Invest like the best with patrick oshaughnessy

367 episodes

1. • 30 AUG 2022

   David Senra - Passion & Pain

   David Senra - Passion & Pain

   My guest today is David Senra. David has studied history’s great founders and entrepreneurs in more depth than anyone I’ve ever met, and I’d wager more than anyone else alive. In this conversation, we cover many of the most common themes he’s discovered studying hundreds of entrepreneurs like Estée Lauder, John Rockefeller, Enzo Ferrari, and Edwin Land. I found this to be one of the most energizing conversations I’ve had in a long time, and one I’ll return to often.

     David’s work and extraordinary energy aligns so well with our mission at Colossus that we’re excited to partner with him. You’ll soon be able to find his podcasts and transcripts at joincolossus.com where we hope you’ll learn as much from him as we have. If you like this conversation, be sure to subscribe to David’s podcast called Founders. Now onto our discussion. Please enjoy this great conversation with David Senra.

     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 Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

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     Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

     -----

     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
   [00:03:01] - [First question] - When he first fell in love with reading
   [00:07:01] - What’s rooted in his own history that’s made him obsessive about studying history’s great entrepreneurs and founders - Founders Podcast
   [00:10:34] - The first time he connected with someone as a positive role model that he was reading about 
   [00:13:45] - How often obsession is apparent in the founders he’s studied across hundreds of biographies 
   [00:18:08] - What is often behind obsession and how people listening can apply the lessons to their own lives
   [00:22:45] - The dynamic and relationship between inspiration and perspiration 
   [00:27:11] - Commonalities between the layers of leadership and support underneath founders
   [00:31:52] - Where else he’s seen ego rear its head in good and bad ways 
   [00:38:34] - How often do great founders break the law or enter gray areas of it 
   [00:41:22] - The role constant learning and listening plays in success
   [00:45:12] - Talking about how anything worth doing is worth doing to excess 
   [00:52:18] - Describing the soul of founders and businesses
   [00:58:39] - What he’s learned about all of these founders as it relates to marketing 
   [01:04:38] - A common story that

2. • 23 AUG 2022

   Robert Smith - Investing in Enterprise Software

   Robert Smith - Investing in Enterprise Software (adsbygoogle = window.adsbygoogle || []).push({});

   My guest today is Robert Smith, the founder, Chairman, and CEO of Vista Equity Partners. An engineer by training, Robert started Vista at the turn of the millennium and built it into one of the world's most successful software-focused investment firms. We discuss the white space left in enterprise software investing, the importance of capital cycles, and what he’s learned building an iconic investing franchise. Please enjoy my discussion with Robert Smith.

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

     -----

     This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

     -----

     Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

     -----

     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
   [00:02:34] - [First question] - What the enterprise software market looks and feels like to him
   [00:05:52] - Whether or not software is becoming a saturated market and what will drive demand over the coming decades
   [00:09:42] - Bringing an engineering mindset to enterprise software investing and culture
   [00:12:36] - A single change he made to a business that stands out most in memory
   [00:14:33] - Qualities that are most critical in defining a good enterprise software company
   [00:18:07] - How the profile of companies he’s bought has changed over the years
   [00:20:33] - Categories of software he tends to gravitate towards 
   [00:23:56] - Evolving his model for considering what multiple to pay for a business and thinking about p/e growth multiples 
   [00:27:17] - Lessons learned about customer churn over his twenty two year career
   [00:29:44] - Capital cycles and how much they truly impact the software world 
   [00:31:53] - What elements of building Vista have most appealed to him over the years  
   [00:34:31] - Changing their investment strategy as the world continues to change
   [00:38:06] - The war for talent and what his senior team would debate most 
   [00:40:01] - Biggest mistakes Vista has made and what they taught him
   [00:41:09] - What has him most insecure or paranoid about the platform he’s built
   [00:43:10] - The advice he’d give on having good relationships with LPs
   [00:44:57] - The largest risk he or Vista has ever intentionally taken 
   [00:46:15] - What he’s learned about having a winning negotiations and sales approach
   [00:49:27] - Who he’d give all of his capital to outside of Vista
   [00:50:06] - How he arrived at the themes he ten

3. • 16 AUG 2022

   Katherine Boyle - Investing for America

   Katherine Boyle - Investing for America

   My guest today is Katherine Boyle, a general partner at Andreessen Horowitz. Katherine started her career as a reporter for The Washington Post before moving into VC at General Catalyst. She now leads a practice at a16z called American Dynamism, investing in companies that are solving critical issues in areas like defense, housing, and education. In the past year, I've spoken to Marc Andreessen, Josh Wolfe, and a number of founders about this need to build societally important businesses so I was excited to explore the topic in even more detail today. Please enjoy my conversation with Katherine Boyle.

