Invest Like the Best with Patrick O'Shaughnessy

My guest this week is Chris Dixon, who has written some of my favorite essays on technology and venture investing. Chris is a prolific investor and thinker, having been an entrepreneur, angel investor, and now partner at the well-known venture capital firm Andreessen Horowitz. Our conversation focuses on major trends in technology, including cryptocurrencies and the future of autonomous vehicles and drones. Chris has a rule of thumb for technology trends: find out what smart people are working on during the weekend, and you’ll know what other will be doing years in the future. After surveying his old essays, it’s clear you use Chris’s writings as a similar litmus test.Hash Power is presented by Fidelity Investments Please enjoy this great conversation with Chris Dixon on the future of tech.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 Books Referenced Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages Who Controls the Internet?: Illusions of a Borderless World Links ReferencedDouglas HofstadterDaniel Dennett How Aristotle Created the Computer New Yorker Cover on automationThe World of Numbers websiteJerry Neumann podcast episodeDavid Tisch podcast ERC-20 Token Standard Eleven Reasons To Be Excited About The Future of Technology Show Notes2:04 (First Question) – Why did Chris choose to study philosophy2:23 – Douglas Hofstadter2:24 – Daniel Dennett3:20 – How Aristotle Created the Computer 3:35 – Where has his thinking and viewpoints changed the most having been in the real world 4:42 – What is the real driving force behind all of the technology that we are creating and will automation kill all of the jobs6:16 – New Yorker Cover on automation6:57 – The World of Numbers website8:36 – A look at his history in networks and network design11:03 – Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages11:07 – Jerry Neumann podcast episode12:32 – Who Controls the Internet?: Illusions of a Borderless World13:06 – What are the market and technological forces that make it difficult to regulate software hardware companies14:39 – The best features of proprietary centralized networks and open networks16:40 – What things are better centralized vs decentralized22:30 – David Tisch podcast23:03 – When it comes to cryptocurrencies, what are the concerns that the protocols themselves hold value and could this lead to centralization of the system problems24:02 – Block size debate (topic)26:40 – ERC-20 Token Standard27:23 – Is the blockchain the answer to the stagnation of the big tech players 34:39 - How does Chris think about the dichotomy of investing in people vs technologies34:59 – Eleven Reasons To Be Excited About The Future of Technology 37:45 – What organizational structures of companies are most compelling 41:50 – Any major trends in technology a cause for concern for Chris 44:09 – What major trends is Chris passionately pursuing 51:15 – If everyone agrees on a future trend of technology, can you still make money investing in them 52:20 – How do you encourage younger people to approach the world and a career differently in this ever-changing world 57:39 – Kindest thing anyone has done for Chris Learn MoreFor 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/bookclubFollow Patrick on twitter at @patrick_oshag

Jim Higgins, founder of Sorin Capital, and Tom Digan, co-lead and former classmate of Patrick, delve into the intricacies of commercial real estate investment. They explore the $7 trillion commercial real estate market, highlighting the resilience of grocery-anchored shopping centers amidst e-commerce challenges. Their contrarian strategies uncover hidden opportunities, emphasizing the importance of liquidity and thorough asset evaluation, especially in retail. They also reflect on the evolution of the hedge fund industry and the advantages of specializing in commercial real estate.

