Invest Like the Best with Patrick O'Shaughnessy

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.

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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

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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

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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

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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

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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) – 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

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

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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.

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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

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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.

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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

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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.

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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

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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.

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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

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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.

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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

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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.

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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

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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.

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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

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My guests today are Bill Gurley and Chetan Puttagunta, both partners at benchmark capital. We review the early stage investing world in the face of coronavirus in a very timely conversation, which is one that will remain valuable once this crisis is done. We discuss enterprise and consumer, funding and growth, and the entrepreneurial spirit in the face of a crisis. Please enjoy.

This episode is brought to by Koyfin.

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Show Notes

1:44 – (First question) – Landscape for venture capital ecosystem

6:47 – The experience in 2009 and the entrepreneurs that tend to rise to the top

8:24 – The relationship between early stage companies and public investors

10:45 – How this crisis impacts enterprise businesses vs the broader corporate sector

14:46 – Advice for early stage companies in a period like this

18:23 – What Chetan was doing during the last downturn and what he learned during it

20:27 – Early stage vs late stage companies in this environment

            22:57 – On the Road to Recap

23:00 – Benefits of being small in a period like this

25:22 – How portfolio companies are responding and pivoting during this period

29:33 – Best practices for remote companies

31:39 – Themes that stand out during this period

34:51 – Closing thoughts 

Learn More

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My guest in this flash podcast is Bryan Krug of Artisan partners. We discuss what has happened so far in the corporate high yield and investment-grade credit markets, and the loan market. We compare today’s environment to the financial crisis and other past crises with lots of nuances that I hope will be helpful to bond and equity investors. Please enjoy.

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Show Notes

1:08 – (First question) – An overview of what he covers in the corporate credit markets

1:52 – How things have changed in the last couple of weeks

3:56 – Composition of the high yield market

7:07 – Major sectors of the high yield market outside of energy

8:39 – How do they price the risk in securities right now

11:21 – How do they handicap a great unknown

13:00 – Risk for broader contagion in the overall credit markets

14:49 – What’s the downside potential here

16:31 – Potential for upside

18:33 – How does he view companies that are drawing down on their entire line of credit

19:44 – An overview of the loan market

20:42 – What warning signs equity investors should be watching for in the bond markets

21:57 – What do credit spreads look like today compared to before this crisis

Learn More

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This week, I’ll be recording and immediately releasing a series of conversations on business and market reactions to the spread of coronavirus. The conversations will be on oil and gas, corporate credit, and the reaction within the venture capital community. Today’s conversation is with Matt Smith, Ian Singer, and Kobi Platt of Deep Basin Capital. We are investors in Deep Basin, and they were past guests on the podcast. We discuss the new price war in the oil markets and the impact it might have on equities and especially on U.S. oil producers. Please enjoy.

This episode is brought to by Koyfin.

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Show Notes

1:59 – (First question) – An overview of the global oil market and demand

3:37 – Supply and demand shocks we’ve seen lately

6:22 – What happened this weekend with Russia and Saudi Arabia and why the outcome was so shocking

9:45 – The knock-on effects of this activity on equities

14:24 – Impact on US energy production

18:29 – What other industries will feel the effect of reduced production in the US

20:35 – Defining a price war and how victory is defined

27:53 – Saudi Arabia’s calculus in this energy fight.

31:11 – How does all of this change what factors they use to analyze companies

35:43 – What it actually looks like within the commodities markets to trade energy

40:01 – What uncertainty is most intriguing to each of them

43:00 – The long-term interest in investing in the energy sector

Learn More

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My guest this week is Peter Zeihan, the author of a new book, the Disunited Nations.  Peter was an extremely popular guest on the show last year and after reading his new book, I knew we had a lot to discuss in round 2.  In this conversation, we discuss two ways of ruling the world, the coming American disinterest in global affairs, and which country are poised to do well int eh future.  We explore military and non-military technologies, political changes, and up and coming alliances like that between the United States and Mexico.  As with last time, peter packs more information into an hour than just about anybody.  Please enjoy our conversation.

This episode is brought to by Koyfin.

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Show Notes

1:57 – (First question) – What makes for a successful country

6:02 – Five first-tier countries that are well positioned

7:14 – Ruling the world, US carrot model vs British stick model

9:39 – How other countries will use these models in the future

12:59 – The surprising reliance of Iran and Russia on the US

15:24– Key points of his research on the Middle East

18:36 – Advice for how those operating in the US should think about future business investments

23:05 – The future of manufacturing partnerships with the US and the focus on Mexico

27:30 – What Coronavirus has taught us about the world economy

30:01 – What the primaries and election are teaching us

35:09 – What role does Africa play in the future

38:36 – Strong and weak players in Europe and how Brexit has impacted things

44:41 – The future for nuclear power

46:27 – The outlook for South America

50:42 – The trends and future in military technology

55:03 – Non-military technology that will have a major impact

58:26 – Skills young people should focus on for the future

1:00:07 – Coronavirus as a dress rehearsal for large scale disruptions to the world

Learn More

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My guest this week is Jeff Lawson, the Founder, and CEO of Twilio. Twilio is a 15-billion-dollar company offering a cloud communications platform to its customers.  Twilio is used by customers like Lyft, Twitch, and Yelp to make communications in their products easy.  Jeff and I talk about why it pays to be a platform, how to be a platform, and how to sculpt a company culture. This is a must-listen for anyone building a business whether it’s a tech business or not.

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Show Notes

1:18 – (First Question) –  Company vowels and draw the owl

5:26 – Significance of API’s

12:14 – How non-software businesses can transition into the space

         17:50 - Agile way of working at ING Belgium (video)

18:38 – How they strategize their product build

23:27 – The idea of asking your developer and why it’s so important to them

33:02 – How they codified their business culture

45:12 – Parting advice for people building platforms

48:13 – Kindest thing anyone has done for Jeff 

Learn More

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Niko Canner is the founder of Incandescent where he and his team help the leaders of large companies in the areas of strategy and innovation. He was also the founder of Katzenbach Partners and a member of Bridgewater’s management committee. Niko is a fantastic writer, and I highly recommend you check out his blog “On Human Enterprise,” which has posts on many of the most interesting aspects of business and personal purpose. This conversation was inspired by many of those posts. Please enjoy.

