Invest Like the Best with Patrick O'Shaughnessy

My guest today is Gaurav Kapadia, founder of investment firm XN. Gaurav is a veteran of the investing arena. We cover his lessons while rising to partner at TPG Axon, co-founding Soroban Capital, and his decision to launch XN in 2020. We then discuss his approach to building XN around a culture of rigor and kindness, the importance of relationships in investing, and finding investments that are obvious in retrospect. Please enjoy my great conversation with Gaurav Kapadia.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:05] - [First question] - What lead to kindness and rigor becoming pillars in XN’s company culture

[00:05:30] - The types of situations where it’s hardest to be kind or rigorous

[00:07:58] - Asking one question that can stump a founder can be a display of rigor

[00:08:58] - An example of looking at a situation and reducing the problem to a single variable

[00:12:51] - How he trains investors and team members to consider outcomes that would be obvious in hindsight

[00:14:28] - Developing the art of interacting with company management

[00:17:54] - Dimensions that typically find their way into his presentations and what tends to create complexity

[00:21:13] - Whether or not rigor has declined in public markets over the years

[00:21:55] - Why fewer talented people are going into public markets

[00:23:01] - What it felt like when he first started XN and being successful at a young age

[00:28:58] - Being impressed with his peers and rooting for each other

[00:30:33] - The nature of public versus private investing today writ large

[00:32:32] - How he gets to know a company when he’s never heard of them before

[00:35:20] - Reasons he won’t invest from a personal policy standpoint

[00:36:01] - Common problems he encounters that companies are dealing with

[00:37:32] - Defining the strike zone of companies to invest in where he can be best-in-class

[00:39:10] - The insane valuations of public markets in recent years especially in tech

[00:40:42] - Why there are so few great businesses and common attributes of the great ones

[00:44:12] - Biggest problems in the investment industry writ large

[00:45:48] - The most remarkable business he’s ever seen

[00:49:22] - How he would teach investors to deploy XN’s operating partner model

[00:51:32] - His perspective and thoughts on diversity in the investing industry

[00:56:58] - A business or institution he would own outright personally

[00:57:37] - What outside of investing most has his attention lately

[00:59:50] - Key touchpoints of coming from Queens and going to Hunter

[01:02:15] - What stands out looking back on his relationship with h...

My guest today is Jess Lee. Jess is a partner at Sequoia Capital as well as their Chief Product Officer. Before becoming an investor, Jess co-founded fashion app, Polyvore, and was an early product manager for Google Maps. Most recently, she founded All Raise, a non-profit that is changing the gender balance in tech. Our discussion ranges from Burning Man to Marvel to Sequoia’s mobile app and I hope that Jess’s passion for delighting users rubs off on you. Please enjoy my conversation with Jess Lee.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:35] - [First question] - Why more investment firms don’t have a product mindset

[00:05:22] - How to approach building a productized version of capital

[00:08:00] - Ways Ampersand measures success and judging their own performance

[00:08:49] - Driving reasons that Sequoia wins deals beyond their brand name

[00:10:28] - How her work as CPO at Sequoia has changed her investing approach

[00:12:28] - Everything she’s learned about community and its relevance to business

[00:17:48] - What the gold standards are for studying strongly built communities

[00:19:42] - What it is about Comic-Con that works so well from a community standard

[00:21:18] - The role that scarcity plays in communities writ large

[00:23:10] - Product mindset and customer obsession

[00:24:33] - Knowing when it’s okay to begin expanding

[00:28:12] - Rates of change in her investment progress and dollars going to female founders

[00:29:36] - Systemic bias and what’s driving a lack of fund...

My guest today is Will Marshall, the co-founder and CEO of Planet. Will founded Planet in 2010 with a small team of NASA scientists to build a constellation of satellites that would image the entire Earth every day. Since then, Planet has successfully built and deployed 450 satellites into space, which the company is using to create a time series of images for every place on Earth.

Our conversation covers the untold space story. How space is going through an internet moment where cost reductions and performance enhancements have led to a seismic shift in what’s possible above our atmosphere, and how that can drastically improve life on Earth through unique datasets like the one Planet is piecing together.

Once you listen to Will speak about Planet’s progress and mission, it’s hard to think of a more underappreciated company in business today.

Please enjoy this great conversation with Will Marshall.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:57] - [First question] - His thoughts on the renaissance of the space industry

[00:05:09] - The earliest days of Planet and why he started the business

[00:09:22] - Unique data units captured by their satellites

[00:13:35] - The real estate of space and interesting angles to consider

[00:15:59] - How customers interface with Planet and their early use cases

[00:20:57] - Thoughts on the sovereignty of space and the laws that exist currently

[00:23:43] - Figuring out the dynamics and pricing of Planet’s business model

[00:27:34] - Examples of stress and tensions when working in space

[00:29:08] - The future of privacy and concerns we should have there collectively

[00:30:29] - Five different types of satellites and their functions

[00:31:39] - The most sci-fi potential futures that Planet may unlock someday

[00:32:54] - Indexing the Earth and using data to train machine learning algorithms

[00:34:02] - What he’s learned about Earth that is most surprising

[00:37:12] - Contributing factors to a 70% decline in life on the planet in 40 years

[00:38:35] - Ways that going public might impact Planet’s long term goals

[00:40:23] - The hardware story of building various prototypes of satellites

[00:42:18] - How much is built in house versus outsourced to fabricate their satellites

[00:43:48] - Complimentary space trends that are compounding beyond imagery

[00:45:32] - Whether or not they plan on making their data open-source

[00:47:15] - Democratizing their data and allowing other companies to build on top of it

[00:48:30] - The kindest thing anyone has ever done for him

My guest today is Orlando Bravo, co-founder and Managing Partner of leading private equity firm, Thoma Bravo. Thoma Bravo manages over $90bn of assets and is best known for investing in software and technology businesses. It was Orlando who led the firm’s early entry into software buyouts some twenty years ago, and he has overseen more than 350 software acquisitions since. There are few, if any, people better placed to discuss private equity and software investing. Please enjoy this excellent discussion with Orlando Bravo.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:36] - [First question] - His belief about an opportunity/capital mismatch in private equity

[00:04:26] - Adjusting his own approach to take advantage of seemingly niche opportunities

[00:06:13] - Differences between software businesses they invest in versus traditional ones

[00:08:25] - Outline of how he runs their four-hour portfolio meetings

[00:09:53] - Overview of the very first deal he ever made in the software sector

[00:14:01] - The dissonance between the average SaaS company and the ones they try to manage

[00:18:22] - Major contributors that allow for their higher margins

[00:20:16] - Common mistakes of companies that mis-invest capital for growth only

[00:22:28] - Defining what market leader means writ large

[00:23:45] - Why the subsector of cyber security is such a good opportunity set

[00:26:25] - The evolving nature of the private equity world in general

[00:28:41] - Where returns will come from going forward

[00:31:47] - How good the opportunity for returns in this style of investing today is

[00:35:32] - Lessons learned on knowing when to exit or sell a position

[00:37:59] - How short their holding periods can be and how much influence they can have in such a short time

[00:40:04] - Surprising things about deal-making that he’s learned over his career

[00:41:20] - Difficulties and points of frictions in deals that still exist for him today

[00:43:11] - What part of the deal-making process he loves the most

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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