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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:
    Sarah Tavel - Consumer & Marketplace Investing - [Invest Like the Best, EP.168] Apr 07, 2020
    Show notes

    My guest this week is Sarah Tavel, a general partner at Benchmark, working alongside past guests Bill Gurley and Chetan Puttagunta. Sarah has a long history as both an investor and as an operator. She was an early product leader at Pinterest before joining Benchmark. Sarah has become one of my go-to resources for topics like networks, consumer technology, and marketplaces among many other topics. I’ve used her framework for how to think about client engagement, company data, and marketplace liquidity and quality over and over again in my business life. I’m so excited to finally have her on the show. 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

    1:24 – (First question) - Lessons learned from watching the food delivery space

    5:44 – Hip camp and how they are thinking about the space rental sector

    5:45 - The a16z Marketplace 100

    7:47 – Valuing private companies vs public companies

    9:37 – Building marketplaces

    14:24 – Tipping a market

    14:30 – Bill Gurley Podcast Episode

    18:09 – How to incorporate reputation scores into a network

    19:55 – Search ranking as a tool for marketplaces

    21:00 – Size of marketplaces vs their competitors

    22:15 – Niching of marketplaces

    22:21 - Chetan Puttagunta Podcast Episode

    23:26 – State of the consumer social sector

    27:50 – The LinkedIn problem and how she would build a social platform

    30:42 – Things that are piquing her interest in the consumer space

    32:20 – Lessons learned about scaling while working at Pinterest

    38:42 – Pricing and the marketplace

    41:25 – Identifying and optimizing a Core Action in a digital business

    44:18 – Accruing benefits and mounting losses as part of the product design

    47:48 – Her investment in Reci

    52:18 – How should companies gather the best data from their business

    56:03 – Lessons to SaaS investing

    56:29 – Kindest thing anyone has done for Sarah

    57:45 – Most interesting philosophy lesson

    58:09 – Creating a Kingdom of Ends

    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


    [BONUS] Boyd Varty - 40 Days and 40 Nights Apr 05, 2020
    Show notes

    In the midst of the worldwide quarantine, my friend Boyd Varty decided to begin an adventure he has been considering for a long time: a 40 day and 40 night stay in the African wilderness. I’m releasing this short conversation with Boyd to pique your interest in his daily dispatches. He will be taking short audio journal-like recordings and sharing them with the world as he goes. As of today they are several that you can listen to by subscribing to the Track Your Life podcast on Spotify or wherever you get your podcasts. Please enjoy this short chat with my good friend Boyd Varty.

    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

    (0:31) – The start of his 40-day trip

    (1:42) – Origin of the word quarantine and how it led to this journey

    (3:07) – History of this idea

    (6:14) – The logistics of this 40-day venture

    (9:59) – His experience doing this before and how it changed his psyche

    (12:07) – What is he most fearful of

    (13:22) – How he feels about sharing this experience when he returns

    (15:47) – The mental preparation to this journey

    (15:48) – Priya Parker Podcast Episode

    (15:49) – The Art of Gathering: How We Meet and Why It Matters

    (17:33) – How can outsiders make a connection to Boyd while he’s in this isolation

    (19:55) – How can people actually follow him on this journey

    (20:23) – Track Your Life with Boyd Varty Podcast – Apple Podcasts | Spotify

    (20:33) – Instagram - @boyd_varty

    (20:36) – boydvarty.com

    (20:43) – 40daysand40nights.com

    (21:05) – The story of the 17 lions

    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


    Gavin Baker – Investing Through a Bear Market - [Invest Like the Best, EP.167] Apr 02, 2020
    Show notes

    My guest today is with past guest Gavin Baker, the founder and CIO of Atreides Management, LP. We discuss investing during a bear market and the major ways in which the COVID19 outbreak has dramatically altered the investment landscape. Please enjoy my second conversation with Gavin Baker.

    This episode is brought to by Koyfin.

    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

    (1:40) – How he sees the markets right now

    (3:06) – How he handles information uncertainty and the value spreads

    (5:53) – Trading in today’s market and the volatility

    (9:45) – How the economic activity squares with the amount of stimulus being pumped into the market

    (13:11) – Market Wizards: Interviews with Top Traders

    (13:56) – Asset tests for individual companies in this environment

    (19:09) – This Time Is Different: Eight Centuries of Financial Folly

    (20:45) – His take on software companies during the crisis

    (28:57) – Fast pace of change during extreme times of duress

    (35:14) – Space as a service

    (39:52) – Attention and time inside digital universes and how investors can take advantage

    (46:17) – Why chaos is a ladder

    (50:42) – It Was a Very Good Year: Extraordinary Moments in Stock Market History

    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


    D.A. Wallach – Investing in Healthcare - [Invest Like the Best, EP.166] Mar 31, 2020
    Show notes

    My guest today is D.A. Wallach, one of the more interesting investors I’ve come across. He is the former lead singer of the group Chester French and the former artist-in-residence at Spotify, where he was also an early investor. While he’s also an early investor in companies like SpaceX, his focus the last 5 years has been on early stage health care investing, which is the topic of this conversation. We discuss the entire life sciences and heath care investing ecosystem. This was recorded in the very early days of the Coronavirus outbreak so while we touch on it briefly it isn’t the primary focus, and I intend on returning to more traditional episodes like this one in the coming weeks, meant to be evergreen conversations. Please enjoy my conversation with D.A. Wallach.