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Show Notes

1:17 – (First Question) – The story of Doctor V

            3:24 – Aravind and the Choice of Great Achievement

4:00 – Becoming the perfect instrument

6:05 – What is Niko planning to be the perfect instrument of

8:18 – How should individuals think about finding what they can be the perfect instrument of

            8:59 – Brett Victor – Inventing on Principle

10:59 – How do businesses apply this principle

13:20 – Making choices easier

16:43 – Era’s to a company and when it’s time to start a new one

19:52 – How can business culture be cultivated and useful

22:53 – Cultures at the tail end of a distribution

24:33 – Can hierarchy be fluid, or does it need to be a dedicated corporate structure

27:47 – My Unlikeliest Favorite Business Book

            28:03 – The Millionaire Real Estate Agent: It's Not About the Money...It's About Being the Best You Can Be!

30:46 – The Red Test and how it can be used by businesses

36:54 - Ten Principles for How to Run a Company

42:25 – Dealing with the sponsor owner brief in the software world

45:24 – How does one choose customers

46:32 – Bill Hubbard passage – A Theory for Practice: Architecture in Three Discourses

49:09 – Kindest thing anyone has done for Niko

Learn More

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For the 100th episode, I’ve brought back my good friend Brent Beshore. Brent was the 10th guest on the podcast, after we met because of a mutual interest in capital allocation. I quickly learned that Brent was one of the most unique and thoughtful investors around. He was an entrepreneur from the moment he left school, trying many different things before finding a fit buying smaller business with the intention of owning them forever. What amazes me about Brent is his encyclopedic understanding of business and the nuances of different business models and deal structures. This comes from reps. He and his team have looked at about 12,000 deals over the years, at every kind of business that you could imagine. I’ve been with him when he goes through this process and it’s fun to hear what makes certain businesses stand out from others, which is largely the topic of this conversation. You all know transparency is key for me, so it’s important to know that my family and I are investors in a fund called permanent equity, run by Brent and his firm Adventure.es. To commemorate this milestone episode, I can think of no one better than Brent, because he exemplifies what has made this podcast so fun for me: learning from other people who are willing to share what they themselves have learned through fun, blood, sweat, and tears. Please enjoy our conversation, and thank you so much for coming along on this journey. I can’t tell you how much it means to me.

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Show Notes

2:02 - (First Question) – How does he think about optimizing risk in terms of the capital stack when looking at deals

5:27 – What conditions would they add debt down the road after investing in a company

6:52 – What business sectors are most intriguing for Morgan to invest in right now

            6:57 – Trent Griffin Podcast

9:34 – Why no HVAC businesses if it’s such an attractive sector

13:56 – thoughts on rolling up similar businesses and horizontal scale

16:04 – Another industry Brent would focus on

18:02 – Difference between property management in larger cities vs smaller metro areas

18:51 – What role does profit margin play when Brent is evaluating a business

22:46 – The appeal of a hyper cyclical business

            22:52 – Brent Beshore Podcast Episode

27:27 – Favorite counter cyclical business

28:14 – How they judge assets, tangible vs intangible assets

33:58 – How does he think about wage inflation when considering the cost of a business

37:21 – His fascination with pet crematoriums

38:57 – History of the permanent equity fund and the changes by having a larger pool of capital

43:48 – Pitching investors on a new structure for the business

46:14 – How will this business model scale

Learn More

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My guest this week is a good friend and a business mentor of mine. Chetan Puttagunta is a general partner at Benchmark Capital and has a remarkable track record of investing in early-stage software businesses, including several like Mulesoft, MongoDB, and Elastic that went on to be public companies.

Chetan has been my key guide for understanding the world of enterprise software as we at O’Shaughnessy Asset Management have built an investing platform called Canvas. His advice has been critical to our early success. In this episode, we explore the history of software and software investing, and go into the details on how to build and grow new software businesses. We discuss product, sales and marketing, recruiting, scaling, and everything in between.

Please enjoy this great conversation with one of my favorite business and investing thinkers.

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Show Notes

1:34 – (First Question) – How Chetan found MongoDB and decided to invest in it

8:01 – The evolution of databases in the growth of technology

16:19 – Market penetration of this space and what investors should be thinking about

21:46 – Advice how companies can build software effectively

25:12 – Tactics to effectively implement empathy led product building

30:33 – Companies asking users what to build vs telling users what they want

34:26 – The need for the right capital, and patient capital in particular

37:55 – Creating the perfect customer experience

44:37 – Common reasons they don’t invest in a company

48:48 – Lessons on scaling, especially in sales and marketing

52:47 – Best recruiting pipeline strategies

59:56 – Pitfalls of unit economic traps

            1:00:23 – The Dangerous Seduction of the Lifetime Value (LTV) Formula

            1:01:34– The Hierarchy of Engagement

1:02:18 – What has changed for Chetan in his time working with the team at Benchmark

1:06:009 – Later stage life cycle business considerations and Amazon’s AWS

1:13:29 – The business model of open-source software

1:15:54 – Being default open

1:17:53 – Kindest thing anyone has done for Chetan

Learn More

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My guest today is Rebecca Kaden, a partner at famed venture firm union square ventures. USV is known for thesis-driven investing, which is the topic of our conversation. Rebecca walks us through the evolution of USV’s thesis into its third generation, and from there we explore many of the most interesting and exciting areas of business, technology, and learning. Please enjoy our conversation

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Show Notes

1:11 – (First Question) – An overview of Union Square Ventures Thesis 3.0

7:49 – Core changes that can help any community

9:59 – Ways to fix the broken education system

13:41 – Gap between job preparedness and the education system

14:44 – Companies creating education systems to prepare people for careers in their field

18:49 – Most unique technological solution for people to educate themselves

22:00 – Ways to improve access to capital

26:49 – The distribution problem in capital markets

28:19 – How does she assess an early-stage company and its team’s ability to assess their ability to maximize distribution

30:56 – Digital marketing and why it could be broken

34:22 – Examples of masterful marketing

36:07 – How they are focused on improving wellbeing, their first focus on healthcare

39:35 – Wellbeing on their focus on community

            41:29– The Art of Community: Seven Principles for Belonging

45:30 – Her thoughts on mentorship

48:23 – What she has learned in her time at USV

51:50 – Kindest thing anyone has done for Rebecca

Learn More

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My guest today is Matt Clifford. He’s the co-founder of Entrepreneur First, the world’s leading talent investor. They invest “pre-company” by helping the best people in cities around the world find a co-founder, develop an idea, and start a company. So far, they’ve helped 1000 people start 200 companies worth a combined $1.5B. This conversation covers their entire ecosystem and holds lessons for anyone building a business. I especially loved Matt’s ideas on the history of ambition.

