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Invest Like the Best with Patrick O'Shaughnessy

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/
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Invest Like the Best with Patrick O'Shaughnessy
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Now displaying: 2022
Aug 9, 2022

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.

 

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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

[00:02:34] - [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 kindest thing anyone has ever done for him

Aug 2, 2022

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.

 

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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

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 the line between recurring and non-recurring revenue

[00:37:42] - The biggest changes for him moving from outside client capital to just managing his own

[00:39:09] - 3 companies that Housatonic Partners has owned for more than 25 years

[00:40:29] - What made Karen Moriarty so good for so long 

[00:42:36] - The crossover between public and private investing and the virtues of each sector

[00:45:35] - How he thinks about the function of Compounding Labs and what he wants it to become 

[00:47:10] - What is at the top of his wish list of the companies he wants to explore 

[00:49:15] - Which companies he’d still be fascinated to learn about that don’t fit the criteria he’s laid out today 

[00:50:25] - The development of investor conviction over time and what he’s learned about it

[00:52:19] - Lessons learned about producing great media

[00:53:43] - What he can teach us about deep research on companies with analysts

[00:55:10] - Adjusting his thinking and investing in a high variance world

Jul 26, 2022

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

Jul 19, 2022

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

Jul 14, 2022

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 ColossusWill’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

Jul 12, 2022

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

Jul 5, 2022

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.

 

-----

 

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

[00:02:35] - [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 

[00:25:14] - The formative experiences or lenses that inform her investing decisions

[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 funds towards female founders 

[00:32:26] - How she applies community building lessons to All Raise

[00:33:20] - The internal learning culture in Sequoia that others could adopt and benefit from

[00:37:01] - Which Marvel superheroes her Sequoia partners would be  

[00:39:05] - Seeds of motivation for Arc and what it is

[00:43:06] - When you should innovate and when you shouldn’t reinvent the wheel 

[00:44:31] - The best ways she’s seen companies manage and support human capital

[00:45:36] - Biggest mistakes made when managing human capital 

[00:46:42] - What working on Google Maps taught her about product development 

[00:48:42] - Someone she admires and has learned the most from in All Raise  

[00:50:02] - Measuring success at Sequoia over the next ten years  

[00:52:20] - The kindest thing anyone has ever done for her

[00:53:42] - What it was that made the people who believed in her take a chance on her 

[00:55:03] - Things in pop culture today that most has her attention

Jun 28, 2022

My guest today is Ken Stanley. Ken is a Professor in Computer Science and a pioneer in the field of neuroevolution. He is also the co-author of a book called, Why Greatness Cannot Be Planned, which details a provocative idea that setting big, audacious goals can reduce the odds of achieving something great. We discuss that revelation in detail and how to apply it in our day-to-day lives. Please enjoy this great discussion with Ken Stanley.

 

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, 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

[00:02:36] - [First question] - The best way to change the world is to stop trying to change it

[00:06:26] - The kinds of goals his work addresses and the ones it doesn’t

[00:08:46] - Almost no prerequisite to any major invention was invented with that major invention in mind

[00:14:04] - Picbreeder

[00:17:21] - How looking for specific results often makes arriving at them a longer process

[00:24:00] - The importance of the individual in a web of invention and disruption

[00:28:30] - How generations progressed in Picbreeder when consensus mechanisms were inserted into the process 

[00:31:24] - Examples of stepping stones that were invented that became something even greater

[00:36:02] - What his research means for how we should conduct ourselves writ large

[00:44:17] - Thoughts on necessity being the mother of all invention

[00:50:08] - The ways that society is arranged is psychologically toxic

[00:55:14] - The role that constraints play in creative output and outcomes in general; Brett Victor - Inventing on Principle

[01:01:10] - What the constraints are that he sets for himself in AI development

[01:04:44] - To know what’s new you need to know what’s not new

[01:06:47] - The kindest thing anyone has ever done for him

[01:08:28] - How he would allocate resources to create more innovation in the world

Jun 21, 2022

My guest today is Lydia Jett, Managing Partner of SoftBank Investment Advisers. Lydia leads the team’s consumer, internet, and e-commerce investments and has worked with many of the most significant consumer platforms in the world, including as a board member of Coupang and Flipkart. We cover all aspects of e-commerce and explore Lydia’s evolution as an investor alongside Masa Son at SoftBank. Please enjoy my conversation with Lydia Jett. 

 

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, 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.

 

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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

[00:02:34] - [First question] - What curiosity thread she’s been pulling on thus far in her career

[00:05:17] - The biggest felt differences doing things one way for a decade and changing now

[00:07:08] - Learning about tailwinds and what the predominant ones are that exist today

[00:08:38] - How much room to go there is left in the world transitioning to e-commerce

[00:10:44] - Competitive frontiers that exist today in e-commerce

[00:12:14] - What drives companies that grow faster than their competitors

[00:13:15] - What areas the world’s most innovative e-commerce companies are focused on

[00:16:38] - Unique characteristics that they select for in ecommerce CEOs and founders

[00:17:44] - Which country she would send an American investor to in order to learn more

[00:19:03] - Upside down approaches to e-commerce that aren’t common in America yet

