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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:
    Abby Johnson – Future of Finance - [Invest Like the Best, EP.116] Jan 08, 2019
    Show notes

    Over the summer. I spent time with Abby Johnson, who is the chairman and CEO of Fidelity Investments and several other business leads at Fidelity to understand how a very large firm like theirs is navigating change in our industry. What follows is a condensed version of my various conversations with Abby and her team. We discuss the big buzzwords like blockchain and machine learning, but also thoughts on leadership, client centricity and measures of success.

    I hope you enjoyed this exploration

    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

    1:16 - (First Question) – [Abby] A look at the early part of Abby’s career

    2:45 – Analyzing the skill of capital allocators

    3:27 – A look at the asset management world of today and what to focus on today

    7:23 – A set of decision-making principles that guide Abby

    12:55 – Their strategy around the digitization of the world

    16:07 – Balance between robo-advisors and humans and the markers of a good relationship

    18:24 – What is the future of the role of the human in these relationships

    20:15 – Their interest in emerging technologies like Blockchain

    24:50 – Will crypto be its own asset class in the future

    25:58 – [TOM] State of the business and the most interesting points of change

    28:14 – Who is winning the battle for the next generation of investors

    29:24 – How much of the change in financial business is cyclical

    30:17 – What are businesses doing right to bridge that generational gap

    31:01 – What does the future of the asset management industry look like

    32:13 – What technologies could impact the asset management business the most

    33:44 – The difference between machine learning and AI in this format

    35:26 – In what way will AI impact these processes and replace humans

    36:41 – What has him most excited about the future

    37:54 – Advice for people thinking about pursuing a career in financial services

    39:20 – Markers of a business that would be attractive for the next generation to consider working for

    40:33 – The importance of brand when thinking about their business and those they work with

    41:57 – Ways of engendering trust from a branding prospective

    43:20 – Kindest thing anyone has done for Tom

    44:28 – [VIPIN] Building a team around AI

    45:21 – Markers for a good data strategy

    47:25 – Kindest thing anyone has done for Vipin

    48:58 - [ABBY] – How Fidelity thinks about data as an investing initiative

    50:24 – Differentiating attributes of good analysts and if they’ve changed

    51:34 – Investor she has always enjoyed learning from

    52:37 – Favorite Peter Lynch story

    53:17 – Business lessons that people could take away from Abby

    54:59 – The role of women in financial services and what can be done to improve the situation there

    57:35 – Trends that Abby is most excited to explore

    1:00:22 – Positives and negatives of being part of a family business

    1:01:46 – Kindest thing anyone has done for Abby

    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


    Keith Rabois - If You Can’t Sell Them, Compete with Them - [Invest Like the Best, EP.115] Dec 18, 2018
    Show notes

    My guest this week is Keith Rabois. Keith is currently an investment partner at Khosla Ventures, but has a storied and diverse background as an investor, entrepreneur, and executive. He has worked in senior positions at Paypal, LinkedIn, and Square; has led investments in companies like Stripe, YouTube, Palantir, and AirBnB; and started the company OpenDoor, which aims to transform the process of selling a home through technology.

    One fun fact about Keith is that he may have the most impressive list of bosses I’ve ever seen, which we discuss during the episode.

    We cover a lot, but one thing we kept returning to was business strategy. Keith’s frameworks for gaining and building strategic power helped me clarify my thinking on the topic, and his examples of contrarian thinking will hopefully make you question some commonly held beliefs.

    Please enjoy our conversation.

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:35 (First Question) – A look at his investing philosophy

    3:16 – Favorite examples of his own investment history

    4:40 – 7 Powers: The Foundations of Business Strategy

    5:07 – Understanding what is anomalous in a given investment

    7:07 – How much a secret needs to be protected within a business

    11:51 – Why accumulating advantage with data is of interest to Keith

    15:12 – Digital health companies and ideas that he finds compelling

    16:17 – Nuance around financial services that investors should be mindful of

    17:56 – How do they evaluate managers ability to recruit talent

    19:36 – How similar are the roles of entrepreneur, board member, investor, etc that Keith has had in his career

    24:02 – Ways that Keith is a contrarian, including his feelings on “lean startup.”