Please enjoy our conversation.

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Show Notes

1:20 – (First Question) – An overview on talent investing

4:37 – The history of ambition

10:08 – How do they search for ambitious people

12:21 – What happens early on for these formed teams

17:43 – Assigning an idea to a talented team

20:52 – Opportunities in deep technology

27:16 – A closer look at the hardware and machinery of the deep technology changes

30:54 – The geographical focus of venture capital investments

37:16 – Problems with the way early-stage investment world works

41:22 – People who are creating value in a management company and how they manage their investments

55:12 – Advice to people creating investment companies and pricing power

1:00:31 – The power of cities

1:02:46 – Topics they cover in their newsletter; technological sovereignty as one example

1:04:11 – Experience and thoughts on China

            1:06:51 – A.I. Nationalism

1:12:03 – Kindest thing anyone has done for Matt

Learn More

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My guest today is Peter Buffett. Peter is a musician, composer, author, and philanthropist. Peter is an Emmy Award winner, New York Times best-selling author and co-chair of the NoVo Foundation. We discuss music, community, philanthropy, and finding one's note in life. This is a very different episode much more about life in general, with no business or investing discussed. Like his father Warren, Peter has the gene for phrasing ideas in memorable ways, and I think you’ll find many great phrases in this chat that will stick with you. I’ve been thinking about Peter's idea making sure those in your life are safe, seen, and celebrated ever since our chat.

Please enjoy.

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Show Notes

1:27 - (First Question) – Welcome and small talk

1:35 – Why Peter is in Kingston and how it plays into his foundation work

4:01 – How moving from the city to the country changed Peter

6:27 – Seeing connections vs living abstractions

7:30 – What is the Nova Foundation

11:03 – Historical points that inform his views

13:51 – Identifying qualitative negative side effects and which ones they are attacking

17:51 – What makes for effective community 

20:22 – Linkage between consumption and individualism

23:55 – The cultivation of work ethic, curiosity, and education

            23:57 – Life Is What You Make It: Find Your Own Path to Fulfillment

27:22 – Early exploration of his curiosity

32:26 – What has music taught Peter about music that is unique to that experience

34:26 – Most memorable question a person has asked Peter at his concert and conversation series

36:46 – What makes for good relationships, in particular marriage

42:03 – What keeps people from putting in the work into a relationship

45:11 – What he has learned about being a good friend

46:29 – How does one person have a relationship with a large community

49:21 – Dark sides of the philanthropic world

            49:54 – The Charitable-Industrial Complex

53:21 – Dignity: Seeking Respect in Back Row America

55:55 – What one spot would he send everyone to learn

57:48 – Traumas and helping people find their note

            57:49 – The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma

            1:00:38 – How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence

1:02:24 – What is he most interested in right now: how to best use Nova’s funds

1:04:45 – Lessons from family

1:07:22 – Kindest thing anyone has done for Peter

Learn More

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My guest today is Ben Savage, a partner at Clocktower ventures. Ben is focused on financial technology, fintech, investing which is the topic of our conversation. I’ve been making the fintech is rounds of late, and plan on making a few of these conversations public. Ben is the first in what may be a mini-series because of the sheer amount I learned in our discussion. We cover all aspects of the fintech ecosystem. I hope you enjoy.

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 Show Notes

1:15 (First Question) – The market portfolio and how technology will move us away from liquid markets

7:24 – Businesses that are making assets that weren’t investable, investable

            9:11 – Ryan Caldbeck Podcast Episode

12:03 – Most interesting places where technology is creating investment opportunities

18:33 – Assets that are likely to tap into new sources of beta

23:46 – How well are investors prepared for the changes that are coming

28:35 – Trends in asset management with technology

33:05 – View on cryptocurrency and blockchain

36:45 – Places where startups can reduce costs/fees and create efficiencies

40:17 – Views on private equity markets and their future

45:40 – Privilege of access problem

48:50 – Verticals in fintech that are interesting to him

59:53 – The importance of focus and niche

1:02:26 – Kindest thing anyone has done for Ben

Learn More

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My guest this week is Jeff Ma. Jeff was on the famous MIT Blackjack team from the book Bringing Down the House but has spent his career in an around fields of analytics and data science. He’s studied sports betting and analytics, built companies for analyzing human capital, and ran the data science and analytics group at Twitter. Here are links to his book, blog, and podcast. Our discussion is about a number of fascinating ways data is being used to make decisions in the worlds of sports and business. Please enjoy!

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Show Notes

1:20 - (First Question) – How quantitative analytics have evolved in sports and how they’re being used

4:26 – Best role of humans in the analysis process

8:38 – Sports that are most interesting to observe through analytics

10:26 – How does luck play into sports analysis

11:54 – Team analytics vs better analytics

12:38 – Concentration of success among sports betters and their moats

14:58 – Favorite lessons learned from professional gamblers

16:45 – How analytics got introduced into gambling

19:21 – Understanding one’s own biases

24:04 – How he became VP of analytics at Twitter

28:37 – Primary lessons from the work evaluating human capital and talent with analytics

            28:59 – Niel Roberson Podcast Episode

31:40 – How to model people for success when hiring

33:29 – How to hire the right data scientists’ team

37:54 – Most interesting problems they tackled at twitter

42:31 – Responsibility of social platforms to police itself

45:34 – Areas that would interest him in the future as an investor

49:24 – Kindest thing anyone has done for Jeff

51:50 – Values instilled in him by his parents.

