My guests this week don't need to be introduced. In celebration of the one year anniversary of invest like the best, I asked Josh Brown, Mike Batnick, and Barry Ritholtz to join me for a hour, during which I spent more time laughing than asking questions. I chose this team because they are the pioneers of mold breaking honesty and personality in our industry. They all figured out that just being themselves yields incredible results. This is a strategy that everyone should try, but very few do. Honesty and transparency require vulnerability, which is hard for most of us. I still struggle with it. But the evidence is in. The Ritholtz team has grown as fast as almost any RIA. Listen to this and tell me you wouldn't want to spend your career working with people this friendly, funny and open. Hell, I want to give them some money just so I have an excuse to drop by more often.  Thanks to everyone who has listened in the past year. We are past 1.25mm listens, and growing fast. You own this thing as much as I do, because the size helps me penetrate deeper and get the best people, which begets more listeners. This podcast is one hell of a discovery machine, and the first year was our warm up. We have a ton of new angles, formats, and events coming in year two. Stay tuned. But first, time to laugh in celebration of year one. Please enjoy my conversation with team Ritholtz For comprehensive show notes on this episode go to http://investorfieldguide.com/ritholtz For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Links Referenced Barry @ritholtz on twitter a16z Podcast Scott Galloway and Aswath Damodaran on Bitcoin vs Gold Latest 'These Are the Goods' post   Show Notes 2:35 – (First question) – What stock best represents you  5:09 – How was this team assembled at Ritholtz  8:50 – Why larger asset management firms are slow to pivot on new technology  10:00 – The humor of Barry @ritholtz on twitter  11:48 – What technology channels are working best 13:08 – What would happen in a Ritholtz stock picking contest 15:19 – How do you keep investors from wanting to move money into or out of buzzworthy trades 20:23 – Pricing out the news and the value premium 23:41 – Why people want complexity and activity in their portfolios 29:51 – People always want to be a part of the next frontier, example bitcoin             31:08 – a16z Podcast 33:13 – Exploring research in action and living the investments 39:35 – Biggest argument against bitcoin could be the underlying utility and what will make it successful 45:13 – The Hindenburg Omen             46:34 - Scott Galloway and Aswath Damodaran on Bitcoin vs Gold 47:38 – How the relationship with clients has evolved 49:50 – Mike’s new book project that he is working on 51:41 – Why the Mark Twain chapter is the most interesting in his book thus far 53:32 – How a business should balance sales and marketing 58:09 – Who would they draft to the Ritholtz team             58:22 – Latest These Are the Goods post 1:05:18 – Kindest thing anyone has done   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 Pat Dorsey, who was the longtime director of equity research at Morningstar, where he specialized in economic moats: sources of sustained competitive advantage that allow a few companies to deliver huge returns over time. Several years ago he left Morningstar to form his own asset management firm, Dorsey asset management, and build a portfolio of companies with wide moats like those he studied at Morningstar. And while moats are critical, equally important is how companies allocate the capital generated--or made possible--by the existence of the moat.   A special thank you to Brian Bares who introduced me to Pat, and to Will Thorndike--an earlier guest on the show. In the vast majority of conversations you hear on this show, I'm meeting the guest for the first time. I mention this to encourage you to connect me with anyone whose story or way of looking at the world might resonate. Always feel free to contact me with ideas.   Pat and I begin our discussion with the key differences between the sell side and the buy side, and then discuss all aspects of moats and capital allocation.    For comprehensive show notes on this episode go to http://investorfieldguide.com/dorsey For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes 2:23 – (First question) – Transition from the sell side to the buy side and the biggest surprise  3:40 – What is a moat  5:16 – What part of the stock market universe has a moat  6:57 – Pat’s framework for identifying moat, starting with intangibles  8:32 – The power of brands  9:44 – what chance does an upstart have to come in and usurp a well-established brand    12:24 – Switching costs as part of the framework for identifying a moat  14:55 – The third component of identifying a moat, network effects, and what businesses should do to effectively build one  17:29 – Last component, cost advantages/economies of scale  19:29 – How do you analyze these four components into an investing framework that can be built into an actual strategy  21:13 – How does Pat think about this from a mis-pricing standpoint  23:37  – How does Pat incorporate current price of a company in consideration for future returns when pricing a moat  25:39 – How should a company with a moat operate to protect that characteristic, especially when it comes to their capital allocation  26:51 – Which characteristic of a moat does Pat find most intriguing  30:35 – What makes for good and smart capital allocation  35:58 – What is Pat’s process for identifying the best investment opportunities  38:38 – What are good economics when looking at a company  41:03 – If Pat could take any business, but have to swap leadership, what would he choose.  