Invest Like the Best with Patrick O'Shaughnessy

Latest Episodes:

John Collison – Growing the Internet Economy - [Invest Like the Best, EP.178] Jun 16, 2020

Show notes

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

Jeremy Grantham – An Uncertain Crisis - [Invest Like the Best, EP.177] Jun 09, 2020

Show notes

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

Ben Thompson – Platforms, Ecosystems, and Aggregators - [Invest Like the Best, EP.176] Jun 02, 2020

Show notes

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

Shishir Mehrotra – The Art and Science of the Bundle - [Invest Like the Best, EP.175] May 26, 2020

Show notes

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

Hamilton Helmer – Power + Business - [Invest Like the Best, EP.174] May 19, 2020

Show notes

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

Tobi Lutke – Building a Modern Business - [Invest Like the Best, EP.173] May 12, 2020

Show notes

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

Ali Hamed – An Update on Private Credit - [Invest Like the Best, EP.172] May 05, 2020

Show notes

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

Chris Bloomstran - An Update on Public Markets - [Invest Like the Best, EP.171] Apr 30, 2020

Show notes

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

Josh Kopelman - The Past, Present, And Future Of Seed Investing - [Invest Like the Best, EP.170] Apr 28, 2020

Show notes

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

Manny Stotz - Frontier Markets Investing - [Invest Like the Best, EP.169] Apr 21, 2020

Show notes

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