[00:20:15] - Subcategories and sub sectors she’s most drawn towards lately

[00:23:05] - Lessons learned about business models that don’t work in e-commerce

[00:27:47] - What western investors should know about Coupang 

[00:30:12] - Everything she’s learned about vertical integration

[00:33:01] - Everything she’s learned and cares about in regards to margins

[00:34:24] - Evaluating a younger company’s ability to drive margins in the future

[00:37:17] - The most extreme version of efficiency gain she’s seen deployed

[00:39:06] - Whether or not the public perception of SoftBank’s simplified approach is accurate

[00:41:27] - The role the size of assets plays at SoftBank

[00:47:42] - Focusing on efficiency and smart allocation first before trying to scale 

[00:50:33] - Companies as products that investors buy and defining what great looks like

[00:53:16] - The danger of premature optimization around a set of KPIs 

[00:55:46] - How important the specific founder is for their given e-commerce company

[00:58:18] - Why e-commerce companies tend to start from a worse place than offline ones

[00:59:45] - Ways that she’s changed from working alongside Masayoshi Son for a year

[01:03:31] - Who comes most to mind as a great investor    

[01:05:23] - The kindest thing that anyone has ever done for her

Jun 14, 2022

My guests today are Josh Wolfe and Chris Power. Josh will be a familiar voice to many of you and is the co-founder and General Partner of Lux Capital. Chris is the founder and CEO of advanced manufacturing start-up, Hadrian. Most of our discussion centers on the need to modernize the factories that supply our space and defense industries. But given the current market environment, we also talk about capital conditions and the responsibility to build products that really matter. Please enjoy this conversation with Josh Wolfe and Chris Power.

 

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, 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

[00:02:40] - [First question] - An overview of the precision manufacturing industry writ large

[00:08:28] - Why the manufacturing sector has so many great investment opportunities

[00:12:58] - Anduril Breakdown; What Hadrian in its final form will unlock for manufacturing

[00:16:08] - What the demand side looks like for manufacturers in its current state today 

[00:18:29] - How the nature of demand will shift for this style of manufacturing in the future

[00:22:51] - Important rare earth materials, supply chain constraints, and the revival of commodities 

[00:27:55] - The key set of jobs being done by mom and pop shops that could be innovated on and done within a Hadrian factory 

[00:30:35] - What is going on inside of a Hadrian factory and how they will evolve over time 

[00:32:10] - Prosecuting diligence on someone's ability to execute on their behalf

[00:37:14] - The PhD arrogance trap and how a Hadrian machine will be better in five years from now

[00:39:44] - Units of innovation and optimization driven by software 

[00:41:43] - Walkthrough of the bubble and anti-bubble concept and funding companies in today’s markets  

[00:48:08] - Breadth of ability versus focus and selling parts to buyers early on

[00:50:42] - Lessons learned and advice for understanding the focus problem 

[00:52:32] - Whether or not the climbing costs of experimentation is a bad thing

[00:56:39] - Fat startup vs. lean startups and making the hardest irreversible decision during Hadrian’s early days

[00:58:31] - Enduring more schlep work than less being a good signal

[00:59:06] - Chris’ thoughts on the future of Hadrian and defining the exciting and scary edges of the spectrum of outcomes

[01:03:36] - Josh’s thoughts on the future of Hadrian and defining the exciting and scary edges of the spectrum of outcomes

[01:07:22] - The kindest thing anyone has ever done for Chris

Jun 7, 2022

My guest today is Martin Casado. Martin is a general partner at Andreessen Horowitz where he focuses on digital infrastructure. Before joining a16z, Martin pioneered software-defined networking and co-founded Nicira, which was bought by VMware for $1.3 billion in 2012. Martin has studied, built, and invested in digital infrastructure his whole career and is the perfect person to discuss the most interesting aspects of the industry. Please enjoy this great conversation with Martin Casado.

 

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, 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.

 

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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

[00:02:43] - [First question] - The state of the digital infrastructure industry today 

[00:04:02] - The major stages and eras of cloud technology 

[00:06:30] - Overview of Dropbox’s story and the two major trends at the time of its emergence

[00:10:12] - Lost margin and lost market cap from big users of the public cloud 

[00:12:14] - Whether or not there is a headwind coming for public cloud providers

[00:14:07] - The base level primitives of the digital world and innovation within those areas

[00:17:33] - How entrepreneurs might go after the biggest public cloud providers

[00:19:37] - His view on API first companies and granular monetizable units in growing markets

[00:23:20] - Developer facing tools and what works well when going to market 

[00:25:34] - Lessons learned about successfully building relationships between a company and developers as a buying class 

[00:27:12] - The difference between a front-end and back-end developer and what is changing in their responsibilities 

[00:28:45] - What he looks for as an investor when he’s processing a new API first company

[00:30:31] - Common redflags and disqualifying observations for an API first company 

[00:31:59] - Pricing usage and building a revenue model around one of these businesses

[00:33:49] - Reasons why this proliferation is happening and important parts of the data stack

[00:36:35] - Frank Slootman Episode; Snowflake’s offering for their users, their explosive growth, and primitives in their sector

[00:39:06] - The history of digital security and potential opportunities as an investor

[00:40:19] - How digital infrastructure intersects with the real world and hardware world

