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

My guest this week is one of my best and oldest friends, Jeremiah Lowin. Jeremiah has had a fascinating career, starting with advanced work in statistics before moving into the risk management field in the hedge fund world. Through his career he has studied data, risk, statistics, and machine learning—the last of which is the topic of our conversation today.  He has now left the world of finance to found a company called Prefect, which is a framework for building data infrastructure. Prefect was inspired by observing frictions between data scientists and data engineers, and solves these problems with a functional API for defining and executing data workflows. These problems, while wonky, are ones I can relate to working in quantitative investing—and others that suffer from them out there will be nodding their heads. In full and fair disclosure, both me and my family are investors in Jeremiah’s business. You won’t have to worry about that potential conflict of interest in today’s conversation, though, because our focus is on the deployment of machine learning technologies in the realm of investing. What I love about talking to Jeremiah is that he is an optimist and a skeptic. He loves working with new statistical learning technologies, but often thinks they are overhyped or entirely unsuited to the tasks they are being used for. We get into some deep detail on how tests are set up, the importance of data, and how the minimization of error is a guiding light in machine learning and perhaps all of human learning, too. Let’s dive in. 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 2:06 - (First Question) – What do people need to think about when considering using machine learning tools 3:19 – Types of problems that AI is perfect for 6:09 – Walking through an actual test and understanding the terminology 11:52 – Data in training: training set, test set, validation set 13:55 – The difference between machine learning and classical academic finance modelling 16:09 – What will the future of investing look like using these technologies 19:53 – The concept of stationarity 21:31 – Why you shouldn’t take for granted label formation in tests 24:12 – Ability for a model to shrug 26:13 – Hyper parameter tuning 28:16 – Categories of types of models 30:49 – Idea of a nearest neighbor or K-Means Algorithm 34:48 – Trees as the ultimate utility player in this landscape 38:00 – Features and data sets as the driver of edge in Machine Learning 40:12 – Key considerations when working through time series 42:05 – Pitfalls he has seen when folks try to build predictive market investing models 44:36 – Getting started 46:29 – Looking back at his career, what are some of the frontier vs settled applications of machine learning he has implemented 49:49 – Does intereptability matter in all of this 52:31 – How gradient decent fits into this whole picture     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, to mark the two-year anniversary of the podcast, I offer a quick summary looking back and forward.

My guest this week is Kathryn Minshew, the co-founder and CEO of the Muse, and the co-author of The New Rules for Work: the Modern Playbook for Navigating Your Career. I’ve learned in business is that the quality of people and the culture they create dictate outcomes. Having made plenty of mistakes hiring, and having had many enormous successes, I am always interested in best practices for finding and successfully recruiting the right people. Given that Kathryn runs a jobs marketplace and has written a book on the topic, she is the perfect person to explore some the core concepts around pairing people with the right positions. We discuss how companies should market to prospective employees, how employees should represent themselves to employers, and the most common mistakes she sees across the hiring landscape. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes 1:31 - (First Question) Largest changes in the nature of work and how people approach finding the right job for them 3:27 – Can this work be jammed into a formula 5:18 – What strategies is she sharing with employers when it comes to hiring 8:31 – How long should the process take 9:33 – Biggest mistakes employers make in this process 10:39 – Besides the usual stuff, what can perspective employees do to bolster their chances 12:50 – How much more efficient will matching technology get in the years to come 16:00 – What will be the largest changes to work itself 19:09 – Will we move away from full time work into parsels of work units 20:50 – Most successful piece of content or content strategy the Muse has employed 22:34 – Advice for early stage entrepreneurs 26:24 – Kindest thing anyone has done for Kathryn   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

