381 episodes

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

Invest Like the Best with Patrick O'Shaughnessy Colossus

    • Investing

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

    Ron Howard and Brian Grazer - Box Office Business

    Ron Howard and Brian Grazer - Box Office Business

    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. 
     
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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
    [00:02:44] - [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  

    • 52 min
    Shane Battier - The No-Stats All-Star

    Shane Battier - The No-Stats All-Star

    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.
     
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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
    [00:03:53] - [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 play

    • 54 min
    Parker Conrad - Building a Compound Company

    Parker Conrad - Building a Compound Company

    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.
     
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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. 
     
    -----
     
    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

    • 1 hr
    Bob Elliott - A Macro Tour

    Bob Elliott - A Macro Tour

    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.
     
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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
    [00:02:45] - [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 

    • 1 hr 20 min
    Kirsten Green - Investing in Consumer Change

    Kirsten Green - Investing in Consumer Change

    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.
     
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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
    [00:02:35] - [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

    • 1 hr 9 min
    Jason Droege - Building Uber Eats

    Jason Droege - Building Uber Eats

    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.
     
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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.
     
    -----
     
    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 Ube

    • 1 hr 4 min

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