Learn More

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My guest today is Vaughn Tan, who studies quality, innovation, and organizational behavior. His resume is bonkers. He’s a PhD from Harvard, Was an infantry signals logistician in the Republic of Singapore Army, then worked at Google on advertising, Earth, Maps, spaceflight, and Fusion Tables. He’s also been a wood sculptor. But the topic of our conversation is how to foster quality and innovation in ourselves and inside of companies—lessons he learned in part by studying inside some of the world’s best restaurants. If you enjoy this conversation, I recommend you also check out his new book, The Uncertainty Mindset Innovation Insights from the Frontiers of Food. Please enjoy my conversation with Vaughn Tan.

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Show Notes

1:33 - (First Question) – Interesting ways to identify high quality

5:06 – The current problem with the way we think about the world

8:56 – How people think about their careers and college

11:21 – Uncertainty vs risk, and productive discomfort

19:08 – Cultivation of discomfort for an individual

24:05 – Successful innovation cultures

32:25 – Analyzing quality and restaurant bread

37:43 – The Slug idea

40:43 – His research project where he observed restaurants

45:44 – How do people mandate their own structure in the face of uncertainty

53:46 – How employees should approach this rent-to-buy hiring structure

57:17 – Example of someone who took advantage of uncertainty time

1:00:05 – Playful adults

            1:00:07 – Jerry Neumann Podcast Episode

1:03:10 – Other changes companies can make to their culture to be more innovative

1:08:19 – The difference between simplicity and complexity

1:11:12 – How he applies his thinking into several different ideas, like Cannabis

1:16:17 – Asking the right question

            1:19:05 – Andy Rachleff Podcast Episode

1:20:19 – Kindest thing anyone has done for Vaughn

Learn More

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My guest this week is Gavin Baker, the founder, and manager of Atreides Management. I met Gavin in the same way I meet many of the most interesting people, on twitter. His focus is on consumer and technology growth investing, which is the topic of our conversation. We discuss many of the largest trends in these sectors, several fascinating investment cases, and also explore the videogame industry in detail—which I found especially interesting. Please enjoy my conversation with Gavin Baker.

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Show Notes

1:16 – (first question) – His unique view on the markets

4:00 – Distilling Apple as a growth investment

6:44 – What is the most important lever for Apple looking forward

9:01 – His view on Intel

11:03 – Most important technological changes that may dictate his investing strategy

16:20 – How do you look at a big idea, like AR, and then apply to an individual business

            18:21 – Fortnite isn't a game, it's a place

            18:26– Fortnite Is the Future, but Probably Not for the Reasons You Think

18:56 – His insight into video games and their ability to control attention

28:36 – How do you invest in the gaming sector

40:06 – Favorite video games

32:07 – Why gaming and customer sector allows him to find Alpha richness

34:17 – Being in the top 1% of knowledge before investing in a company

36:24 – His view on value investing today and, in the future,

41:15 – Increase of regulatory capture 

42:01 – Headwinds to the tech companies today

43:50 – Thoughts on the Chinese internet market and how it impacts US markets

45:36 – How often companies look at China for ideas

46:21 – Role of alternative data in his process

49:36 – Big trends today we should be paying attention to

54:20 – the most interesting company he does not own

58:48 – Advice for new investors

1:00:17 – Non-obvious tech resources - TechMeme

1:00:50 – Favorite sci-fi character

1:01:19 – Kindest thing anyone has done for him

Learn More

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All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of O'shaughnessy asset management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of O'shaughnessy asset management may maintain positions in the securities discussed in this podcast. Clients of the podcast guest’s firm may also maintain positions in the securities discussed in this podcast.

My guests this week are Kevin Systrom and Mike Krieger, the co-founders of Instagram. I met Kevin and Mike a few months ago over a shared interest in business and investing. I have found them both to be extremely good people who have a rare talent for finding and solving interesting problems. Indeed, problem-solving and jobs-to-be-done is a big part of our conversation. I realized walking into the podcast that Kevin and Mike have a rare set of experiences: having both built and sold an extremely successful product from scratch, but then also operated and scaled inside one of the largest businesses in the world. This means they have unique knowledge to offer just about anyone interested in business and products. We dig into all those lessons here. I am working on hosting more founders and CEOs on the podcast, and can’t think of a better pair to show you why I want to do so. Please enjoy my conversation with Kevin and Mike. 

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Show Notes

1:38 – (first question) – Projects they’ve been working on since leaving Instagram

5:22 – How they can apply what they are learning in machine learning

7:18 – Most interesting experience diving back into data and machine learning

8:42 – How startups compare today to when they founded Instagram

13:23 – Judging founders and whether they know how to use their data effectively

14:26 – The jobs-to-be-done framework

19:14 – Laying out a vision vs solving problems that pop up

25:20 – Developing and sharing the principles of the company with the team

30:48 – Creating a community when it includes almost the entire world

39:03 – The most popular ways people used the platform

41:24 – What was the jobs-to-be-done rational behind the stories feature

44:15 – Interesting things that they saw as Instagram entered the developing world

46:40 – Their thoughts on how Instagram shaped culture and if they focused on those

52:58 – The new waves that they are observing right now

55:11 – How their thinking on leadership and teams changed during their time at Instagram and Facebook

1:03:23 – The pillars of a good business, including humility and confidence

1:06:06 – Focus on growth and distribution in a startup

1:10:01 – How early were they thinking about monetization on this free platform

1:13:43 – How do they think about how they invest their money and allocate resources

1:17:36 – Mentors for Kevin and Mike

1:20:30 – Their passion for learning to fly and the someday/maybe list

1:23:01 – Their interest in coffee

1:26:24 – Advice for everyone else

1:30:00 – Kindest thing anyone has done for them

Learn More

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My guest this week is Daniel Ek, the founder and CEO of Spotify.

In my conversations with Daniel, I’ve found him to be one of the most interesting and thoughtful business leaders in the world. You’ll see what I mean as you listen to our conversation.

We talk about Spotify plenty, but what I so enjoy about Daniel is his way of thinking in systems and frameworks. He is committed to evolution, innovation, and growth for both himself and for Spotify and is on my shortlist of CEOs to emulate.

This was one of my favorite conversations on the podcast, I hope you enjoy it.

