Invest Like the Best with Patrick O'Shaughnessy

Colossus | Investing & Business Podcasts
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Jan 16, 2018 • 1h 14min

Preston Byrne - Crypto-pocalypse - [Invest Like the Best, EP.72]

My guest this week is Preston Byrne. Preston is vocal critic of crazy prices and projects in the world cryptocurrencies. His background is in the legal world and also as a founder and former COO of Monax, which made the first open-source permissioned blockchain client. As Preston says, he is a “blockchain without bitcoin” guy, who believes that this crypto mania will end in some sort of apocalypse for token holders and ICO issuers . We tackle several issues, from his broad skepticism of crypto assets, to the potential regulatory reaction from major governments, to types of coins like stable coins, which Preston views as analogous to perpetual motion machines.  Please enjoy our conversation and for any crypto investors out there, let me know if this conversation affects your opinion of the investing prospects for cryptocurrencies.  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   Links Referenced Bitcoin white paper The Bear Case for Crypto Hash Power series Zero Hedge Preston tweet on Reverse network effect   Show Notes 2:12 - (First Question) –Ponzi scheme vs pyramid scheme vs Nakimoto scheme  5:29 – Why there are regulatory challenges to cryptocurrency             5:33 – The Bear Case for Crypto  9:59 – Who are the most influential people supporting this and how are they swaying the regulatory minefield on this issue             10:28 – Hash Power series  13:23 – Looking into the idea of a digital asset and the difference between blockchain and the token itself  16:09 – What about the idea that cryptocurrency’s only feature is that it’s censorship resistant  18:39 – Why cryptocurrencies become less usable the more successful they are             18:59 – Zero Hedge  21:04 – Why can’t we rely on offchain solutions to solve the scaling issue  22:29 – The idea of bubbles and what happens next in this one            25:41 – What are the incentives to build technology to support cryptocurrencies  29:23 – Explaining Ripple  31:21 – What would precipitate a massive reversal in the inflated valuations of cryptocurrencies  34:52 – Understanding reverse network effects             34:36 – Preston tweet on Reverse network effect 37:45 – The principles behind Stablecoin 42:20 – What has been the greatest lesson that Preston has learned about blockchain he wish he knew when he first got started 44:05 – How embedded will blockchain be by 2024/2025 45:12 – ICO’s, why Preston is not a fan and if there are any positives to them 50:20 – What are the conditions under which these things will be viewed legally. 54:00 – Preston’s history owning cryptocurrencies 55:35 – What has Preston most excited in the space 59:02 – Utility settlement coin 1:00:36 – Why the fascination with marmots 1:02:10 – What to reference before getting started with cryptocurrencies 1:04:03 – Understanding supply chains in block chain 1:07:14 – Some smart people on block chain to follow 1:08:24 – Kindest thing anyone has done for Preston Learn More For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag  
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Jan 9, 2018 • 1h 19min

Ali Hamed – Creative Investing - [Invest Like the Best, EP.71]

Ali Hamed, the young founder of CoVenture, dives into the world of creative investing. He discusses how to spot unique opportunities, from financing perishable produce to rolling up Instagram accounts. Ali shares insights on the importance of empathy in product design and contrasts different investment stages. He emphasizes the need for sustainable business practices over one-off trades and reveals his experiences in fundraising and crypto. This conversation inspires listeners to think outside the box and find new ways to earn success.
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Jan 2, 2018 • 56min

Sheel Tyle - The Future of Venture Capital - [Invest Like the Best, EP.70]

Sheel Tyle is the sole general partner at Amplo, a venture capital firm focused on mission-driven entrepreneurs. At just 26, he has already made significant waves in venture capital, previously co-heading seed investing at NEA. In this discussion, he shares insights on the potential of African markets, the importance of authentic networking, and innovative technologies like driverless cars. Tyle emphasizes the necessity for founders to engage with their communities and the strategic decisions involved in navigating venture capital funding.
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Dec 26, 2017 • 1h 1min

Chris Dixon – The Future of Tech - [Invest Like the Best, EP.69]

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
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Dec 19, 2017 • 1h 29min

Sorin Capital – Retail Contrarians - [Invest Like the Best, EP.68]

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.
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Dec 12, 2017 • 60min

Franklin Foer – World Without Mind - [Invest Like the Best, EP.67]

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
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Dec 5, 2017 • 1h 10min

Adam Ludwin - A Sober View on Crypto - [Invest Like the Best, EP.66]

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
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Nov 28, 2017 • 60min

Joanne Wilson - Angel Investing and Trend Spotting - [Invest Like the Best, EP.65]

Joanne Wilson, a dynamic angel investor and trend spotter known for supporting female founders, shares her insights from investing in over 90 companies. She discusses how she identifies emerging trends in food and culture, revealing her unique blend of instinct and observation. Joanne also delves into the common traits of successful entrepreneurs, emphasizing the importance of relentless problem-solving and adaptability. She reflects on the challenges female founders face in fundraising and highlights the potential of niche markets in today’s economy.
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Nov 21, 2017 • 1h 9min

Connor Leonard - Capital Light Compounders & Reinvestment Moats - [Invest Like the Best, EP.64]

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
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Nov 14, 2017 • 1h

Dhani Jones - Adventures in Sports, Business, and Investing - [Invest Like the Best, EP.63]

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

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