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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:
    Michael Mauboussin – The Four Sources of Alpha - [Invest Like the Best, EP.126] Mar 26, 2019
    Show notes

    My guest this week for the third time is Michael Mauboussin. If there is a major question about markets and investing, Michael has usually written one of the best pieces of research on that topic. Today’s conversation is a mix of several of his research pieces, but focuses on the sources of alpha. The framing of the conversation is the brilliant question “who is on the other side” of a given trade. If you are buying, who is selling, and why? Knowing the answer to this question is one key to understanding where excess return comes from. As is usual with Michael, we also explore tons of other interesting ideas that will serve as food for thought. Please enjoy.

    For more episodes go to InvestorFieldGuide.com/podcast.

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

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:23 - (First Question) – An outline of the syllabus for the course he teaches

    4:02 – What are smart people missing when it comes to decision making

    5:33 – Why Michael went down the path of defining major investing concepts

    7:41 – On the impossibility of informational inefficient markets

    9:14 – Beware behavioral finance

    12:03 – What are the behavioral errors that people can take advantage of in a trade

    15:14 – Timing opportunities

    17:25 – Modest Proposal Podcast Episode

    17:47 – Where the analytical edge comes from

    21:16 – Is there an advantage to exhibit time arbitrage

    23:53 – Technical arbitrage

    29:34 – What impact do flows into ETFs play on the market

    32:25 – Informational edge and how you source that edge

    36:39 – Biggest changes that he has seen on the buy side

    43:18 - How would Michael apply this as a sports GM

    48:35 – His views on stock buybacks

    51:02 – The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success

    52:55 – EBIT to EBITDA paper

    54:43 – What Does a PE Multiple Mean?

    59:28 – The concept of benign myths

    1:02:06 – What the future holds of Michael

    1:04:17 – The Myth of Capitalism: Monopolies and the Death of Competition

    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


    Annie Duke – Wanna Bet? - [Invest Like the Best, EP.125] Mar 19, 2019
    Show notes

    My guest this week is with Annie Duke, and the topic of our discussion is how to improve decision making.

    We break decisions down into their component parts: values, beliefs, decisions, randomness, and outcomes. After diving into each, we discuss how to make better decisions, how to work in group settings, and how to harness power of tribes and identity to improve our behavior.

    Annie has thought about this as much as anyone, and her various tricks for getting us to think in probabilities and to stop evaluating decisions based on outcomes that have been tainted by randomness will be useful for anyone listening.

    Please enjoy.

    For more episodes go to InvestorFieldGuide.com/podcast.

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

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:23 - (First Question) – Why people don’t take the best investing advice

    2:11 – Investing tribes

    4:21 – Jay Van Bavel twitter

    6:34 – Rule setting as a way of crafting an investment strategy

    11:13 – How much control do we have in choosing our values

    15:52 – Anatomy of a decision

    19:28 – Her concept of resulting

    26:47 - How beliefs impact your decision making

    34:28 – Tact’s for making the best decision

    42:40 – Ego and decision making

    47:06 – People who are exceptional at changing their decision making

    48:18 – How often do people who change their decision making, stick with the rules of the game

    50:07 – Finite and Infinite Games

    50:28 – Psychology of making decision that involves other people

    59:20 - Never close doors on other people

    1:01:57 – Best decision that Annie made

    1:04:24 – Kindest thing anyone has done for Annie

    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


    Michael Mayer – Pseudonymous Social Capital and Bottomless Coffee - [Invest Like the Best, EP.124] Mar 12, 2019
    Show notes

    My guest this week is unique and so requires a short story.

    I met our guest Michael Mayer because of twitter. I followed and enjoyed one of several pseudonymous accounts that he maintains to experiment with ideas. His various accounts have wide followings.

    I think many of the best accounts on twitter are anonymous or pseudonymous, and I’ve always made a point to get to know the ones I like best. As it turns out, Michael was also an entrepreneur. He’d been building a new company and was raising a small amount of outside capital.

    I didn’t invest personally, in part because he raised it so quickly after I spoke with him. Ever since, I’ve gotten to know him better and followed his company, Bottomless, with interest. You know that I am always hyper transparent about any potential conflicts of interest, so it’s worth noting that while I am not an investor in this company, I expect to be at some point in the future.

    The topic of our conversation is both his social media activity and his company. I am a coffee fanatic, and the problem he is solving is one I live. I order a weekly bag of coffee beans, but I often have too much coffee or run out. Bottomless solves this by shipping you a simple scale which you keep wherever you store your coffee, connect to your Wi-Fi, and set your bag of coffee on. It automatically orders new coffee for you at the right time. Thus the name: Bottomless. If you like the conversation, check out bottomless.com

    With this podcast, all I’m really trying to do is find, meet, and learn from interesting people. Michael certainly qualifies. I hope you enjoy this unique episode.