    27:04 – Is problem identification a specific skill set

    28:29 – Objection with experimentation/iteration

    30:02 – Bad ideas in venture

    31:36 – What he likes about Apple

    31:51 – Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs

    32:26 - Interview questions for identifying great talent

    35:41 – Elements of good design

    37:14 – Impact of platforms on opening new opportunities

    38:42 – His take on valuation in the early stage environment

    40:33 – Advice he would give people early in their careers

    43:58 – Do high growth companies get beat by established larger businesses

    45:25 – Popular narratives that he thinks are just wrong

    48:22 – His thoughts on how people should learn, balancing experience vs information gathering

    50:00 – Other investors that are taking a unique approach to investing

    51:57 – Reflecting on the entrepreneur as a client model of private equity

    55:04 – Books that he recommends that is least known

    55:18 – The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It

    56:30 – Kindest thing anyone has done for Keith

    Learn More

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

    Follow Patrick on twitter at @patrick_oshag


    Bryan Krug – High Yield Credit Investing - [Invest Like the Best, EP.114] Dec 11, 2018
    Show notes

    My guest today is Bryan Krug, who manages the Artisan Partners Credit Team and overseas more than $3B in high yield credit investments for the firm. This was my first conversation on high yield, so I took it as an opportunity to get an overview on the investment universe and home in on the tools used for analysis and security selection. As an equity investor, I think one of the most fruitful areas of research is into ways that companies fail or go wrong, and credit investors focus almost entirely on this potential for impairment. My guess is that all equity investors will learn something useful from this conversation. Please enjoy.

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    2:11 – Overview of the high yield debt markets

    5:05 – Why should investors consider this investment class

    7:11 – How analyzing a company’s debt is different from what equity analysts look for

    8:42 – Primary factors when exploring a company’s ability to de-lever

    9:43 – What is their alpha vs others in the space

    12:02 – Deep dive into the quantitative factors for them to look into a deal

    14:25 – Benchmarks he uses

    16:08 – Portfolio construction

    17:15 – Their preference for broadband providers over cable tv networks

    20:01 – What piques his interest about spreads

    21:50 – The ratings of debt

    25:40 – A recent example of an opportunity and how the mispricing was identified

    29:17 – Most valuable data sets in this world

    31:51 – Favorite part of this process

    32:26 – Most surprising new learning

    33:01 Maintaining your advantage

    34:49 – The biggest pools of error in this industry

    48:00 – What industries interest Bryan

    40:50 – Dedication to this market

    41:45 – Evolution of his healthy skepticism

    42:38 – Can things in the debt market help to project what will happen in the equity markets

    44:56 – Current view of the world based on what is happening in the credit markets

    45:51 – Categories of convenience that he cares about

    49:15 – Anything that has him worried in high yield markets

    50:38 – Kindest thing anyone has done for Bryan

    Learn More

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

    Follow Patrick on twitter at @patrick_oshag


    Maureen Chiquet – Leadership Through Hard Conversations - [Invest Like the Best, EP.113] Dec 04, 2018
    Show notes

    My guest this week is Maureen Chiquet, the former longtime CEO of Chanel. Maureen also spent much of her career at the Gap, growing Old Navy from scratch, and serving as the president of Banana Republic. The topic of discussion is her experience running large businesses and of finding one’s way in a career and as a leader of others. I hope you enjoy this unique conversation and that it encourages you to, among other things, travel somewhere new and interesting in the coming year.