I intentionally avoid the world of quantitative investing on this podcast. The whole point of this format is to learn about many different fields, and the vast majority of my time is already spent in quant world. Occasionally I’ve broken this rule because of something unique, including this week’s conversation with Richard Craib, the founder and CEO of Numerai. If you listen to the podcast often you’ll have heard me reference Numerai, a hedge fund which blends quant investing, cryptocurrencies, crowdsourcing, and machine learning — talk about a PR company’s dream. One important note: Numerai is both incredibly open and very secretive. You may sense a bit of frustration on my part, but that is only because, as a fellow quant who loves details about data and modeling, we couldn’t go deeper into the details on the record. We discuss how Numerai has created an incentive structure to work with data scientists around the world in an attempt to build better investing models. The idea of having data scientists stake cryptocurrency in support of the quality of their models is fascinating. Like many hedge funds, Numerai doesn’t share its track record, so we don’t know if this works—but I hope you, like me, use this conversation as inspiration for how different technologies can intersect. Hash Power is presented by Fidelity Investments Please enjoy my conversation with Richard Craib.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes 2:32 - (First Question) – How he came up with Numerai and how its related to his background 4:08 – How he works with and models the data for his system 5:24 – Describing machine learning as it relates to his work, and specifically linear regression 7:11 – The important stages in his sequence 8:46 – How the scale in the number of data scientists they use is different from other areas 11:30 – Which is the most important aspect of creating alpha; their data, algorithm work, proprietary ensembling of those algorithms. 14:30 – The idea of staking in blockchain 17:30 – Does the magnitude of the stake matter in blockchain 19:10 – Understanding the full incentive structure for both staked and unstaked work 21:07 – How is the prize pool determined 22:29 – Philosophy on how to source interesting data 26:11 – His thoughts on the crowd model and the wisdom of crowds 27:12 – The size of stakers for Numerai 27:51 – Interpreting the models and knowing when something is broken 30:03 – How they think about people not submitting their models 31:48 – Their model building 32:39 – Most interesting set of things they are working on to improve the overall process             35:38 – The Market for "Lemons": Quality Uncertainty and the Market Mechanism 37:11 – How people can come along with their own data 39:00 – His thoughts on the quantitative investment community 40:44 – What else is interesting him in the hedge fund world 44:03 – Building a marketplace and staving off competition 46:16 – Kindest thing anyone has done for him   Learn More For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week has a fascinating background. He has a PhD in biology but has split his time as both an investor and an operator. As an investor, he’s involved in companies like Airbnb, Coinbase, Instacart, Opendoor, Stripe, Square, and Pinterest—not too shabby. As an operator, he helped both Google and Twitter scale their businesses, in the case of Twitter from 100 employees to 1500 over two years. He’s just written a book about these experiences called the High Growth Handbook.  Our talk centered on what makes for a good investment and more specifically how Elad identifies an interesting market. Operators and early stage investors will find lots of nuggets in this fun 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 1:31 - (First Question) – Process for evaluating a young business             2:43 – Andy Rachleff Podcast Episode 3:09 – Data factors for evaluating a business 5:08 – Reference checks 6:42 – Advice for companies that are reliant on product cyclicality             7:01 – Where to Go After Product-Market Fit: An Interview with Marc Andreessen 7:31 – High Growth Handbook 9:30 -   Lessons learned from marketing and growing companies 12:09 – How do you hire the best people to improve your distribution 13:16 – How does he think about lifetime customer value vs customer acquisition cost 15:57 – Should companies just focus on the high margin power users 16:35 – Best ways to organize a company hierarchy 19:16 – His interest and background in the area of longevity research 21:52 – Changes he has made in his own life as a result of this longevity research 22:56 – Most effective use of a CEO’s time 24:58 – How he evaluates or identifies interesting markets for potential businesses 28:03 – Any markets that fit his criteria that are underappreciated by investors 30:02 – Worst practices for businesses 32:19 – Kindest thing anyone has done for him 33:20 – What would be the topic of his next book 34:40 – Biggest lessons he’s learned about markets   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

