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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.joincolossus.com
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Now displaying: 2022
Dec 6, 2022

My guest today is Bill Lenehan. Bill is the CEO of Four Corners Property Trust, a listed REIT and one of the leading owners of restaurant real estate in the US. Their portfolio is made up of 982 properties across 47 states. Real estate is something most of us own, whether as an investment or a home, and Bill’s insight into the asset class at this particular moment in time is fascinating to hear. Please enjoy my conversation with Bill Lenehan.

 

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. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:03:19] - [First question] - Recent increases in mortgage rates and a frozen housing market

[00:08:55] - Projected real estate trends over the next decade

[00:13:38] - How a company’s ROI can be more consistent with backing from a real estate firm

[00:16:41] - Risk-return rate and risk exposure in real estate compared to other asset classes

[00:20:09] - The skills, traits, and circumstances that make a top-level real estate investor

[00:22:38] - Stand-out learnings from his time at Farallon Capital Management

[00:33:20] - The value of shopping malls and offices in a post-COVID, e-commerce US

[00:39:27] - Pros and cons of different types of real estate investments, including REITs

[00:43:22] - The impact of climate change on the real estate market

[00:45:39] - The role of modern technology in investing and in real estate infrastructure

[00:51:10] - Hard costs of building and renovating for the future

[00:54:20] - How hard costs and supply levels impact rates of return and housing costs

[00:57:17] - How the retail industry is adapting to consumer trends

[01:01:23] - Why retailers need to adapt to a changing economy and how they’ll do it

[01:04:03] - The relative magnitude of change in today’s real estate market

[01:06:51] - The role health and wellness plays in real estate and finance

[01:09:28] - What it feels like to be investing in 2022

[01:12:23] - The kindest thing anyone has ever done for him

Nov 29, 2022

Today I’m joined by two Hollywood greats, Ron Howard and Brian Grazer. They have produced, directed, written, and acted in a number of the most popular films and tv shows ever made, including Apollo 13, A Beautiful Mind, 24, and Frost/Nixon. Their partnership is one of the longest running in Hollywood, and the business they founded in 1985, Imagine Entertainment, has won 49 EMMY awards, 11 Golden Globes, and 10 Academy Awards. There are few better storytellers in the world and it was a thrill to talk about curiosity, trust, and business building with them both. Please enjoy this great conversation with Ron Howard and Brian Grazer.

 

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

 

-----

 

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

[00:02:44] - [First question] - The value of trust and how Ron built it up over time with Brian

[00:08:34] - The spark that allowed Brian to trust and work with Ron 

[00:14:45] - Ray Stark calling Brian and threatening him over their mermaid movie

[00:16:37] - Keeping their creative spark alive as their business scaled and matured 

[00:20:20] - Principals like the universality concept that they return to most commonly 

[00:23:24] - Seemingly bottomless wells of inspiration that they both pull from

[00:26:18] - Curiosity precedes innovation and the curiosity conversations Brian has

[00:30:15] - The pitch format Brian uses to try and secure a guest for a curiosity talk

[00:32:16] - The role of engaging with conversations or ideas Brian disagrees with 

[00:33:56] - How curiosity shapes the nitty gritty of Ron’s directing and producing 

[00:37:41] - The biggest mistakes they’ve come across that people make telling stories

[00:40:27] - Pinpointing the defining moments of their careers outside of the obvious wins

[00:44:27] - Thoughts about how the industry has changed across their careers

[00:47:19] - How they’ve gotten better at taking a project from nothing to the finish line 

[00:49:53] - The kindest things anyone has ever done for them  

Nov 22, 2022

Today’s episode is a special one, in a format that may turn into a series. It is a conversation between Ravi Gupta and Shane Battier. Ravi is a partner at Sequoia, one of our most popular past guests, and a good friend. Shane is Ravi’s friend, and one of the most successful basketball players ever, having won championships and awards at the high school, college, and NBA levels.

 

I spent 10 years as a purely quantitative investor, so naturally I was obsessed with data in sports. When I was meeting with prospective investors, Michael Lewis’s book Moneyball—which chronicled the data analytics revolution in baseball—was my go-to analogy to explain what I did… “Moneyball, but for investing.” I used that line for years.

 

I’ve learned firsthand that it’s wise to follow your curiosity, no matter how strange or different it may be. The podcast is my curiosity tour, and years ago it led me to Sam Hinkie—who is himself on the Mt. Rushmore of analytics in sports. Sam introduced me to Ravi. Then Ravi sent me Michael Lewis’ article written about Shane called “The No Stats All-Star.” I highly recommend you read it.

 

All this serendipity around friends, data, investing, and sports gave me an idea: why not ask Ravi to interview Shane? There were so many valuable ideas in the Michael Lewis article, I thought we’d get even more in a real taped interview with someone that knew Shane well, and that’s exactly what happened. Ravi likes the idea of playing for the front of the jersey, not the back. It is hard to imagine someone that lived that more than Shane. Shane shares his story, lessons learned from various coaches, and using data as an advantage. He also explains the four kinds of teams he’s encountered, which I found simple, and memorable.  I hope you enjoy this great conversation, and if you have ideas for other iconic duos we could bring on in a similar format, DM me on Twitter. Thanks to Ravi and Shane for kicking off Thanksgiving week for us all.