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Show Notes

1:21 – (first question) – Management lessons from a Dubai chocolate maker

4:54 – Trends shaping the business landscape today: globalization, automation, and digitation

7:51 – How he thinks about the vertical integration of his business and scale

10:37 – Are companies doing a good job adjusting to the changes in the global business landscape

14:44 – How does Spotify view scale moving forward

17:59 – What trends has he seen among creators as a result of the Spotify platform

20:32 – The community benefit that has been created by the platform

23:47 – Intimacy of audio

25:31 – Creating an environment that continues to spur innovation

29:12 – Star vs constellation business strategy

32:21 – Measuring network health

35:12 – Spotify Originals and what his competition in the video market is doing

39:36 – How podcasts play into the growth strategy

43:04 – How did he solve the problem of competing with free

47:21 – Is their strategy repeatable, going after fractured suppliers

49:02 – Role of the CEO in a startup

51:22 – Others who have taught him great business lessons

53:18 – Kindest thing anyone has done for Daniel

Learn More

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My guest this week is George Rzepecki, the found and managing partner Raba, an Africa focused investment firm. George is making investments across Africa in early-stage companies. Africa represents a fascinating opportunity: a huge and diverse population and enormous room for per capita GDP growth. We cover all aspects of investing in the continent, including unique potential rewards and risks.

Please enjoy our conversation.

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Show Notes

1:18 – (first question) – Interest in emerging markets and the tech landscape in Africa

4:57 – Similarities across all of the different metro markets across Africa

8:05 – Why has the continent lagged behind the rest of the world

10:49 – What is the history and landscape of capital in the African continent

13:32 – The market opportunity given the demographics

15:44 – US investment/involvement in Africa

18:06 – Kinds of companies that he likes to invest in

23:26 – Initiatives and investments that could help lift the population out of poverty: finance

29:33 – The public marketplace landscape in Africa

31:49 – Capacity on the private side

34:24 – How the valuation of deals compares to other markets

36:13 – Unique risks in the investments they are making

38:28 – Most exciting trends or changes he is seeing

40:22 – The professional investor environment

43:25 – How to learn more and get involved

            43:49 – China Africa Research Initiative

            44:17 – China Africa Project

            44:38 – Factfulness: Ten Reasons We're Wrong About the World--and Why Things Are Better Than You Think

Learn More

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My guest today is Chad Cascarilla, the CEO and co-founder of Paxos, which describes itself as a financial technology company “mobilizing assets at the speed of the internet.“ Thanks to more than 20 years of investing and financial services experience, Chad has a unique perspective on integrating blockchain technology with traditional systems. He also has one of my favorite bitcoin origin stories, which we explore. Before Paxos, Charles co-founded institutional asset management complex Cedar Hill Capital Partners in 2005 and its blockchain-focused venture capital subsidiary, Liberty City Ventures (LCV). Our conversation is less about cryptocurrencies and more about the history, current state, and potential future states of our financial system. Please enjoy.

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Show Notes

1:32 - (First Question) – His work in the finance world before crypto’s

5:12 – Experience navigating the subprime mortgage trend and what it taught him about blockchain

9:59 – The levers that matter in the financial services industry today vs when he first started

14:07 – Open vs closed money in financial services

19:16 – How slowdowns are different in the modern era

23:06 – What would lead to a major winding down of global debt

27:09 – What would be his focus as a traditional investor

29:21 – How he first got involved with bitcoin

            29:47 – Elliott Wave Newsletter

31:53 – His measured view of Bitcoin and living through the volatility of it

            32:03 – Bitcoin: A Peer-to-Peer Electronic Cash System

35:57 – Allocation of a portfolio which includes crypto

36:54 – His involvement and feelings on gold

37:56 – The formation of Paxos and the problem it exists to solve

41:34 – How Paxos is impacting the space

44:12 – Advantages of a private blockchain

43:59 – What is Pax Gold and how does it work

48:53 – Bad ways and situations to own gold

52:12 – Using a stable coin

56:00 – Biggest problem they are working on now

57:23 – What should people be paying attention to in the crypto currency space

            59:23 – Coindesk Research Archive

59:39 – Has the influx of interest in crypto helped in other spaces

1:02:11 – Other lessons people should learn from his career

1:04:53 – Kindest thing anyone has done for Chad

Learn More

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My guest this week is Bill Gurley, general partner at Benchmark Capital. Our conversation is about one specific issue that has popped up as a topic of interest in the investing community in recent months: the comparison between bringing a company public through a traditional IPO vs. what’s known as a direct listing.

As a third party observer with no real dog in the hunt (as we don’t buy IPOs at O’Shaughnessy Asset Management), I thought this was a small and nuanced issue. I’ve therefore been surprised by the strength of opinions on both sides of this issue as I’ve explored it behind the scenes this past week. It feels almost like I’ve encountered a political third rail, where one side throws a lot of vitriol towards the other. 

To be clear, this episode is very much in favor of direct listings instead of traditional IPOs. For those that want a good discussion of the IPO process and its upsides, check out episode 173 of the Exponent podcast with Ben Thompson. 

Now please enjoy my very interesting conversation with Bill Gurley

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Show Notes

1:22 - (First Question) – His view on the IPO process

5:42 – Will now be the turning point for IPO’s

6:40 – The engagement between a new company going public and their counterparty and the IPO process

13:38 – The math of capital costs

18:18 – Banks that underprice the IPO’s

20:45 – The psychology of IPO’s

23:14 – The pop in the IPO and the media

24:54 – The value that shareholders give vs VC’s

25:37 – The Green Shoots

28:17 – The lock-up

31:40 – Direct listings vs IPO’s

            36:07 – Spotify’s CEO Reveals Why He’s Not Doing a Traditional IPO

38:23 – The capital raised in an IPO and diluting the company

40:18 – Privilege access and buy-side firms

43:33 – What will actually lead to changes in the IPO space

44:48 – Why he became so interested in the IPO space

Learn More

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My guest this week is Albert Wenger, a managing partner at Union Square Ventures and the author of the book World After Capital.

Albert studied economics at Harvard and earned a PhD in information from technology, but if you’d asked me to guess before looking those up, I’d have guessed that he studied philosophy because of how widely he has thought about the world and the impact of technology.