My guest this week is Franklin Foer, the author the recently published book “World Without Mind.” The topic of our conversation is one that I’ve been thinking through often this past year: the impact that large technology companies have on our minds and behavior. This conversation is only indirectly related to markets, but given that the companies we discuss are now several of the largest by market cap in the global stock market, what happens to them likely impacts all of our portfolios whether we own them or not. Given that these companies compete for our attention and dollars, they also affect our businesses. As an example, My friend Brent Beshore and his team at Adventures wrote a long and incredibly thoughtful piece on how they think about Amazon as a force in the market, and how they plan on navigating around such a fierce competitor. Franklin’s book, especially the early history, is very thought-provoking, so it was no surprise that our conversation was too. Please enjoy our talk on the tech giants. 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   Links Referenced Free PDF of The Whole Earth Catalog Amazon Must Be Stopped (New Republic) Hannah Arendt Philosophy Time Well Spent   Books Referenced World Without Mind: The Existential Threat of Big Tech The Whole Earth Catalog The Lessons of History   Show Notes 1:40 - (First Question) – As part of Jonathan’s new book, World Without Mind: The Existential Threat of Big Tech, exploring the idea of the whole earth catalogue.             4:09 – The Whole Earth Catalog             4:36 – Free PDF of The Whole Earth Catalog 4:49 – What happened next for Brand and how he laid the early groundwork for today’s modern Silicon Valley 7:43 – Franklin’s personal journey into writing this book             10:00 – Amazon Must Be Stopped (New Republic) 11:48 – Thoughts on the advancement of technology in our world 15:52 -  Filling the gap into Brand’s influence on Silicon Valley from the early 80’s to today 18:57 – How does the current state of the free internet without gatekeepers hold up for the next generation 20:53 – Is there a chance that technology’s unlimited mining of our attention is not the horrible thing we often make it out to be 24:47 – What are the ways we can have a free internet and other technologies, but not let them get perverted 28:09 – How will people respond to our tech monopolies 31:54 – The Lessons of History and the rise and fall of centrist powers 33:02 -  A look at Franklin’s work and how its impacted by the reliant on a few large tech companies 35:28 – The dangers that tech giants like Facebook, Amazon, etc, have created for us 40:45 – Is there a technology, company, or trend that Franklin is really excited for 42:19 – Will there be movements that emphasis detachment from technology 44:05 – Why most innovations have happened to people thinking in a very separated or contemplative mode 45:58 – What’s the most exciting thing that Franklin is thinking about now 49:30 – What was the most memorable content in researching this book that Franklin would suggest other check out             49:59 – Hannah Arendt Philosophy 52:37 – Are there specific things that Franklin does to be more contemplative             53:26 – Time Well Spent 54:47 – Kindest thing anyone has done for Franklin   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 Adam Ludwin, the founder and CEO of Chain, a blockchain technology company targeted at large enterprises. Before shifting his career to focus solely on crypto, Adam was a venture capitalist focused on FinTech, which is how he came across the Bitcoin whitepaper earlier than most. I called this episode “a Sober View on Crypto” because Adam’s take is so balanced. He is certainly long crypto, both in his portfolio and career, but he is very skeptical of much of what is happening in the ecosystem today. For example, he offers the best reason I’ve heard for not launching an ICO or investing in them.  If you haven’t read Adam’s widely shared open letter to Jamie Dimon, it has become a must-read piece for crypto-enthusiasts. Read it as soon as you can. I edited out an earlier chunk of our conversation as it was largely introductory. If you need a broader introduction to cryptocurrencies, I suggest starting with episode one of Hash Power and working your way forward. One key insight from Adam in our offline discussion what how cryptocurrencies function very much like equities or bonds. Just as equity financing enables the activity of joint stock corporations, cryptocurrencies enable activity in decentralized applications. We pick up our discussion with Adam discussing whether anyone really uses these decentralized apps today. Hash Power is presented by Fidelity Investments   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) – Will anyone use cryptocurrency in the real world at a large scale 3:43 – The idea of censorship resistance 12:29 – Will society be accepting of this technology 14:39 – Why decentralized apps can’t be acquired 18:24 – The idea of exponential vs linear improvements on a trend and if there are limits to the growth of decentralized technologies 23:26 – The struggle