[00:42:14] - What he’s most excited about that digital infrastructure might unlock in the future

[00:43:33] - How to screen out people for their potential to deliver transformative technology

[00:45:38] - What he’d like to know about the future that he isn’t sure of yet 

[00:47:45] - Things he’s most intrigued about by cryptocurrencies as an infrastructure person

[00:51:36] - Where he’s most bullish and bearish relative to his peers in digital infrastructure

[00:52:49] - The kindest thing anyone has ever done for him

May 31, 2022

My guest today is Aswath Damodaran, a Professor of Finance at NYU’s Stern School of Business. Aswath is one of the clearest teachers of investing and finance in our industry and through his blog, books, and YouTube has open-sourced his wisdom for decades. This conversation is a masterclass of key investing concepts. We discuss inflation, narratives, disruption, the evolution of alpha and edge, and his thoughts on ESG. Please enjoy this great conversation with Aswath Damodaran.

 

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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This 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.

 

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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 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

[00:02:43] - [First question] - How he thinks about inflation as a now dominant force

[00:04:33] - Why inflation is so important across the spectrum

[00:09:02] - Big lessons from other periods of historically high inflation writ large

[00:10:45] - Reasons why equities as an asset class struggle in high inflation environments

[00:15:21] - The relationship betweens goods versus services in times of high inflation

[00:16:59] - Broader economic implications especially for income inequality

[00:19:03] - The Fed taking inflation seriously now when they didn’t and thoughts on the policy response to today’s situation

[00:21:05] - How smart companies are defensively adjusting to inflation

[00:24:38] - Thoughts on returns on invested capital with emphasis on invested capital 

[00:27:46] - The importance of a capital allocation skill-set for executive team members

[00:29:32] - Further historic lessons and how he’s being defensive against inflation

[00:33:09] - Lessons learned about Amazon valuing them every year since their inception

[00:37:50] - How to figure out a new company’s narrative and the story they’re telling

[00:42:25] - Whenever he sees Thanos in the Avengers he thinks of Amazon

[00:44:51] - Thoughts on Facebook, Apple and Microsoft

[00:48:26] - The evolution of edge and the search for alpha

[00:54:37] - Whether or not there’s utility in studying other investors 

[00:57:16] - Skill versus luck and the most common valuation mistakes he’s made

[00:59:09] - Assuming long-term growth rates and changing company life cycles

[01:02:02] - Momentum and Value investing in today’s market

[01:07:24] - Differences between interest rates and discount rates in regards to inflation

[01:10:29] - Thoughts on equity risk premium in a market like this

[01:12:00] - How today’s market affects early stage equity investment

[01:14:36] - The growing popularity of ESG and his seemingly contrarian view on it

[01:24:03] - Nature of disruption as a force and companies that are protected from it

[01:28:24] - Assigning a disruption risk premium when valuing companies

[01:31:17] - Characteristics that will define the most successful leaders over the next decade

[01:32:52] - What he makes of Elon Musk buying Twitter

[01:34:24] - Other major topics he has a divergent view on 

[01:38:37] - Narrative And Numbers; The kindest thing anyone has ever done for him

[01:38:55] - Teaching with a goal of changing mindsets 

May 26, 2022

Today, we are running a special episode of Business Breakdowns. With geopolitics playing an increasingly important role in society again, this episode with Anduril’s CEO offers an inside look at the state of the defense industry and how it is changing. If you enjoy this episode, subscribe to Business Breakdowns on your preferred podcast player, where you’ll find past episodes on Block, Goldman Sachs, AutoZone and many others.

 

Today, we are breaking down Anduril. Anduril builds high tech defense systems for the US Department of Defense and its allies. Crucially, it does so with speed that emanates from Silicon Valley. Founded in 2017 by Palmer Luckey, who previously built and sold Oculus to Facebook, Anduril has achieved the rare feat of challenging the established order in the defense industry.

 

To break down Anduril, I’m joined by the company’s CEO and co-founder, Brian Schimpf. We discuss the history of the defense industry, how Anduril’s business is counter positioned against the legacy cost-plus model, and what Brian has learned about selling to the DoD. Please enjoy this breakdown of Anduril.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. If you're ready to go deeper on any company and you appreciate the value of primary research, head to tegus.co/breakdowns for a free trial.

 

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This episode is brought to you by Daloopa. Daloopa streamlines a major pain point for investors. By capturing all of a company's KPIs and adjusted financials into their database - Daloopa makes it easy to quickly update your models for what matters. Daloopa uses AI to find every KPI disclosed - from charts, to text, and even from footnotes of investor presentations. Daloopa updates these KPIs and data points in your existing Excel models in one click, regardless of your source or format. Test Daloopa for free at daloopa.com/Patrick.

 

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Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, 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: @JoinColossus | @patrick_oshag | @jspujji | @zbfuss

 

Show Notes

[00:02:52] - [First question] - The history of defense technology and the technological and competitive landscape when he set out to build Anduril

[00:08:22] - What the early experience was like when approaching the government and finding an early adopter

[00:12:44] - Necessity being the mother of invention when it came to developing drones

[00:16:37] - What it’s like to develop hardware and software products at the same time 

[00:20:26] - How the defense business complex works economically and overview of the detailed cost plus model

[00:24:44] - The state of military technology and military conflict today writ large

[00:31:10] - Are we heading to a future where warfare is mostly machine against machine? 