 

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

 

-----

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:03:53] - [First question] - What people measure in basketball, what matters when it comes to winning, and why he was called a replaceable cog in the No-Stats All-Star

[00:08:38] - Some of the plays that impact the overall points during a basketball game

[00:11:44] - The role that preparation and understanding game analytics plays in the ability to do something different and succeed at it

[00:14:33] - The power of curiosity and obsessing over details

[00:16:16] - Embracing his role and how being a role player applies to life outside of the court

[00:20:47] - Where his obsession for winning and being a good team mate comes from 

[00:23:23] - Some of the things great leaders and coaches did to inspire him 

[00:28:51] - An overview of the four types of teams and fundamental aspects of them

[00:34:50] - What a person can do to elevate their team and make it a winning one 

[00:37:43] - Antifragility and the letter Shane wrote for Ravi when Amazon bought Whole Foods

[00:41:08] - Riding the thin line between winning a championship and being irrelevant 

[00:44:56] - How to get everyone rallied around a long-term shared mission effectively  

[00:46:48] - Finding a No-Stats All-Star in a company and what to look for in one

[00:52:34] - The kindest thing anyone has ever done for him

Nov 15, 2022

My guest today is Parker Conrad, co-founder and CEO of Rippling. I wanted to speak to Parker because he is building Rippling in a way that we don’t come across often. Rather than focus narrowly on one product, he is building a suite of interrelated products simultaneously to carry out the functions of HR, Finance, and IT for companies. He calls it a compound company and we discuss the idea, as well as some of his other non-traditional theories, in detail. Please enjoy this conversation with Parker Conrad.

 

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

 

-----

 

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

[00:02:36] - [First question] - Overview of what a compound startup is 

[00:06:32] - What he’s learned about picking customers effectively 

[00:08:48] - Key chapters when it comes to building a compound startup 

[00:13:48] - What great looks like at the base level infrastructure of employee data

[00:20:15] - His overall philosophy on product development writ large 

[00:25:09] - His role as a capital allocator and distributing resources to his teams

[00:27:19] - The amount of products they offer and whether or not there’s a tradeoff between time, cost, and quality when building software

[00:31:36] - Possibly incorporating an app-like store on top of their existing infrastructure 

[00:34:43] - Speed and the kinds of people that can sustain it for long periods of time

[00:36:30] - What motivates him on a personal level and harnessing motivation in general

[00:42:31] - Whether or not there’s an end to feeling hurt by false public perceptions when building in public

[00:44:12] - The intersection of leadership and communication inside of a business and what he’s learned about great communication 

[00:48:00] - The paradox of how focusing on non-scalable actions perpetuates growth and productivity and his views on productivity-per-person

[00:50:36] - The best example of a moment that required the most grit and perseverance while building his company 

[00:52:28] - How to successfully get former founders to come work for him 

[00:54:47] - What good private equity investors do 

[00:58:31] - The kindest thing anyone has ever done for him

Nov 8, 2022

My guest today is Bob Elliott, the CEO and CIO of Unlimited, which creates low-cost index ETFs for alternative investment strategies. Prior to co-founding Unlimited, Bob was a senior investment executive at Bridgewater Associates where he served on their investment committee and led Ray Dalio’s personal research team for a decade. His breadth and depth of experience makes him a great person to assess the current macro landscape. We discuss the relationship between rates, inflation, and asset classes, Bob's approach to identifying data with the most signal, and finish with his view on quantitative strategies in private markets. Please enjoy this great discussion with Bob Elliott.

 

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

 

-----

 

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

[00:02:45] - [First question] - The Economic Organization of a POW Camp and key lessons one can learn from the paper

[00:07:22] - The way that supply and demand clears a price and how that plays into his thinking about investing across asset classes 

[00:09:58] - Whether or not he has a generalized investing worldview or framework

[00:11:46] - Deciding on what data is signal and matters most when analyzing markets 

[00:15:46] - A crash course on easy money and tight money regimes and the implications of both in a macro environment 

[00:20:28] - The rise and role of inflation and what should be done about it

[00:24:00] - What the next couple of years will look like if we draw lessons from history

[00:30:12] - Why gold could ever belong in someone's portfolio when it doesn’t produce or yield anything back to the investor 

[00:35:08] - Supply and demand constraints and the state of the housing market today 

[00:40:42] - What might happen in future labor markets given our current macro environment

[00:46:27] - Currencies, energy, geopolitics, and what he’s most focused on globally

[00:52:19] - What movements in the charts are worrying him the most 

[00:56:04] - The original “All Weather” portfolio and what one would look like if he built it today

[01:02:05] - How his career has taught him to find talented individuals who might deliver alpha

[01:07:19] - Lessons learned from early-stage and venture investing and thoughts on that world now

[01:12:41] - Why there hasn’t been an iconic early-stage technology investing firm driven by systematic strategies

[01:16:10] - The kindest thing anyone has ever done for him 

Nov 1, 2022

My guest today is Kirsten Green, founder and managing partner at Forerunner Ventures. Kirsten launched Forerunner in 2012 and has built it into a leading consumer-focused venture firm with early investments in consumer brands like Dollar Shave Club, Bonobos, Faire, and Warby Parker. Our conversation is an exploration of consumer behavior and how to invest behind change in our society. We also discuss frameworks for identifying brands early, how to build deal flow, and the shift in power between buyers and sellers. Please enjoy my conversation with Kirsten Green.