    For more episodes go to InvestorFieldGuide.com/podcast.

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

    Follow Patrick on Twitter at @patrick_oshag

    Show Notes

    1:31 – (First question) – Where is interest in healthcare started

    4:04 – How to categorize health services

    5:13 – The product of medicine

    6:56 – How medicine is changing in 2020

    10:17 – What is enabling innovation in medicine

    12:41 – Manufacturing of solutions, gene therapy example

    17:16 – Using CRISPR

    19:47 – Pros and cons, and the morality of gene intervention

    23:44 – How progress is being made in medical breakthroughs

    26:51 – What is the business and investment world seeing on the longevity side

    30:15 – What is next in the wearable medical tracking trend

    33:04 – The personalization of medical treatments

    34:31 – How he thinks about all of this from an investing standpoint

    36:37 – Exiting these companies

    39:41 – How he thinks about founders in this space

    42:35 – Drug prices

    42:46 – The Paradox of Pricing

    46:45 – What will lead to a change in the pricing of drugs

    49:05 – The delivery side of healthcare

    51:09 – Investments that could improve the delivery side of healthcare

    53:33 – Thoughts on the anti-interventionist line of thinking in the medical world

    57:50 – Lessons from his health portfolio

    1:02:33 – Other frontiers that pique his interest, including gut biome

    1:06:46 – His career in music

    1:08:20 – Lessons he learned during his time in the music industry

    1:10:19 – Opportunities in the music industry as an investor

    1:12:29 – Kindest thing anyone has done for DA

    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


    Chad Cascarilla – Update on Tail Risk - [Invest Like the Best, EP.165] Mar 25, 2020
    Show notes

    My guest today is Chad Cascarilla, here to discuss some of the tail risks in the economy and markets as of March 24th in the midst of the Coronavirus pandemic. Chad was one of the most successful investors during the global financial crisis with a specialty in the banking and finance systems. He now runs Paxos, a trust company which trades and custodies unique products like pax gold, bitcoin, and other tokenized assets including simple pax dollars. I feel it is important to avoid confirmation bias in times like this and not just talk to people are optimistic or long, and while I still believe this is ultimately a positive and optimistic conversation, Chad acknowledges and outlines scenarios that few are talking about yet in the markets.

    This episode is brought to by Koyfin.

    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

    (2:04) – (First question) – Today’s market and the porridge scenario

    (7:38) – Risks to the market that people aren’t focused on

    (10:54) – What lessons from 2008 do we need to heed this time

    (13:07) – How does he think about inflation on the other side of this crisis

    (16:02) – What does a too cold recovery look like

    (20:35) – Benefits of nationalizing the banks vs pumping liquidity

    (24:13) – What does the just right recovery look like

    (25:24) – Assets that might be ideal to hold in a too hot or too cold scenario

    (29:00) – His take on how Bitcoin has performed during this crisis

    (31:53) – The US’s inherent strengths compared to the rest of the global economy

    (34:50) – Advice for people

    (38:59) – Paxos.com

    (39:48) – What is he monitoring to see which way things shake out

    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


    Brent Beshore – Update on Small Business and Private Equity - [Invest Like the Best, EP.164] Mar 20, 2020
    Show notes

    My conversation today is with my close friend Brent Beshore. Brent is a private equity investor who owns and interacts with many small businesses, which have been hit especially hard by COVID. We discuss the various impacts that COVID has had and may have on both small business and the private equity investing community. Brent also proposes some policy actions which he thinks may help those most in need. 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

    1:13 – (First question) – What Brent sees as the current landscape for small businesses

    3:25 – The real problem for small businesses right now

    6:02 – How long can small businesses survive these freezes

    9:14 – Ideas to help businesses stay afloat during a global shutdown

    11:01 – The cost of restarting businesses on the other side of this

    13:41 – Policies that could help

    14:30 – government co-paying some business expenses

    16:05 – Suspending payroll taxes

    16:17 – The small business bond

    18:00 – Wider latitude for banks

    20:03 – How effective would Brent’s ideas actually be at lessening the pain

    22:41 – A look at how things look in the private equity complex

    25:39 – What are the potential opportunities out there

    29:24 – What is a balance sheet product

    32:00 – How this is personally impacting Brent

    34:20 – How this is personally impacting Patrick

    35:45 – Importance of relationships for personal health

    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


    Dan Rasmussen – Investing Through a Crisis - [Invest Like the Best, EP.163] Mar 16, 2020
    Show notes

    My guest this morning is Dan Rasmussen of Verdad Capital. Like me, Dan and his firm focus on quantitative research. Just a month before the COVID crisis hit markets, they completely and published a study on investing during periods of market crisis, which is the topic of this conversation. We discuss what works and what doesn’t during and after acute periods of panic in markets. I think you’ll find it extremely informative. Because Dan’s firm and my own share many beliefs about investing and conduct similar flavors of research, I try to offer devil’s advocate questions throughout. Please enjoy.

