Invest Like the Best with Patrick O'Shaughnessy

My guest this week is Hunter Walk, the co-founder of Homebrew, a unique venture capital firm. Hunter is a tool builder, having spent his career before venture at companies like Google and YouTube. The topic of our conversation is the intersection of creative expression, technology, human behavior, and problem solving.  We discuss his time at the company behind the video game Second Life, building tools for creators at YouTube, and why a very hands-on style of early stage venture investing represents an interesting use of his skillset at this stage of his career.  Please enjoy my conversation with Hunter Walk. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes 1:24 - (First Question) – Background on Second Life and what role Hunter had there 6:10 – The virtual currency system at use in Second Life 9:51 – Measuring how people behaved in this virtual world 12:21 – How closely is the Second Life world mimicking real life 15:13 – The market for platforms that lets people take on creative ventures 17:58 – Investments that interest Homebrew 20:21 – Lessons learned while working at YouTube 28:34 – The idea behind Homebrew 33:44 – How to best describe good problems to solve for 36:10 – The Shadow economy and investing in companies operating there 42:17 – Monetization of attention 47:22 – His interest in fintech companies 54:03 – Major trends of change he’s observed over his first three funds 1:04:13 – What is there take on the state of returns for VC’s 1:09:52 – What is the most common way that founders need help and what advice is more helpful 1:14:35 – Kindest thing anyone has done for Hunter   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

[REPLAY] Modern Monopolies: What It Takes to Dominate the 21st Century Economy, which explores the platform business model (Uber, Airbnb, Github).  Alex is also the founder and CEO of Applico, a company that he started in his dorm room that is since grown into a huge enterprise that helps startups and Fortune 500 innovate with platforms.  Alex and I talk about history and future of businesses and different types of business models.  There’s a lot in here for investors, entrepreneurs, and historians.  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 Books Referenced Modern Monopolies: What It Takes to Dominate the 21st Century Economy The Systems Bible: The Beginner's Guide to Systems Large and Small The Master Switch: The Rise and Fall of Information Empires Zero to One: Notes on Startups, or How to Build the Future   Links Referenced Failed Color App Applico   Show Notes 2:39  – (first question) – Exploring the history of business models from linear to platform. 5:46 – A look at the share of overall business platform companies have taken over             7:06 - Modern Monopolies: What It Takes to Dominate the 21st Century Economy 7:48 – The potential for platform businesses over the next 20 years 9:18 – Detailing the difference between a linear and a platform business 12:08 – Exploring transaction costs and core transactions across different business models 19:49 – Is the platform business model good for investors and VC’s since so many can get crushed when there’s a sole victor, or is it just for the founders and entrepreneurs.  24:35 – How the self-driving car is going to deliver more opportunity for consumer consumption 27:15 – Untapped supplies as the opportunity for new platforms and where we could see new openings 30:24 – How consolidated will things become across all platforms 33:16 – How do platform companies create a moat to keep others from replicating their business strategy 37:03 – Are there platform strategies that specifically don’t work             37:40 - Failed Color App 38:45 – Why complex systems typically don’t scale up and you should think small and easy to get started             38:47 – The Systems Bible: The Beginner's Guide to Systems Large and Small 40:02 – How the origin of so many larger companies started out small and localized, and why it makes investors more comfortable 41:37 – How Alibaba had to tweak their business model to accommodate the Chinese market 44:07 – Why are the modern monopolies better for consumers 47:52 – Exploring platforms that are asset heavy 49:00 – What do you look for as a VC to determine 52:05 – Alex’s take on whether a platform based company like Uber should be more asset heavy 54:31 – Exploring some lesser known platform businesses that Alex finds interesting 56:18 – If there is a demand in the secondary markets for a product, why don’t the primary suppliers simply raise their prices 57:03 – What Alex’s portfolio of platform-based businesses would look like 58:48 – A couple of most influential books Alex has read             59:12 – The Master Switch: The Rise and Fall of Information Empires             59:38 – Zero to One: Notes on Startups, or How to Build the Future and other Peter Thiel books 59:53 – Looking at Applico, how it started and how it become so focused on the platform business model 1:03:56 - Most memorable day for Alex  1:05:13 – Kindest person to Alex in his life 1:06:10 – What platform opportunities could exist in the financial world 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

Cliff Asness, managing and founding principal at AQR Capital Management, discusses the past, present, and future of quant investing. They touch on major changes in factor investing, the balance between sharing and keeping proprietary information, the application of value, momentum, and volatility in asset allocation, attributes of good researchers, transitioning into less exciting aspects of the business, and the importance of understanding HML for value managers.