For the 100th episode, I’ve brought back my good friend Brent Beshore. Brent was the 10th guest on the podcast, after we met because of a mutual interest in capital allocation. I quickly learned that Brent was one of the most unique and thoughtful investors around. He was an entrepreneur from the moment he left school, trying many different things before finding a fit buying smaller business with the intention of owning them forever. What amazes me about Brent is his encyclopedic understanding of business and the nuances of different business models and deal structures. This comes from reps. He and his team have looked at about 12,000 deals over the years, at every kind of business that you could imagine. I’ve been with him when he goes through this process and it’s fun to hear what makes certain businesses stand out from others, which is largely the topic of this conversation. You all know transparency is key for me, so it’s important to know that my family and I are investors in a fund called permanent equity, run by Brent and his firm Adventure.es. To commemorate this milestone episode, I can think of no one better than Brent, because he exemplifies what has made this podcast so fun for me: learning from other people who are willing to share what they themselves have learned through fun, blood, sweat, and tears. Please enjoy our conversation, and thank you so much for coming along on this journey. I can’t tell you how much it means to me. 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 2:02 - (First Question) – How does he think about optimizing risk in terms of the capital stack when looking at deals 5:27 – What conditions would they add debt down the road after investing in a company 6:52 – What business sectors are most intriguing for Morgan to invest in right now             6:57 – Trent Griffin Podcast 9:34 – Why no HVAC businesses if it’s such an attractive sector 13:56 – thoughts on rolling up similar businesses and horizontal scale 16:04 – Another industry Brent would focus on 18:02 – Difference between property management in larger cities vs smaller metro areas 18:51 – What role does profit margin play when Brent is evaluating a business 22:46 – The appeal of a hyper cyclical business             22:52 – Brent Beshore Podcast Episode 27:27 – Favorite counter cyclical business 28:14 – How they judge assets, tangible vs intangible assets 33:58 – How does he think about wage inflation when considering the cost of a business 37:21 – His fascination with pet crematoriums 38:57 – History of the permanent equity fund and the changes by having a larger pool of capital 43:48 – Pitching investors on a new structure for the business 46:14 – How will this business model scale   Learn More 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

Today’s conversation is a continuation of my discussion on applying the lessons of tracking animals in the wild to tracking in your own life. I encourage to listen to that episode first. In this second part, Boyd’s sister Bronwyn joins and offers perspective on business and life. Given that Boyd and Bron grew up in this wild place, their perspective on the world is refreshing and very different. We discuss a wide range of things, But the section on restoration near the end is just phenomenal stuff. Please enjoy part two of my conversation with the Varty family.   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 1:21 - (First Question) – Concept of shame and the role it plays in the lives of the people that visit 3:11 – Bron’s take on shame and if this is uniquely male issue 5:15 – How the Varty’s think about the concept of presence, and time with Nelson Mandela 13:34 – Selfishness as an impediment to presence 20:26 – Tending the cup 20:37 – Life is not a zero-sum game 23:15 – How they run the reserve as a business 30:18 – Importance of motivation as a business 33:55 – Cultivating a culture that makes a business a family 40:15 – How they help other family businesses 45:29 – The idea of restoration as a business and legacy 51:23 -Restoration model in investment 53:49 – The age of restoration will be born on the age of information 54:48 – Places that have given Varty’s deep connections (other than Africa) 1:00:46 – Kindest thing anyone has done for Bron   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

An interesting question that I think about a lot: how do you balance exploring the new with savoring what you already know and love? Most of the time I prefer to explore, but the best part of this podcast experience for me has been meeting people who become close friends. For episodes 99 and 100, I’m bringing back two of the most popular past guest who are both now dear friends.  This week’s episode is split into two parts, today and tomorrow. Today’s episode is with Boyd Varty and tomorrow is with both Boyd and his sister Bronwyn. The incredible Varty family hosted me in South Africa, so you’ll hear birds and elephants in the background as we talk.  This conversation with Boyd is about our shared experience called “track your life” which I couldn’t recommend more highly. We tracked animals on foot for five days, and learned a lot from the environment itself. While we discuss our time together, this is much more about how to live. My original conversation with Boyd had a huge impact on me, and this continues the exploration of Boyd’s idea that we should all be going our own way, in the right way, instead of simply following well trodden paths.  I hope you enjoy this conversation with Boyd and check back tomorrow for another conversation with the Vartys.  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 1:55 - (First Question) – Encounter with five wild dogs 10:19 – The idea of a perfect day on the track 15:59 – The importance of silence 19:42 – Why we could all benefit from the power of silence 21:37 – Side effects of being on the track 23:49 – Following the smaller paths 25:20 – How culture can keep us from forging our own path   29:34 – The stress he puts on the watch at night 33:34 – The power of going from alert to rest and back again             35:11 – Why Zebras Don't Get Ulcers 38:25 – Disconnecting from the modern world and reconnecting with your life’s purpose 41:42 – How much does skill play into finding your life’s calling 43:23 – Common objections to what they do 49:58 – Importance of end of day on the track 52:33 – Silence and feeling of thousands of years of time passing through hallucinogenic 56:22 – His experience with bees 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