 

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

 

-----

 

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] - The insights gleaned from studying consumers in the modern era

[00:07:02] - Whether or not the shift in consumer behavior is similar to a platform shift like mobile

[00:09:58] - Which of her hypothesis going into the research was proven most wrong

[00:11:31] - The leading persona archetype that drives consumer spending 

[00:13:58] - Thoughts about her investing focus after doing all of this research 

[00:16:23] - How much the digital world is good and bad for community

[00:18:50] - Positive and negative impacts digital access has on children

[00:21:17] - The investing criteria that she and her firm have developed for founders and business models they find desirable 

[00:29:20] - An example of the middle of the spectrum between tailwinds and headwinds that may result in them passing on a business

[00:32:00] - The beachhead problem for entry points, encouraging good focus and entry point selection, and who’s done it well 

[00:35:33] - The history of the consumer of how they buy and sell and where the shifts in power have been 

[00:39:47] - Other interesting trends she’s seeing in the seller empowerment era

[00:43:35] - How different her investing models are for linear product businesses

[00:46:45] - Frameworks she’s developed for evaluating a brand early on 

[00:49:57] - The most defining moment in Forerunner’s history and the hardest lesson she’s had to learn 

[00:53:13] - Ways she’s fostered and mentored young investors at Forerunner 

[00:54:04] - What the most underappreciated thing is today about the consumer

[00:54:50] - User and customer development strategies that work well for early stage products

[00:56:26] - Three businesses young investors should study to educate themselves on great consumer businesses; Shoe Dog

[00:59:49] - Where they find the companies Forerunner tends to invest in, and how to build and effective deal flow pipeline 

[01:05:07] - The kindest thing anyone has ever done for her

Oct 25, 2022

My guest today is Jason Droege, a venture partner at Benchmark. Jason’s had a long entrepreneurial career, which most recently culminated in building and leading Uber Eats. He joined Uber in 2014 with a blank piece of paper to grow the business beyond ride sharing. Within six years, he found product market fit with food delivery, refined the service, and scaled Uber Eats to a global $20 billion GMV run rate. Our conversation pulls out the most important lessons learned during that period and how Jason now employs them in his role at Benchmark. Please enjoy this great conversation with Jason Droege.

 

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. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

 

-----

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:02:52] - [First question] - What it was like at a high level building Uber Eats

[00:07:38] - How he would structure entrepreneurial incentives on a platform like Uber for a new leader or team attempting to build on top of it

[00:10:17] - What he learned about selecting competitive frontiers and mistakes made while building Uber Eats

[00:15:17] - Things that Uber Eats got most right that he’s proud of 

[00:18:16] - Constructive mistakes that taught him a lot from his time with Uber Eats

[00:20:36] - What made India such a competitive environment 

[00:22:50] - Building a business with an uncertain end state of unit economics 

[00:26:13] - What improved the most in his playbook for launching in a new city

[00:27:14] - Defining what best means in this competitive sector  

[00:29:01] - Dealing with suppliers in different categories and finding an ideal balance

[00:32:09] - When monogamy between the buyer and supplier matters and when it doesn’t in a marketplace 

[00:33:29] - Other attributes of a marketplace he’d pay special attention to as an investor given what he’s learned building one

[00:36:12] - Defining what founder market fit is and being “fingertippy”

[00:37:29] - His views on the relationships between leaders of businesses and their cultures

[00:40:26] - Why Uber believed in him more than he did 

[00:41:40] - What he learned about marketing to suppliers specifically 

[00:43:44] - Find new businesses by looking for areas that technology hasn’t yet affected

[00:45:18] - Differing views he has on the concept of failure  

[00:47:31] - Thoughts about ideas versus execution and the relative importance of the two

[00:49:10] - Effectively measuring opportunity cost and using it in decision making  

[00:51:14] - What it’s like being inside of a consumer business that people have so many opinions about

[00:56:30] - How he would describe the landscape and state of the market he was in from a higher viewpoint today

[00:58:56] - The most interesting things he’s learned from his time as a partner at Benchmark

[01:00:15] - The kindest thing anyone has ever done for him

Oct 18, 2022

My guest today is Paul Orfalea. Paul founded Kinkos, the popular copy chain, in 1970. He started with a single photocopy shop in California and grew the business into a $2 billion multinational operation over the course of his 30 years in charge. Paul is a non-traditional leader in the best sense and we discuss his philosophy of business building, from why your subordinates should frustrate you, why you shouldn’t love your business and tips he learned on hiring well. Please enjoy this conversation with Paul Orfalea. 

 

Founders podcast on Paul Orfalea.