    This episode is brought to by Koyfin.

    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

    1:54 – (First question) – What he sees in the markets today given the atmosphere right now

    4:26 – An overview of their study: Crisis Investing: How to Maximize Return During Market Panics

    8:38 – How things get more predictable during crisis

    11:15 – The length of these crises and assets they focused on

    12:40 – What happens to bonds and credit during these times

    15:50 – Geography of crises

    18:14 – How does this impact the philosophy of just index investing

    20:40 – Positioning of value in this market

    27:50 – Lessons from other crises

    32:21 – Importance of a blended factor approach

    35:44 – Role of momentum

    38:10 – What else he is paying attention to during this crisis

    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


    Bill Gurley and Chetan Puttagunta – An Update on Consumer & Enterprise Venture Capital - [Invest Like the Best, EP.162] Mar 13, 2020
    Show notes

    My guests today are Bill Gurley and Chetan Puttagunta, both partners at benchmark capital. We review the early stage investing world in the face of coronavirus in a very timely conversation, which is one that will remain valuable once this crisis is done. We discuss enterprise and consumer, funding and growth, and the entrepreneurial spirit in the face of a crisis. Please enjoy.

    This episode is brought to by Koyfin.

    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

    1:44 – (First question) – Landscape for venture capital ecosystem

    6:47 – The experience in 2009 and the entrepreneurs that tend to rise to the top

    8:24 – The relationship between early stage companies and public investors

    10:45 – How this crisis impacts enterprise businesses vs the broader corporate sector

    14:46 – Advice for early stage companies in a period like this

    18:23 – What Chetan was doing during the last downturn and what he learned during it

    20:27 – Early stage vs late stage companies in this environment

    22:57 – On the Road to Recap

    23:00 – Benefits of being small in a period like this

    25:22 – How portfolio companies are responding and pivoting during this period

    29:33 – Best practices for remote companies

    31:39 – Themes that stand out during this period

    34:51 – Closing thoughts

    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 – An Update on Corporate Credit - [Invest Like the Best, EP.161] Mar 13, 2020
    Show notes

    My guest in this flash podcast is Bryan Krug of Artisan partners. We discuss what has happened so far in the corporate high yield and investment-grade credit markets, and the loan market. We compare today’s environment to the financial crisis and other past crises with lots of nuances that I hope will be helpful to bond and equity investors. 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) – An overview of what he covers in the corporate credit markets

    1:52 – How things have changed in the last couple of weeks

    3:56 – Composition of the high yield market

    7:07 – Major sectors of the high yield market outside of energy

    8:39 – How do they price the risk in securities right now

    11:21 – How do they handicap a great unknown

    13:00 – Risk for broader contagion in the overall credit markets

    14:49 – What’s the downside potential here

    16:31 – Potential for upside

    18:33 – How does he view companies that are drawing down on their entire line of credit

    19:44 – An overview of the loan market

    20:42 – What warning signs equity investors should be watching for in the bond markets

    21:57 – What do credit spreads look like today compared to before this crisis

    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


    Deep Basin – Oil Price War and Its Implications - [Invest Like the Best, EP.160] Mar 11, 2020
    Show notes

    This week, I’ll be recording and immediately releasing a series of conversations on business and market reactions to the spread of coronavirus. The conversations will be on oil and gas, corporate credit, and the reaction within the venture capital community. Today’s conversation is with Matt Smith, Ian Singer, and Kobi Platt of Deep Basin Capital. We are investors in Deep Basin, and they were past guests on the podcast. We discuss the new price war in the oil markets and the impact it might have on equities and especially on U.S. oil producers. Please enjoy.

    This episode is brought to by Koyfin.

    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

    1:59 – (First question) – An overview of the global oil market and demand

    3:37 – Supply and demand shocks we’ve seen lately

    6:22 – What happened this weekend with Russia and Saudi Arabia and why the outcome was so shocking

    9:45 – The knock-on effects of this activity on equities

    14:24 – Impact on US energy production

    18:29 – What other industries will feel the effect of reduced production in the US

    20:35 – Defining a price war and how victory is defined

    27:53 – Saudi Arabia’s calculus in this energy fight.

    31:11 – How does all of this change what factors they use to analyze companies

    35:43 – What it actually looks like within the commodities markets to trade energy

    40:01 – What uncertainty is most intriguing to each of them

    43:00 – The long-term interest in investing in the energy sector

    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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