with early adaption of blockchain 25:41 – Best application for bitcoin, storing value 29:52 – Adam’s introduction to cryptoassets and how his thinking has evolved in the space 36:44 – In this hyper frothy market, is there a situation that makes an ICO exciting to Adam 43:51 – Even though it appears to be easy money, Adam explains why you shouldn’t just create an ICO 50:59 – A look at what Chain is doing and what Adam is excited about 53:23 – How does what Adam is working on help to improve the ledger of his clients 1:02:00 – Why you can easily be an early investor in crypto currency 1:04:27 – Kindest thing anyone has done for Adam   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 Joanne Wilson, a New York City based angel investor, writer, podcaster, trend spotter, and self-described “woman around town.” Joanne has had a multifaceted and winding career, and began angel investing a decade ago when she put money into NYC-based media company Curbed media which we discuss in detail. Since then, she’s invested in more than 90 companies and been pitched by countless more. She is an instantly likeable person, you can literally tell in 10 seconds you are going to have a great conversation, so it’s no surprise that part of what makes her unique among angels is a very close relationship with many of the founders she backs. We cover a lot of ground. We talk about the personality traits of entrepreneurs, Joanne’s evolving investment style, her focus on female founders, fashion, business models, restaurants and a lot more. Please my conversation with the Gotham Gal, Joanne Wilson.   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 2:12 - (First Question) – How does Joanne orient herself towards what’s new, in the context of food in New York city 4:10 – Can that mindset of forward thinking be cultivated 5:18 – Latest thing that got Joanne excited before everyone else 6:57 – Why the new frontier is going niche and local 10:23 – Joanne’s first investment 11:48 – Why do VC’s typically stay away from media 12:55 – How Joanne got into her first investment as a customer 14:11 – What is the skillset of making money that Joanne as 14:45 – Can you sense if a founder has that innate ability to just make money 17:04 – Are there common traits in founders 18:07 – Joanne’s progression into angel investing after her first investment 19:58 – Red flags when looking at investments 20:40 – Impression on growth without goals 23:30 – Trends among Joanne’s investments 25:56 – How much knowledge is transferrable between different industries that Joanne invests in 27:06 – The dichotomy and unique challenges between raising capital with female founders vs male founders 29:07 – How does Joanne balance her time and stay engaged with all of her investments 30:50 – Time when Joanne has helped a founder side step a pothole 31:35 – Most memorable first impression Joanne experienced 35:05 – How often does someone not have the right idea but is still worth investing in 37:19 – Why Joanne won’t start a fund 38:22 – Data on female founders returns and time 40:38 – Criteria for identifying emerging trends, especially in the more creative/artistic fields  43:29 – The changing costs of launching a brand, in the contest of fashion 47:11 – What has Joanne most excited right now       48:11 – Interesting facts about the fashion business  52:01 – Kindest thing anyone has done for Joanne   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 conversation is an ode to old school, fundamental public market investing. My conversation is with IMC’s Connor Leonard, who spends most waking hours thinking and reading about markets. His mandate is to invest purely as if it was his own money, with no pressure to hug a benchmark, and no pressure to do much of anything other than earn strong long-term returns. The portfolio that results from this approach is highly concentrated and unique. Connor’s strategy is to sort companies into four categories based on their type of sustainable competitive advantage. As you’ll hear, the vast majority fall into the first category, which means they don’t have such an advantage and therefore should be largely set aside. We spend the majority of our conversation talking about the other three categories: 1) companies with a legacy moat, 2) companies with a re-investment moat, and 3) an interesting category Connor calls “capital light compounders,” which we explore in detail. When you step back and think about public markets, you realize how amazing it is that we can, from afar, buy an interest in so many companies around the world. A select few go on to deliver outstanding returns. This conversation highlights how hard that can be, but also how fun and ultimately rewarding. Please enjoy my talk with Connor Leonard.                                                