364 episodes

Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at https://joincolossus.com/

Invest Like the Best with Patrick O'Shaughnessy Colossus

    • Business
    • 4.8 • 2K Ratings

Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at https://joincolossus.com/

    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.
     
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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
    [00:02:34] - [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

    • 1 hr 17 min
    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.
     
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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.
     
    -----
     
    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

    • 59 min
    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

    • 1 hr 11 min
    Matthew Ball - A Manual to The Metaverse

    Matthew Ball - A Manual to The Metaverse

    My guest today is Matthew Ball. Matt is an investor, the former head of strategy at Amazon studios, and one of the brightest minds in the media industry. Through his essays and now his book, which launches today, Matt has established himself as the foremost authority on the Metaverse, which has stormed into the public eye since I first had him on the show two years ago. The Metaverse is the focus of our discussion and I hope you enjoy this encyclopedic tour through all of its details as much as I did.
     
    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, 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
    [00:02:37] - [First question] - Which most represents the Metaverse: Minecraft, Ready Player One, Fortnite, or Facebook’s Horizon
    [00:05:58] - Facebook trying to own the concept of the Metaverse by changing their name 
    [00:09:22] - Defining what the Metaverse is and a good working definition of it
    [00:11:33] - The state of the engines behind 3D output and the history of them 
    [00:16:32] - The role IP played in bootstrapping the first Metaverses 
    [00:18:32] - Where the ability to create digital environments will lead, and what Unreal 7 could look like compared to Unreal 5 today
    [00:21:03] - Natural limits of the Metaverse compared to real-world experiences
    [00:24:16] - Other sensory inputs that will need to be improved for digital immersion
    [00:26:59] - Why the initial excitement of trying something like Oculus wears off over time, both for casual gamers and those excited about this new frontier
    [00:31:40] - Changes in technology and new projects that have him most excited that will empower the digital infrastructure for Metaverses
    [00:37:14] - What interoperability means and why it has its own chapter in his book
    [00:31:52] - How Roblox connects with Fortnite and how far down we need to go to build a bridge between digital worlds
    [00:46:13] - What will drive commerce in the Metaverse and the possibility for a singular currency standard
    [00:51:35] - Considering the demand for the Metaverse and whether or not it will be a constraint on adoption and success
    [00:57:37] - What the modern equivalent of a lemonade stand will be in the Metaverse
    [00:59:58] - The lower adoption rates for more participatory media consumption
    [01:03:19] - Potential pitfalls and the dark side of the metaverse
    [01:06:14] - Who the categorical winners of the Metaverse might be   
    [01:14:15] - The top things he would suggest exploring to best understand the Metaverse

    • 1 hr 20 min
    TransDigm: Foundations with Nick Howley [50X, EP.1]

    TransDigm: Foundations with Nick Howley [50X, EP.1]

    Today we are dropping a special episode in the Invest Like the Best feed. You will hear the first episode of 50X – a new series from Will Thorndike and the team at Compounding Labs, in partnership with Colossus. Will’s book, The Outsiders, is one of the best business and investing books you will find. Now you will hear him continuing his work in the hosting chair as he looks in detail at investments that have appreciated at least 50-fold.
    First up is TransDigm, an aerospace components manufacturer that has returned over 1,750X since its inception nearly three decades earlier. In this episode, Will is joined by Nick Howley, TransDigm’s long-time CEO and Chairman. Make sure to subscribe to 50X in your preferred podcast player.
     
    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. The team at Tegus has built a full company intelligence platform aimed at streamlining the investment research process. In preparation for the 50X series, we actively used Tegus to gain qualitative insights beyond traditional reported data. To learn more and enjoy a free trial, visit tegus.co/50x. 
     
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    50X is a podcast that dissects the anatomy of extraordinary long-term investments. The show is hosted by Will Thorndike and the team at Compounding Labs, and brought to you in partnership with Colossus.
     
    In each episode of 50X, we look in detail at an investment that has appreciated at least 50-fold. From the seat of the professional investor and occasionally the CEO, we explore its origins, evolution, and eventual outcome, studying key themes around long-term value creation ranging from operations, capital allocation, and culture to pivotal buy and sell decisions. To enhance the quality and depth of our interviews, we rigorously study each asset in advance, diving into all available public and private resources.
     
