Invest Like the Best with Patrick O'Shaughnessy

My guest this week is Keith Rabois. Keith is currently an investment partner at Khosla Ventures, but has a storied and diverse background as an investor, entrepreneur, and executive. He has worked in senior positions at Paypal, LinkedIn, and Square; has led investments in companies like Stripe, YouTube, Palantir, and AirBnB; and started the company OpenDoor, which aims to transform the process of selling a home through technology. One fun fact about Keith is that he may have the most impressive list of bosses I’ve ever seen, which we discuss during the episode. We cover a lot, but one thing we kept returning to was business strategy. Keith’s frameworks for gaining and building strategic power helped me clarify my thinking on the topic, and his examples of contrarian thinking will hopefully make you question some commonly held beliefs. 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 1:35  (First Question) – A look at his investing philosophy 3:16  – Favorite examples of his own investment history             4:40 – 7 Powers: The Foundations of Business Strategy 5:07 – Understanding what is anomalous in a given investment 7:07 – How much a secret needs to be protected within a business 11:51 – Why accumulating advantage with data is of interest to Keith 15:12 – Digital health companies and ideas that he finds compelling 16:17 – Nuance around financial services that investors should be mindful of 17:56 – How do they evaluate managers ability to recruit talent 19:36 – How similar are the roles of entrepreneur, board member, investor, etc that Keith has had in his career 24:02 – Ways that Keith is a contrarian, including his feelings on “lean startup.” 27:04 – Is problem identification a specific skill set 28:29 – Objection with experimentation/iteration 30:02 – Bad ideas in venture 31:36 – What he likes about Apple             31:51 – Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs 32:26 - Interview questions for identifying great talent 35:41 – Elements of good design 37:14 – Impact of platforms on opening new opportunities 38:42 – His take on valuation in the early stage environment 40:33 – Advice he would give people early in their careers 43:58 – Do high growth companies get beat by established larger businesses 45:25 – Popular narratives that he thinks are just wrong 48:22 – His thoughts on how people should learn, balancing experience vs information gathering 50:00 – Other investors that are taking a unique approach to investing 51:57 – Reflecting on the entrepreneur as a client model of private equity 55:04 – Books that he recommends that is least known             55:18 – The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It 56:30 – Kindest thing anyone has done for Keith   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 Bryan Krug, who manages the Artisan Partners Credit Team and overseas more than $3B in high yield credit investments for the firm. This was my first conversation on high yield, so I took it as an opportunity to get an overview on the investment universe and home in on the tools used for analysis and security selection. As an equity investor, I think one of the most fruitful areas of research is into ways that companies fail or go wrong, and credit investors focus almost entirely on this potential for impairment. My guess is that all equity investors will learn something useful from this conversation. 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 2:11 – Overview of the high yield debt markets 5:05 – Why should investors consider this investment class 7:11 – How analyzing a company’s debt is different from what equity analysts look for 8:42 – Primary factors when exploring a company’s ability to de-lever 9:43 – What is their alpha vs others in the space 12:02 – Deep dive into the quantitative factors for them to look into a deal 14:25 – Benchmarks he uses 16:08 – Portfolio construction 17:15 – Their preference for broadband providers over cable tv networks 20:01 – What piques his interest about spreads 21:50 – The ratings of debt 25:40 – A recent example of an opportunity and how the mispricing was identified 29:17 – Most valuable data sets in this world 31:51 – Favorite part of this process 32:26 – Most surprising new learning 33:01 Maintaining your advantage 34:49 – The biggest pools of error in this industry 48:00 – What industries interest Bryan 40:50 – Dedication to this market 41:45 – Evolution of his healthy skepticism 42:38 – Can things in the debt market help to project what will happen in the equity markets 44:56 – Current view of the world based on what is happening in the credit markets 45:51 – Categories of convenience that he cares about 49:15 – Anything that has him worried in high yield markets 50:38 – Kindest thing anyone has done for Bryan   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 Maureen Chiquet, the former longtime CEO of Chanel. Maureen also spent much of her career at the Gap, growing Old Navy from scratch, and serving as the president of Banana Republic. The topic of discussion is her experience running large businesses and of finding one’s way in a career and as a leader of others. I hope you enjoy this unique conversation and that it encourages you to, among other things, travel somewhere new and interesting in the coming year. 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) – The importance of being able to put yourself in other people’s shoes             3:05 – Scott Norton Podcast Episode 4:36 – Most memorable sale from her early career 5:03 – The intersection of facts and emotions in sales 6:40 – Most important emotions in business 7:30 – The importance of identity as part of the selling/marketing of sales and products 9:10 – Difference in strategy for luxury brands vs others             9:21 – The Luxury Strategy: Break the Rules of Marketing to Build Luxury Brands 10:55 – Striking a balance between tradition and innovation 13:46 – Advice for new brand company related to rarity 14:59 – Importance of being organic with your brand purpose             15:01 – Wild Company: The Untold Story of Banana Republic 16:26 – Maureen’s purpose over the years 18:44 – How to harness your purpose for your job 20:53 – Her process for writing and desire to do TV 24:01 – Her time with Micky Drexler 27:40 – As a leader, guiding people to succeed. 32:33 – Strategy for shifting culture at a company 37:54 – The importance of courageous conversations we should all be having 43:45 – Markers of courageous conversations 46:43 – How she thinks about introspection 50:12 – What draws here to certain locations 55:15 – Advice for younger people starting out their career 57:11 – Kindest thing anyone has done for Maureen   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 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