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

     The content here is for informational purposes only and should not be taken as legal, business, tax or investment advice, or be used to evaluate any investment or security and is not directed at any investors or potential investors in any a16z fund. For more details, please see a16z.com/disclosures.

     -----

     This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

     -----

     Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

     -----

     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
   [00:02:42] - [First question] - The origin and overview of the term American Dynamism 
   [00:05:01] - Why the shift to a move slow and make sure nothing breaks mentality
   [00:07:31] - What about the American system today feels broken and stale 
   [00:09:48] - Becoming a journalist at The Washington Post 
   [00:11:35] - Describing the power landscape of media as it exists today  
   [00:12:28] - Major categories of American Dynamism that matter most  
   [00:14:29] - What matters more or less to her as an investor in  these categories 
   [00:17:31] - Whether or not there’s anything fundamentally broken about our government
   [00:19:36] - The Systems Bible; What excites her about aerospace and defense and what creates opportunity and demand in these sectors
   [00:22:44] - Explanation of what it means when the factory is the product 
   [00:23:47] - How much is flowing into aerospace and defense currently 
   [00:26:01] - An overview of how lobbying works and who does it and why
   [00:29:07] - Whether or not she considers these sectors from a bottom up perspective as in investor   
   [00:30:32] - What other categories she feels pulled towards 
   [00:33:09] - The biggest problems that currently exist in the K-12 school sys

4. • 9 AUG 2022

   Ravi Gupta - Focus

   Ravi Gupta - Focus

   My guest today is Ravi Gupta. Ravi spent a decade in private equity at KKR before joining Instacart as their first CFO and COO. He navigated them through a critical moment in their history and returned to investing in 2019 as a partner at Sequoia. Our discussion gets to the heart of what it means to build and invest in great businesses, and we talk a lot about the personal side of the journey, which tends to get overlooked. Please enjoy this great conversation with Ravi Gupta.

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

     -----

     This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

     -----

     Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

     -----

     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
   [00:02:34] - [First question] - Why it’s important to keep the main thing the main thing
   [00:04:59] - His first exposure to this idea; How Will You Measure Your Life
   [00:07:50] - Thoughts on the conflict of the main thing for a business and a person
   [00:11:45] - The most painful episode of enacting this philosophy at Instacart 
   [00:16:13] - How this concept has manifested in his life as an investor at Sequoia 
   [00:19:16] - Amazon’s 14 leadership principles vs. his concept of focus
   [00:21:55] - What good main things share in common and their attributes; Frank Slootman Episode
   [00:24:48] - Whether or not the feedback loop for things that work are very short 
   [00:26:04] - The nature of joy and competitiveness in company culture 
   [00:29:01] - How he assesses the depth that motivation runs through people and companies
   [00:32:43] - Analysis of his own motivations in life 
   [00:35:34] - Differences and shortcomings of virtuous and vicious motivators 
   [00:37:15] - How to accurately figure out someones motivators in a short period of time
   [00:40:22] - Being Demanding and Supportive; Why these words pair so well together
   [00:45:55] - What he’s looking for in companies given all of the ideas discussed so far
   [00:51:11] - How his ideology manifests inside of Sequoia 
   [00:58:44] - What it’s like to mentor an apprentice and how to do it well
   [01:02:40] - Adjusting behaviors to meet current markets where they’re at 
   [01:06:13] - Defining what a great product is
   [01:07:56] - What he did to turn around Instacart by narrowing their focus
   [01:12:28] - The things that most drove the switchover at Instacart
   [01:14:53] - The k

5. • 2 AUG 2022

   Will Thorndike - The Power of Long Holding Periods

   Will Thorndike - The Power of Long Holding Periods

   My guest today is Will Thorndike. I first spoke to Will in 2017 about his excellent book The Outsiders and his career in private equity. I titled that conversation: How Skilled Capital Allocators Compound Capital. In many ways this conversation continues where that one left off. Through the lens of his new project, a podcast called 50X, we explore the power of multi-decade holding periods and the shared characteristics of businesses that are able to compound returns at high rates for abnormally long periods of time. Please enjoy this discussion with my friend, Will Thorndike, and if you haven’t subscribed to 50X, I highly recommend doing so.