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:15 - (First Question) – The importance of being able to put yourself in other people’s shoes

    3:05 – Scott Norton Podcast Episode

    4:36 – Most memorable sale from her early career

    5:03 – The intersection of facts and emotions in sales

    6:40 – Most important emotions in business

    7:30 – The importance of identity as part of the selling/marketing of sales and products

    9:10 – Difference in strategy for luxury brands vs others

    9:21 – The Luxury Strategy: Break the Rules of Marketing to Build Luxury Brands

    10:55 – Striking a balance between tradition and innovation

    13:46 – Advice for new brand company related to rarity

    14:59 – Importance of being organic with your brand purpose

    15:01 – Wild Company: The Untold Story of Banana Republic

    16:26 – Maureen’s purpose over the years

    18:44 – How to harness your purpose for your job

    20:53 – Her process for writing and desire to do TV

    24:01 – Her time with Micky Drexler

    27:40 – As a leader, guiding people to succeed.

    32:33 – Strategy for shifting culture at a company

    37:54 – The importance of courageous conversations we should all be having

    43:45 – Markers of courageous conversations

    46:43 – How she thinks about introspection

    50:12 – What draws here to certain locations

    55:15 – Advice for younger people starting out their career

    57:11 – Kindest thing anyone has done for Maureen

    Learn More

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

    Follow Patrick on twitter at @patrick_oshag


    Hunter Walk – Building Picks and Shovels - [Invest Like the Best, EP.112] Nov 27, 2018
    Show notes

    My guest this week is Hunter Walk, the co-founder of Homebrew, a unique venture capital firm. Hunter is a tool builder, having spent his career before venture at companies like Google and YouTube. The topic of our conversation is the intersection of creative expression, technology, human behavior, and problem solving.

    We discuss his time at the company behind the video game Second Life, building tools for creators at YouTube, and why a very hands-on style of early stage venture investing represents an interesting use of his skillset at this stage of his career.

    Please enjoy my conversation with Hunter Walk.

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:24 - (First Question) – Background on Second Life and what role Hunter had there

    6:10 – The virtual currency system at use in Second Life

    9:51 – Measuring how people behaved in this virtual world

    12:21 – How closely is the Second Life world mimicking real life

    15:13 – The market for platforms that lets people take on creative ventures

    17:58 – Investments that interest Homebrew

    20:21 – Lessons learned while working at YouTube

    28:34 – The idea behind Homebrew

    33:44 – How to best describe good problems to solve for

    36:10 – The Shadow economy and investing in companies operating there

    42:17 – Monetization of attention

    47:22 – His interest in fintech companies

    54:03 – Major trends of change he’s observed over his first three funds

    1:04:13 – What is there take on the state of returns for VC’s

    1:09:52 – What is the most common way that founders need help and what advice is more helpful

    1:14:35 – Kindest thing anyone has done for Hunter

    Learn More

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

    Follow Patrick on twitter at @patrick_oshag


    [REPLAY] Alex Moazed – Building Modern Monopolies - [Invest Like the Best, EP.25] Nov 20, 2018
    Show notes

    [REPLAY]

    Modern Monopolies: What It Takes to Dominate the 21st Century Economy, which explores the platform business model (Uber, Airbnb, Github). Alex is also the founder and CEO of Applico, a company that he started in his dorm room that is since grown into a huge enterprise that helps startups and Fortune 500 innovate with platforms. Alex and I talk about history and future of businesses and different types of business models. There’s a lot in here for investors, entrepreneurs, and historians. Please enjoy!

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

    Follow Patrick on twitter at @patrick_oshag

    Books Referenced

    Modern Monopolies: What It Takes to Dominate the 21st Century Economy

    The Systems Bible: The Beginner's Guide to Systems Large and Small

    The Master Switch: The Rise and Fall of Information Empires

    Zero to One: Notes on Startups, or How to Build the Future

    Links Referenced

    Failed Color App

    Applico

    Show Notes

    2:39 – (first question) – Exploring the history of business models from linear to platform.