 

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. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/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

[00:02:58] - [First question] - What it was like to be a very bad student in highschool

[00:04:22] - When he first realized he was unemployable

[00:05:02] - The origin story of the very first Kinko’s

[00:06:13] - What the ideal progression of an entrepreneur is in his mind 

[00:06:57] - Recognizing real customer problems and what he enjoys most about sales

[00:07:53] - Finding what has worked well in each Kinko’s and coaching managers

[00:08:54] - Something he found that a manager was doing that blew him away

[00:10:22] - Getting messages from his brain to everyone else in the Kinko’s network 

[00:11:45] - The difference of working on and not in the business

[00:13:22] - What he got better at when it came to managing people 

[00:13:57] - Why a good salesperson will sell you broke  

[00:14:41] - Disagreeableness as a positive characteristic for people in business

[00:15:08] - Whether or not candor is different from disagreeableness

[00:15:36] - Why he teaches, what he teaches, and his teaching style

[00:18:31] - Explaining the Federal Reserve in two minutes  

[00:19:47] - What students most commonly want from him  

[00:20:06] - Whether or not making yourself inaccessible as a leader is good for promoting a self-starter attitude amongst team members 

[00:21:39] - The story about tearing down a sign that was antagonistic to a customer

[00:21:58] - The role of anger in his career and something he’s worked on over time

[00:22:31] - Where Kinko’s falls on the spectrum of bad to great businesses

[00:24:09] - Characteristics he’d look for in founders to back a business early

[00:25:08] - Qualities of a business he’d cultivate more or less if he could start over

[00:26:18] - Lessons learned about using the word employee

[00:26:42] - His strategy for where to go next once he had his original concept

[00:27:21] - The most clever marketing strategy he ever deployed or designed

[00:27:45] - Learning to spread the glory instead of the money  

[00:28:30] - The state of entrepreneurship today compared to when he started 

[00:29:50] - How he instilled frugality and the saving mentality in the business 

[00:30:42] - What motivated him across his career

[00:31:35] - Why being in it for the money seems odd in today’s lens

[00:32:34] - Who he most admired or most admires today 

[00:32:51] - Let My People Go Surfing: The Education of a Reluctant Businessman

[00:33:08] - Preserving the alignment of integrity and action 

[00:33:42] - What it felt like to sell a business he’d worked so hard on 

[00:34:57] - How good he is naturally with numbers and math being dyslexic 

[00:37:17] - Defining success as having your adult children want to hang out with you and what stood out about his parents to him 

[00:38:05] - His parents’ impression of him while he was building Kinko’s 

[00:38:34] - What has his interest and keeps his interest most 

[00:39:56] - The most interesting person he’s ever worked with at Kinko’s

[00:40:48] - What he would have done differently if he started from scratch

[00:41:24] - Something that is most underappreciated about the United States 

[00:43:00] - The kindest thing anyone has ever done for him 

[00:43:57] - A big lesson he’s earned in a deeper way that he wishes he could share with others

Oct 11, 2022

My guest today is Madhavan Ramanujam. Madhavan quite literally wrote the book on how to price products, it’s called “Monetizing Innovations” and his concepts have been used by companies across the world like Porsche, Uber, LinkedIn, and SuperHuman. Our conversation is a masterclass on pricing. We discuss common mistakes when pricing products, why you need to focus on benefits rather than features, and how to pick the right monetization model. Please enjoy my conversation with Madhavan Ramanujam.

 

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. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. 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

[00:02:48] - [First question] - How he arrived at a radically different way of building products

[00:05:07] - An example of coming up with a price before the product

[00:08:35] - Distinctions between a willingness to pay and positive feedback 

[00:10:29] - How to make sure you’re talking to the right potential customer in the first place

[00:13:32] - Productizing for different customer segments 

[00:16:16] - Questions companies should be asking to get accurate feedback

[00:21:18] - What he’s learned about the motivations of potential buyers

[00:22:43] - What leaders, killers, and fillers are

[00:24:37] - Some of the biggest mistakes companies make while following his formula

[00:25:35] - A rule of thumb for what is a benefit versus a feature

[00:27:35] - Five distinct pricing models for charging a customer

[00:30:46] - Whether or not the value piece of all of this revolves around time and money

[00:33:27] - What he tells entrepreneurs about pricing their products that most surprises them 

[00:35:16] - Defining the first four categories of failure 

[00:40:13] - Reasons why so many innovations fail to monetize and pricing being a CEO topic

[00:41:51] - Good rules that leaders can use to have a general sense for effective pricing 

[00:47:38] - Behavioral changes and observations as the absolute price move up and down 

[00:50:36] - Is there a pricing genius we should take note of?

[00:53:18] - The single question every leader should ask themselves

[00:53:46] - The kindest thing anyone has ever done for him

Oct 4, 2022

My guest today is Scott Wilson. Scott is the CIO of Washington University’s endowment, which manages over $13 billion. In this conversation we discuss WashU’s non-traditional endowment model and cover a variety of asset classes and geographies. We talk about the qualities Scott looks for in managers, lessons from investing in Asia and emerging markets, and red flags in the venture space. Please enjoy this conversation with Scott Wilson.

