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Invest Like the Best with Patrick O'Shaughnessy

Latest episodes

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Mar 25, 2020 • 44min

Chad Cascarilla – Update on Tail Risk - [Invest Like the Best, EP.165]

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
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Mar 20, 2020 • 38min

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

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
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Mar 16, 2020 • 43min

Dan Rasmussen – Investing Through a Crisis - [Invest Like the Best, EP.163]

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
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Mar 13, 2020 • 39min

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

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
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Mar 13, 2020 • 28min

Bryan Krug – An Update on Corporate Credit - [Invest Like the Best, EP.161]

Bryan Krug, an expert in corporate high-yield and investment-grade credit markets, discusses the changes in the corporate credit market due to coronavirus, the composition of the high-yield market, and the sectors most at risk. They explore the challenges of incorporating uncertainties into investment decisions and the risks of credit downgrades. They also discuss factors to watch in bond issues and historical extremes of high-yield spreads, as well as analyze market volatility and spreads amid the coronavirus pandemic.
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Mar 11, 2020 • 50min

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

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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Mar 10, 2020 • 1h 4min

Peter Zeihan - Dis-United Nations - [Invest Like the Best, EP.159]

My guest this week is Peter Zeihan, the author of a new book, the Disunited Nations.  Peter was an extremely popular guest on the show last year and after reading his new book, I knew we had a lot to discuss in round 2.  In this conversation, we discuss two ways of ruling the world, the coming American disinterest in global affairs, and which country are poised to do well int eh future.  We explore military and non-military technologies, political changes, and up and coming alliances like that between the United States and Mexico.  As with last time, peter packs more information into an hour than just about anybody.  Please enjoy our conversation. 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 1:57 – (First question) – What makes for a successful country 6:02 – Five first-tier countries that are well positioned 7:14 – Ruling the world, US carrot model vs British stick model 9:39 – How other countries will use these models in the future 12:59 – The surprising reliance of Iran and Russia on the US 15:24– Key points of his research on the Middle East 18:36 – Advice for how those operating in the US should think about future business investments 23:05 – The future of manufacturing partnerships with the US and the focus on Mexico 27:30 – What Coronavirus has taught us about the world economy 30:01 – What the primaries and election are teaching us 35:09 – What role does Africa play in the future 38:36 – Strong and weak players in Europe and how Brexit has impacted things 44:41 – The future for nuclear power 46:27 – The outlook for South America 50:42 – The trends and future in military technology 55:03 – Non-military technology that will have a major impact 58:26 – Skills young people should focus on for the future 1:00:07 – Coronavirus as a dress rehearsal for large scale disruptions to the 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
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Mar 3, 2020 • 52min

Jeff Lawson – How to Build a Platform - [Invest Like the Best, EP.158]

My guest this week is Jeff Lawson, the Founder, and CEO of Twilio. Twilio is a 15-billion-dollar company offering a cloud communications platform to its customers.  Twilio is used by customers like Lyft, Twitch, and Yelp to make communications in their products easy.  Jeff and I talk about why it pays to be a platform, how to be a platform, and how to sculpt a company culture. This is a must-listen for anyone building a business whether it’s a tech business or not. 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 1:18 – (First Question) –  Company vowels and draw the owl 5:26 – Significance of API’s 12:14 – How non-software businesses can transition into the space          17:50 - Agile way of working at ING Belgium (video) 18:38 – How they strategize their product build 23:27 – The idea of asking your developer and why it’s so important to them 33:02 – How they codified their business culture 45:12 – Parting advice for people building platforms 48:13 – Kindest thing anyone has done for Jeff  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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Feb 25, 2020 • 52min

Niko Canner – Become a Perfect Instrument - [Invest Like the Best, EP.157]

Niko Canner is the founder of Incandescent where he and his team help the leaders of large companies in the areas of strategy and innovation. He was also the founder of Katzenbach Partners and a member of Bridgewater’s management committee. Niko is a fantastic writer, and I highly recommend you check out his blog “On Human Enterprise,” which has posts on many of the most interesting aspects of business and personal purpose. This conversation was inspired by many of those posts. 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 1:17 – (First Question) – The story of Doctor V             3:24 – Aravind and the Choice of Great Achievement 4:00 – Becoming the perfect instrument 6:05 – What is Niko planning to be the perfect instrument of 8:18 – How should individuals think about finding what they can be the perfect instrument of             8:59 – Brett Victor – Inventing on Principle 10:59 – How do businesses apply this principle 13:20 – Making choices easier 16:43 – Era’s to a company and when it’s time to start a new one 19:52 – How can business culture be cultivated and useful 22:53 – Cultures at the tail end of a distribution 24:33 – Can hierarchy be fluid, or does it need to be a dedicated corporate structure 27:47 – My Unlikeliest Favorite Business Book             28:03 – The Millionaire Real Estate Agent: It's Not About the Money...It's About Being the Best You Can Be! 30:46 – The Red Test and how it can be used by businesses 36:54 - Ten Principles for How to Run a Company 42:25 – Dealing with the sponsor owner brief in the software world 45:24 – How does one choose customers 46:32 – Bill Hubbard passage – A Theory for Practice: Architecture in Three Discourses 49:09 – Kindest thing anyone has done for Niko 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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Feb 4, 2020 • 51min

[REPLAY] What You Learn About Business Deals After: 12,000 Deals Reviewed, 1,500 Deep Dives, 125 Site Visits, and 7 Portfolio Companies with Brent Beshore - [Invest Like the Best, EP.100]

For the 100th episode, I’ve brought back my good friend Brent Beshore. Brent was the 10th guest on the podcast, after we met because of a mutual interest in capital allocation. I quickly learned that Brent was one of the most unique and thoughtful investors around. He was an entrepreneur from the moment he left school, trying many different things before finding a fit buying smaller business with the intention of owning them forever. What amazes me about Brent is his encyclopedic understanding of business and the nuances of different business models and deal structures. This comes from reps. He and his team have looked at about 12,000 deals over the years, at every kind of business that you could imagine. I’ve been with him when he goes through this process and it’s fun to hear what makes certain businesses stand out from others, which is largely the topic of this conversation. You all know transparency is key for me, so it’s important to know that my family and I are investors in a fund called permanent equity, run by Brent and his firm Adventure.es. To commemorate this milestone episode, I can think of no one better than Brent, because he exemplifies what has made this podcast so fun for me: learning from other people who are willing to share what they themselves have learned through fun, blood, sweat, and tears. Please enjoy our conversation, and thank you so much for coming along on this journey. I can’t tell you how much it means to me. 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 2:02 - (First Question) – How does he think about optimizing risk in terms of the capital stack when looking at deals 5:27 – What conditions would they add debt down the road after investing in a company 6:52 – What business sectors are most intriguing for Morgan to invest in right now             6:57 – Trent Griffin Podcast 9:34 – Why no HVAC businesses if it’s such an attractive sector 13:56 – thoughts on rolling up similar businesses and horizontal scale 16:04 – Another industry Brent would focus on 18:02 – Difference between property management in larger cities vs smaller metro areas 18:51 – What role does profit margin play when Brent is evaluating a business 22:46 – The appeal of a hyper cyclical business             22:52 – Brent Beshore Podcast Episode 27:27 – Favorite counter cyclical business 28:14 – How they judge assets, tangible vs intangible assets 33:58 – How does he think about wage inflation when considering the cost of a business 37:21 – His fascination with pet crematoriums 38:57 – History of the permanent equity fund and the changes by having a larger pool of capital 43:48 – Pitching investors on a new structure for the business 46:14 – How will this business model scale 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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