he’s also an early investor in companies like SpaceX, his focus the last 5 years has been on early stage health care investing, which is the topic of this conversation. We discuss the entire life sciences and heath care investing ecosystem. This was recorded in the very early days of the Coronavirus outbreak so while we touch on it briefly it isn’t the primary focus, and I intend on returning to more traditional episodes like this one in the coming weeks, meant to be evergreen conversations. Please enjoy my conversation with D.A. Wallach. 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 1:31 – (First question) – Where is interest in healthcare started 4:04 – How to categorize health services 5:13 – The product of medicine 6:56 – How medicine is changing in 2020 10:17 – What is enabling innovation in medicine 12:41 – Manufacturing of solutions, gene therapy example 17:16 – Using CRISPR 19:47 – Pros and cons, and the morality of gene intervention 23:44 – How progress is being made in medical breakthroughs 26:51 – What is the business and investment world seeing on the longevity side 30:15 – What is next in the wearable medical tracking trend 33:04 – The personalization of medical treatments 34:31 – How he thinks about all of this from an investing standpoint 36:37 – Exiting these companies 39:41 – How he thinks about founders in this space 42:35 – Drug prices             42:46 – The Paradox of Pricing 46:45 – What will lead to a change in the pricing of drugs 49:05 – The delivery side of healthcare 51:09 – Investments that could improve the delivery side of healthcare 53:33 – Thoughts on the anti-interventionist line of thinking in the medical world 57:50 – Lessons from his health portfolio 1:02:33 – Other frontiers that pique his interest, including gut biome 1:06:46 – His career in music 1:08:20 – Lessons he learned during his time in the music industry 1:10:19 – Opportunities in the music industry as an investor 1:12:29 – Kindest thing anyone has done for DA   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
My guest today is Chad Cascarilla, here to discuss some of the tail risks in the economy and markets as of March 24th in the midst of the Coronavirus pandemic. Chad was one of the most successful investors during the global financial crisis with a specialty in the banking and finance systems. He now runs Paxos, a trust company which trades and custodies unique products like pax gold, bitcoin, and other tokenized assets including simple pax dollars. I feel it is important to avoid confirmation bias in times like this and not just talk to people are optimistic or long, and while I still believe this is ultimately a positive and optimistic conversation, Chad acknowledges and outlines scenarios that few are talking about yet in the markets.   This episode is brought to by Koyfin.   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 (2:04) – (First question) – Today’s market and the porridge scenario (7:38) – Risks to the market that people aren’t focused on (10:54) – What lessons from 2008 do we need to heed this time (13:07) – How does he think about inflation on the other side of this crisis (16:02) – What does a too cold recovery look like (20:35) – Benefits of nationalizing the banks vs pumping liquidity (24:13) – What does the just right recovery look like (25:24) – Assets that might be ideal to hold in a too hot or too cold scenario (29:00) – His take on how Bitcoin has performed during this crisis (31:53) – The US’s inherent strengths compared to the rest of the global economy (34:50) – Advice for people             (38:59) – Paxos.com (39:48) – What is he monitoring to see which way things shake out   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
My conversation today is with my close friend Brent Beshore. Brent is a private equity investor who owns and interacts with many small businesses, which have been hit especially hard by COVID. We discuss the various impacts that COVID has had and may have on both small business and the private equity investing community. Brent also proposes some policy actions which he thinks may help those most in need. 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 1:13 – (First question) – What Brent sees as the current landscape for small businesses 3:25 – The real problem for small businesses right now 6:02 – How long can small businesses survive these freezes 9:14 – Ideas to help businesses stay afloat during a global shutdown 11:01 – The cost of restarting businesses on the other side of this   13:41 – Policies that could help             14:30 – government co-paying some business expenses             16:05 – Suspending payroll taxes             16:17 – The small business bond             18:00 – Wider latitude for banks 20:03 – How effective would Brent’s ideas actually be at lessening the pain 22:41 – A look at how things look in the private equity complex 25:39 – What are the potential opportunities out there 29:24 – What is a balance sheet product 32:00 – How this is personally impacting Brent 34:20 – How this is personally impacting Patrick 35:45 – Importance of relationships for personal health 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
My guest this morning is Dan Rasmussen of Verdad Capital. Like me, Dan and his firm focus on quantitative research. Just a month before the COVID crisis hit markets, they completely and published a study on investing during periods of market crisis, which is the topic of this conversation. We discuss what works and what doesn’t during and after acute periods of panic in markets. I think you’ll find it extremely informative. Because Dan’s firm and my own share many beliefs about investing and conduct similar flavors of research, I try to offer devil’s advocate questions throughout. Please enjoy. This episode is brought to by Koyfin. 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 1:54 – (First question) – What he sees in the markets today given the atmosphere right now 4:26 – An overview of their study: Crisis Investing: How to Maximize Return During Market Panics 8:38 – How things get more predictable during crisis 11:15 – The length of these crises and assets they focused on 12:40 – What happens to bonds and credit during these times 15:50 – Geography of crises 18:14 – How does this impact the philosophy of just index investing 20:40 – Positioning of value in this market 27:50 – Lessons from other crises 32:21 – Importance of a blended factor approach 35:44 – Role of momentum 38:10 – What else he is paying attention to during this crisis 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
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Comments (11)

Chris Anderson

fantastic interview. incredibly insightful; great interviewing technique allowing it to flow.so smoothly.

Jul 11th
Reply

Arunkumar Navasiva

Great content!

Mar 4th
Reply

Kevin T

brilliant

Feb 21st
Reply

Timera Boateng

very interesting

Jan 23rd
Reply

Kurt Edwins

this guy is amazing.and thanks Patrick for letting him. from New Zealand.

Jan 15th
Reply

Manny George

akallq

Dec 26th
Reply

Bob

Blew me away. Great episode!

Aug 8th
Reply

ryan weston

Great conversation

Mar 10th
Reply

hemal dani

superb episode

May 25th
Reply

Anthony Roach

Josh Wolfe is fast speaking and has an intelligence like few other. Great show guys, informative and eye-opening. Thank you!

Feb 18th
Reply

IJS

Excellent podcast.

Feb 5th
Reply
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