Ryan Selkis - The Crypto Barbell and Token Curated Registries - [Invest Like the Best, EP.98] This week’s conversation is for those interested in the nitty gritty of cryptocurrencies and for those who, like me, are fascinated by that world but more than a bit skeptical of the investing prospects for the many cryptocurrencies now in existence. My guest is Ryan Selkis, who I met at an event hosted by Union Square Ventures and Blocktower Capital. At that event, in a crowd of many brilliant people, Ryan was consistently asking hard questions and raising counterpoints. I love his perspective because he is both passionate, but realistic, excited about crypto, but worried about many aspects of the ecosystem. We discuss many new topics like his barbell analogy for thinking about different kinds of coins, token curated registries, and the need to better transparency around decentralized projects. Hash Power is presented by Fidelity Investments Please enjoy our conversation.   March for the Fallen Want to meet other curious investors, get in good shape, and support a fantastic cause? Consider joining a great group to hike 28 miles in honor of those who have fallen in defense of our nation.  Learn more and sign up at alphaarchitect.com/mftf.    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 2:55 - (First Question) – how he best explains blockchain technology 4:12 – How does he categorize each cryptocurrency 9:11 – How Numeraii is valued 10:04 – Explaining token curated registries (TCR) 12:58 – How Token Curated Registries are being applied 15:05 – Innovations that will protect against nefarious actors in the crypto space 16:37 – How do you convince investors to commit to TCR’s 18:40 – Biggest headwinds to this industry 22:12 – What are the quality filters to root out the bad actors 25:42 – Thoughts on the ICO market as an alternative to capital raising 29:23 – Litmus test for who should use an ICO to raise capital 34:28 – What is unique about creation of a token vs the normal exchange of cash to determine if a company needs a token 36:21 – How many ICO projects are really necessary 38:28 – How should people form an investment opinion about this space 41:35 – Core mission of his company 44:28 – What are some of the reasons his goals won’t happen 49:30 – Lessons learned while working at Coindesk 49:58 – What is he most excited about for the future of this space 52:56 – 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 is Cathie Wood, the founder of ARK invest. Cathie and her team believe that disruptive innovation is the key to long-term growth and, therefore, alpha in the public markets. Because their style of investing is entirely contingent on what will happen and change in the future, it is about as different a style as exists from the quantitative approach to investing, which relies on what is currently knowable about stocks and businesses.  The future is notoriously hard to predict, so I am always interested to hear about investing approaches which try to model or handicap the future and build portfolios against that work. In this conversation, we explore all the most interesting and exciting technology trends at play in the world today—and how those trends may play out for investors. We discuss genome sequencing, blockchain, software 2.0, mobility as a service, automation, and more.  We also discuss Cathie’s take on building a bridge between the worlds of finance and Silicon Valley, and why starting with a benchmark is anathema to their process. It is hard to deny Cathie’s passion and enthusiasm, and I credit her for building a unique firm culture that emphasizes openness and collaboration. Please enjoy our conversation on investing in innovation.  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 2:30 - (First Question) – Cathie’s idea of bringing open source to Wall Street 4:47 – Deep dive into the platform             6:09 – White Paper on Bitcoin – Could Bitoin serve as the role of money 7:43 – Why disruptive innovation is so inefficiently priced 10:04 – How well does the market discount cash flow of disruptive businesses 14:09 – A look at their investing strategies, starting with top-down.  16:10 – How they picked their 5 categories of technological change, starting with foundational     19:42 – Changes in energy 21:53 – Robotics 24:17 – Excitement over deep learning 28:03 – How they express their top-down ideas from the bottom up 36:06 – Mobility as a service as a key area of focus 45:25 – The power of public mistakes 46:39 – What she looks for when hiring 51:14 – her philosophy on building and maintain a portfolio 56:38 – Behind the growth of the company 1:04:01 – Most exciting area for her right now 1:07:52 – Kindest thing anyone has done for Cathie   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