44:13 – Back to his process of finding investment opportunities  46:05 – Kindest thing anyone has ever done for Pat   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 both veterans of the podcast, Jason Zweig and Morgan Housel. They are two of the best in the world at making the complicated simple, and in that spirit, I’ll keep this introduction short. Morgan shifted from public markets to the private markets a year ago when he joined the Collaborative Fund, so we begin with what he has learned about venture capital in his first year on the job.   For comprehensive show notes on this episode go to http://investorfieldguide.com/writers For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Books Referenced The Devil's Financial Dictionary Modern Monopolies: What It Takes to Dominate the 21st Century Economy Thinking, Fast and Slow Shoe Dog: A Memoir by the Creator of Nike Life and Fate   Online References A Rediscovered Masterpiece by Benjamin Graham Rishi Ganti podcast Small Companies Are Gone, But Should they Be Forgotten (Zweig Column)   Show Notes 1:43 – (First question) – Morgan on why he got disenchanted with the investment industry and shifted to venture capital 4:05 – Jason’s thoughts about investing in the private markets             5:19 - A Rediscovered Masterpiece by Benjamin Graham 7:57 – Morgan’s thoughts on how private market investments differ from public market investments 10:24 – Exploring valuations of businesses and what they say about broader trends in the market 13:21 – How much does Jason think about individual companies when exploring the overall market trends             18:41 – The Devil's Financial Dictionary 19:28 –What does it take to be a successful founder 23:40 – How does Jason look at activities that are work related vs just for pleasure 25:33 – If Jason had to start a business, what would he do 27:22 – What business would Morgan start 29:18 – Problems with the financial planning industry 30:56 -  The role of stress in personal and business development             31:04 – Modern Monopolies: What It Takes to Dominate the 21st Century Economy 38:17 – Are there signs that let you know when to cut and run vs when to keep slogging along with something             42:02 – Thinking, Fast and Slow             44:03 – Shoe Dog: A Memoir by the Creator of Nike 44:20 – Principals to approach learning 50:10 – The idea of keeping your identity small in a world where social media encourages one-upmanship 53:56 – Last significant thing Morgan changed his mind about 55:23 – Why Morgan chooses passive investing with stocks, but as a VC, essentially is a stock picker in private markets             1:00:44 – Rishi Ganti podcast 1:02:14 – What major thing did Jason change his mind about             1:02:30 – Small Companies Are Gone, But Should they Be Forgotten (Zweig Column) 1:06:33 – What was the most interesting idea Jason and Morgan have been tackling and what data helped to spark that interest             1:09:32 – Life and Fate

This week's conversation is about performance. More specifically, it is about the ins and outs of steady progress and growth. My guest is Brad Stulberg who coauthored the book Peak Performance, which combines research from many fields into a description of how athletes, creatives and others continue to push boundaries in their respective crafts. As someone who is intermittently lazy, the growth equation framework that Brad and I explore has impacted me often since I first read the book several months ago. I hope you enjoy this conversation, which isn't about investing, but which is, at its heart, still about the power of compounding.    Books Referenced Outliers: The Story of Success Peak: Secrets from the New Science of Expertise   Online References Jool Health   Show Notes 1:32 – (First question) – How Vick Stretcher influenced the book, Peak Performance 4:32 – Looking at some of the preliminary research at the science of purpose 7:58 – The idea of a growth equation and the components that can lead to success 11:47 – How the introduction of stress can help in all sorts of creative and entrepreneurial pursuits. 13:39 – The ratio between physical and mental as an impact on this formula 14:56 – Just manageable challenges and the role that they play in the growth equation 18:06 – The idea of just manageable challenges through the example of an athlete 22:19 – Favorite example of a crazy feat of physical performance, stress on older athletes operating at high levels 23:30 – Thoughts about outside influences like mentors/coaches and how they help high performance individuals advance 25:51 – Describe catabolic and anabolic states and why anabolic is so important 29:13 – How the relationship of catabolic and anabolic states also helps the mind 30:47 – How does the idea of practice play into the growth equation 32:49 – Exploring the nuances of practice and why you don’t go all out             32:56 – Outliers: The Story of Success 33:00 - Peak: Secrets from the New Science of Expertise 34:24 – The idea of designing of a day 42:06 – What role can environment play on us 43:40 – How far is it healthy to run 46:25 – How does ego play into all of this 48:06 – The idea of camaraderie and study of Air Force Cadets highlighting this 49:28 – Fatigue and why it is believed to happen in the mind and not the body 54:00 – Most memorable day 55:43 - Method for finding purpose             56:29 – Jool Health 58:26 – Kindest thing anyone has ever done for Brad   Learn More For more comprehensive show notes on this episode go to http://investorfieldguide.com/brad For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