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   Books Referenced Margin of Safety: Risk-Averse Value Investing Strategies for the Thoughtful Investor The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success        Links Referenced Pat Dorsey Podcast Episode David Tisch podcast    Will Thorndike Podcast episode   Show Notes 2:31 - (First Question) –   Trends in value investing             2:52 – Margin of Safety: Risk-Averse Value Investing Strategies for the Thoughtful Investor 4:43 – A look at Connor’s backstory and the history of IMC, parent company of Golden Corral 8:01 – Why Connor loves the public markets so much   9:21 – The concept of intrinsic value when looking at companies 12:36 – How Connor categorizes MOATS             13:21 – Pat Dorsey Podcast Episode 14:27 – Legacy MOATS 16:11 – Reinvestment MOATS 17:58 – Capital light compounder MOAT 20:00 – Why classifieds are an interesting business model 25:12 – Looking at platform businesses 26:56 – Looking at companies in the 500 million to 5 billion range and what makes it so enticing 30:34 – What is the process that gets Connor to find investment opportunities             35:53 – David Tisch podcast   36:15 – How Connor looks at industry classifications 41:30 – Connor’s strategy for running his portfolio 46:36 – The circumstances in which Conno would buy a legacy MOAT company             46:49 – Will Thorndike Podcast episode             46:51 – The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success     49:21 – How do you pick managers that will beat the markets 52:21 – Second reason to buy a legacy MOAT 54:48 – Comparing the reinvestment MOAT and Capital A compounder in Connor’s portfolio 58:16 – Connor’s Mt Rushmore of Capital Allocators 1:00:03 – Impactful mentorships for Connor 1:01:52 – kindest thing anyone has done for Connor 103:04 – What in the discussion with founder of IMC got him the job   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 unique. As you will hear early and often, he is programmed to go his own way, to, as he says, go one way when everyone else is going another. His name is Dhani Jones, a name I knew as a Notre Dame football fan, because he won a championship with our arch-rivals, the University of Michigan, in the late 90’s. Dhani went on to a long and successful career in the NFL, but even more interesting has been his many pursuits in business and investing outside of football. Like my conversation with Tim Urban, I’ll remember this conversation as a reminder to use a first principles mindset. Dhani seems to have this fresh mindset baked into his character, and as you’ll hear this has led to many a great adventure. Please enjoy my conversation with athlete, businessman, investor, philanthropist, movie buff, and bowtie wearer, Dhani Jones.                                                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 1:30 - (First Question) –  A introduction into Dhani Jones and everything he’s done 5:35 – How did Dhani change throughout his football career 9:55 – The power of your mind in every aspect of life 10:34 – Most memorable experience in the NFL 13:10 – Making the transition from the NFL to the business world 18:20 – Looking at Bowtie Cause 22:40 – The role of creative agencies in Dhani’s ventures and why story telling is so important for him 26:48 – Looking at some of the TV stuff that Dhani has done, particularly around travel 28:21 – Dhani’s favorite movie 30:35 – Back to the joy of travel and “Dhani Tackles the Globe.” 36:54 – How does Dhani think about risk 38:56 – Some of the other sports and activities Dhani did while filming his show 41:45 – The psychological benefit of travel in your personal and business life 44:41 – Looking into the business part of Dhani’s career 51:19 – How to expand diversity in the financial world 54:56 – Kindest thing anyone has done for Dhani   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 episode is a continuation of the Hash Power series. It is the first of what we will call a Hash Power single—a series of conversations each with a single guest on a specific topic. In this case my guest is Chris Burniske, and the topic is cryptoasset valuation. This conversation is loaded with information, I think you are going to love it. Chris recently released book called Cryptoassets, which is a must read for those interested in this field. Chris was at one point the only tradintional buy side analyst covering bitcoin, and is now a partner at a new crypto firm called Placeholder. Chris has developed new frameworks for evaluating and valuing cryptocurrencies, marrying techniques and ways of thinking for several different asset classes to assess the newest asset class. Chris prefers the term cryptoassets because as you’ll hear, several of these tokens aren’t really currencies at all. We discuss the differences between cryptocurrencies, cryptocommodities, and cryptotokens. We begin our conversation with a deep dive into the equation of exchange, which Chris has been using as a starting point for understanding utility value.  