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Invest Like the Best with Patrick O'Shaughnessy

Latest episodes

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May 19, 2020 • 59min

Hamilton Helmer – Power + Business - [Invest Like the Best, EP.174]

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
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May 12, 2020 • 1h 6min

Tobi Lutke – Building a Modern Business - [Invest Like the Best, EP.173]

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) – Daniel 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
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May 5, 2020 • 45min

Ali Hamed – An Update on Private Credit - [Invest Like the Best, EP.172]

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
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Apr 30, 2020 • 58min

Chris Bloomstran - An Update on Public Markets - [Invest Like the Best, EP.171]

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
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Apr 28, 2020 • 56min

Josh Kopelman - The Past, Present, And Future Of Seed Investing - [Invest Like the Best, EP.170]

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
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Apr 21, 2020 • 1h 1min

Manny Stotz - Frontier Markets Investing - [Invest Like the Best, EP.169]

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
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Apr 7, 2020 • 1h 1min

Sarah Tavel - Consumer & Marketplace Investing - [Invest Like the Best, EP.168]

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
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Apr 5, 2020 • 25min

[BONUS] Boyd Varty - 40 Days and 40 Nights

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
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Apr 2, 2020 • 53min

Gavin Baker – Investing Through a Bear Market - [Invest Like the Best, EP.167]

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
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Mar 31, 2020 • 1h 15min

D.A. Wallach – Investing in Healthcare - [Invest Like the Best, EP.166]

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

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