 

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. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. 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

[00:02:38] - [First question] - What he learned about markets from quant fixed income trading 

[00:04:42] - How his experience shaped his degree of skepticism of the world

[00:05:15] - The story that brought him to Grinnell College 

[00:06:45] - What his education was like back in 2010 and what seemed sensible and insane when he arrived

[00:08:05] - The style of investment he learned at Grinnell compared to his style now

[00:09:37] - His philosophy around trying to have more direct ownership

[00:11:00] - Why their co-investment approach is outperforming the rest 

[00:12:03] - Lessons learned about choosing good partners and doing it effectively over time

[00:13:51] - Things that are most enjoyable about getting to know new managers 

[00:14:25] - The role that global travel and having boots on the ground plays in his success

[00:16:17] - Why they spend so much time in frontier and emerging markets

[00:18:21] - Lessons learned from investing in China and thoughts on it today 

[00:20:10] - What else he’s learned in continental Asia outside of China

[00:21:02] - Interests and red flags when it comes to investing in the venture space

[00:23:16] - The worst things he sees from venture investors 

[00:24:39] - Whether or not venture investors should care more 

[00:26:16] - The virtues and vices in private equity and his thoughts on that space

[00:27:55] - What percentage of investors in private equity are investors versus just involved to try and engineer returns

[00:28:59] - His impressions on hedge funds and the evolution of the hedge fund model

[00:31:18] - The role that credit can play in a portfolio like the one he manages now 

[00:33:10] - Common characteristics of managers that perform well in credit 

[00:34:20] - How he thinks about the sources of returns in the “other” portfolio category 

[00:36:34] - Everything he’s learned about asset managers acting as asset gatherers

[00:39:35] - Ways he fights convergence and tracking error overseeing so much capital 

[00:41:49] - What it’s like to go through the bad side of tracking error

[00:44:27] - Thoughts on how the macro environment influences allocating time and resources

[00:45:43] - What he sees as a normal level of tracking error for endowments and foundations

[00:46:59] - Why such big pools of institutional capital tend to look so similar 

[00:48:10] - Whether or not real estate sits somewhere between stocks and bonds

[00:49:07] - The cultivation of a talented investment team and effectively teaching investing 

[00:51:10] - Colliding managers in a fun and spirited way at meetings 

[00:52:16] - An investing trip from his career that he finds most memorable

[00:53:34] - Whether or not the factors that sort winners from losers will be different today compared to a decade ago

[00:52:50] - The kindest thing anyone has ever done for him

Sep 27, 2022

My guests today are Julio Vasconcellos and Mate Pencz, who are partners at Canary and Atlantico, leading early-stage investment firms in Latin America. They’re also both successful entrepreneurs. Mate is the co-founder and CEO of Brazilian real estate unicorn, Loft. Julio was Facebook’s first country lead for Brazil, an entrepreneur in residence at Benchmark, and the former founder of Peixe Urbano which sold to Baidu. This conversation was a great opportunity to dive into the state of investing and business in Latin America today, what it looks like on the ground, and cover the most interesting findings from Atlantico's annual report on Digital Transformation in the region. Please enjoy my conversation with Julio and Mate.

 

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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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

[00:02:39] - [First question] - A broad perspective on what is interesting in Latin American investing today - Latin America Digital Report 2022

[00:05:15] - What makes up the existing 1.5% tech penetration index in Lat Am

[00:06:11] - Florian Hagenbuch, Mate Pencz - Everything Will be Bought Online (Loft); David Velez - Building the Branchless Network (Nubank); How important it is to parse by country when it comes to building businesses in LatAm 

[00:08:31] - Overview of LatAm as a microcosm of fintech innovation happening really fast and what is most exciting in that sphere 

[00:12:28] - Why the adoption of PIX was so successful and how it maps onto the banking system

[00:14:27] - What PIX’s widespread adoption will enable for the coming wave of entrepreneurs 

[00:18:30] - Demographics, GDP, growth rates, and inequality in LatAm

[00:22:30] - Shifting to remote work and how it’ll affect LatAm workers and talent

[00:25:25] - Macro tailwinds that matter when it comes to returns in these markes

[00:30:06] - What it feels like for an entrepreneur today compared to when Loft launched 

[00:32:36] - Deeper themes and what needs to be unlocked for LatAm’s tech sector to look more like the US or China with big tech giants 

[00:37:04] - The opportunity set in developing a software that serves small and medium businesses in LatAm

[00:40:12] - Sources of available funding for venture and private equity  

[00:42:54] - What valuations look like and whether or not there’s an entry multiple discount

[00:45:12] - Seeking evidence that crypto is used in more valuable ways in emerging markets 

[00:48:00] - Areas where LatAm is operating in a future state more so than elsewhere

[00:50:28] - What the right amount of global firm participation in capital partnerships looks like

[00:52:38] - Big standout lessons from their operating days 

[00:55:53] - What is most exciting and concerning about their investing style and investing writ large in LatAm 

[00:58:51] - The kindest thing anyone has ever done for Julio

Sep 20, 2022

My guest today is Trina Spear, a former investor at Blackstone and the co-founder and CEO of FIGS. FIGS is a multi-billion-dollar public company that built a category-leading brand selling scrubs to healthcare professionals. It was a problem hiding in plain sight and FIGS solved it through vertical integration and customer obsession. Trina shares so many interesting, simple lessons that are often ignored in business. Please enjoy my great conversation with Trina Spear.