    5:46 – A look at the share of overall business platform companies have taken over

    7:06 - Modern Monopolies: What It Takes to Dominate the 21st Century Economy

    7:48 – The potential for platform businesses over the next 20 years

    9:18 – Detailing the difference between a linear and a platform business

    12:08 – Exploring transaction costs and core transactions across different business models

    19:49 – Is the platform business model good for investors and VC’s since so many can get crushed when there’s a sole victor, or is it just for the founders and entrepreneurs.

    24:35 – How the self-driving car is going to deliver more opportunity for consumer consumption

    27:15 – Untapped supplies as the opportunity for new platforms and where we could see new openings

    30:24 – How consolidated will things become across all platforms

    33:16 – How do platform companies create a moat to keep others from replicating their business strategy

    37:03 – Are there platform strategies that specifically don’t work

    37:40 - Failed Color App

    38:45 – Why complex systems typically don’t scale up and you should think small and easy to get started

    38:47 – The Systems Bible: The Beginner's Guide to Systems Large and Small

    40:02 – How the origin of so many larger companies started out small and localized, and why it makes investors more comfortable

    41:37 – How Alibaba had to tweak their business model to accommodate the Chinese market

    44:07 – Why are the modern monopolies better for consumers

    47:52 – Exploring platforms that are asset heavy

    49:00 – What do you look for as a VC to determine

    52:05 – Alex’s take on whether a platform based company like Uber should be more asset heavy

    54:31 – Exploring some lesser known platform businesses that Alex finds interesting

    56:18 – If there is a demand in the secondary markets for a product, why don’t the primary suppliers simply raise their prices

    57:03 – What Alex’s portfolio of platform-based businesses would look like

    58:48 – A couple of most influential books Alex has read

    59:12 – The Master Switch: The Rise and Fall of Information Empires

    59:38 – Zero to One: Notes on Startups, or How to Build the Future and other Peter Thiel books

    59:53 – Looking at Applico, how it started and how it become so focused on the platform business model

    1:03:56 - Most memorable day for Alex

    1:05:13 – Kindest person to Alex in his life

    1:06:10 – What platform opportunities could exist in the financial world

    Learn More

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

    Follow Patrick on twitter at @patrick_oshag


    Cliff Asness – The Past, The Present & Future of Quant [Invest Like the Best, EP.111] Nov 13, 2018
    Show notes

    My guest this week is Cliff Asness, the managing and founding principal at AQR Capital Management. 20 years after its founding in 1998, AQR manages $226 Billion dollars across a number of quantitatively based investing strategies. Cliff was an original quant researcher and he has long been one of the financial writers and thinkers that I look to for education and for inspiration. I distinctly remember reading one paper in particular—value and momentum everywhere—somewhat early in my career and thinking: this is the kind of research I want to do forever. You can always tell when talking to Cliff or hearing him speak that he just loves researching markets. There is a deep intellectual honesty in his work, and a respect for thinkers at different ends of the market spectrum, from Gene Fama and Ken French, to Jack Bogle, to Dick Thaler and Robert Shiller. Our conversation is about all things quant—past, present, and future. Cliff touches on many of the big issues facing quant investing and tells some great strong along the way. I hope you enjoy our discussion. 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

    1:47 - (First Question) – Favorite superhero

    2:43 – Why ‘Ka nama kaa lajerama’ is part of his twitter profile.

    3:38 – How portfolios have shifted the way they use factors in a portfolio

    10:15 – What are good questions clients are asking right now

    13:24 – Contrarian Factor Timing Is Deceptively Difficult

    15:40 – Does technology impact investing strategy

    22:14 – When to share information vs keep it proprietary for clients sake

    26:40 – How their research process is governed

    31:14 – How they will incorporate machine learning into their process

    34:21 – What they will do when red flags show up

    37:01 – Wackiest question from a client

    41:47 – The Three Sharpe Ratio Strategy

    41:53 – Liquid Alt Ragnarök

    48:10 – Does his thinking change when it comes to asset allocation vs portfolio building