[REPLAY] My guest this week is Peter Attia, M.D., whose mission is to understand and improve human lifespan and healthspan (or quality of life).  Reading Peter’s research, you find that there are many similarities between health and investing—ideas like compounding—which we explore in detail. We spend a lot of time on mind, body, spirit and performance as it relates to living a better life. Of particular interest is the strategic problem that we face when studying longevity. As Peter puts it in our conversation: we are the species of interest, but we can’t conduct the kinds of experiments on humans—randomized trials, with control groups—that we apply to solve other big problems. So we have to back our way into a better understanding of longevity and quality of life. To that end, we discuss what we can learn from studying centenarians, the problem of progress in science, a drug called Rapamycin (which Peter believes could be revolutionary), eating, the importance of muscle mass, and the idea of distressed tolerance.  We emerge with a framework for thinking about health and well-being which can hopefully help us all live longer, better lives. Please enjoy! For comprehensive show notes on this episode go to http://investorfieldguide.com/attia 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 Posts From Peter Attia That You Should Read Do Calories Matter How You Move Defines How You Live 2016 Update Long List of Questions Answered: Part 1 and Part 2 Links Referenced The Scientific Method-Richard Feynman Knowing Versus Understanding-Feynman again Books Referenced Barbarians at the Gate: The Fall of RJR Nabisco Diffusion of Innovations Good Calories, Bad Calories Show Notes 2:31  – (first question) – Getting Peter to define the concept of wealth and how it might have changed in his life 5:01 – How do you increase the number of really good people in your life. 6:50 – Looking at the relationship between healthspan and lifespan and a chart that Peter created on this specific topic. 11:11 – Drilling down into the different dimensions and aspects of this chart that could be most important for people, especially how compounding plays into our health. 16:57 – The difference between strategies and tactics that will help you extend lifespan 17:54 – The Scientific Method-Richard Feynman 21:41 – Different types of intermittent fasting 28:59 – What role does repair play in health 34:17 – Barbarians at the Gate: The Fall of RJR Nabisco 36:01 – Looking back, what health trends today will look absurd 36:19 – Diffusion of Innovations 39:24 – What are the primary benefits of weight lifting 40:21 – The importance of glucose disposal 45:07 – Good Calories, Bad Calories 46:31 – What is the state of progress in the scientific community 52:14 – Peter is asked about how he guards against getting too attached to old beliefs 1:01:51 – A look at how performance relates to healthspan 1:03:34 –Peter’s first great auto-racing experience 1:09:17 – Looking into Peter’s medical practice and understanding his thinking that goes into helping people 1:18:11 – The most memorable day in Peter’s career 1:22:31 – The kindest thing anyone has done for Peter 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 Ryan Caldbeck, a private equity investor who wants to bring quantitative rigor to the private markets. Ryan is the CEO of Circle Up, which uses a system it calls Helio to identify attractive investments in early stage consumer brands.  While I am of course a fan of quantitative investing, I also know from experience how much harder private markets are than public markets when it comes to the transactions themselves. We discuss this and many other potential roadblocks to bringing models to private markets. Using many individual companies as examples, Ryan explains some of the major predictive factors they’ve uncovered in their research. We also discuss which parts of the private markets might be infiltrated by quant processes first, and which may never be.  I expect many more to go on a journey similar to Ryan’s in the years to come. They serve as an interesting example for ambitious investors out there. 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 1:39 - (First Question) – Formation of Helio 6:57 – How they handle the relationship building needed to make investments in private markets 10:26 – Why consumer and retail are interesting spaces to apply their quantitative approach in private markets 12:54 – Searching for new relevant data 16:14 – How do they stay ahead of the commoditization of uniqueness             16:21 – Pattern Recognition and Machine Learning             17:24 – Sam Hinkie Podcast Episode 18:00 – Dominant predictive factors in this world 21:05 – Which is more important, relative value or rate of change 21:48 – What does the data say about online sales vs offline (being in a store) 23:30 – Variable that consumer investors think matters but it doesn’t 24:53 – Valuing companies and accounting for mispricing’s             25:36 – Michael Recce Podcast Episode 26:41 – Goes through the process using Liquid Ivy as an example 28:46 – Most interesting sub-categories 29:33 – Future for this model             32:10 – Albert Wenger Podcast Episode 35:19 – Other categories outside consumer and retail interest Ryan 36:28 – Biggest challenges for CircleUp as a business 38:46 – Handicapping their earnings expectations 41:36 – Take on the VC/PE landscape 43:03 – The types of models that are most interesting to the team 45:05 – Quantitative elements of brand that are most interesting 47:30 – Most unique brand and distribution strategy he’s come across 53:27 – Who has influenced Ryan the most 54:37 – His personal values 55:51 – More people who had an influence on Ryan             56:05 – The Innovator's Dilemma: The Revolutionary Book That Will Change the Way You Do Business 57:07 – Thoughts on goal setting at the company 59:29 – Unchangeable factors that shape their long-term vision 1:02:01 – Most interesting individual conversation as part of this journey 1:04:02 – If he could only keep one dataset, what would he keep 1:05:09 – kindest thing anyone has done for Ryan   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 aspires to be the Larry David of investing, and we discuss why. Howard Lindzon is hard to categorize. He’s primarily an early stage investor right now, but he’s participated in all types of investing. He describes himself as a trend follower and always has a unique take on popular topics.  