[00:33:34] - Comparing the ghost drone system to predator drones

[00:38:40] - Guiding principles as a firm and deciding on their product roadmap

[00:43:25] - An overview of their product lineup and what they’ve built so far 

[00:48:13] - Having an open innovation policy to promote competition

[00:49:37] - The nuance of politics when it comes to building and running their business

[00:51:56] - Most difficult decisions he’s had to make through Anduril’s history 

[00:53:51] - How he overcame Anduril’s lowest points and biggest challenges 

[00:58:38] - Thoughts on effectively compounding hardware innovation 

[01:02:23] - A moment he’s most proud of and regrets most in Anduril’s history

[01:04:20] - Lessons learned from observing Palantir and SpaceX 

[01:08:37] - The kindest thing anyone has ever done for him

May 24, 2022

My guest today is Tobi Lütke, co-founder and CEO of Shopify. Having first spoken to Tobi at the beginning of the pandemic, just two months into it, this felt an opportune moment to revisit Shopify and the world through Tobi’s eyes. Among many things, we discuss Shopify’s evolution into the world of atoms-based building through Shopify’s fulfillment network, the value of infrastructure writ large, and the impact of market volatility on day-to-day business building. Please enjoy my conversation with Tobi Lütke.

 

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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This 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 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

[00:02:44] - [First question] - His interest in infrastructure as a whole and why it’s underrated

[00:07:18] - Whether or not we’re currently building enough digital infrastructure 

[00:09:45] - Base level principles for decision making around building infrastructure 

[00:13:17] - How much room is left for innovation and whether or not we’ll just reinvent basic human instincts

[00:15:22] - Ways new ideas are fed into a product funnel at Shopify and greenlit

[00:19:34] - Solving eCommerce infrastructure and what he attributes to Shopify’s success

[00:24:23] - Overview of the Shopify Network and how it’s evolved over time 

[00:31:04] - Lessons learned in an atom-driven world in regards to fulfillment and logistics

[00:34:37] - Common ways bits thinkers are often wrong when solving atom problems

[00:35:50] - Spreadsheets tend to win meetings and how the ROI on a fulfillment network impacts its ecosystem

[00:40:26] - Navigating becoming an aggregator that sits on top of their merchants and whether or not there are plans to participate as a distributor

[00:45:45] - Fair market value, what it’s been like managing through such a volatile market, and important takeaways

[00:50:54] - Thoughts on capital allocation decisions as Shopify continues to grow

[00:53:25] - Advice for company leaders effectively communicating with their teams about stock-based compensation 

[00:59:04] - How much COVID altered their trajectory and what he’s most interested in as he looks out to the future

[01:03:45] - What he’s learned about blockchains and the crypto space given recent events

[01:08:45] - A new idea he’s encountered recently that he’s fallen in love with 

May 17, 2022

My guests today are Tyler Cowen and Daniel Gross. Tyler is an economics professor and creator of one of the most popular economics blogs on the internet. Daniel is the founder of start-up accelerator Pioneer, having previously been a director at Apple and a partner at Y Combinator. Both Daniel and Tyler are prolific talent spotters and that is the focus of our discussion and their new book, which is called Talent. Please enjoy this conversation with Tyler Cowen and Daniel Gross.

 

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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This 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

[00:02:38] - [First question] - Defining what talent is to them writ large

[00:03:34] - The differences between means and ends in regards to talent

[00:04:14] - What the Diet Coke idea is and why it’s relevant

[00:06:32] - Types of energy that are valuable and the subtle differences between them 

[00:07:40] - Thoughts on using a moneyball-like approach to acquiring and evaluating talent 

[00:11:49] - The talent market and thinking about pricing talent specifically

[00:13:14] - What is seemingly overpriced in today’s talent landscape

[00:15:50] - Relationship between experience and/or age when it comes to talent

[00:20:34] - Lessons about the utility of intelligence and where they’ve lead them wrong

[00:23:35] - What’s beneath being an outsider and why it’s important

[00:24:46] - Why what people do in their downtime is worth considering  

[00:28:27] - Whether or not references should be held in higher regard than interviews

[00:31:41] - Things to try and get out of a reference call as an objective

[00:32:40] - Disabilities and what lead them write that chapter specifically

[00:35:01] - Whether or not talented people are happier  

[00:38:40] - Lack of contentment and it’s dynamic influence over individuals

[00:41:01] - Where they think the other is most talented

[00:43:33] - Thinking about the physical side of mental performance

[00:45:49] - What was frustrating about writing the book

[00:48:25] - How they evaluate talent most differently now after having finished the book

[00:50:41] - What makes for a good bat signal and how to cast one well 

[00:53:27] - Personality inventories and what they would and wouldn’t recommend  

[00:54:15] - Geographical frictions and their role in high success rates

[00:56:08] - Antonio Gracias; Existing supply constraints on talent development

[01:00:01] - How they would redesign the current attractors of talent that we rely on today

[01:01:18] - Assembly line development and how we can improve and scale talent filters

[01:02:29] - The biggest open questions for talent today writ large

[01:05:16] - The kindest thing anyone has ever done for Tyler

May 10, 2022

My guest today is Jeff Jordan, General Partner at Andreessen Horowitz. Jeff has one of the most interesting set of experiences of guests that I’ve had on the show. As an operator, he has been the General Manager of eBay.com, President of PayPal, and CEO of OpenTable. As an investor, he was one of the first General Partners at a16z and sits on the board of Airbnb, Instacart, Pinterest, and other notable firms. Given his vast experience, he is the firm’s go-to-expert on all things marketplaces, which is the common thread in our conversation. Please enjoy this great discussion with Jeff Jordan.