    For more episodes go to InvestorFieldGuide.com/podcast.

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

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    2:06 - (First Question) – Why he writes under a pseudonym online

    2:58 – Positive impacts of writing this way

    3:45 – His background

    5:02 – Habits he improved upon

    7:03 – Where did his exploration into technology and start-ups come from

    7:33 – Algorithms to Live By: The Computer Science of Human Decisions

    10:32 – Elements of business that interest him most

    13:26 – Building social capital vs the current state of education

    17:06 – What information does he like to consume

    18:17 – Zero to One: Notes on Startups, or How to Build the Future

    18:34 – Jerry Neumann blog Reaction Wheel | Podcast episode

    18:39 – Kevin Simler’s blog Melting Asphalt| Podcast Episode

    21:01 – Why the current education system is busted

    22:54 – Formation of his business

    24:04 – Importance of making things legible

    25:54 – On demand delivery vs subscription business models

    30:16 – Early day in developing the scale for his business

    33:50 – What he learned about coffee roasters

    35:29 – thoughts on supplier power

    36:17 – The customer relationship

    39:50 – Best objections to his business

    41:58 – Biggest operational/emotional challenges

    42:56 – Best moment

    44:39 – Time at Y combinator

    46:28 – His unique co-founder story

    49:47 – Marketing strategies and acquisition costs

    51:37 – The idea of a commercial loop

    53:27 – Discarded ideas, such as spaced repetition social networks

    57:38 – Having a long-term plan vs reformatting a business into success

    1:00:35 – What works on twitter based on his experience

    1:03:09 – Most controversial opinion

    1:05:59 – 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


    Peter Zeihan – The Future of Geopolitics - [Invest Like the Best, EP.123] Mar 05, 2019
    Show notes

    Peter is a geopolitical strategist who combines expertise in demography, economics, energy, politics, technology, and security to assess an uncertain future. Before founding his own strategy firm, Peter helped develop the analytical models for Stratfor, one of the world’s premier private intelligence companies.

    I came across Peter via his books the Accidental Superpower and the Absent Superpower. We discuss America’s changing place in the world and four additional countries poised to do well in the future. Spoiler alert: he believes the U.S. is particularly well positioned.

    While we don’t discuss equity markets per se, all of what we talk about will obviously impact companies across the world for the remainder of our careers. 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

    1:32 - (First Question) – His model of the world

    4:05 – What makes for a strategically advantaged country

    5:35 – History of the Bretton Woods agreement and the order that it created

    8:47 – The security apparatus that has made globalization of manufacturing possible

    12:04 – The US’s pullback from being the naval police of global trade

    12:08 – The Absent Superpower: The Shale Revolution and a World Without America

    14:57 – How energy has played into America’s disinterest abroad

    21:52 – Moving towards global disorder

    24:55 – Characterizing factors that will impact countries in any collapse

    27:38 – How this manifest in physical conflict

    32:44 – How the new world order will end the ease of innovation we are accustomed to today

    34:13 – What gets the US to reengage before this new world order

    38:08 – Demographics that make a country prepared for this, Japan as an example

    40:57 – A look at China

    43:59 – What the story is about Argentina

    45:52 – How North America fares based on their geography and relationships

    49:50 – The trader wars that are currently ongoing

    52:17 – US political system

    56:15 – Most important policy issues moving forward

    58:27 – His view on American infrastructure

    1:00:33 – Technologies that interest him the most

    1:02:55 – What he is watching most closely in his research, starting with media

    1:05:59 – What are and should be the countries of the future

    1:06:55 – Kindest thing anyone has done for Peter

    1:07:32 – Favorite places he’s been

    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


    Michael Kitces – The Past, Present & Future of Financial Advice - [Invest Like the Best, EP.122] Feb 26, 2019
    Show notes

    My guest this week is Michael Kitces, who is one of our industries go-to experts on all things financial advise and financial planning.

    We discuss the past, present, and future of financial advise, financial technology, and investing. If you are a financial advisor or use one, this conversation is full of great history and perspective. Please enjoy.

    For more episodes go to InvestorFieldGuide.com/podcast.