Our conversation is about how technology is changing the world from an Industrial Age to a knowledge age. We explore how cryptocurrencies, low cost computing, and regulation will impact our future and why the transition may require delicate care.

I loved this conversation because of my obsession with the concept of scarcity. We explore what has been scarce through time and what may be scarce in the future. Albert is one of the most interesting thinkers I’ve come across and was a pleasure to speak with. I hope you enjoy our conversation.

Hash Power is presented by Fidelity Investments

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Links Referenced

World After Capital

Show Notes

2:16 – (First Question) –  Defining what it means to be human

            2:58 – World After Capital

3:56 – Trans-humans vs neo-humans

4:37 – The concept of Qualia

5:25 – Albert’s investment philosophy=

8:27 – How Albert began his exploration into cryptocurrencies

12:59 – Most exciting things blockchains could enable

14:27 – How does Albert view blockchain technology from the view of an venture capital investor

17:00 -  Why Albert thinks that the dominate cryptocurrency of our time may not exist just yet and what he is looking for in protocols that will become the leader in the space

20:16 – What are the central functions that will be important in cryptocurrencies

21:22 -   The state of regulation in the cryptocurrency space

27:37 – What has Albert most excited for the future of blockchain

29:10 – The idea of universal basic income

32:26 – How do you solve the problem of giving money value in a world of universal basic income

35:00 – How scarcity has changed over time

39:01 – Role of financial capital in the last 200 years of civilization

42:39 – Are we as a society only capable of solving problems once they become an immediate threat

44:15 – Explaining the idea of attention as a scarce resource

47:56 – The two key drivers of change; zero marginal cost distribution and universality of computational power

53:13 -  What should we as investors and inventors be focusing on as the new objective function

57:24 – Scariest aspect of this transition into the knowledge age

59:45 – Three basic freedoms we all seek; informational, economic, psychological

1:02:13 – Fermi’s paradox and the scarcity of attention

1:02:56 – How Albert thinks about his own day and wellbeing given all of this information

1:05:01 – Kindest thing anyone has done for Albert

Learn More

For more episodes go to InvestorFieldGuide.com/podcast. 

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My guest this week are Matt Smith and Ian singer of Deep Basin Capital, a hedge fund specializing in the energy sector.

I first met Matt almost 10 years and, in that time, I’ve grown to respect him as much as any investor that I’ve ever met. Now having spent time with Ian, who specializes in oil and gas field exploration companies and the rest of the Deep Basin team, I have similar respect and admiration for all of them.

Deep Basin does almost the exact opposite of what us quants do. In fact, their entire goal is to build a portfolio of mostly idiosyncratic or stock specific risk, the very thing us quants mostly remove from portfolios. Deep Basin positions the portfolio to make a series of carefully constructed bets, long and short, without taking market risk, style-factor risk, or even commodity risk. They use a hybrid fundamental and quantitative process which we explore in detail.  This is definitely another good example of who we are all up against in public markets.

What makes this story unique is that we are investors in Deep Basin’s management company and so have a clear interest in their ongoing success. Listeners know that I want to be as transparent as possible on this podcast so we event spend a little time telling the story about how it all came together a few years ago.

I have learned a ton about investing from my countless hours with this team and hope that this conversation gives you a glimpse into what is happening at the cutting edge of investing in the world of hedge funds.

Please enjoy my conversation with Deep Basin

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.

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Books Referenced

Expectations Investing: Reading Stock Prices for Better Returns

Show Notes

2:47 – (First Question) –  Looking at the universe of the energy space that they are focusing on

7:48 – Breaking down the important components and their labels in this space

10:27 – What makes energy companies distinct from the broader market.

12:52 – How the isolate unique value creation

14:58 – Ian’s take on the upstream part of the business where he has spent a lot of time

18:35 – How does Deep Basin use data and what edge do they derive from it.

21:31 – What insight are they looking for from updated well data

23:59 – How do they use combine the business value that they measure with the market price that is being forecasted

            24:40 – Expectations Investing: Reading Stock Prices for Better Returns

29:34 – How do they build an actual portfolio

31:51 – Their systematic approach to energy investing

37:53 – What are their thoughts about using leverage when making investments in the energy space

40:53 – A look at the changes to the hedge fund industry over the entirety of their careers

45:46 – Defining the culture of Deep Basin

49:15 – The story of how OSAM and the O’Shaughnessy’s came to be investors in the Deep Basin

54:13 – Kindest thing anyone has done for each of them

Learn More

For more episodes go to InvestorFieldGuide.com/podcast. 

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My guest this week is Pat Dorsey, who was the longtime director of equity research at Morningstar, where he specialized in economic moats: sources of sustained competitive advantage that allow a few companies to deliver huge returns over time. Several years ago he left Morningstar to form his own asset management firm, Dorsey asset management, and build a portfolio of companies with wide moats like those he studied at Morningstar. And while moats are critical, equally important is how companies allocate the capital generated--or made possible--by the existence of the moat.  

A special thank you to Brian Bares who introduced me to Pat, and to Will Thorndike--an earlier guest on the show. In the vast majority of conversations you hear on this show, I'm meeting the guest for the first time. I mention this to encourage you to connect me with anyone whose story or way of looking at the world might resonate. Always feel free to contact me with ideas.  

Pat and I begin our discussion with the key differences between the sell side and the buy side, and then discuss all aspects of moats and capital allocation. 

For comprehensive show notes on this episode go to http://investorfieldguide.com/dorsey

For more episodes go to InvestorFieldGuide.com/podcast.

To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier.

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

2:23 – (First question) – Transition from the sell side to the buy side and the biggest surprise 

3:40 – What is a moat 

5:16 – What part of the stock market universe has a moat 

6:57 – Pat’s framework for identifying moat, starting with intangibles 

8:32 – The power of brands 

9:44 – what chance does an upstart have to come in and usurp a well-established brand   

12:24 – Switching costs as part of the framework for identifying a moat 

14:55 – The third component of identifying a moat, network effects, and what businesses should do to effectively build one 

17:29 – Last component, cost advantages/economies of scale 

19:29 – How do you analyze these four components into an investing framework that can be built into an actual strategy 

21:13 – How does Pat think about this from a mis-pricing standpoint 

23:37  – How does Pat incorporate current price of a company in consideration for future returns when pricing a moat 

25:39 – How should a company with a moat operate to protect that characteristic, especially when it comes to their capital allocation 

26:51 – Which characteristic of a moat does Pat find most intriguing 

30:35 – What makes for good and smart capital allocation 

35:58 – What is Pat’s process for identifying the best investment opportunities 

38:38 – What are good economics when looking at a company 

41:03 – If Pat could take any business, but have to swap leadership, what would he choose. 

