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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.joincolossus.com
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Now displaying: April, 2020
Apr 30, 2020

My guest today for a flash update is Chris Bloomstran, the founder and CIO of Semper Augustus and a popular past guest on the show. We talk about his view on the state of the public equity market, why it will be hard for the market to deliver great returns for the next decade relative to the last, and where opportunities may lie. 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

(1:42) – (First question) – Adjustments to his portfolio in the age of a pandemic

            (6:41) – Chris Bloomstran Podcast Episode

            (9:36) – The Federal Reserve Act

(12:32) – Surprising action in the markets during the crisis

            (13:08) – 2020 Investment Letter

(15:02) – Why we won’t see the same performance in tech over the future as we’ve seen the last decade

(21:00) – The carnage in energy sector and return potential

(30:06) – Berkshires activity since the crisis started

(35:48) – Where sectors are valued in the current market

(41:12) – Expectation for deflation over inflation 

(48:54) – Characteristics to look for in businesses to own over the next 10 years

(52:05) – Economic factors they are focusing on

 

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

Apr 28, 2020

My guest today is Josh Kopelman, the founder of famed venture capital firm First Round Capital. Prior to starting First Round, which has invested at the earliest stages in companies like Square, Uber, and Roblox, Josh was a three-time entrepreneur, so our conversation spans early-stage investing, business building, and entrepreneurship. I’ll not sure forget his analogy distinguishing between navigators and cartographers, nor the rest of the interesting ideas he shared after seeing and investing in so many great businesses. We also discuss how First Round has bucked the trend to build what I’d call a platform adjacent to the core investing business which does a lot for their entrepreneurs and is a model for other professional investing firms, both in venture and elsewhere. Please enjoy my conversation with Josh Kopelman. 

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

(2:05) – (First question) – How pandemic has impacted their investing strategies

(3:54) – How this stressful environment impacts founders

(6:23) – His early career as a founder and how startup culture has changed

(10:15) – Most important lessons from his entrepreneurial career and building from just an idea

(11:50) – How to analyze a founder

(14:05) – Common disagreements when it comes to deciding on an investment

(15:33) – How many opportunities they evaluate in a meeting

(16:16) – The curvy road to their investment in Roadblox

(17:52) – Whether the concept for a platform is overused

(19:36) – Founders asking what google search they should build on

(20:46) – Solving existing or forecasted problems

(25:39) – How the startup scene is impacted by the huge legacy tech companies

(30:28) – What makes a great early stage investor

(32:19) – Do they focus on founders or themes

(33:19) – Where will valuations and returns come back to after the pandemic

(36:30) – How are business models evolving in technology entrepreneurship

            (36:31) – Matt Clifford Podcast Episode

(39:40) – The Dorm Room Fund

(43:02) – Whether investment funds should have their own platform

(47:31) – Product mistakes in software building

(51:52) – What he’s most excited about for the future

(54:05) – The 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

Apr 21, 2020

My guest today is Manny Stotz, the founder of Kingsway Capital. Manny is one of the leading investors in Frontier Markets, investing in equities in countries like Egypt, Bangladesh, and Pakistan. We discuss the opportunity in these markets from all angles: demographics, valuations, sectors and beyond. It is important to note that we recorded this conversation before COVID, and these markets have fallen 30% without a similar rebound in prices that we’ve seen in the U.S. As you listen you’ll hear why this may be relevant for the companies Manny focuses on and may accentuate the opportunity in Frontier Markets even relative to the numbers quoted in this conversation. Listeners will know my interest in Frontier Markets runs deep, so I was excited to have one of the categories leading investors join me.

Please enjoy my conversation with Manny Stotz.

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

2:07 – (First question) – How Kingsway was conceived, their focus on frontier emerging markets, and his career path

11:57 – What are the best company builders good at when it comes to fostering a brand

18:30 – How country-specific factors impact the tailwind

25:43 – How markets are faring in these special circumstances

32:09 – Building a book in many of the markets they trade-in

37:10 – Understanding your edge in frontier markets, showing up

39:59 – Importance of solid distribution for the companies he invests in

42:12 – Concentration in various markets

44:10 – Moving beyond consumer brands in these markets

47:14 – Some of the most interesting countries they are looking into and the country business model

            47:42 – Guns, Germs, and Steel: The Fates of Human Societies

            47:44 – Civilization: The West and the Rest

            47:46 – Why Nations Fail: The Origins of Power, Prosperity, and Poverty

53:21 – New topics he’s excited to learn about that will impact his business over the next 10-20 years

55:37 – Best way for people to get involved and invest in these markets

58:17 – 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

Apr 7, 2020

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

Apr 5, 2020

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

Apr 2, 2020

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

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