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

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:08 - (First Question) – History of financial planning/advice model

    5:26 – Fee changes in the 1970’s

    10:01 – The start of the AUM model

    10:44 – Value proposition for financial advisors beyond trading vs robo-advsiors

    11:49 – Why Robo-Advisors Will Be No Threat To Real Advisors

    18:20 – Why are humans still dominating the space

    23:58 – Future of advisor fees

    32:50 – Viability of the human driven flat fee model

    37:50 – The dominance of flat fee models

    43:13 – What services are financial advisors offering to justify their fees

    47:17 – Dimensions to divide potential customers

    52:20 – Exciting updates on the investment side that will help differentiate managers

    55:37 – Any investment function beyond the basics that is intriguing to him

    58:45 – Most interesting problems to be solved on the investing and non-investing sides

    1:04:52 – Advice for young advisors

    1:09:24 – How does he invest his own money

    1:11:31 – Kindest thing anyone has done for Michael

    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


    Alex Danco – Scarcity, Abundance and Bubbles - [Invest Like the Best, EP.121] Feb 12, 2019
    Show notes

    My guest this week is Alex Danco. Alex is a member of the Discover Team at Social Capital, has a background in biology, and has written about all things tech and business. While Alex is only 30, it seems like he has spent decades thinking about all the topics that we discuss, from changing business models, to railroads, to the shift from products to functions, and the rise and fall of asset bubbles. I hope you enjoy this wide ranging 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

    1:15 - (First Question) – A look at his day job on the discover team

    2:20 – 40 problems doc

    4:27 – How companies get on the list and the turnover

    5:21 – Hardest problem they are looking at…housing

    11:37 – The investment component that fixes housing

    15:35 – Where we are in the technology cycle in the view of abundance vs scarcity

    20:54 – Change in distribution and the business vs utility business idea.

    28:40 – Bifurcation of small and larger businesses

    32:48 – New forms of scarcity today

    38:31 – The trend of massive company incumbency

    41:07 – The utility of bubbles

    49:08 – His favorite bubble

    51:18 – Challenges and nuances of bubbles

    53:35 – Zero to One Notes on Start-Ups, or How to Build the Future

    1:02:22 – Future for VC funding in Silicon Valley

    1:04:07 – Advice for business builders

    1:08:23 – The Three True Outcomes

    1:13:04 – His background in biology and innovation in that space that is coming

    1:19:46 – Company examples that are of interest to him and that encapsulate his way of investing

    1:24:56 – Kindest thing anyone has done for Alex

    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 Wasserman – Real Estate Investing - [Invest Like the Best, EP.120] Feb 05, 2019
    Show notes

    My guest this week is Keith Wasserman, co-founder of the real estate investment firm Gelt.

    This was my first fully dedicated conversation on direct real estate investing, so we cover many different topics, including the pros and cons of different types of real estate, current valuations, risk vs. reward, tax protection, and the most interesting emergent areas.

    You can tell Keith is an entrepreneur at heart so I enjoyed his energy and all that he has learned. Please enjoy.

    For more episodes go to InvestorFieldGuide.com/podcast.

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

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:15 - (First Question) – Their interest in apartments and mobile homes as investments

    2:32 – The returns spectrum for different classes of real estate

    4:03 – His early entrepreneurial ventures and the start of Gelt

    7:45 – Don’t be afraid of negotiating

    8:34 – Going through early deals in real estate

    11:57 – How he determines when it’s time to sell a property

    14:13 – How do they think about taxes in their investment offerings

    16:57 – Depreciation strategies in real estate investing

    18:27 – The evolution of the types of real estate properties they’ve invested in

    21:41 – Most important factors when evaluating a building to invest in

    23:50 – Barriers to entry

    25:41 – Changes in his cost of capital

    28:51 – Cost of debt and deciding how much to put into a building

    30:33 – A look at the competition

    34:51 – Effective marketing strategies

    37:07 – How demographics impact their strategies

    39:11 – The co-living space

    40:34 – Cloud kitchens and how he would invest in these

    46:11 – How autonomous vehicles will impact real estate

    47:52 – Pros and cons of developing new properties vs buying existing ones

    49:59 – Early stage investing interest

    53:48 – Favorite business/entrepreneur story

    55:10 – Advice for younger entrepreneurs

    57:09 – 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


    Alex Mittal – Early Stage Investing - [Invest Like the Best, EP.119] Jan 29, 2019
    Show notes

    My guest this week is Alex Mittal, co-founder of Funders Club. Following past guest Jeremiah Lowin, Alex is my second elementary school friend to appear on the podcast—a trend I hope continues.

    Funders club is a unique venture firm, because it is build around a network of investors and entrepreneurs who submit deals for consideration and invest together. But as you’ll hear, Alex and his co-founder Boris aren’t just building an open platform for early stage investing: they also then take a very traditional venture approach, making investing decisions themselves when it comes to building a centralized portfolio.

    Our conversation is about what Alex has learned investing in almost 300 early stage companies over the past 7 years.

    Please enjoy.

    For more episodes go to InvestorFieldGuide.com/podcast.