 

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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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

[00:02:28] - [First question] - The original insight that lead to founding FIGS

[00:04:28] - Why obvious opportunities can go so long before being seized 

[00:06:23] - Key dimensions needed to improve the product and the early days 

[00:09:02] - Basic overview of a clothing retailer’s financial profile

[00:10:49] - Financing the business and the early stage cash flow cycle 

[00:13:04] - Strategies to manage workflow and making sacrifices

[00:14:43] - Advice for people trying to build their brands in a hands-on way 

[00:17:14] - The biggest calculated risk she took in the first five years

[00:19:00] - Building a foundation that allowed for such explosive growth

[00:21:44] - The story that allowed FIGS to connect with their customers

[00:24:43] - Painting a picture of the size and scope of healthcare apparel

[00:26:22] - Things lazy companies do and thoughts on product variety

[00:28:54] - Defining SKU productivity and what to do with low productivity products 

[00:30:21] - Chip Wilson Book; Lessons learned from reading Chip’s story

[00:31:58] - Balancing a healthy relationship with your CFO

[00:33:59] - Where she sees the most runway to tackle and continue to execute

[00:35:46] - A women-lead industry and her time spent with Meg Whitman

[00:38:13] - The most essential jobs she feels she has and shouldn’t do as the CEO

[00:40:03] - Thoughts about relationships with investors and messaging 

[00:42:14] - What she’d be most focus on in founders if she was just an investor 

[00:43:57] - The most stressful thing that has ever come across her desk 

[00:44:41] - What types of things bring her the most joy in building FIGS

[00:45:27] - Philosophy of hiring given their small team and when it’s okay to hire

[00:46:56] - Whether or not there’s a role for non A players in businesses

[00:47:48] - The kindest thing anyone has ever done for her

Sep 15, 2022

Today, we are sharing an episode of Web3 Breakdowns with you. My Invest Like the Best conversation with Gabe Leydon last year was one of my favorites and became one of our most popular. Since that conversation, Gabe has become one of the most interesting builders in web3 that I know so I was excited to have him back to share his views of the space and how it might grow. If you enjoy this episode, subscribe to Web3 Breakdowns on your preferred podcast player.

 

My guest today is Gabe Leydon, who’s episode last year was one of our most popular ever. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I know. He was the co-founder of Machine Zone, which pioneered free-to-play hits like Mobile Strike and Game of War. Over the past year, he has been in stealth mode building a web2 meets web3 video game company called Limit Break, which is founded on a brand new business model that he calls free-to-own. We dive into his vision for the future of gaming, how it could onboard a billion users onto the Ethereum network, and why the LTVs of crypto gamers are so far higher than their web2 counterparts. Please enjoy this conversation with Gabe Leydon.

 

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 Coinbase Prime. Coinbase Prime combines advanced trading, battle-tested custody, financing, and prime services in a single solution. Clients have used our comprehensive investing platform to execute some of the largest trades in the industry because they are the only publicly-traded company with experience trading and custodying crypto assets at scale. Get started with Coinbase Prime today at coinbase.com/prime.

 

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Web3 Breakdowns is a property of Colossus, LLC. For more episodes of Web3 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: @Web3Breakdowns | @ericgoldenx | @patrick_oshag 

 

Show Notes

[00:02:19] - [First question] - What free-to-own gaming means and why it’s exciting 

[00:11:40] - Pre-existing behavior that sets up free-to-own for success

[00:12:32] - The progression from PFP NFTs to clubs and the road ahead

[00:14:16] - Overview of the business and monetization model for free-to-own games

[00:17:51] - The story of DigiDaigaku, their mechanics, the drops, and what lead to their creation

[00:22:14] - Balancing supply and demand in a free-to-own market

[00:24:35] - Creativity and extensions of the DigiDaigaku NFTs

[00:26:13] - Tiering, breeding and the role the Genesis series will play in the Digi universe

[00:27:32] - The level of brand marketing NFTs will unlock for businesses

[00:29:57] - How free-to-own will be the primary monetization method for brands

[00:31:21] - A future with a global marketing shift towards digital property and economies

[00:33:06] - Why most of the winning PFP projects are of unique characters

[00:35:50] - His Twitter strategy and how he’s created such a fervor around him

[00:42:40] - What will define the legendary marketers over the coming decade 

[00:43:06] - Interoperability needed to make real-world NFT uses appealing to consumers 

[00:44:44] - Whether or not we’ll see more token-gated business in the future 

[00:45:40] - Stable Diffusion and his impression of the new AI art generating bots

[00:48:56] - What great distribution looks like in a digitally native world

[00:50:03] - The emphasis of innovation taking place in the metaverse being a bad thing

[00:53:24] - Things he most admires in adjacent games and creators in his world

[00:54:25] - Unique game mechanics that Web3 technology unlocks 

[00:56:16] - NFTs will be the gateway for people to acquire crypto

Sep 13, 2022

My guest today is Harley Finkelstein. Harley is the President of Shopify and has been with the company since its early years. He is a lawyer by training but an entrepreneur by calling and that is the focus of our discussion. We discuss the different dimensions of entrepreneurship and Shopify’s role in promoting it, as well as exploring the company’s transition to public markets, and what the last few years have been like. Please enjoy my discussion with Harley Finkelstein. 