Several weeks ago my conversation with Leigh Drogen on quant investing proved timely and popular--because everyone in asset management is facing the rise of big data, and the use of data science in investing strategies. Because of the rise of quants, many are asking themselves how to survive and thrive in a changing industry. In short, how can traditional managers compete with quants? This second conversation with Leigh was set up to answer many of the questions posed in the first one. If quants are taking over, what should other investors do about it? Leigh proposes a method by which old school asset managers can restructure their thinking and their process to compete with and even beat purely quantitative competitors. The method involves pulling the best from both worlds and combining them into a hybrid structure. But it will be impossible without a wholesale change in mindset, which is where we begin. Please enjoy round two with Leigh Drogen.   Links Referenced Revenge of the Humans Part II: A New Blueprint For Discretionary Management   Show Notes 2:14 – (First question) –  What role will ego and mindset play for traditional hedge funds looking to transition into quantitative investing strategies 4:21 – Describes the traditional process that hedge funds use to make investment decisions and how the internal politics can hamper it 6:08 – What value has portfolio managers played at hedge funds traditionally as the quarterback of a fund 9:57 – A look at what Leigh has seen as he sits with teams 12:20 – A look at places that have tried to simply add quant to their firm’s strategies without “tearing it down to the studs” and properly integrating them into the process 15:00 – Leigh is asked to define the basics of a good investment firm’s strategies 16:57 – Strategies for writing down core beliefs, whether it’s for yourself or your firm 17:49 – Exploring the second step, finding a differentiating view and how to succeed with it. 21:43 – The importance of force ranking and structuring the unstructured 26:14 – Building factor models 29:42 – How the portfolio manager position should have less room for subjectivity than at the analyst level 33:44 – Is anyone integrating this kind of high level data at the portfolio manager level into the decision making the way Leigh describes 35:07 – What blind spots are created by systematizing their processes 36:18 – Why much of this applies more to shorter and structured periods 38:23 – Shifting to portfolio constructions and what Leigh would do to create the right mix 43:39 – Shifting to management structures in these firms starting with the role of the CIO 45:24 – Looking at the different quant roles that exist in a firm and what they should be responsible for; data engineers, data analysts, pure quants, and quantitative engineer 48:20 – If you are an undergrad or grad student right now interested in asset management, what are the roles you should be thinking about targeting 49:25 – Why communication skills are still so important, no matter what role you are in 50:25 – With all of the tools and skills that Leigh has at his disposal at Estimize, why not institute an active strategy 52:01 – What has Leigh observed in the dispersion of skill in the Estimized data set 53:47 – What is the relationship between specialization and accuracy among funds 55:29 – The pros and cons of the generalist 56:56 – A look at Leigh’s background into War Theory and what lessons that he still draws on today 1:00:19 – How the field of study around war and battle relates to the investing world   Learn More For more episodes go to InvestorFieldGuide.com/podcast.  For complete shownotes, go to InvestorFieldGuide.com/leigh.  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 a version of me—a funnier, cooler version who has a PhD and served as an active duty marine. Lots of you will already be familiar with Wes Gray, and those of you who are not are in for a treat. Wes is the founder of Alpha Architect, a firm which manages quantitative equity strategies for clients using factors like value and momentum. He also advocates for a more concentrated, pure approach to factor investing, which listeners know is music to my ears. While we share a lot of the same views on markets and investing, you will still find this refreshing. The conversation was easy to structure--I just took all the questions clients and prospective investors always ask of me and my firm, and turned them on Wes. These range from very specific questions on quant investing to big existential ones. I listened to this on a long drive home and laughed out loud in the car at least 5 times. You are going to love it all. I close this introduction by offering you an opportunity which is not for the faint of heart. On September 16th, I will be joining Wes and his crew on a 28-mile trek called “March for the Fallen” which is a small but important way of honoring those who have given their lives in service of our country. Wes and I invite you to join as well. If you are interested, check out the post on Wes’s site with all the details. I will link to it in the shownotes at investorfieldguide.com/wes. If you are still interested, then email me with the subject heading “March for the Fallen.” I told you Wes is a much cooler version of me, and true to form he will be doing the hike with a 40-pound rucksack. I will be doing the version without a rucksack. Either way, it will be a day of comradery and remembrance that we won’t soon forget. Join us.   Books Referenced The Devil Dogs at Belleau Wood: U.S. Marines in World War I Thinking, Fast and Slow   Online References The Limits of Arbitrage   Show Notes 3:07 – (First question) – Exploring the mindset that is ingrained into Marines 3:16 – The Devil Dogs at Belleau Wood: U.S. Marines in World War I 5:27 – Most memorable experience growing up in the mountains of Colorado 6:29 – What experiences in the military have transferred to what Wes sees in the public markets 6:48 – Thinking, Fast and Slow 7:51 – Wes’s first foray into stocks 10:51 – What was the transition into the quantitative investing space 12:29 – How Wes would describe quantitative investing and what the landscape looks like today 17:10 – What is the nature of the strategies Wes uses, like high-frequency and market-making, and what makes them stand out in those 20:57 – What about the human capital arms race in this space and how different firms are attracting