 

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

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

[00:02:48] - The notion of perfect competition in marketplaces

[00:04:31] - How to build a marketplace while thinking about perfect competition

[00:05:32] - Promoting price discovery at eBay

[00:06:52] - Features of a marketplace he focuses on 

[00:08:38] - Best way to do lead generation 

[00:10:20] - Red flags for marketplace businesses 

[00:11:00] - Major business lessons learned while at Disney 

[00:12:10] - Learning to be an operator while at eBay; Leaving It All on the Field

[00:14:45] - How he got hired at OpenTable

[00:16:22] - Taking OpenTable public and being its first public company CEO

[00:17:44] - What they did well in financing OpenTable

[00:18:54] - Communications between company leaders and its investors 

[00:19:45] - Going from operator to investor

[00:22:08] - Lessons from the early years of becoming an investor and pricing companies

[00:24:12] - Power of network effects on a startup

[00:26:56] - Healthy tensions inside of a network

[00:29:23] - When the supply side is the more difficult part of the equation

[00:30:27] - Characteristics of founders when it comes to marketplaces

[00:33:30] - The importance of being a perpetual learner as a founder

[00:35:36] - When he starts focusing on unit economics and margin profile in a new marketplace

[00:37:45] - Increasing convenience for a buyer as a business strategy 

[00:42:14] - Categories that could use better marketplace solutions

[00:44:36] - Layers of growth inside a business

[00:50:26] - Lessons with the unique business model of Pinterest

[00:52:03] - Unique aspects of the Andreessen Horowitz business model

[00:55:54] - Finding and recruiting talented general partner investors 

[00:57:37] - The morning basketball game and community strengthening

[01:01:36] - Defining great mentor relationships

[01:04:54] - Kindest thing anyone has done for him

[01:06:05] - Lessons from his parents

May 3, 2022

My guest today is Eric Glyman, co-founder and CEO of Ramp. Ramp is best known for its corporate cards but it has a range of software products to help finance teams save money and time. Since its founding in 2019, the business has grown rapidly and was last valued at $8 billion. Eric and I discuss Ramp’s initial marketing wedge, how the business has dealt with such fast growth, and why they hold stablecoins on their balance sheet. Please enjoy my conversation with Eric Glyman.

 

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

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

[00:02:41] - [First question] - What was most notably awry about the industry before Ramp

[00:04:45] - Breakdown of Visa; The business model of the Black Card compared to the business card offering of Ramp

[00:08:40] - Causes and what he attributes their early success to

[00:11:30] - Description of Ramp’s software in the beginning and the evolution of co-building it

[00:16:34] - How he’s gone about building the company and team fast enough to handle their explosive growth curve

[00:19:47] - Approaching all aspects of recruiting and acquiring such great talent

[00:21:39] - Thoughts on the biggest mistake he’s made while building Ramp

[00:24:05] - Lessons learned about marketing that this journey has taught him

[00:26:13] - Learning to manage a senior team and advice for managing rapid growth

[00:28:58] - Unique aspects of Ramp’s approach to the financing side 

[00:32:56] - Why they are storing some of their balance sheet in stablecoins 

[00:34:47] - What the idealized end state of Ramp looks like

[00:37:26] - How the data and information he sees indicates trends in the economy writ large

[00:39:33] - Providing secondary liquidity to employees in a world where companies stay private for longer periods of time

[00:43:03] - Aspects of company building that are still unnecessarily hard

[00:44:55] - What has him most excited about Ramp in the next 12-18 months

[00:46:42] - The kindest thing anyone has ever done for him

Apr 26, 2022

My guest today is Dmitry Balyasny. Dmitry is the Managing Partner and CIO of Balyasny Asset Management, otherwise known as BAM. BAM runs a multi-strategy, multi-PM model that aims to produce consistent absolute returns. Since its founding in 2001, it has produced only one negative year and become one of the largest firms of its kind. Please enjoy my conversation with Dmitry Balyasny. 