I’ve often heard that good investors are a bit like journalists: doggedly collecting evidence and building an understanding of how all the pieces of a company or investment fit together. My guest this week is one of my favorite writers and journalists, Bethany McLean. Across her career, Bethany has covered many of the most interesting stories in business and investing, including Enron (which became the famous book and documentary, the Smartest Guys in the Room), Valeant, Wells Fargo, SAC Capital, Fannie Mae and Freddie Mac, the great financial crisis, and most recently, fracking and the energy revolution. Given how deeply she has investigated all of these topics-- and thought about the common threads across them all--this was an amazing conversation. When talking to her, you can feel how much she cares and how diligent and fair she is when analyzing a topic. In addition to all of the great stories already listed, we discuss the art of persistence and other lessons she has learned about businesses and people gone bad. I especially loved her evolving take on housing in America. Please enjoy my conversation with Bethany McLean   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Links Referenced The Hunt for Steve Cohen   Books Referenced Free Radicals: The Secret Anarchy of Science Saudi America: The Truth About Fracking and How It's Changing the World Twilight in the Desert: The Coming Saudi Oil Shock and the World Economy All the Devils Are Here: The Hidden History of the Financial Crisis   Show Notes 2:22 - (First Question) – Differences and similarities between investors and journalists 3:19 – What has more of an impact on business practices, exposing negatives or reporting positive 4:57 – first story that got Bethany intrigued with finding bad behaviors 6:19 – The process of getting to know the people who know more than the market 7:43 – Mindsets: Optimism vs. Complacency vs. Pessimism 8:18 – First short seller that garnered her interest 8:57 – The process that led to The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron 10:36 – How to ask questions 12:18 – Importance of preparation 14:20 – Difference between a visionary and a fraud 15:42 – Free Radicals: The Secret Anarchy of Science 16:23 – Any standout frauds that told a really compelling story 17:33 – Looking into Valient 19:32 –Writing about the #MeToo movement 19:34 - Disgraced ex-BofA exec raises uncomfortable questions about #MeToo 21:49 – Thoughts on the spectrum of chasing this story 23:26 – Ways journalist can fairly impact this movement 24:14 – The romance of owning a home in America and what it has meant for the market 24:34 – Shaky Ground: The Strange Saga of the U.S. Mortgage Giants 28:27 – What has changed on her thinking about housing 30:24 – What role does Fannie and Freddie have in the market today 31:13 – Her desire to look into energy 32:26 – Saudi America: The Truth About Fracking and How It's Changing the World 35:05 – What have been the changes in energy market in the US 34:40 – Twilight in the Desert: The Coming Saudi Oil Shock and the World Economy 37:01 – Where are we in the life cycle of energy production 38:29 – Technologies that shaped industrial revolution in America 41:10 – Why is Peter Elkin the best investigative journalist 42:24 – Most relentless she has ever been 43:58 – Who is doing it right 44:38 – All the Devils Are Here: The Hidden History of the Financial Crisis 45:36 – Her take on reporting the The Hunt for Steve Cohen story 49:01 – How her views have evolved over her career and lessons learned 50:40 – Are there ways to prevent success from leading people down a bad path 53:48 – The role of empathy in her career 55:13 – Kindest thing anyone has done for Bethany’s career

A very short introduction today because my guest is anonymous. Suffice it to say he manages a large pool of private capital. He goes by the pseudonym “modest proposal” and his twitter presence is one of the reasons I first got on and now stay on the platform. He is level headed, smart, and skeptical by nature, all of which made for a great conversation. We discuss how difficult the market has become for active investors, thematic investment opportunities, and the potential sources of market mispricings. Please enjoy our conversation, and let me know which other anonymous accounts you’d like to hear from. 