 

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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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

[00:02:26] - [First question] - His interpretation and definition of a person’s life's work 

[00:05:50] - The story of the riverstone and the average polished executive 

[00:08:36] - The thing he can’t help but do; and focusing on our compulsions

[00:13:12] - How he would boil things down to the most simple entrepreneurial formula; Distilled

[00:16:38] - What is harder and easier about new business formation today 

[00:21:03] - The countervailing forces for small-to-medium business entrepreneurship 

[00:24:31] - What he’s learned about operationalizing ideas and mentor lessons

[00:29:08] - A piece of fortune cookie advice that he finds terrible

[00:30:49] - How Brands Grow; his philosophy on marketing & distribution  

[00:35:27] - The most effective distribution strategies he’s seen work in Shopify that might be portable to other businesses

[00:38:43] - What it was like getting their first app developer for the Shopify app store

[00:41:17] - The state of ecommerce today writ large and what trends are interesting 

[00:45:46] - Lessons learned about the digital places that people are buying 

[00:49:06] - What it’s been like as an executive working at a company that had their stock price explode over the pandemic 

[00:52:25] - Tips for communicating effectively with Wall Street

[00:54:14] - An investor that stands out in memory that really impressed him

[00:55:10] - Important aspects of his world that are worth mentioning 

[00:57:04] - Lessons learned about motivating people through DJing 

[00:59:12] - Whether or not reading the crowd can apply to business

[01:03:49] - The kindest thing anyone has ever done for him

Sep 6, 2022

My guest today is Mitch Lasky. Mitch is a partner at Benchmark and one of the leading figures in the video game industry. Over the last 30 years, he has built, led, and invested in a number of the best gaming companies in the world, including Activision, EA, Riot, Snapchat, and Discord. I couldn’t think of a better person to break down the anatomy of great gaming businesses and Mitch does not disappoint. His insights are remarkable. Please enjoy this excellent conversation with Mitch Lasky.

 

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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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] - Why there aren’t more famous gaming investors

[00:05:08] - The most important features of the modern gaming business model

[00:07:11] - Developing his aesthetic taste and investing decision skill

[00:08:03] - What makes a game fun 

[00:09:26] - How delivering a pleasurable active user experience differs from passive content and media

[00:11:09] - The developers of Doom being the first real modern video game company

[00:13:09] - Half-Life’s important role in the development of the gaming industry

[00:14:50] - The powerful notion of the platform-based publisher model

[00:17:54] - How some of the big game aggregators get started in the first place

[00:19:58] - What Riot can teach non-gaming businesses about business writ large

[00:21:10] - Ways that the change from physical games to downloads changed monetization

[00:25:19] - How to quantify an economic model in the new paradigm of superfan monetization

[00:28:27] - What the shift in gaming platforms has done to the business model

[00:31:47] - The impact of Apple’s privacy changes on gaming revenue

[00:34:11] - How the access to professional game engines and a lower friction environment will change the industry

[00:37:04] - Whether or not there is a step beyond mobile

[00:39:42] - Ways platforms like Twitch and Discord have influenced gaming

[00:42:26] - What he’s learned about games that allow them to seemingly exist forever

[00:45:17] - Signs of a healthy gaming community

[00:46:21] - The role of celebrities and influencers and generating retained audiences

[00:47:45] - Whether or not crypto will unlock new opportunities for in-game monetization 

[00:52:50] - Key categories of motivators that could replace a ponzi-style in-game inflation 

[00:54:36] - Contrasting League of Legends versus a Ready Player One style world

[00:58:22] - Emerging technologies and trends that may revolutionize the industry 

[01:00:29] - A future with further consolidation on distribution and power

[01:02:41] - The most genius game pattern he’s ever played

[01:04:44] - What attributes will define the great game investors in the coming decades

[01:06:59] - How much his experience lends itself to investing in other sectors

[01:11:07] - The kindest thing anyone has ever done for him

Aug 30, 2022

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

 

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

 

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

 

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

 

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

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:03:01] - [First question] - When he first fell in love with reading

[00:07:01] - What’s rooted in his own history that’s made him obsessive about studying history’s great entrepreneurs and founders - Founders Podcast

[00:10:34] - The first time he connected with someone as a positive role model that he was reading about 

[00:13:45] - How often obsession is apparent in the founders he’s studied across hundreds of biographies 

[00:18:08] - What is often behind obsession and how people listening can apply the lessons to their own lives

[00:22:45] - The dynamic and relationship between inspiration and perspiration 

[00:27:11] - Commonalities between the layers of leadership and support underneath founders

[00:31:52] - Where else he’s seen ego rear its head in good and bad ways 

[00:38:34] - How often do great founders break the law or enter gray areas of it 

[00:41:22] - The role constant learning and listening plays in success

[00:45:12] - Talking about how anything worth doing is worth doing to excess 

[00:52:18] - Describing the soul of founders and businesses

[00:58:39] - What he’s learned about all of these founders as it relates to marketing 

[01:04:38] - A common story that process is often art 

[01:08:10] - Who his idols are in podcasting specifically 

[01:14:55] - Major aspects of people he’s studied that haven’t been discussed yet

[01:19:55] - The kindest thing anyone has ever done for him

Aug 23, 2022

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

 

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

 

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

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:02:34] - [First question] - What the enterprise software market looks and feels like to him

