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    Business

    Invest Like the Best with Patrick O’Shaughnessy

    Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can’t find anywhere else. If you’re a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.colossus.com

    Advertise
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    Latest Episodes:
    Tobi Lütke - Embrace the Unexpected - [Invest Like the Best, EP. 278] May 24, 2022
    Show notes

    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.

    -----

    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 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


    Tyler Cowen & Daniel Gross - Identifying Talent - [Invest Like the Best, EP. 277] May 17, 2022
    Show notes

    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.

    -----

    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 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

    [00:31:41] - 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


    Jeff Jordan - Building & Investing in Marketplaces - [Invest Like the Best, EP. 276] May 10, 2022
    Show notes

    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.

    -----

    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

    [00:33:30] - 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


    Eric Glyman - Reimagining Corporate Finance - [Invest Like the Best, EP. 275] May 03, 2022
    Show notes

    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


    Dmitry Balyasny - Building a Better Model - [Invest Like the Best, EP. 274] Apr 26, 2022
    Show notes

    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


    Henry Ward - Transforming Private Markets - [Invest Like the Best, EP. 273] Apr 21, 2022
    Show notes

    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

    [00:22:45] - 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


    Alexandr Wang - A Primer on AI - [Invest Like the Best, EP. 272] Apr 12, 2022
    Show notes

    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

    [00:27:16] - 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


    Antonio Gracias - Pro-Entropic Investing - [Invest Like the Best, EP. 271] Apr 05, 2022
    Show notes

    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

    [00:18:53] - 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

    [00:42:02] - 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

    [00:53:07] - 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


    David Rubenstein - Life, Leadership, and LBOs - [Invest Like the Best, EP. 270] Mar 29, 2022
    Show notes

    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.

    -----

    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

    [00:14:11] - 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

    [00:32:17] - 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


    Gaurav Kapadia - Everything Compounds - [Invest Like the Best, EP. 269] Mar 22, 2022
    Show notes

    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.


    -----

    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


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