the top talent 23:21 – What the approach is for Wes and what his research suggests is the best predictor of performance in stocks 25:36 – Wes’s approach to portfolio construction 33:19 – What is the thinking behind the number of and the size of names in the QVAL ETF 36:20 – Why the data suggests momentum is the better pick 37:36 – Why price-to-book sucks relative to other value factors 39:55 – What things worry Wes about the future of this strategy 44:39 – How does Wes think about research and what to explore next. 50:05 – Who would Wes have manage his money since he thinks Vanguard is not the best choice 57:01 – Exploring his firm Alpha Architect, how it started and has evolved since launch 57:39 – The Limits of Arbitrage 1:08:15 – How the influx of people to passive investments are impacting the overall market, especially for active investment strategies 1:13:13 – Wes’s most memorable day of his career both in the military and as an investor 1:17:19– Kindest thing anyone has ever done for Wes     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 Rishi Ganti, who invests in what he calls esoteric assets. I'm not sure what to do other than laugh in amazement at his professional credentials -- PhD in economics, CFA, CPA, lawyer, speaks six languages, and so on. The best part is he isn't lording those over anyone and in fact casts some shade on the whole idea of credentials in our conversation. He just did it all because he's a learning fiend. Rishi's core idea about markets is this: avoid markets at all costs. As he explains off the bat, the minute there are multiple buyers for anything, prices get efficient very quickly and there opportunity to find alpha shrinks. Instead he searches for what esoteric assets: things without a market, orphaned assets that require high human capital and human touch. We explore several interesting examples, from charter school financing to A stark realization I had during he episode is how big the worlds asset base is. Almost all of our attention goes to the most highly refined ones: stocks and bonds. But there is a whole other world out there. The closing sections, on what Rishi would do if not investing, and his answer for the kindest thing anyone has done for him were among the best answers I've heard.   Show Notes 3:30 – (First question) – Rishi’s broad take on markets and whether or not he really likes them 5:30 – Defining esoteric markets 8:31 – Looking at the mountain of assets that are most impacted or made most efficient by markets and how Rishi describes each level of that pyramid 12:28 – Looking at an esoteric asset at the early part of Rishi’s career 16:23 – Why is there little competition in these types of investment opportunities 23:06 – How they created a market and turned an esoteric asset into a return opportunity, starting with the charter school funding example 31:54 – Looking at how this is done internationally 38:55 – What they consider a platform 41:08 – How they are able to provide their service and skirt the government, legally 44:18 – A simplified explanation of what Orthogon does 50:30 – What are the main reasons people don’t want to go down this road since it seems like an obvious choice 59:00 – Looking at the most memorable experiences in esoteric investing 1:01:10 – What value has Rishi found in his extensive education, credentials, and certifications 1:07:31 – Another topic that Rishi finds interesting and he’d want to lecture on if he could other than investing. 1:09:48 – What is the right formula and types of goals you should consider in planning your life 1:14:39 – Kindest thing anyone has done for Rishi 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 am drawn to a group of investors that I call practitioner philosophers. These are people who have gotten their hands dirty in their respective fields, but despite being doers, they still often sit back and ponder the big questions in business and life. My guest this week is one such practitioner philosopher, NYC based venture capitalist Jerry Neumann. I came across Jerry's essays a year ago, and he is on a very short list of writers whose work I read without fail and almost always more than once. You can think about this conversation on business, investing, and venture capital as a big funnel. We start very broad, discussing where we may be in a large 70-year economic cycle. We then break down the so-called power law which seems to govern venture capital returns and business outcomes. Then we get even more specific, discussing Jerry's process for evaluating early stage companies, and the particulars of what might make a good venture capitalist. I say "might" because as Jerry explains often, nothing is certain, and luck may always play a huge role. I just loved this conversation. It is the type that without the podcast as an excuse would be a very odd and intense one if I were just meeting someone for the first time. You'll find no small talk or even medium talk here. This is a meaty discussion with one of the smartest and most straightforward people I've come across.   Books Referenced Carlotta’s Perez - Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages Thomas Hughes – Networks of Power: Electrification in the Western Society, 1880 – 1930 Frank Knight – Risk, Uncertainty, and Profit Jeffrey West - Scale: The Universal Laws of Growth, Innovation, Sustainability, and the Pace of Life in Organisms, Cities, Economies, and Companies   Links Referenced Deployment Age Oswald Spangler About Men; Corporate Man Howard Mark’s 2x2 matrix of superior investment results Michael E. Porter - How Competitive Forces Shape Strategy DJ Teece: Profiting from Technological Innovation Porter’s Five Forces   Show Notes 3:27 – (First question) – Start with Jerry’s essay the Deployment Age and a look at what it means for where we sit today (looking forward as investors)? 