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

     -----

     This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

     -----

     Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

     -----

     Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 
   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
   [00:02:45] - [First question] - How working on The Outsiders project shaped his thinking
   [00:06:29] - His interest in long-term holding periods and dealing with multi-decade time horizons
   [00:09:42] - Shared characteristics among compounding machines
   [00:11:23] - Defining capital efficiency and the return on tangible capital metric 
   [00:13:02] - An example of an attractive business that requires a lot maintenance CapEx
   [00:14:22] - Thoughts on the measurement of intangibles and whether or not he’d avoid great businesses that are intangible heavy 
   [00:15:25] - Tangible ways capital efficiency rolls into compounding capacity 
   [00:17:45] - Being patient early on and things that reveal themselves after doing thorough year long research in a company like TransDigm
   [00:20:32] - Lessons learned about good game selection for companies 
   [00:22:47] - Common features of customers that tend to be served by the businesses he invests in 
   [00:23:43] - Evaluating culture and its ability to propagate forward in the public equity markets 
   [00:25:09] - An example of a decentralized structure and why it works so well
   [00:27:53] - Successful decentralized companies regularly assemble general managers and compare their results and share ideas
   [00:28:46] - Thoughts about software as a business model and lessons learned about this industry across his career
   [00:30:00] - What the best serial acquirers do for long-term holders
   [00:31:46] - Advantages of using debt for financing and acquisitions  
   [00:33:39] - How different the future might be for young CEOs with capital allocator mindsets
   [00:35:40] - Other forms of recurring revenue he’s seen and things that are one

6. • 26 JULY 2022

   Alok Vasudev - Searching for White Space

   Alok Vasudev - Searching for White Space

   My guest today is Alok Vasudev. Alok is an early-stage investor who has been in the crypto space for a very long time. Before co-founding Standard Crypto, he was an investor at Benchmark and S28 Capital. Given Alok's experience and the prevailing mood right now in crypto, this is a particularly interesting discussion on the ecosystem writ large. We discuss whether the bubble can be thought of as productive speculation, his views on skeptics in the space, and look at some big, potentially, underestimated ideas. Please enjoy my conversation with Alok Vasudev.

     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.

     -----

     Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

     -----

     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
   [00:02:31] - [First question] - His history in venture and thoughts on the crypto ecosystem
   [00:06:06] - What it means to be great at searching for white space as a venture capitalist
   [00:08:00] - Things his original venture peers would say he was best and worst at
   [00:09:24] - How he would address crypto skeptics broadly given today’s market
   [00:13:35] - Whether or not it’s appropriate to look at each crypto token as a stock 
   [00:15:32] - The pool of demand for Dai and the end use-case itself for the stablecoin 
   [00:17:01] - What matters to him the most in the world of stablecoins 
   [00:19:59] - Defining sound and unsound collateral 
   [00:21:02] - Why the US doesn’t digitize the dollar and how being a government entity would impede some of their capabilities 
   [00:23:21] - What a community operated computer unlocks compared to a standalone one
   [00:27:09] - What persistence and resilience from community computers open up  
   [00:29:30] - Something going on that people aren’t talking about yet in regards to blockchains
   [00:33:54] - The notion of productive speculation and what it means 
   [00:36:03] - One of the best historical examples of productive speculation
   [00:42:29] - How things outside of the blockchain become integrated and connected to it
   [00:45:43] - Ways crypto will impact the gaming world over the coming years
   [00:49:10] - Handicapping a potential future where NFTs work and blockchains don’t benefit
   [00:51:42] - Thoughts on the world of art, IP, NFTs, and its changing landscape
   [00:54:43] - Whether or not there are companies being built that can streamline and facilitate this form of connection between artists and their fanbases
   [00:58:13] - Other controversial opinions he holds in the crypto community 
   [01:03:13] - What he’s most bullish and bearish on right now
   [01:07:29] - The kindest thing anyone has ever done for him

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