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    Business

    Invest Like the Best with Patrick O’Shaughnessy

    Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can’t find anywhere else. If you’re a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.colossus.com

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    Latest Episodes:
    Jason Zweig and Morgan Housel - Business vs. Investing - [Invest Like the Best, EP.50] Aug 15, 2017
    Show notes

    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


    Brad Stulberg - Just Manageable Challenges - [Invest Like the Best, EP.49] Aug 08, 2017
    Show notes

    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


    Leigh Drogen - Sink or Swim--How to Combine Quant and Traditional Asset Management Techniques - Invest Like the Best, EP.48] Aug 01, 2017
    Show notes

    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


    Wes Gray - Compound Your Face Off - [Invest Like the Best, EP.47] Jul 25, 2017
    Show notes

    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


    Rishi Ganti - Esoteric Assets - [Invest Like the Best, EP.46] Jul 18, 2017
    Show notes

    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


    Jerry Neumann - The Deployment Age, Power Laws, and Venture Capital - [Invest Like the Best, EP.45] Jul 11, 2017
    Show notes

    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


    Top Ten Lessons After Almost a Year - [Invest Like the Best, EP.44] Jul 05, 2017
    Show notes

    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.


    Scott Norton - Seek to Learn That Which Cannot be Taught - [Invest Like the Best, EP.43] Jun 27, 2017
    Show notes

    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


    Andy Rachleff - Building Something People Want to Buy - [Invest Like the Best, EP.42] Jun 20, 2017
    Show notes

    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


    Leigh Drogen - Quant vs Traditional Investors and How Alphas Become Betas - [Invest Like the Best, EP.41] Jun 13, 2017
    Show notes

    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


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