3:40 - Deployment Age 4:26 - Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages 9:28 – What time in history can you compare our current deployment age to and what does that say about the next 10, 20, and 30 years? 9:40 – Oswald Spangler 11:09 – About Men; Corporate Man 18:06 - Networks of Power: Electrification in the Western Society, 1880 – 1930 20:40 - What lessons should venture capitalists make from these deployment age cycles 25:27 - Risk, Uncertainty, and Profit 26:50 – Howard Mark’s 2x2 matrix of superior investment results 32:56 – Nassim Taleb: Powerlaw 42:31 – Venture Follow-on and the Kelly Criterion (Jerry's Blog) 44:34 - How have you have actually done this, Jerry? What is your process like and your focuses? 54:00 – Are there any circumstances where it is wise for friends and family to make venture investments? 59:20 - What is this idea of who profits from innovations? 56:12 - DJ Teece: Profiting from Technological Innovation 1:02:57 – Understanding complimentary assets 1:05:06 - Porter’s Five Forces 1:09:24 - Are Augmented and Virtual Reality interesting areas for venture capital and why? 1:15:28– What makes a successful venture capitalist? What makes you special? 1:26:03 – Kindest thing anyone has ever done for Jerry   Learn More For comprehensive show notes on this episode go to http://investorfieldguide.com/jerry For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

A future guest just told me, every band has a song about being in a band, so today I give you my version. I won’t do this often, and only do it this week in case listenership drops due to the holiday—I didn’t want any guest to have a smaller than normal audience. I have now been doing this for almost one year, and have learned a tremendous amount. Since the whole idea behind the show is to learn in public, I am going to share a few of the lessons I’ve learned with you today. I’ll shape it as a top ten list, which ends with a fun story about my recent dinner with Warren Buffett. You’ll notice that many of these are just good business and life lessons applied to something specific: a podcast. I hope you can pull the essence of one or more of these and change how you do things, especially if you create any sort of content as part of your job.

If you told me a year ago that I’d be learning critical life and business lessons from the founder of a ketchup company, and that thirty to fifty thousand people would listen to our conversation, well, I’d have told you that’s impossible. But the fact that it is true proves many of the points laid out by this week’s guest Scott Norton, co-founder of Sir Kensington’s which was recently acquired by Uni-Lever. Sir Kensington’s, which makes “condiments with character” is no ordinary Ketchup company, and Scott is no ordinary founder. We talk about the most elemental aspects of business: product, relationships, sales, marketing, and culture. I love that we can do so through the lens of such a seemingly simple product, something that we use all the time with our families at a BBQ. Scott’s observations on culture, the importance of relationships in sales, and competitive edge are all memorable. But above all, I’ll remember his line: seek to learn that which cannot be taught. And I will continually return to the mental image of the Temple of Poseidon. Oh, and as a bonus we also talk about biking around Asia, which like all of Scott’s stories comes complete with thought provoking lessons. Enjoy this unique conversation with one of the most interesting people I’ve met on this journey. We begin with the history of ketchup.   For comprehensive show notes on this episode go to http://investorfieldguide.com/norton 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 They Call Me Supermensch: A Backstage Pass to the Amazing Worlds of Film, Food, and Rock’n’Roll (Movie)   Books Referenced Getting to Yes: Negotiating Agreement Without Giving In How to Win Friends & Influence People They Call Me Supermensch: A Backstage Pass to the Amazing Worlds of Film, Food, and Rock’n’Roll (Book)   Show Notes 2:40 – (First question) – A look at the history of ketchup 5:16 – The milestones of ketchup’s history in the US 10:26 – What were the early days like to compete in a market where the leaders have such a stronghold on the consumer 14:41 – Effective ways to negotiate 14:57 – Getting to Yes: Negotiating Agreement Without Giving In 16:32 – How may stages were there in the early products 19:04 – A look at kaizen and what it means to Scott 20:38 – Scandinavian business principles that they bring to the company 23:40 – As the company has grown, has Scott seen downsides to the stakeholder model especially when competing against larger companies that use the shareholder model 28:19 – How did they use outside capital in getting started 31:07 – What was the most memorable story from the early days of disrupting this legacy industry, especially as it relates to the sales of this product  33:30 – How to Win Friends & Influence People 33:58 – How do you create trust and show the benefits of your product in sales 37:48 – How culture started for the company, how it’s shifted since then and what competitive advantage the right culture creates 41:47 – Some of the best outcomes are the result of mindset and culture 43:28 – What new frontiers is Scott and the company looking at today 51:41 – The power of giving and how it will bring large returns, especially when you don’t expect them as part of the giving 53:04 – They Call Me Supermensch: A Backstage Pass to the Amazing Worlds of Film, Food, and Rock’n’Roll (Book and Movie) 55:37 – Look at Scott’s decision to bike around Asia and what he experienced during that time 1:02:49 – Best advice for someone in their early 20’s   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 Andy Rachleff, who is the CEO of the automated investing platform Wealthfront. Andy was also a co-founder and long-time partner at Benchmark capital--one of the most interesting and successful venture capital firms in the world. We spend most of our conversation discussing venture capital investing and entrepreneurship. Andy coined the now ubiquitous term “product/market fit,” and has great insight into how investors and entrepreneurs should think about business. In that vein, we discuss both what we refer to as the value hypothesis: building a product or service that customers love, and the growth hypothesis: scaling that product or service to a large market. We finish our conversation by talking about Andy and his teams mission at Wealthfront, and this conversation is perfectly timed, as Wealthfront just released a new feature that allows investors to buy factor portfolios, similar to Smart Beta ETFs. Above all, I’ll remember Andy’s advice to “put the gun in the other person’s hand,” a strategy that we explore in the middle of our talk.   