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 Factors from Scratch: A look back, and forward, at how, when, and why factors work Josh Wolf Podcast Episode Mike Zapata Podcast Episode Michael Mauboussin Podcast Episode   Show Notes 1:55 - (First Question) - How value investing has changed 5:45 – How does he apply the lens of market over-reaction to the current market today             5:47 – Factors from Scratch: A look back, and forward, at how, when, and why factors work             7:06 – Josh Wolf Podcast Episode 8:35 – Areas where he prepares most             8:36 – Mike Zapata Podcast Episode 12:18 – Where markets may be over reacting in media 20:10 – How does he invest on this thinking             20:44 – Michael Mauboussin Podcast Episode 22:35 – Other parts of media that he finds interesting 27:35 – Aggregation theory and how it plays into his investment philosophy 31:06 – Structuring a long-short portfolio in today’s media market 35:59 – Customer acquisition costs and how it’s impacting retailers 40:51 – The role of physical locations in a world that was upended by virtual retailers 49:41 – Consumer Internet Story thesis and what he’s seen during his career 58:11 – Why the FANG stocks can’t win in the niches 1:02:25 – The distrusted 50 1:05:00 – How he thinks about Capital Allocation and buybacks 1:11:08 – His view on international equity markets 1:13:58 – His take on the asset management business 1:19:38 – Allocation of a portfolio in between periods of conviction 1:21:08 – People that he has learned the most from 1:23:54 – How do you identify people who are capable of evolving after a rough spot 1:26:53 - How does he force himself to adapt to new conditions and evolve 1:30:31 - Thoughts in investing in cannabis industry 1:32:31 – Conditions where he would get interested in crypto currency 1:36:20 – 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

With Patrick out of the country this week, we thought we'd play an old favorite that many of you have not heard. Please Enjoy!     This week we explore a rare and underappreciated skill through the lens of an incredible story. My guest is Eric Maddox, whose name you probably don’t know but won’t soon forget. Just trust me that you need to listen to this entire episode, and listen carefully—because that is what the episode is ultimately all about: how to listen to others, with care and empathy, in the age of distraction. Sometimes it’s fun not to know what’s coming and be surprised, so I won’t say anymore. After the episode, you can learn more about Eric at Ericmaddox.com. On his wall, Eric has a framed Cuban cigar, he starts his story by explaining the significance of that cigar. Enjoy this episode, and try Eric’s method. It has worked wonders for me. Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/maddox/ 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 episode covers a new set of topics. The conversation, with Niel Robertson, covers media, e-sports, content distribution, marketing, and a lot more. Niel started a software company out of his bedroom when he was 14, and sold his first company in 1999 for $280 million, when he was 24 years old. He has started and sold other companies to Twitter and Cisco. He started another large business that ultimately failed. He’s been an investor, venture partner, and serial entrepreneur. You can find more in the shownotes.  As I often do, I cut the long background section from the interview so we can get right to the meat of things, but Niel concluded that section saying: “I think that could be all summed up by I just liked building things and I can't stop doing it.” In addition to the overall media landscape, we discuss the role that the biggest media platforms will play, and where other opportunities may exist. We cover digital collectibles stored on blockchain, and what type of digital assets may be leased to others. We close with a discussion of leadership, company structure, content creation, and something you should do each year. Please enjoy this unique conversation with Niel Robertson.   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 The Start-up of You: Adapt to the Future, Invest in Yourself, and Transform Your Career   Show Notes 2:30 - (First Question) – Overview of the media landscape as it relates to influencer marketing 6:42 – How does he think about this space as an investor 12:21 – What is the future of distribution of products 17:01 - An overview of the e-sports ecosystem 18:20 – The shift of people watching others play video games 20:06 – Will we see power shift from the platform to the influencer 27:03 – Why Amazon is the sleeper in this game 29:38 – Reviewing some of the other platforms, starting with Snapchat 30:54 – Twitter 32:06 – Other platforms that should be focused on…Pinterest 33:38 – His interest in blockchain and digital collectibles 36:34 – Who will be disrupted by digital collectibles 37:55 – Why does the decentralization of these assets matter 39:49 – The tokenization of assets 42:11 – What companies have the largest hurdles to innovate in these spaces 44:57 – His thoughts on leadership             46:44 – The Start-up of You: Adapt to the Future, Invest in Yourself, and Transform Your Career 47:52 – Advice for content creators and content aggregators 50:10 – His thoughts on companies that aggregate top content creators 53:17 – His experience owning restaurants 55:46 – His experience in motocross 57:31 – Kindest thing anyone has done for Neil   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 Eric Balchunas, the senior ETF analyst for Bloomberg and the author of the Institutional ETF toolbox. This episode is intended for those in the asset or wealth management industry who have considered using ETFs