[00:05:52] - Whether or not software is becoming a saturated market and what will drive demand over the coming decades

[00:09:42] - Bringing an engineering mindset to enterprise software investing and culture

[00:12:36] - A single change he made to a business that stands out most in memory

[00:14:33] - Qualities that are most critical in defining a good enterprise software company

[00:18:07] - How the profile of companies he’s bought has changed over the years

[00:20:33] - Categories of software he tends to gravitate towards 

[00:23:56] - Evolving his model for considering what multiple to pay for a business and thinking about p/e growth multiples 

[00:27:17] - Lessons learned about customer churn over his twenty two year career

[00:29:44] - Capital cycles and how much they truly impact the software world 

[00:31:53] - What elements of building Vista have most appealed to him over the years  

[00:34:31] - Changing their investment strategy as the world continues to change

[00:38:06] - The war for talent and what his senior team would debate most 

[00:40:01] - Biggest mistakes Vista has made and what they taught him

[00:41:09] - What has him most insecure or paranoid about the platform he’s built

[00:43:10] - The advice he’d give on having good relationships with LPs

[00:44:57] - The largest risk he or Vista has ever intentionally taken 

[00:46:15] - What he’s learned about having a winning negotiations and sales approach

[00:49:27] - Who he’d give all of his capital to outside of Vista

[00:50:06] - How he arrived at the themes he tends to be philanthropic towards

[00:53:08] - The work he does in the foster world

[00:54:49] - The kindest thing anyone has ever done for him

Aug 16, 2022

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

 

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

 

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

 

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

 

-----

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:02:42] - [First question] - The origin and overview of the term American Dynamism 

[00:05:01] - Why the shift to a move slow and make sure nothing breaks mentality

[00:07:31] - What about the American system today feels broken and stale 

[00:09:48] - Becoming a journalist at The Washington Post 

[00:11:35] - Describing the power landscape of media as it exists today  

[00:12:28] - Major categories of American Dynamism that matter most  

[00:14:29] - What matters more or less to her as an investor in  these categories 

[00:17:31] - Whether or not there’s anything fundamentally broken about our government

[00:19:36] - The Systems Bible; What excites her about aerospace and defense and what creates opportunity and demand in these sectors

[00:22:44] - Explanation of what it means when the factory is the product 

[00:23:47] - How much is flowing into aerospace and defense currently 

[00:26:01] - An overview of how lobbying works and who does it and why

[00:29:07] - Whether or not she considers these sectors from a bottom up perspective as in investor   

[00:30:32] - What other categories she feels pulled towards 

[00:33:09] - The biggest problems that currently exist in the K-12 school system 

[00:35:34] - Thoughts on how states are competing citizens and how it plays into American Dynamism

[00:37:34] - The role immigration will play in range of outcomes in these main categories 

[00:39:32] - Key takeaways about housing in light of American Dynamism  

[00:42:09] - Her interpretation of the chart that shows inflation in categories over time

[00:44:40] - How different the investing dynamics are in all of these categories and thoughts on valuation in this world 

[00:47:56] - Whether or not expected returns and risk profiles are different in this area 

[00:48:36] - The importance of effective a founder’s storytelling, knowledge and customer empathy

[00:49:55] - Overview of the anatomy of a great story  

[00:51:30] - The story she tells founders at this stage so establish a partnership 

[00:52:46] - The kindest thing that anyone has ever done for her

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.

 

-----

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:02:34] - [First question] - Why it’s important to keep the main thing the main thing

[00:04:59] - His first exposure to this idea; How Will You Measure Your Life

[00:07:50] - Thoughts on the conflict of the main thing for a business and a person

[00:11:45] - The most painful episode of enacting this philosophy at Instacart 

[00:16:13] - How this concept has manifested in his life as an investor at Sequoia 

[00:19:16] - Amazon’s 14 leadership principles vs. his concept of focus

[00:21:55] - What good main things share in common and their attributes; Frank Slootman Episode

[00:24:48] - Whether or not the feedback loop for things that work are very short 

[00:26:04] - The nature of joy and competitiveness in company culture 

[00:29:01] - How he assesses the depth that motivation runs through people and companies

[00:32:43] - Analysis of his own motivations in life 

[00:35:34] - Differences and shortcomings of virtuous and vicious motivators 

[00:37:15] - How to accurately figure out someones motivators in a short period of time

[00:40:22] - Being Demanding and Supportive; Why these words pair so well together

[00:45:55] - What he’s looking for in companies given all of the ideas discussed so far

[00:51:11] - How his ideology manifests inside of Sequoia 

[00:58:44] - What it’s like to mentor an apprentice and how to do it well

[01:02:40] - Adjusting behaviors to meet current markets where they’re at 

[01:06:13] - Defining what a great product is

[01:07:56] - What he did to turn around Instacart by narrowing their focus

[01:12:28] - The things that most drove the switchover at Instacart

[01:14:53] - The 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.

 

-----

 

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

 

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

 

-----

 

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

 

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

 

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

 

Follow us on Twitter: @patrick_oshag | @JoinColossus

 

Show Notes

[00:02:31] - [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

 

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

 

-----

 

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

 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, 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.

 

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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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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

[00:02:33] - [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.

 

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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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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

[00:02:35] - [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

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