For comprehensive show notes on this episode go to http://investorfieldguide.com/andy 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 Four Steps to the Epiphany The Lean Startup: How Today's Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses Millennial Money: How Young Investors Can Build a Fortune Diffusion of Innovations Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers   Show Notes 2:36 – (First question) – The partnership setup and how they came to be 5 equal partners 7:57 – Why benchmark would not take on the chairman role in companies they invested in 9:28 – What made John Doerr the greatest capitalist investor ever 11:59 – Looking at the venture process and what made it an attractive investment for Benchmark, using eBay as an example. 18:06 – If you are willing to help other people, without an expectation of return, it can create other opportunities 20:08 – Andy is asked to explain the idea of Product Market Fit, a term that he coined 22:18 – How does one go about finding a Product Market Fit             23:05 – The Four Steps to the Epiphany             23:19 – The Lean Startup: How Today's Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses 25:55 – What are the components of the Growth hypothesis 26:51 – Why you can learn more professionally from success vs failure 28:13 – What it’s like to shift from venture capitalist to operator/CEO 30:24 – The rate at which technology gets adopted and what will help Wealthfront             30:53 – Millennial Money: How Young Investors Can Build a Fortune             31:26 – Diffusion of Innovations             31:38 – Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers 32:38 – What does it look like to innovate on top of current platforms 41:07 – Will platforms like Wealthfront help to democratize access to private markets 44:23 – Kindest thing anyone has done for Andy     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 joked that this show should be called “this is who you are up against,” because I am so often having conversations with brilliant people across the investment landscape who are effectively my competition and yours. This week’s conversation fits that description because it gives you an inside view into how things work among some of Wall Street’s most competitive investment firms. My guest is Leigh Drogen, who has worked as a statistical arbitrage portfolio manager and who founded and now runs Estimize, a data company which works with some of the world’s largest hedge funds. Our conversation centers on the massive shift from what we call discretionary portfolio management—basically stock picking—to a landscape that is increasingly dominated by quantitative investors of various types. We talk about how any investor might hope to earn alpha, and how doing so is harder and harder. There are so many great stories in this episode, told by someone with the perfect career experience to know how the system actually works. After many episodes where I’ve been learning on the fly about topics like venture capital, permanent equity, or health, this episode marks a return to my world of quantitative investing. I think you’ll learn a lot, and that you’ll likely finish with an even deeper appreciation of just the type of investors that we are all up against.  Books Referenced Revenge of the Humans: How Discretionary Managers Can Crush Systematics   Links Referenced The Undoing Project: A Friendship That Changed Our Minds Force Rank (App) Founder of Estimize Explains How He Plans To Disrupt The World Of Wall Street Research   Show Notes 2:45 – (First question) – A look at Leigh’s early career and how he got started in investing 3:13 – Revenge of the Humans: How Discretionary Managers Can Crush Systematics 8:04 – What happened when things stopped working towards the end of 2007. 9:35 – The proper dimensions to separate any sort of potential Alpha edge 11:15 – The traits that help a fund perform well 11:42 – The Undoing Project: A Friendship That Changed Our Minds 14:05 – Force Rank (App) 14:49 – How the scientific process plays into Leigh’s research strategies 19:18 – Explain what Estimize is and what it does 20:55 – How people are compensated for the estimates 23:33 – The scale of how many estimates they get per company 24:57 – Why you need to be part of this informational arms race if you hope to survive 28:30 – What happens if everyone buys Estimize data and the Alpha built into it goes away 31:04 – What has been the evolution in these hedge fund platform type companies 35:00 – If Leigh was designing a firm from scratch, what would it look like 37:25 – Understanding Numerai and crowdsourcing in funds 41:41 – What is an example of interesting data set that Leigh as come across 45:38 – What is the potential for a hybrid model between a quant only with a discretionary picker. 51:35 – How do you know when something is busted or broken? 55:33 – Exploring his most memorable individual day in his career – Flash Crash 58:16 – With all the algorithms and automation, will we continue to see more of these unforeseeable dislocations like the flash crash? 