in their portfolios, or for the individual investor who likes to stay up to date on trends in the market for asset management products. We cover all aspects of ETFs in some detail, and luckily in ways that have little overlap with a few other recent ETF-centric episodes on two of my favorite podcasts: the Meb Faber Show and Capital Allocators with Ted Seides with Matt Hougan and Tom Lydon respectively. We open with Eric’s favorite ETF tickers, discuss the pros and cons of ETFs versus other investment vehicles, and explore the largest areas of opportunities for new ETFs coming to market in the years to come. ETFs have become the vehicle of choice for many investors, so it was about time we covered them in depth in this forum. As you’ll hear, Eric is the right person to teach the world about ETFs, thanks to deep domain knowledge and unflagging enthusiasm. Please enjoy my conversation with Eric Balchunas on the past, present, and future of ETFs. 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 Quantitative Momentum: A Practitioner's Guide to Building a Momentum-Based Stock Selection System Links Referenced Chart – There Are Now More Indexes Than Stocks Show Notes 2:32 - (First Question) – Eric’s favorite ETF tickers 4:07 – How Eric got started into his career and how it led him into the ETF world 8:04 – An overview of the ETF landscape 10:10 – Active managed ETFs             12:17 – Chart – There Are Now More Indexes Than Stocks 13:32 – Key variables he thinks about when assessing a new ETF 15:18 – Evaluating shiny object ETFs 17:30 – The appeal of ETFs 20:18 – Future regulatory concern of the tax treatments of ETFs 22:10 – The liquidity advantage of ETFs and why that can actually be bad for investors 24:19 – What would Eric do to build the perfect ETF 26:03 – What are the future trends for new ETF’s launched 29:40 – Categories that work well in the ALT world of ETFs 31:32 – Most effective marketing strategy for ETFs 35:50 – Quantitative Momentum: A Practitioner's Guide to Building a Momentum-Based Stock Selection System 36:28 – How will the winning asset managers have done differently in this space 41:56 – How the next downturn could impact ETFs 46:17 – Do ETF’s create pricing distortions 50:33 – What trend is Eric most interested in right now 53:21 – Alpha through Beta 55:51 – Kindest thing anyone has done for Eric 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 Kyle Samani and Tushar Jain, both managing partners at Multicoin Capital. I’ve taken a bit of a break from crypto because I hadn’t sensed many new angles to explore in this forum, from an investor’s point of view. I felt that while things keep evolving, the major investment theses have been established and explored. Kyle and Tushar are interesting because of their often divergent views. For example, Kyle has been an outspoken supporter of Ethereum relative to bitcoin. This conversation, which is meant for those still curious about crypto, offers lots of new food for thought. We discuss smart contract platforms, network effects, the coming platform wars, and why blockchains may not matter in ten years. Please enjoy my conversation with the partners of Multicoin Capital. 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 Paths to Tens of Trillions An (Institutional) Investor’s Take on Cryptoassets On the Network Effects of Store Value If SaaS Products Sell Themselves, Why Do We Need Sales? Money, blockchains, and social scalability Nakamoto Institute Token Economy Multicoin.capital Crypto Cannon              Show Notes 2:11 - (First Question) – What would get the entire cryptocurrencies ecosphere to 5-10 trillion dollars             2:53 – Paths to Tens of Trillions 4:37 – What will be the effective uses for crypto currencies, store value vs utility value             4:38 – An (Institutional) Investor’s Take on Cryptoassets 8:48 – Why they are negative on bitcoin and more positive on Ethereum 10:07 – Where will start to see widespread adaption of the utility value of cryptocurrencies 14:44 – What is the major breakthrough that cryptocurrencies create 21:21 – How do we gain confidence that a utility token will become a sound investment 25:16 – The different type of network effects             25:47 – On the Network Effects of Store Value 31:18 – How do you convince institutional investors to consider the crypto space 34:21 – Factors that they care about when first evaluating a crypto currency 39:21 – How does technological development and marketing factor into their decision when picking a crypto currency             40:31 – If SaaS Products Sell Themselves, Why Do We Need Sales? 41:42 – Where these two men disagree the most right now 44:07 – Why there’s a chance blockchain technology as we know it today could be irrelevant             44:25 – Money, blockchains, and social scalability 47:56 – Most compelling trends in this world today 51:51 – A favorite resource or person people can look into if they want to learn more             52:22 – Nakamoto Institute             52:57 – Token Economy             53:24 – Multicoin.capital             53:30 – Crypto Cannon          54:14 – Kindest thing anyone has done for them   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