 

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

 

-----

 

This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Listeners can redeem a $1k off coupon at vanta.com/patrick

 

-----

 

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

[00:02:53] - [First question] - The origin story of his firm and the key stages of evolution

[00:06:43] - Describing the difference between good and great in platform hedge funds 

[00:10:25] - How a multi-strategy, multi-investor group works and managing capital allocation

[00:13:58] - What he’s trying to solve at the end of the day as their CIO

[00:16:21] - How close they are to their idealized end-state 

[00:18:26] - Typical amounts of leverage associated with these types of models

[00:20:22] - Lessons learned about incentivizing talented investors

[00:22:39] - Ways he tends to attract risk takers and their levels of variance

[00:28:15] - Other characteristics that are common amongst great PMs

[00:30:42] - The nature and source of edge and how it’s changed most over time

[00:33:19] - Some of the hardest portfolio and business decisions he’s had to make 

[00:37:59] - One of his most important business decisions on the firm side

[00:40:09] - How they’ve thought about shorting as a firm in general and more recently

[00:43:52] - How interest rates affect this style of investing

[00:45:29] - His view on the opportunity set in private markets and what does and doesn’t excite him about it

[00:49:42] - How reading Ayn Rand most shaped his thinking

[00:50:36] - Things Ayn most got right and most got wrong in his mind

[00:51:24] - What the war in Ukraine has felt like for him as a Ukrainian-American

[00:52:08] - Ways the future still has him excited as he continues to build his firm

[00:53:53] - Where his trading instincts draw him today and areas of interest

[00:55:11] - His most memorable trade of all time

[00:56:37] - In which order the major asset classes will be affected by digital innovation

[00:58:13] - The kindest thing anyone has ever done for him

Apr 21, 2022

My guest today is Henry Ward, co-founder and CEO of Carta. Started in 2012, Carta helps companies and investors manage their cap tables, equity plans, and ownership. Last year, they launched CartaX, a platform for private companies and their employees to access secondary market liquidity. Our discussion is a detailed exploration of private market infrastructure and Henry’s views on building an enduring business. Please enjoy my conversation with Henry Ward.

 

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

 

-----

 

This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Listeners can redeem a $1k off coupon at vanta.com/patrick

 

-----

 

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] - The first key mental moment of how Carta came to him

[00:05:30] - Initial thoughts on how to position Carta as a business model

[00:06:47] - Historical divergence between private and public market infrastructure

[00:08:33] - What a price discovery process for primary shares could look like in the future

[00:11:09] - The end state Carta is trying to effect in their perfect state

[00:13:29] - Why it’s so hard for private company staff to manage their illiquid wealth

[00:15:45] - Lessons and challenges in the new market creation business

[00:17:57] - The nature and dynamics of supply and demand in this space

[00:20:16] - Restrictions that prevent retail investors from participating in private markets and why there’s more alpha in private markets

[00:22:45] - How Carta is mapped onto the success of its customers

[00:25:27] - Deciding on what is a good idea and what isn’t when it comes to focus

[00:28:07] - Describing the One of N versus N of One market frameworks and principles of this philosophy that manifests in how he runs Carta

[00:32:11] - How working at Carta would differ from a payroll-type company

[00:35:37] - Characterizing his leadership and management styles

[00:37:57] - The types of circumstances that bring out his tough side

[00:39:33] - Making hard decisions in a bottom up management model 

[00:44:05] - How he spends his time while building Carta

[00:45:02] - What a great product looks like to him

[00:47:10] - The Systems Bible; Defining what a great team looks like

[00:49:13] - What he’s learned about being great at Go-To-Market

[00:51:26] - Effective ways to beat competitors and build relationship pipelines

[00:53:49] - Things he likes the least about leading a company of this size 

[00:55:13] - What he fears most as he thinks about the future of Carta

[00:55:45] - Advice for entrepreneurs when thinking about data in modern businesses

[00:58:26] - The biggest missing pieces in capital market structure writ large

[01:00:17] - What’s next for CartaX and what he’ll be pushing to make it work 

[01:02:10] - Lessons learned from serving venture investors 

[01:04:25] - Whether or not investment banks are their competitors

[01:05:18] - Public market dislocation and how long it will last

[01:06:58] - The kindest thing anyone has ever done for him

Apr 12, 2022

My guest today is Alexandr Wang, the CEO and founder of Scale AI. Alexandr founded Scale in 2016, having been inspired to accelerate the development of AI through his work at Quora and his studies at MIT. Specifically, Alexandr realized there was a lack of infrastructure solutions for producing high quality data, the lifeblood for AI models. Today, Scale provides data solutions to leading AI teams at Meta, Microsoft, OpenAI, Flexport, the US Air Force, and many others. This time last year, the business was valued at over $7 billion. 

 

Our conversation is a primer on AI. We discuss the building blocks beneath successful artificial intelligence, AI’s role in both the public and private sector, and why data is the new code. We also cover the similarities and differences between AI and software from an investing perspective and what inspiration Scale takes from AWS. Please enjoy my great discussion with Alexandr Wang.



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

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

[00:03:04] - [First question] - The role that AI and data play in geopolitics and foreign policy

[00:07:21] - The end state of a digital arms race akin to nuclear weapons

[00:08:53] - Current state of things writ large and how the public and private sectors differ

[00:11:33] - The flow and importance of talent when scaling AI and whether it’s more important than software 

[00:14:29] - His thoughts on how to communicate categories of what AI can do well and what is still a ways out

[00:20:18] - The process of creating an AI model and the stages of development

[00:23:19] - A growing trend of data becoming more valuable than code itself

[00:27:16] - Principles of building a great engine for gathering data

[00:29:04] - The state of technology around annotating data writ large

[00:31:31] - What Scale does as a business and their product lineup

[00:35:08] - The Storage and Compute equivalents in the AI space

[00:37:08] - How Scale fills the gap in producing better and cleaner data

[00:39:52] - What Scale will look like in 10 years if their vision is fully realized

