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

Invest Like the Best with Patrick O'Shaughnessy Colossus

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

    James Reinhart – Lessons in Process Power – [Founder’s Field Guide, EP. 32]

    James Reinhart – Lessons in Process Power – [Founder’s Field Guide, EP. 32]

    My guest today is James Reinhart, founder, and CEO of thredUP, an online thrift marketplace. thredUP’s online store is distinct in the way the company touches every product, processing every piece of clothing at their own facilities instead of focusing solely on being a marketplace connecting buyers and sellers. We talk about the competitive advantages of building processing plants from the ground up, how James turned thredUP from having negative gross margins to very strong unit economics, and the future of retail more broadly. I hope you enjoy this conversation with James Reinhart.
     
    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 Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick."
    -----
     
    Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, 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
    [00:02:47] - [First question] - An overview of thredUP
    [00:03:44] - Origination of the idea
    [00:04:43] - Initial reactions to the concept
    [00:05:22] - Early days trying to acquire the first customers
    [00:07:32] - The evolution of their margins
    [00:11:04] - Providing convenience for the customer
    [00:13:01] - Lessons on working capital and inventory 
    [00:14:27] - How consumers use the money they receive within the platform
    [00:15:47] - The evolution of the operations of the business and scaling
    [00:20:20] - When it’s time to shift from human capital to automation
    [00:22:00] - The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time
    [00:22:39] - Competitive Advantage: Creating and Sustaining Superior Performance
    [00:23:15] - Removing the hurdles for acquiring more buyers 
    [00:27:19] - Convincing investors on this concept
    [00:30:44] - The most difficult time for him psychologically in creating the business
    [00:31:56] - How he thinks about capital allocation
    [00:32:12] - The Startup Way: How Modern Companies Use Entrepreneurial Management to Transform Culture and Drive Long-Term Growth
    [00:33:51] - Overview of the clothing landscape and what would surprise most people
    [00:38:00] - Expanding their business from here 
    [00:40:36] - Improving how the raw material is sourced for apparel
    [00:42:45] - The nature of work 
    [00:42:56] - Dustin Moskovitz Podcast Episode
    [00:49:04] - What he’s most excited about for the future
    [00:50:35] - Kindest thing anyone has done for him

    Andrew Sugrue - Investing in Paradigm Shifts - [Invest Like the Best, EP. 224]

    Andrew Sugrue - Investing in Paradigm Shifts - [Invest Like the Best, EP. 224]

    My guest today is Andrew Sugrue, co-founder, and partner at Avenir Growth Capital. Avenir is a growth equity firm focused on backing category-defining businesses. In our conversation, we cover Andrew’s investing career, what he learned from Julian Robertson, how counter-positioning could drive unique distribution, and the difference between good and bad growth. We also spend time examining the business model of two of Andrew’s portfolio businesses, SavageXFenty and Latch. There are so many great lessons for investors and operators to take away from Andrew. Please enjoy my conversation with Andrew Sugrue.
     
    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've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.
    ------
    This episode is brought to you by MIT Investment Management Company – MITIMCo, the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term. 
     
    MITIMCo is also searching for an exceptional new teammate to join their internal investment team. Visit mitimco.org to learn more – click “Join” to learn more about the Global Investor Role on MITIMCo’s team or and click “Emerging Managers” to learn more about their emerging manager activities.
    ------
    Invest Like the Best is a property of Colossus, Inc. 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
    [00:03:31] - [First question] - His journey leading up to his current firm
    [00:05:55] - Lessons learned from time spent with Julian Robinson
    [00:07:54] - The chip on his shoulder that helped keep him driven
    [00:08:40] - Transforming his early motivators into a sustainable career-long fuel
    [00:10:46] - The first things in mind when approaching a new business or person
    [00:14:00] - Analysis of Savage Lingerie and learning about how that sector operates 
    [00:20:27] - Amazon producing a one-hour special Savage infomercial 
    [00:23:16] - Lessons learned from Savage that can be applied to other direct to consumer brands
    [00:25:04] - Having a celebrity at the forefront of your brand
    [00:26:41] - Levers and overview of apparel company income statements and how they can shape the way you grow and operate the business
    [00:30:08] - Apparel companies always being tied to identity
    [00:31:03] - Analysis of Latch and learning about the relationship between hardware and software
    [00:33:40] - How Latch works and why you might need it
    [00:38:56] - Other businesses that may benefit from understanding the events that drive demand and using it as an opportunity for customer acquisition
    [00:40:12] - The concept of density of demand and the power behind it
    [00:41:33] - Other areas of operations density of demand could be applied 
    [00:44:11] - Shared components that unite Avenir’s portfolio companies 
    [00:46:14] - How he thinks about the world of private investment, having lived such a diverse career 
    [00:50:22] - Developing relationships growing such a concentrated portfolio
    [00:51:35] - Macro thoughts on the state of investing today
    [00:52:59] - Defining and identifying characteristics of bad growth
    [00:54:05] - The kindest thing an

    Alyssa Ravasio - Supply, Demand, and the Outdoors - [Founder’s Field Guide, EP. 31]

    Alyssa Ravasio - Supply, Demand, and the Outdoors - [Founder’s Field Guide, EP. 31]

    My guest today is Alyssa Ravasio, co-founder and CEO of Hipcamp, a platform to discover and book your next camping trip. I was excited for this conversation as it combines two of my favorite passions – the outdoors and internet marketplaces. In our discussion, we cover how Alyssa bootstrapped demand in the early days of Hipcamp, the importance of creating not just great experiences but magical ones, and the evolution of Hipcamp’s business model. After listening to this episode, I’m sure the first thing you’ll want to do is get outside in nature. Please enjoy my conversation with Alyssa Ravasio.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2 report at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.
     