You can see all crypto related conversations at investorfieldguide.com/Hashpower. Please enjoy this conversation with Chris Burniske. Hash Power is presented by Fidelity Investments   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   Books Referenced Cryptoassets: The Innovative Investor's Guide to Bitcoin and Beyond   Links Referenced Hash Power Podcast Documentary Nic Carter (twitter) Cryptoasset Valuations (Medium)   Show Notes 4:58 - (First Question) – Chris’s overall method for evaluating cryptocurrencies             5:14– Cryptoassets: The Innovative Investor's Guide to Bitcoin and Beyond 6:47 – The equation exchange 11:19 – Bonding 12:35 – How bonding may represent a more efficient way of representing consensus over proof of work 14:29 – Why the amount being bonded and held should be taken out of the float 16:58 – Using bitcoin as an example to figure out remittances in the PQ side 18:31 – Looking at the velocity of various crypto-assets 21:04 – Chris’s impression of the different way of categorizing various crypto assets 24:37 – Explaining Auger as an example of a cryptotoken 25:38 – How could these networks be impacted by not having any censorship 27:57 – Exploring the gap between expectation vs reality in the value of crypto currency 30:43 – Other ways of valuing these crypto assets             30:50 – Hash Power Podcast Documentary 33:32 – Explaining the idea of billion dollar a day onchain transactions 36:05 – How to measure the value of the underlying network             36:37 – Nic Carter (twitter) 37:13 – What are the variables that matter when investing in cryptocurrency on a long-term horizon 39:24 – Determining when it’s better for a network to be centralized vs decentralized 42:03 – Networks that Chris is most excited about 44:06 – Understanding the consumption side of the steam marketplace 46:01 – Deep dive into the Aragon network 47:27 – How does Chris evaluate existential risk of networks 51:09 – Could these assets really ever go to zero? 54:07 – Is there a scenario in which velocity gets so high that it negatively effects the price 56:10 – What are the unknowns of cryptocurrency that Chris is most interested in             56:24 – Cryptoasset Valuations (Medium)   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

Brad Katsuyama, founder of the IEX exchange and the central figure in Michael Lewis’s 'Flash Boys', discusses the complexities of the stock market and the impact of high-frequency trading. He shares his discovery of latency problems in trading and the journey to develop IEX, which aims for fairer trading practices. Katsuyama also delves into the challenges of entrepreneurship, balancing business with personal life, and the evolving dynamics of financial markets. His insights into investor relationships and ethical trading provide valuable lessons for aspiring entrepreneurs.

This week’s episode is part of an experiment and so requires a longer than normal introduction. I’ve come to view this podcast as a learning tool, a means to understand a new topic in a short window of time. One of those areas is venture capital and startups—an area that one year ago was completely foreign to me. I think the best way to learn is aggressive immersion in a topic along with some consequences, what we often call some skin in the game. Accordingly, this is a conversation with the founder of a startup in which I am an investor.The founder is Brett Maloley and his company is called Ladder. Ladder represents an overlap of many topics we’ve explore together over the last year. We’ve talked about venture capital, health and wellbeing, the difficultly of fundraising and power law outcomes in startups. We also spent an entire episode, with Alex Moazed, talking about the business model that Ladder is pursing: what Alex calls platform business model and what my favorite technology writer Ben Thompson calls the Aggregator model.I hope you enjoy this collective experiment, which is largely the result of what I’ve learned from past guests and from all of your support which helps me meet those great people in the first place. Let’s dive in to my conversation with the founder of Ladder, Brett Maloley, who starts by describing how he got his start in the fitness world. Show Notes5:25 – (First question) – Brett describes his history in the fitness industry10:04 – Realized he could fix the commercial fitness industry by changing it12:46 – Explain how Ladder works14:14 – What does the ratio of digital to in-person coaching need to be in order to be effective coaching17:12 – Explaining the platform business model as a whole and how to scale these types of business22:15 – Origin of health clubs24:01 – Current state of the health fitness space through some key stats26:44 – What happened where gyms were able to start charging a lot less for memberships30:20 – How Ladder is going to attract customers in the beginning36:10 – How to drive engagement37:46 – The opportunity for coaches on the platform40:28 – How will ladder ensure the quality of coaches on the platform remains high42:41 – Exploring the value of the data45:32 – How will Ladder work with gyms in the scope of how a new business can take advantage of existing businesses48:58 – Comparing Ladder to crossfit and what is not sustainable about 53:14 – Difference between a franchise model vs a license model55:12 – Strategy for building an audience59:56 – Competitors to this business1:03:39 – Brett’s thoughts on brand broadly speaking and how he’s worked to shape Ladder’s brand1:05:00 – Best individual experience of the platform so far