    50:17 – Parallels Between the Cross-Sectional Predictability of Stock and Country Returns

    53:01 – Sin a Little

    57:14 – Trends in fees and pricing

    1:02:43 – Thoughts on private equity markets

    1:11:03 – Common attributes of really good researchers

    1:13:21 – What is he most curious about right now

    1:15:43 – What excites him outside of finance

    1:17:00 – How much he discusses his work with his kids

    1:18:35 – The Devil in HML’s details

    1:19:36 – 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


    [REPLAY] Peter Attia, M.D. - How to Live a Longer, Higher Quality Life - [Invest Like the Best, EP.27] Nov 06, 2018
    Show notes

    [REPLAY]

    My guest this week is Peter Attia, M.D., whose mission is to understand and improve human lifespan and healthspan (or quality of life). Reading Peter’s research, you find that there are many similarities between health and investing—ideas like compounding—which we explore in detail.

    We spend a lot of time on mind, body, spirit and performance as it relates to living a better life. Of particular interest is the strategic problem that we face when studying longevity. As Peter puts it in our conversation: we are the species of interest, but we can’t conduct the kinds of experiments on humans—randomized trials, with control groups—that we apply to solve other big problems. So we have to back our way into a better understanding of longevity and quality of life.

    To that end, we discuss what we can learn from studying centenarians, the problem of progress in science, a drug called Rapamycin (which Peter believes could be revolutionary), eating, the importance of muscle mass, and the idea of distressed tolerance. We emerge with a framework for thinking about health and well-being which can hopefully help us all live longer, better lives. Please enjoy!

    For comprehensive show notes on this episode go to http://investorfieldguide.com/attia

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

    Follow Patrick on twitter at @patrick_oshag

    Posts From Peter Attia That You Should Read

    Do Calories Matter

    How You Move Defines How You Live

    2016 Update

    Long List of Questions Answered: Part 1 and Part 2

    Links Referenced

    The Scientific Method-Richard Feynman

    Knowing Versus Understanding-Feynman again

    Books Referenced

    Barbarians at the Gate: The Fall of RJR Nabisco

    Diffusion of Innovations

    Good Calories, Bad Calories

    Show Notes

    2:31 – (first question) – Getting Peter to define the concept of wealth and how it might have changed in his life

    5:01 – How do you increase the number of really good people in your life.

    6:50 – Looking at the relationship between healthspan and lifespan and a chart that Peter created on this specific topic.

    11:11 – Drilling down into the different dimensions and aspects of this chart that could be most important for people, especially how compounding plays into our health.

    16:57 – The difference between strategies and tactics that will help you extend lifespan

    17:54 – The Scientific Method-Richard Feynman

    21:41 – Different types of intermittent fasting

    28:59 – What role does repair play in health

    34:17 – Barbarians at the Gate: The Fall of RJR Nabisco

    36:01 – Looking back, what health trends today will look absurd

    36:19 – Diffusion of Innovations

    39:24 – What are the primary benefits of weight lifting

    40:21 – The importance of glucose disposal

    45:07 – Good Calories, Bad Calories

    46:31 – What is the state of progress in the scientific community

    52:14 – Peter is asked about how he guards against getting too attached to old beliefs

    1:01:51 – A look at how performance relates to healthspan

    1:03:34 –Peter’s first great auto-racing experience

    1:09:17 – Looking into Peter’s medical practice and understanding his thinking that goes into helping people

    1:18:11 – The most memorable day in Peter’s career

    1:22:31 – The kindest thing anyone has done for Peter

    Learn More

    For more episodes go to InvestorFieldGuide.com/podcast.

    Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

    Follow Patrick on twitter at @patrick_oshag


    Ryan Caldbeck – Quant in Private Markets - [Invest Like the Best, EP.110] Oct 30, 2018
    Show notes

    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


    Howard Lindzon – Fintech and Trend Following - [Invest Like the Best, EP.109] Oct 23, 2018
    Show notes

    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


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