[00:41:11] - Where AI is in the S curve of acceleration and where AI and software intersect

[00:44:32] - Questions to ask about how to incorporate AI and data sets in your business

[00:46:23] - What worries him about the proliferation of technology that makes AI more accessible to the masses

[00:48:27] - The most interesting AI model he’s ever come across and collapsing the friction between human intent and programmable outcomes

[00:51:51] - The kindest thing anyone has ever done for him 

Apr 5, 2022

My guest today is Antonio Gracias, founder, CIO, and CEO of Valor Equity Partners. Antonio is perhaps best known for his role at Tesla, as the earliest institutional investor and Director from 2007 to 2021. But he has deep operating and investing experience, having first acquired and managed a number of manufacturing and technology companies during his 20s. And it was during those formative years that Antonio and his team developed the skills that led to Valor, which provides operational expertise to the high growth private companies they invest in.

 

Our conversation is a deep exploration of the drivers behind Antonio and Valor’s success. We dive into his concept of pro-entropic investing, what he learned as a 25-year-old running a manufacturing business, and trust me when I say, you don't want to miss his answer to the kindest thing ever. Please enjoy this great conversation with Antonio Gracias.

 

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

 

-----

 

This episode is brought to you by Lemon.io. The team at  Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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
[00:02:51] - [First question] - Defining what a pro-entropic company is

[00:07:26] - Understanding external forces of chaos and why they’ll continue to increase

[00:11:32] - What he’s learned about identifying and investing in pro-entropic companies

[00:13:43] - Investing with entropy in mind can be a bet on unchanging aspects of human nature

[00:15:08] - Defining durability in contrast with resiliency and entropy

[00:17:27] - Timing and valuation matters less and less as you ascend the entropic scale

[00:18:53] - Coming from a traditional background and the origin of Valor

[00:22:05] - The theory of constraints and why it’s so powerful; The Goal

[00:26:32] - Transitioning into a private equity structure and Valor’s 2001-2005 era

[00:30:42] - Asymmetric information and developing a stage deployment of capital strategy

[00:32:51] - The importance of understanding people and psychological ideas for investing he finds useful

[00:36:59] - Understanding the psychology of founders that have successful outcomes

[00:39:07] - Vision setting, narrative building, and qualities of effective and dangerous leaders

[00:42:02] - Decision making bias and combating bias effectively in practice 

[00:44:30] - Where security and control figures into his thinking

[00:45:45] - Identity in relation to ego; the tools he uses to combat identity related decisions

[00:49:04] - Lessons learned from the Japanese language versus Western languages

[00:50:37] - What he’s gotten better at when it comes to getting to the heart of what’s actually going on in a company and accepting reality

[00:53:07] - Questions he returns to when he’s getting to know a company

[00:56:16] - An episode of operational deployment that most stands out in memory

[00:58:54] - Key concepts that most stick with him from working alongside Elon Musk

[01:01:32] - Why there aren’t more Musk’s or Bezos’ in the world

[01:04:20] - Ensuring Valor invests in the best companies going forward

[01:06:06] - How to pass the torch of what Valor is to others when his time is done

[01:08:25] - The kindest thing anyone has ever done for him 

Mar 29, 2022

My guest today is David Rubenstein, co-founder of The Carlyle Group - one of the largest private equity firms in the world. David has worked in the White House, built a $300 billion investment institution, become a prominent philanthropist, published books, and even hosts his own TV show. It was a thrill to sit down with him and cover the whole spectrum of his experience as a father, investor, historian, and titan of American business. Please enjoy this great conversation with David Rubenstein.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

-----

 

This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Listeners can redeem a $1k off coupon at vanta.com/patrick

 

-----

 

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

[00:03:02] - [First question] - What his perspective on the world today is compared to the last forty years

[00:05:35] - The long term implications of the Ukraine war on a global scale

[00:07:54] - Concerns and thoughts on the US’s role in a radically different world

[00:10:07] - How inflation and reduced globalization impacts business behavior in the US

[00:12:58] - Why he chooses to learn by listening to people who are incredibly versed in their respective fields and what started it

[00:14:11] - His method when interviewing people and how it’s changed over time

[00:15:03] - How his interest in leadership as a topic began; How to Lead

[00:17:55] - The time he was the most personally in awe of a leader

[00:19:05] - The most basic ingredients for strong leadership

[00:21:34] - Learning from Oprah and developing his own interviewing style

[00:24:25] - His leadership style while running Carlyle and key variables that drove Carlyle’s success

[00:28:41] - The ways that were most effective in terms of investment for Carlyle’s brand

[00:29:50] - How should a new investor think about the relationship between government and business

[00:31:25] - Best ways for a business to interact with the government and common traits of those who do it well

[00:32:17] - What he’s learned about leadership that he thinks is the most portable for other people

[00:34:04] - His interest in masters of leadership and what he has learned from them

[00:35:08] - How Carlyle retained their talent and building relationships with LP investors

[00:37:20] - Lessons from working in media with what worked and what didn’t; How to Invest