44:13 – Back to his process of finding investment opportunities 

46:05 – Kindest thing anyone has ever done for Pat

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

Read more at https://investlikethebest.libsyn.com/pat-dorsey-buying-companies-with-economic-moats-invest-like-the-best-ep51#oBGdOp1br4EMtORd.99

My guest this week is Joe McLean, the founder of Intersect Capital, which provides financial advisory services to a variety of clients, including a number of NBA players and other professional athletes. 

What I loved about this conversation was the weaving of sport, coaching, and finance into a cohesive whole. There’s so much to take from this discussion—from the importance of service and low self-orientation to the impact of strict standards for who you work with, to common mistakes we all tend to make with money.

Please enjoy my conversation with Joe McLean.

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

1:18 - (First Question) – His backstory and the combination of athleticism and finance

2:43 – His time in Ireland

3:29 – Moving away from basketball and into finance

6:08 – What the Intersect business is today and his early lessons

7:55 – Most important coach/mentor

8:59 – Where the name Intersect came from

10:22 – Setting high standards early on

12:35 – Biggest mistakes he saw in his early clients

14:04 – Developing his value proposition to clients

14:24 – Michael Kitces Podcast Episode

16:57 – Process when he’s working with a client signing a new athletic contract

19:53 – The concept of a Pro’s Pro and Top 50 Reasons Professional Athletes Remain Wealthy

22:40 – Managing clients’ interest in creating businesses off their brand

24:20 – The role media plays in athletes’ long-term strategies

25:40 – Getting early clients into compliance with his strategy

28:24 – Daily maintenance role he plays with clients

32:24 – What has impressed him most from his young clients

33:36 – What makes for a great coach

34:50 – The meaning of “all in” to Joe

35:54 – His assessment of the financial services industry today

37:32 – Where his value in service came from

39:05 – Longer term vision for his business

40:33 – Unique ways he finds himself helping his clients

43:49 – Watching his client’s mentor the next generation

45:10 – Historical players and teams he personally admires

46:22 – Athletes and venture capital investing

47:38 – Who makes up his trust network

49:09 – What he’s most excited about for the future of the business

49:46 – Kindest thing anyone has done for Joe

50:24 – Biggest impact a coach had on his life

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

This week’s guest is, Zack Kanter, the founder and CEO of the Stedi.  Zack and I decided not to talk much about his business on this podcast and opted instead to explore more generally, so a bit of an introduction to what they do may be helpful here for some extra context. Stedi is a platform for exchanging and automating 300+ types of business-to-business transactions - transactions like purchase orders, invoices, etc. It’s a modern take on an archaic protocol called EDI - electronic data interchange, something I’d never even heard of until several months ago. Learning about EDI is a bit like finding out about the Matrix - every physical object you come across, from the food you ate for breakfast to the clothes you’re wearing and consumer electronics you use - anything with a barcode on it - was likely touched by EDI, often dozens of times before making it into your hands. Stedi is the first update to this messaging later in decades.

Our conversation in this podcast is about business in general, starting with Zack’s fascination with Walmart and Amazon. I should also not that my family is a recent investor in Stedi, and I’m thankful to have learned a great deal from him over the past few months. 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

1:52 - (First Question) – Interest in Walmart and Amazon

            4:02 – Sam Walton: Made In America

4:49 – What from their success can be applied elsewhere

11:07– The idea of tempo with a business

17:17 – Ability for a business to expand laterally

24:33 - Magic of Amazon as a constitution

26:24 – The concept of the OODA loop

            26:40 – Boyd: The Fighter Pilot Who Changed the Art of War

31:51 – Orientation within software businesses

            32:24 – The Systems Bible: The Beginner's Guide to Systems Large and Small

38:03 – Lessons in building software

            38:37– Certain to Win: The Strategy of John Boyd, Applied to Business

41:51 – Setting a common vision for a company

44:14 – Changing the dynamic of teams and how different size teams can accomplish different things

48:00 – How leaders should think about build vs buy

51:07 – The different types of value propositions

53:07 – Utility for companies

57:31 – Concept of network health and the best question from VCs

1:04:04 – Massive projects are less frequent in a world where we can do a lot quickly

            1:04:08 – Wait but Why

1:09:37 – Just in time vs just in case learning framework

1:11:55 – His favorite question

1:13:39 – Why is most commonly heard advice wrong

1:18:06 – Kindest thing anyone has done for Zack

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 Chris Bloomstran, the president and chief investment officer of Semper Augustus Investments Group. He became famous in investing circles a few years back for his incredibly detailed investigations of Berkshire Hathaway. While we do cover Berkshire towards the end of the conversation, we spend most of our time talking about what makes for a quality business. I loved some of his angles on the current landscape, including our discussion of companies like Richemont and Disney which are actively taking distribution back in house. 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

1:18 - (First Question) – Largest investing error

4:52 – Defining quality investor and their investment strategy

11:48 – Incremental return on capital and other themes that they focus on with investments

15:33 – Importance of unique business models

22:58 – Ownership of the customer relationship

28:06 – Bringing distribution back in house

29:55 – Doing something unique with owned distribution

32:40 – His thoughts on growth and value

            32:42 – Chuck Akre podcast episode

37:12 – History of his interest in Berkshire Hathaway and he characterizes the business

53:29 – How is Berkshire protected into the future

59:17 – Most important trends in adjustments

1:08:00 – Which sectors or industries would he focus on

1:10:02 – Most intriguing business he’s unlikely to own

1:11:44 – 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 Brian Christian, the author of two of my favorite recent books: Algorithms to Live By and The Most Human Human. Our conversation covers the present and future of how humans interact with and use computers. Brian’s thoughts on the nature of intelligence and what it means to be human continue to make me think about what works, and life, will be like in the future. I hope you 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.