1:01:00 – Bloomberg article about passive investing rates 1:07:50 – What is Leigh most excited about the future 1:13:15 – Kindest thing anyone has ever done for Leigh            1:13:41 – Founder of Estimize Explains How He Plans To Disrupt The World Of Wall Street Research   Learn More For comprehensive show notes on this episode go to http://investorfieldguide.com/drogen 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 is very unique. It is the first episode devoted to bonds, just not the kind of bonds you are used to. My guest is Ira Judelson, who is the leading bail bondsman in New York City. I met Ira through my friend and former podcast guest Danny Moses, who is also a part of this conversation. I have always had a passion for understanding how different businesses work. In this case, this week we are exploring a different business, but also a different world. Ira’s story is larger than life. He is as authentic and hard working as they come. In both his book and this conversation, there is a lot about family, loyalty, and hard work—principles which really resonate with me. You’ll emerge from this hour with an appreciation of hustle and what it takes to get ahead. I can’t stop thinking about our discussion on how sources of power in any career morph through time, a framework that can help anyone think about their work and where to apply effort. The conversation goes all over the place, but suffice it to say we discuss bond collateral, Dominique Strauss-Kahn, and DMX—and that is but one small fraction. Please enjoy my conversation with Ira Judelson and Danny Moses.   For comprehensive show notes on this episode go to http://investorfieldguide.com/ira 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 Fixer: The Notorious Life of a Front-Page Bail Bondsman   Links Referenced Rao’s Restaurant   Show Notes 1:55 – (First question) – The role that Rao’s restaurant has meant to Ira’s business and career   6:11 – A look at Ira’s bail bonds business and how that industry works             6:22 – The Fixer: The Notorious Life of a Front-Page Bail Bondsman   8:31 – The story of how a pizzeria was a bad piece of collateral   11:10 – How often does Ira deal with bail jumpers   12:10 – What is the size of the open liabilities   13:14 – How long will the open liabilities last   14:55 – Ira’s relationship with his clients and the importance of character in this business   17:46 – the amazing story of how Ira got started in this business   31:05 – His early years of being a bail bondsman and how important his wife was to his success   29:52 – How Ira balances family with this kind of work   32:22 – Ira’s ability to be amazingly efficient on the phone when in social settings and a work call comes in   33:14 – Ira is the fixer   36:40 – Exploring the “Sources of Power” and where the balance for Ira of who he knows vs who he has shifted in this line of work.      38:29 – The importance of intense reliability, consistency and empathy, and why Ira can trust his clients may be considered bad people   30:19 – Two cases where Ira got emotionally involved   47:26 – Why Ira is not worried about people coming after him   48:57 – When a bunch of detainees were wailing to wait an extra day in jail for Ira because his wife was pregnant with their first daughter   54:06 – Ira’s relationships with Ja Rule and DMX   58:32 – What does Ira enjoy most about the business still   1:01:51 – Will Ira ever stop?   1:04:02 – What advice would Ira give to someone early in their career just getting started   1:08:42 – The importance in having a willingness to fail mixed with the passion for what you are doing   1:10:11 – Ira’s health scare and what it taught him about appreciating life

This week's conversation was especially fun. I have a long history with my guest, Dave Chilton, but this was the first time we'd met in person. I'd heard stories about him from people I work with for twenty years, so getting to finally spend time with him was a real treat. I'll let him reveal the connection. This episode will also be fun for listeners in the US, as Dave is one of the best-known people in Canada because of his famous book the wealthy barber and his more recent stint as a dragon on Dragon’s Den, which is Canada's version of shark tank. I called this episode the human blitzkrieg because of Dave's relentlessly positive style and curiosity. He has dabbled in many parts of the business and investing worlds. He is one of the most successful authors in history, has invested in dozens of interesting businesses, and is a Jedi master in the long-lost art of the phone conversation. We discuss business, investing, and writing. If you enjoy this conversation and have any aspirations as a writer, I highly recommend you check out the series of videos Dave and his son recently released called the Chilton method, which I will link in the show notes. I have no financial interest in this recommendation, and neither does Dave! He put it together in large part to stop people from calling him for advice. We discuss a few of the hundred plus lessons from his course in this conversation. As you'll be able to tell early and often, it is hard not to have a good time with Dave.   For comprehensive show notes on this episode go to http://investorfieldguide.com/chilton 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 David Salem. David was the founding president and CIO for The Investment Fund for Foundations, which served 800 endowed charities under David’s 18-year tenure. He's now the CIO of the Windhorse Group, which focuses on long-term, value oriented investing. This conversation wanders into and explores many different areas of investing and life. The theme is how to think about asset allocation and investing holistically--from first principles--but we talk a lot about motivation, incentives, human behavior, and the fear of missing out as key variables in money management. We discuss the history of the Yale and Harvard endowment models and how their success has affected the asset management world for better or worse. I had never heard such an interesting take on two very important institutions. I also can't stop thinking about David’s "Mt. Everest" question, which we explore early in our conversation. I'd love to hear your answers to that question, so email me or message me with your thoughts.   