    -----
    This episode is brought to you by DigitalOcean. DigitalOcean provides founders and creators with the platform they need to get their website and apps off the ground, all with low-bandwidth pricing to save them money over other cloud providers.
     
    If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders.
    -----
    Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, 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
    [00:02:57] - [First question] - The original insight that led to founding Hipcamp
    [00:06:15] - What she studied in college and primary lessons learned there
    [00:08:18] - Specific features of studying the internet that influenced her trajectory
    [00:10:14] - Deciding what to attack first when developing Hipcamp’s infrastructure
    [00:14:12] - Dimensions and market size of the outdoor industry
    [00:15:48] - Organizing fragmented data into a useable schema and data set
    [00:18:24] - What customers cared about most in the early days of Hipcamp
    [00:20:00] - Managing focus and liquidity of the initial marketplace
    [00:22:58] - Helping landowners manage the logistics of their property placements
    [00:25:16] - Liability insurance in the outdoor industry
    [00:27:35] - The biggest challenge faced in developing an outdoor marketplace
    [00:30:03] - Amplifying and accelerating naturally grooved distribution
    [00:32:32] - Identifying the top correlates of making magic happen
    [00:34:55] - An ideal future for Hipcamp five years from now
    [00:38:28] - What bad supply looks like and creating quality standards 
    [00:42:08] - Their business model and revenue stream
    [00:44:45] - Deciding on their take rate and the debate around booking fees
    [00:46:14] - Lessons learned along the way as a leader
    [00:47:42] - Unit economics from the host’s perspective
    [00:52:33] - The most interesting businesses built on top of Hipcamp
    [00:53:35] - Why is Hipcamp’s mission so important to her
    [00:57:11] - The kindest thing anyone has ever done for her

    Josh Buckley - Identifying Legendary Start-ups - [Invest Like the Best, EP. 223]

    Josh Buckley - Identifying Legendary Start-ups - [Invest Like the Best, EP. 223]

    My guest today is Josh Buckley. Josh is the new CEO of Product Hunt and an investor in many breakout companies like Rippling, Lattice, Boom Supersonic, and Relativity Space. In our conversation, we cover how video game companies are at the forefront of new business models, what current companies can learn from video game companies, Josh’s investing philosophy, and the three things he looks for when trying to identify the next legendary startup. Josh’s long experience operating his video game business, Mino Games, gives him such an interesting perspective as an investor, and I really enjoyed exploring that with him. Please enjoy my conversation with Josh Buckley.
     
    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've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.
    ------
    This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.
     
    With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more.
    ------
     
    Invest Like the Best is a property of Colossus, Inc. 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
    [00:03:56] - [First question] - His start as an entrepreneur in online game
    [00:05:09] - His parent's reaction to selling his first company at fifteen
    [00:05:57] - Starting a second video game company 
    [00:07:40] - The video game industry being ahead of the curve in performance marketing, distribution, and operations
    [00:08:49] - Notable two year lag between gaming innovation and other consumer sectors
    [00:10:50] - What is happening today in gaming that may be a glimpse into the future
    [00:12:41] - Key elements for creating a great gaming experience
    [00:15:29] - Building a meta game on top of the game itself to maximize engagement
    [00:17:23] - Monetizing free to play games through in-game purchases
    [00:20:25] - The most portable idea from fifteen years in gaming that can be applied to business
    [00:22:02] - A future shift towards usage-based pricing models
    [00:23:03] - His overall investment philosophy and strategy
    [00:26:45] - Example of small a market with a high growth rate
    [00:27:38] - Key elements of system elements and design when evaluating a business
    [00:31:07] - What a flywheel looks like and investing in one such as  Next Health 
    [00:33:24] - Working core actions versus giving credit ones that aren’t yet working but may drive desirable outcomes
    [00:34:13] - Why don’t more investing firms have a flywheel?
    [00:39:04] - Product Hunt as a standalone business and part of a self-reinforcing ecosystem
    [00:40:17] - Emerging systems and ecosystem edges in the digital landscape
    [00:42:17] - Potential barriers for crypto becoming widely adopted in a variety of ways
    [00:44:29] - New frontiers and platform shifts like crypto that may unlock new doors for companies
    [00:45:13] - Which person has rewired his brain in his lifetime the most
    [00:47:13] - Weirdness around Stripe and P

    Thomas Tull - New Physics of Business - [Founder’s Field Guide, EP. 30]

    Thomas Tull - New Physics of Business - [Founder’s Field Guide, EP. 30]