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Show Notes

1:11 - (First Question) – Summarizing his collection of interests that led to his three books

2:59 – Biggest questions in AI

3:43 – Defining AGI (Artificial General Intelligence) and its history

            5:18 – Computing Machinery and Intelligence

7:54 – The idea of the most human human

9:59 – Tactics that have changed the most in learning to be the most human human

16:10 –Tests for measuring AGI and updates made to them

20:12 – Concerns for once we have AGI

26:06 – Self-awareness as a threshold for AGI

31:58 – Skeptics’ take on AGI

37:14 – Advice for people building careers and how AGI will impact work

38:16 – Explore/Exploit trade-off

44:57 – How to explore/exploit applies to business concepts

49:16 – Impacts of AGI on the economy

52:40 – Highlights from his second book

57:39 – Kindest thing anyone has done for Brian

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

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My guest this week is Eric Sorensen, the CEO of Panagora asset management, which manages more than $46B for clients across a variety of strategies.

Eric began his career serving in the Air Force as both a pilot and instructor in high-performance jet aircraft. He then accumulated 40 years of quantitative research and investment experience, with a Ph.D. along the way.

Please enjoy our conversation on the changing landscape of quantitative investment strategies.

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

1:15 - (First Question) – His background in the Air Force

            1:23 – Boyd: The Fighter Pilot Who Changed the Art of War

3:18 – Training people on high-performance machines

4:47 – Traits that made for better pilots

5:51 – The evolution of quantitative equity research and its stages

7:56 – How his research led to becoming a practitioner

9:10 - The early feature sets in his research

10:44 – Tradeoffs in the spectrum of interpretability

12:08 – Early days of his practitioner career

13:24 – Risk Premia and the 5 C’s

14:28 – Quantitative Equity Portfolio Management: Modern Techniques and Applications

17:13 – Applying the 5 C’s to value investing

18:38 – Knowing when a strategy/signal is broken

21:24 – What does this strategy plan mean for his firm today

24:56 – Mixing expert systems and portfolio construction

30:07 – Natural language processing

32:00 – The cultivating the power and creativity to ask good questions

35:13 – The concept of a research graveyard

37:45 – State of risk premia today

40:04 – Active equity process

46:37 – Frontiers of research that he’s excited about

48:53 – Safe havens for non-quantitative investors

52:16– Advice for young quants

54:36 – Quants on the buy-side that he admires

55:41 – 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

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Jane McGonigal, PhD is a world-renowned designer of alternate reality games — or, games that are designed to improve real lives and solve real problems.

She is the Author of Reality is Broken: Why Games Make Us Better and How They Can Change the World and is the inventor and co-founder of SuperBetter, a game that has helped nearly a million players tackle real-life health challenges such as depression, anxiety, chronic pain, and traumatic brain injury.

Our conversation is about how to design useful games, how games effect us and our kids, and what the future might hold. 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

1:22 - (First Question) – Her take on the history of gaming and studying the players themselves

3:44 – Where her passion for gaming really started

4:55 – Her take on flow states

7:47 – Kids and gaming

10:32 – Advice for parents when it comes to the role of games

            11:06 – SuperBetter: A Revolutionary Approach to Getting Stronger, Happier, Braver and More Resilient--Powered by the Science of Games

13:53 – Types of games that develop the right skills for kids

16:20 – Four things all games share in common

            16:23 – Reality Is Broken: Why Games Make Us Better and How They Can Change the World   

20:50 – Her take on Carse’s theory about infinite gaming

            21:04 – Finite and Infinite Games

26:28 – How to understand gaming culture if you’ve never played a game before

28:28 – Amazon and gaming

31:18 – How fun makes anything more enjoyable

34:55 – How game designers calibrate feedback loops

39:14 – The good and bad of gamifying life

45:01 – What is the superbetter app

52:43 - Why powerups and bad guys are so important in games

57:03 – Secret identity

59:04 – Playing with boundaries

1:00:36 – Most worried about in the gaming world, and most exited about

1:07:32 – Kindest thing anyone has done for Jane

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 Bill Gurley, a general partner at Benchmark Capital and one my favorite investment thinkers. As you’ll hear, despite enormous success through his career, Bill is clearly still in love with business and investing. Where many might discuss past glories, I’ve been incredibly impressed with how both Bill and his partners emphasize the current portfolio and market landscape. I’m thankful to have had the chance to speak with him in this format. I hope you 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

1:13 - (First Question) – The idea of increasing returns

            1:21 – Competiting Technologies, Increasing Returns, and Lock-in By Historical Events

            2:07 – Complex Systems Theory – Santa Fe Institute

4:35 – Markers that could be a sign of network effect in a company

6:27 – The opportunities for companies to capture network effect

8:46 – Are there certain teams/leaders that are more conducive to leading a network effect company

11:55 – Liquidity quality

13:35 – How important is the revenue model at the beginning

15:59 – Fascination with Nextdoor

            17:56 – Paradox of Choice

18:39 – Finding opportunities

20:17 – Potential marketplaces and assets that could be commoditized

            20:20 – All Markets Are Not Created Equal: 10 Factors To Consider When Evaluating Digital Marketplaces

21:39 – Usage yield on the world’s assets

23:50 – Has technology changed the world of value investing

26:28 – Hyper niche marketplaces

27:52 – Challenges of labor marketplaces

30:12 – User generated content businesses

32:44 – People who are capable of building UGC businesses

33:16 – His interest in Discord

34:31 – Factors of a healthy marketplace

37:57 – Fools’ gold in marketplace businesses

39:04 – How influx of cash is impacting the marketplace business landscape

            40:43 – All Revenue is Not Created Equal: The Keys to the 10X Revenue Club

43:20 – How does the influx of money into the space impact him

46:44 – Spending money to attack top brands

50:32 – Regulatory capture

53:36 – His thoughts on the IPO market

57:49 – How did he realize this was his passion

1:00:42 – Qualifying his passion

1:01:52 – Favorite thing about working with entrepreneurs

102:48 – Honing your craft

1:04:33 – Making yourself a good mentor

1:05:56 – 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