For comprehensive show notes on this episode go to http://investorfieldguide.com/salem 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 Michael Mauboussin, who is the head of global financial strategies at Credit Suisse and is on my short list of must read writers on all things investing. If you read his entire catalogue, Howard Marks's memos, and Buffett's shareholder letters, you be sitting pretty. Michael was also a big reason for the early success of this show appearing as my second guest and now my 37th. He and his team have been prolific in the last six months, publishing several long research reports on the most interesting aspects of the investing landscape. In this conversation, we talk about business moats, industry analysis, and how to combine man and machine when building an investment strategy and portfolio. As I tell Michael at the end, you won't be able to listen to this episode at two times speed, because we go deep quickly. For comprehensive show notes on this episode go to http://investorfieldguide.com/michael 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 guest is Will Thorndike, an author and investor whose book The Outsiders is an all-time favorite of mine. Our conversation is in two parts. First, we dive deep into the lessons of his 8-year research project studying CEOs who were master capital allocators. These CEOs include Henry Singleton, John Malone, Tom Murphy, Katherine Graham, and Warren Buffett. We discuss how these CEOs tended to be contrarians on topics like dividends, buybacks, acquisitions, and the use of debt. As we go through each of the tools in the capital allocators toolkit, you’ll hear several useful lessons for running or evaluating a business. In the second part, we cover Will’s career in private equity. Will founded and continues to run Housatonic Partners, investing in buyouts, recaps, and search funds. Will has been one of the most active search fund investors for decades, and given how much time I’ve spent in past episodes on the searchers or operators in the micro-cap, permanent equity space, it was great to get the perspective of an experienced LP. As always, we also take time to survey the dangers and opportunities in today’s private equity market. For comprehensive show notes on this episode go to http://investorfieldguide.com/thorndike 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 coming weekend is the annual Berkshire Hathaway shareholder meeting in Omaha. That means this week is the perfect opportunity to discuss a topic which will likely figure prominently at Berkshire this weekend: Ted Seides’s famous bet with Buffett. Ted and I discuss the origins of the bet, the nuances beneath the headlines, and whether he’d make the bet again for the next ten years. Along the way, we cover many hot topics like hedge funds, alternatives, fees, and indexing. Please enjoy! For comprehensive show notes on this episode go to http://investorfieldguide.com/bet 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 Danny Moses, who was directly in the middle of the biggest trades in market history, chronicled by Michael Lewis in his book the Big Short. Danny was the head trader on the Frontpoint team led by Steve Eisman, which was one of a small group of firms that figured out, in real time, the dire situation with mortgage-backed securities during the financial crisis, and how to build a portfolio to bet against the U.S. housing market. We cover his part in the Big Short story, but also lots of other interesting ground, including the state of sell-side research and financial markets. I love conversations with traders because they live and breathe market risk. You’ll be able to see why quickly in this great conversation with Danny Moses.   For comprehensive show notes on this episode go to http://investorfieldguide.com/danny 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

In this episode, I continue to pull on one of the most interesting threads that I have uncovered while producing this podcast: the world of permanent equity. My guests today are Royce Yudkoff and Rick Ruback, two Harvard Business School professors who have partnered to create a popular class that teaches students how to search for, acquire, and run a small business directly after graduation. I approach this conversation from an investors standpoint. LP investors usually partner with these searchers to form what is called a search fund. A search fund allows recent MBA grads to spend time looking for a business and ultimately acquire it. The result is a small scale but often high return proposition for investors. I loved our discussion of what to look for in a business and what to avoid. The principles we list are useful for investors of any kind, and will particularly appeal to those from the buy and hold, value investing, and quality investing camps. One point of note which wasn’t captured during the recording. One of the reasons this style of investing isn’t more well known that it is extremely costly upfront. It can take years to find a company, and once found, the transaction costs can be 20% of the total purchase price. Rick calls this category “REALLY private equity. If you enjoy this conversation, be sure to check our Royce and Rick’s book. HBR Guide to Buying a Small Business, which goes into many of the topics we cover in even greater detail.   For comprehensive show notes on this episode go to http://investorfieldguide.com/hbs 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