    Learn more and dive into our research at 50xpodcast.com
     
    Follow us on Twitter: @50Xpodcast and @joincolossus
     
    Show Notes
    [00:00:00] – 50X Introduction 
    [00:02:00] – Sponsorship: Tegus
    [00:07:04] – Episode Introduction 
    [00:09:05] – Nick’s Background pre-TransDigm
    [00:11:56] – Original Acquisition from Imo Industries in 1993
    [00:15:33] – Thesis and Performance under Kelso & Co.’s Ownership
    [00:18:42] – Genesis of Three Key Value Drivers: Price, Productivity, and New Business
    [00:21:07] – Building the Management Team
    [00:24:05] – Early Lessons on Value Drivers
    [00:27:53] – Capital Allocation under Kelso & Co.
    [00:28:51] – Sale to Odyssey Investment Partners in 1998
    [00:30:26] – Strategy under Odyssey’s Ownership
    [00:31:51] – Early Acquisitions and Integration Playbook
    [00:37:26] – Early External Crises
    [00:41:13] – Snapshot at Conclusion of Odyssey’s Ownership in 2003
    [00:43:19] – Building a Decentralized Culture  
    [00:46:23] – Differentiated Approach to Compensation
    [00:52:12] – Sale to Warburg Pincus in 2003
    [00:55:51] – Shift to Inorganic Growth under Warburg’s Ownership
    [00:58:08] – Evolution of M&A Process
    [01:05:37] – Post-Acquisition Expectations and Post-Mortem Process
    [01:09:48] – Divesting Acquired Assets to Maintain Focus
    [01:11:29] – Embedding Value-Generative Culture via Hiring and Training
    [01:13:54] – Quarterly Product Line Reviews
    [01:20:43] – Recap of Private Investment Returns and Snapshot pre-IPO

    • 1 hr 24 min
    Alice Bentinck - Building a Start-Up Machine

    Alice Bentinck - Building a Start-Up Machine

    My guest today is Alice Bentinck, co-founder of Entrepreneur First. Entrepreneur First, or EF, invests pre-company by systematizing the way that talented individuals find co-founders, develop ideas, and scale into companies. They’re an incubator of teams and ideas on a mission to create impactful companies that, without their help, wouldn’t exist. I first spoke with Alice’s co-founder, Matt Clifford, over two years ago and have been fascinated with EF’s model of investing ever since. Please enjoy my conversation with Alice Bentinck.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
     
    -----
     
    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
    [00:02:33] - [First question] - Overview of what Entrepreneur First is today
    [00:05:57] - How she identifies the people to bring into each cohort and convince them to quit their job to join EF for eight weeks
    [00:10:10] - Categories of the main types of people who join the EF program
    [00:12:32] - What she’s learned about negative screening at the first stage of recruits 
    [00:14:07] - Positive signals she looks for in early admissions 
    [00:17:46] - What the program itself feels like as a participant
    [00:21:29] - Reasons partners tend to fail and whether or not EF advises equity splits between founders
    [00:24:49] - How important the idea is that the team will be working on 
    [00:28:04] - Exercises she enjoys doing with the new cohorts around social norms
    [00:30:38] - How the experience looks physically in each city 
    [00:32:57] - Categories of data collected as the cohorts unfold and making investment decisions
    [00:36:46] - Ways the companies mature after EF and what kinds of investors fund the next stage of their startups
    [00:40:55] - Why aren’t there ten EF style initiatives or organizations
    [00:44:26] - Motivations for the change in their holding company structure
    [00:46:48] - The love of product and ideas she’s playing with right now
    [00:51:49] - Cities she has her eye on that EF is not a participant in today and criteria that makes a city desirable for EF
    [00:54:03] - A piece of software that EF could benefit from that doesn’t exist yet
    [00:55:30] - The keys to her harmonious relationship with her co-founder Matt 
    [00:59:01] - National and international impediments that directly impact company building
    [01:01:36] - The kindest thing anyone has ever done for her

    • 1 hr 3 min

Customer Reviews

4.8 out of 5
2K Ratings

2K Ratings

Sonofman311 ,

Love it!

Great podcast, always interesting guest and topics discussed even for folks like me who are not in the investment world.

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Genius

Enough said

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