In this conversation, we cover his investing history and his take on the fintech investing landscape. What I’ll remember most is the idea that we should focus on what is happening versus what we think will happen or might happen. There is a Peter Lynch like quality to some of Howard’s thinking, and a willingness to embrace the weird that I find very appealing. The few times I’ve met Howard, I’ve smiled or laughed most of the time, which is about as nice a thing as I could say about someone. He’s a good example of why I like this podcast format. His investing style bears literally no resemblance to my own, but it got me thinking about a lot of new things. I hope you enjoy our chat. 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) – Why he wants to be the Larry David of investing 2:00 – Why his investing style is best described as trend following 4:05 – The biggest inspirations/influencers on Howard’s investing 6:39 – What made his second mentor, Fred Wilson such a great investor 9:52 – Formation of Wall Strip 12:33 – Why weird is so important in his investment philosophy 14:56 – Understanding his investment philosophy through his investment in Rally Road. 21:02 – His assessment of the fintech space 28:54 – Why fintech pushes away from human nature 30:50 – Major trends in fintech that have his attention 35:02 – What stands out about the teams at these companies he invests in 36:37 – Thoughts on fractionalization plays             36:44 – Capital Allocators podcast episode             36:54 – Venture Stories Podcast 40:03 – Any major trends that are changing and worth attention             42:06 – The Tipping Point: How Little Things Can Make a Big Difference 43:26 – His take on the media landscape 45:10 – 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 guests this week are Ali Hamed, Brian Harwitt and Marc Porzecanski who work together at CoVenture Credit. When I first had Ali on as a podcast guest, we discussed the many aspects of what his firm does, ranging from venture, to crypto, to credit. We glossed over the lending side of the business, but having since learned a lot from them on the topic, I was excited to get the chance to talk with members of their credit team for today’s longer exploration of esoteric high yield lending. I am always proselytizing the value of investor education, s this week we have a podcast first. The CoVenture team has prepared a long series of posts that correspond to our conversation and go even deeper into the topic of credit investing. You can find them in the shownotes at investorfieldguide.com/credit This is entirely differently from any conversation I’ve shared before, so I hope you learn as much as I did. Please enjoy my discussion with team CoVenture Credit. 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) – The formation of their unique credit business 7:09 – Their advantage in seeing both the equity and credit side of their investments 10:23 – Looking at the Returnly deal as an example 14:07 – How they view these deals and are able to sustain them as long-term investments 18:09 – Their interest in payroll deduction lending 20:08 – Finding unique types of default risk 21:31 – What stands out in a platform that makes CoVenture want to take a deeper look 26:43 – Most interesting types of problem they have come across that they have yet to do a deal in 31:35 – What is going to change to make for more thoughtful underwriting of subprime lending 35:51 – Major structures of asset backed lending 39:49 – Whether the home serves as an interesting playground for credit opportunities and whether people will own anything again 42:44 – Mark’s experience working at a huge firm vs his experience at CoVenture 44:31 – How does the current credit cycle impact their view 47:04 – Lending against bitcoin 50:06 – Who is interested in these loans against bitcoin 50:57 – How to set interest rates against a weird asset like this 53:00 – What are the key determents of success in this business 1:02:27 – Kindest thing anyone has team for the team 1:03:52 – How to treat people that you pass 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 this week is Saifedean Ammous, author of the book the Bitcoin Standard. This was one of the more interesting conversations I’ve had in the world of cryptocurrency, primarily because we don’t talk about Bitcoin or Crypto until 25 minutes into the talk. Instead, we focus on history, economics, sound money, low time preference, and gold—all interesting topics. Saif’s thinking on cryptocurrencies other than bitcoin—which is that they are worthless—is unique and thought provoking. His reasoning around why gold shouldn’t be compared to the returns generated by assets like equities was also compelling. If you’ve followed my Hash Power episodes, this is a new a differentiated interpretation of Bitcoin as a technology for the store of value use case. Please enjoy our conversation. 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 2:10 - (First Question) – Explain Sound Money 4:25 – Examples of hard vs easy money 7:36 – the even money trap 9:36 – The benefits of hard money vs today’s standards 14:05 – Why this interests him             14:16 – Gold Wars: The Battle Against Sound Money As Seen From A Swiss Perspective             14:56 – Democracy – The God That Failed: The Economics and Politics of Monarchy, Democracy and Natural Order 16:17 – Correlation between time preference and people’s ability to succeed in life 19:59 – How money markets worked in the late 18th century vs today 27:57 – How he came across Bitcoin and how he thinks of it as a digital gold 35:42 – How will the world transition to a sound money standard 42:15 – The impacts of hyperinflation on crypto currencies 45:04 – The idea of a orderly upgrade of the world currency 48:20 – His thinking on alternative coins 54:05 – What it takes to compete with bitcoin 1:01:43 – How he diversifies 1:04:35 – Stalling bitcoins demand 1:06:11 – Does he apply his thinking of lower time preference elsewhere in his life 1:07:09 – 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

Jeremiah Lowin, a former statistician turned founder of Prefect, discusses machine learning in investing. He addresses data workflows, friction between data scientists and engineers, deploying machine learning in investing, the importance of data and error minimization. The conversation explores applications in finance, model testing, label formation, and the significance of interpretability in machine learning.

This week, to mark the two-year anniversary of the podcast, I offer a quick summary looking back and forward.