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

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:30 - (First Question) – Inception of the Founder’s Club

    1:36 – Jeremiah Lowin Podcast Episode

    3:59 – How the process of their platform works

    5:40 – Role of the network in Founders Club setup and success

    8:26 – What he has learned from all of the data he has access to

    16:00 – Early stage investing and finding the sweet spot

    22:17 – What makes a really intriguing bad idea

    25:23 – Why he remains so excited about Ethereum

    31:18 – More bad ideas

    31:55 – Apoorva Mehta on How I Built This Podcast

    37:15 – Thoughts on retail and logistics and how they fit his Venn diagram of boring and crazy

    43:13 – Chip and electronic design

    45:47 – Companies that are not just increasing efficiencies but actually making foundational changes

    45:54 – Energy and Civilization: A History

    52:34 – What does he look for in founders

    55:26 – Pivot or Fail

    57:05 – Kindest thing anyone has done for Alex

    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


    Eugene Wei – Tech, Media, and Culture - [Invest Like the Best, EP.118] Jan 22, 2019
    Show notes

    My guest this week, Eugene Wei, has one of the most interesting backgrounds of anyone I’ve had on the podcast. He worked at Amazon early in its life, was the head of product at Hulu and Flipboard, and head of video and Oculus.

    Our conversation is about the intersection of technology, media, culture. We discuss Eugene’s concept of invisible asymptotes: why growth slows down (for both companies and people) and how some can burst through. I’d list more of the topics, but we covered so much that you should just listen.

    Finally, I’ll say that after spending a day with Eugene (including a wildly interesting dinner with Eugene, past podcast guest Sam Hinkie, and future podcast guest Kevin Kwok) that he is the type of uniquely interesting and kind person I am always searching for and one that I wish I could bet on somehow. If you know more people like this, reach out and suggest them for this podcast. Now, 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

    1:38 - (First Question) – Idea of cuisine and empire

    1:52 – Cuisine and Empire: Cooking in World History

    4:20 – Key takeaways from the Defiant Ones Documentary

    8;25 – Being convinced to buy a sports coat

    11:10 – The concept of invisible asymptote

    17:43 – How the medium shapes the messaging and the impact of cameras everywhere on society

    17:48– Invisible asymptotes

    17:56 – Selfies as a second language

    22:57 – Proof of work in building a social network

    32:51 – Magnification of inequalities in digital networks

    34:01 – The Lessons of History

    36:47 – His thoughts on the media industry’s impact on society as a whole

    39:42 – His time at Hulu

    44:48 – Places where video could replace text

    47:30 – The need for media for any business looking to grow

    49:35 – Amusing Ourselves to Death: Public Discourse in the Age of Show Business

    53:08 – Personal asymptotes

    57:19 - Habit building and goal setting

    1:00:29 – Travel recommendations

    1:03:24 – Movie recommendations

    1:08:16 – Product recommendations and what makes them indispensable

    1:10:44 – Creation: Life and How to Make It

    1:13:23 – Thoughts on the art of conversation

    1:14:59 – The Most Human Human: What Artificial Intelligence Teaches Us About Being Alive

    1:18:30 – Kindest thing anyone has done for Eugene

    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


    Michael Duda – Investing In Brands - [Invest Like the Best, EP.117] Jan 15, 2019
    Show notes

    My guest this week is Michael Duda, and the topic of our conversation is the role that brand plays in business and investing. Michael has worked on and invested in a wide-range of brands including Birchbox, Casper, Harry's, Citibank, DirecTV, Google, TripAdvisor, Under Armour and vineyard vines. His background in advertising made this a unique and interesting conversation. please enjoy.

    For more episodes go to InvestorFieldGuide.com/podcast.

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

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:11 - (First Question) – Mission of Bullish

    2:15 – Typical relationship they have with companies

    3:01 – Defining brand

    4:35 – Ryan Caldbeck Podcast Episode

    5:51 – A dive into how brands make people feel

    7:54 – Does the emphasis on brand still matter to consumers and if so, where

    10:01 – Process of building up a brand

    14:53 – What has changed most in the planning of a brand strategy

    18:35 – How does his thinking impact his investing strategy

    21:48 – Where does he differ from the rest of the market

    23:34 – Advice he would give to companies in general

    26:18 – How advertising has changed in the current landscape

    28:35 – The screening process for picking potential investments

    35:16 – How they analyze valuation

    37:31 – Unusual traits he likes in founders

    40:12 – Categories most ripe for young companies to disrupt

    44:03 – Most interesting marketing channel for direct to consumer businesses

    46:45 – Marketing piece he is most proud of

    49:23 – Companies that embody the best of what has been discussed

    52:31 – His love for people in business

    53:41 – Kindest thing done for Michael

    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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