    My guest today is Thomas Tull, the founder of Tulco LLC, an investment holding company that invests in businesses with high growth potential and helps them apply machine learning and data analytics. Thomas is also the founder and former CEO of Legendary Entertainment, the production company behind the Dark Knight, Hangover, Inception, 300, and many more iconic movies which he sold in 2016. In our discussion, we cover the movie industry’s value chain, the recipe for trying to make a successful movie and how Legendary pioneered the use of data analytics to improve those odds, and Thomas’ concept of the new physics of business and why it matters for what he’s now building at Tulco. Please enjoy my conversation with Thomas Tull.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2 report at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.
    -----
    This episode is brought to you by DigitalOcean. DigitalOcean provides founders and creators with the platform they need to get their website and apps off the ground, all with low-bandwidth pricing to save them money over other cloud providers.
     
    If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders.
    -----
    Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, 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
    [00:03:06] - [First question] - His overarching career philosophy and theme
    [00:04:07] - Attacking a previously established industry in a new way
    [00:05:20] - The origin story of Legendary and stepping into the film industry
    [00:07:56] - Stakeholders involved in producing a movie and pre-existing profit pools when Legendary was founded
    [00:12:44] - Topline and downstream revenue distribution of intellectual property from then versus now
    [00:19:46] - Lessons learned about intellectual property writ large  
    [00:19:03] - What makes Chris Nolan such an exceptional storyteller
    [00:23:42] - Power and defensibility of cinematic universes and transmedia storytelling
    [00:22:21] - Applying quantitative data analysis to film production and marketing
    [00:25:55] - Competitive frontiers in movie studios and his advantageous skillset
    [00:28:10] - Potential investment opportunities in media or media adjacent businesses
    [00:29:26] - Interesting new tools that could be developed in entertainment technology
    [00:31:00] - His favorite mind-blowing and awe-inspiring movies
    [00:32:41] - Telling Jackie Robinson’s story in the film, 42
    [00:35:30] - Jackie Robinson and Chadwick Boseman’s quiet dignity
    [00:36:56] - Building the holding company Tulco 
    [00:39:02] - The new physics of business that can’t be ignored
    [00:42:40] - Modern velocity in the current era of business
    [00:46:03] - Interweaving an antifragile mindset into the company culture
    [00:47:55] - Who Tulco Labs is and what they do
    [00:49:12] - What gets him most excited about exploring a new business for the first time
    [00:50:48] - Unique characteristics he seeks out in a management team
    [00:52:31] - Trends that m

    Paul Enright - The Buy Side Primer - [Invest Like the Best, EP. 222]

    Paul Enright - The Buy Side Primer - [Invest Like the Best, EP. 222]

    My guest today is Paul Enright, managing partner at Krainos Capital, his family office. Before running his own family office, Paul worked on the buy-side at Viking Global for over a decade managing their consumer and technology portfolios and before that at Morgan Stanley on the sell-side.
     
    I thought Paul would be the perfect person to help me demystify the world of high finance – explaining the difference between the buy-side and sell-side, how long/shorts differ from long onlys, and walking through the various jobs in the investing world. In addition to setting that foundation, we also cover the evolution of the buy-side, what makes someone a great researcher verse a great stock picker, and various portfolio construction methodologies. Paul brings such a wealth of knowledge and experience to the table. I think this episode will be enjoyable for investing novices and professionals alike.
     
    Please enjoy my conversation with Paul Enright.
     
    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've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.
    ------
    This episode is brought to you by MIT Investment Management Company – also known as MITIMCo, the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term. MITIMCo doesn’t care how small, new, or un-institutional your firm is if you have the potential to generate amazing results that support MIT’s pursuit of world-class education, cutting-edge research, and groundbreaking innovation.
     
    Despite their willingness to invest early, they do not ask for GP economics, and they commit their initial capital for ten years.
     
    Visit www.mitimco.org and their new emerging managers page to learn more.
    ------
    Invest Like the Best is a property of Colossus, Inc. 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
    [00:03:39] - [First question] - His history in both the buy and sell side
    [00:05:20] - Different types of roles on the buy side and sell side
    [00:06:48] - Interest sets that best align with being a buyer or a seller
    [00:07:57] - The emotional experience of being on the buy side and exposed to risk
    [00:08:53] - How the nature of buying and portfolio construction has changed 
    [00:10;15] - What Regulation Fair Disclosure (Reg FD) is
    [00:12:46] - Key terminology and definitions of long-only and long-short funds
    [00:17:40] - Varying clusters of long-short funds and defining each type
    [00:21:48] - Differences in exposure between a platform model versus a traditional long-short stock picking sense
    [00:25:16] - Skill sets that are most important to have when navigating this space
    [00:29:03] - What is good and what is great when it comes to “digging”
    [00:31:20] - Why the quality of one’s analysis matters
    [00:33:10] - Having a potential edge when deciding based on someone else’s analysis
    [00:35:19] - Foundational building blocks of an effective pitch 
    [00:37:20] - Finding wrongly identified stocks and reaping the rewards
    [00:40:49] - Overview of good portfolio construction and lessons learned over the years
    [00:44:06] - Why hedge funds ten

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