[00:38:55] - How he approached writing How to Invest

[00:41:13] - The importance of intuition when evaluating backers and why geniuses aren’t always chosen

[00:43:04] - Big aspects of American history and why he finds it so interesting; The American Story

[00:44:17] - Key drivers of American outcomes and biggest areas for improvement

[00:47:00] - Lessons he learned going from humble beginnings to amassing wealth and how he’s teaching his children about it

[00:49:20] - The state of private equity and what are its best and highest functions today

[00:51:03] - Experience and impressions on the emerging cryptosphere

[00:52:25] - What makes for a good chairman and why he is always drawn to that role

[00:53:42] - The most interesting system outside of the US that he’s observed

[00:55:33] - What he has learned about being a giving pledge signer and philanthropy

[00:57:02] - His interest in Monticello and the Magna Carta

[00:59:13] - View on how speeches from leaders have changed over the years; Citizenship in a Republic

[01:01:24] - What subject he would write his next book on

[01:03:58] - Thoughts on the line between giving your life for your country versus your state

[01:05:17] - The American Experiment

[01:06:10] - Looking back on his career at a time where he felt the most alive

[01:08:07] - The kindest thing anyone has ever done for him

Mar 22, 2022

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.

 

-----

 

This episode is brought to you by Tegus. Tegus is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

-----

 

This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Invest Like the Best listeners can redeem a $1k off coupon at vanta.com/patrick

 

-----

 

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 his parents and how hard they worked to build a better life for their family

[01:04:10] - Two things that manifest in a system that is seemingly rigged towards the wealthy and the problem with generational wealth

[01:05:29] - What has him most excited and optimistic about the future in the investing landscape today

[01:08:16] - Investing mentors deserve gratitude for believing in their pupils

[01:09:12] - The kindest thing anyone has ever done for him  

Mar 15, 2022

My guest today is Marko Papic, partner and chief strategist at Clocktower Group, where he leads the firm’s research on macroeconomics and markets. Marko has spent his career at the intersection of finance and geopolitics, making him a perfect person to speak to about current events in Ukraine and their potential impact further afield. Along with Russia and Ukraine, we discuss the Fed, inflation, China, the green energy transition, and the US’s position in the global order. Please enjoy this discussion with Marko Papic.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

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This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/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

[00:02:48] - [First question] - His thoughts on what’s happened so far between Russia and Ukraine

[00:06:18] - The geopolitical motivations for Russia and what they can gain from the conflict 

[00:10:52] - How his impressions of warfare have evolved watching this play out

[00:13:45] - What to consider about nuclear war and different types of nuclear weapons

[00:16:31] - The economic warfare from the West against Russia and its implications

[00:21:06] - Whether or not the world is de-globalizing and how interconnected we all are

[00:24:45] - How we should view post-covid inflation, specifically in the US

[00:30:34] - The ways the Fed’s role has evolved 

[00:33:25] - Impacts of liquidity on asset prices and why it’s such a key factor in markets

[00:34:16] - China’s positioning and how the Ukraine conflict could alter their plans

[00:40:58] - Thoughts on Taiwan and how global supply chains might change

[00:44:47] - Why so few people believe that China has peaked; Young China 

[00:48:52] - His take on income equality in the US and why it’s the number one issue

[00:53:03] - What the US could do to improve itself as a country most going forward

[00:55:35] - Having a green energy transition view is crucial and the surrounding politics

[00:59:22] - The preconditions for doing well in atoms-based innovation

[01:01:13] - What he’s watching most carefully about the conflict in Ukraine

[01:02:51] - The kindest thing anyone has ever done for him

Mar 8, 2022

My guest today is Garry Tan, founder and managing partner of early-stage venture firm, Initialized Capital. Before starting Initialized, Garry was a partner at Y Combinator, employee number 10 at Palantir, and co-founder of YC backed blog platform Posterous. Our discussion covers what’s missing in the investment world, how to best systematize venture investments, and what he learned from Paul Graham. Please enjoy my conversation with Garry Tan.

 

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 is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.

 

-----

 

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

 

-----

 

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

[00:02:45] - [First question] - Why he’s interested by software and the global brain

[00:06:23] - How the shift from global to local manifests in his investing and company activities

[00:11:42] - Ways to increase throughput that would benefit everybody in the investing world 

[00:17:13] - What software he would build if there were no limitations and what happens at the systems level of securing deals at Initialize 

[00:23:33] - Why there is no objective application process for early-stage capital and how much human judgment we can remove from approving funding

[00:26:49] - Shared characteristics amongst new inventions he finds favorable 

[00:31:49] - Whether he’s able to evaluate an idea without a prototype

[00:33:33] - Why travel planning software was the worst idea of 2012 and what he sees as the bad idea of today

[00:36:06] - The most common reasons for failure in these types of businesses

[00:39:07] - Is big enabling technology shifts what manifests in successful outcomes?

[00:40:37] - The role of media and how it intersects with investing

[00:44:29] - What he attributes to the success of his firm and thriving in chaos

[00:48:11] - Would he press a button that would have made his childhood easy, and whether he’s met founders who haven’t come across adversity in their lives 

[00:50:00] - His thoughts on the world today via the lens of his portfolio

[00:53:12] - The kindest thing anyone has ever done for him 

 

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