283 episodes

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
    • 4.8 • 1.9K Ratings

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/

    Christina Cacioppo - Building the New Standard in Security – [Founder’s Field Guide, EP. 38]

    Christina Cacioppo - Building the New Standard in Security – [Founder’s Field Guide, EP. 38]

    My guest today is Christina Cacioppo, founder of Vanta, a security and compliance software business founded in 2017. In our conversation, Christina brings to life the idea of “finding a problem that exists and fixing it.” We dive into the experiences that led her to launch Vanta, the strategy she took to build, price, and distribute the product, and we touch on her lessons from running a growing organization. I always admire the drive that founders have when they set off to build something -- Christina fits that mold, and you will hear about how she embarked on a self-taught journey early in her career. I hope you enjoy my conversation with Christina.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.
     
    See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders.
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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
    [00:02:44] - [First question] - How she first found her interest in business
    [00:04:09] - Early days exploring business for the first time
    [00:07:09] - Lessons learned from USV that have been applied to Vanta
    [00:07:42] - The next stage of her learning journey after USV
    [00:09:20] - Making a massive pivot in life and teaching herself to code
    [00:10:53] - The four-year road that lead to building Vanta
    [00:12:39] - First encounters with the software security problem space
    [00:15:21] - Origins of SOC 2, what it means, and what it does
    [00:17:11] - What software security means writ large
    [00:19:32] - Who demands a SOC 2 and why
    [00:20:57] - How Vanta improved a broken process and productized it
    [00:23:33] - What V1 of Vanta looked like
    [00:26:30] - Understanding the value of using spreadsheets first
    [00:27:48] - From static to streaming and finding product-market fit
    [00:29:22] - Monitoring whether or not a company is SOC 2 compliant in real-time
    [00:32:19] - Auditors that still exist in the compliance space today
    [00:33:39] - The pace of onboarding new clients onto the Vanta software 
    [00:34:53] - Figuring out a price point for the service Vanta offers
    [00:37:06] - Developing the business model and scaling it
    [00:39:18] - Lessons learned and innovations created about effective sales organization
    [00:41:52] - Hardest hills to climb in building Vanta
    [00:43:17] - Building competitive advantage into the framework of the business
    [00:46:07] - Overview of the frontier of software security
    [00:47:43] - General thoughts on competitive advantage as a whole
    [00:49:43] - Quality control of decision making in Vanta
    [00:50:40] - Downstream effects of structural and organizational business design
    [00:52:30] - Hard lessons learned going from being academic to pragmatic
    [00:53:36] - What the future could look like for Vanta bas

    • 1 hr 3 min
    John Harris - Resilience and Imagination

    John Harris - Resilience and Imagination

    My guest today is John Harris, Managing Partner of Ruane, Cunniff & Goldfarb, where the flagship Sequoia Fund has an incredible 50-year track record running a highly concentrated portfolio of equities. In our conversation, we cover John’s approach to finding businesses that can be owned for the long-term, what goes into their diligence process, and the importance of resilience for investors. I think many of the stock pickers will enjoy many of the points on good management, good businesses, and using imagination. I hope you enjoy my conversation with John.
     
    For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.
    ------
    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.
     
    ------
    This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick.
     
    ------
    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
    [00:03:48] - [First question] - How markets undervalue long-duration growth of companies
    [00:07:21] - Why should one even do DCFs at all
    [00:10:01] - Defining homework when studying a business and what getting better as you do your homework tends to look like
    [00:12:24] - How the market still underestimates how the quality of a company reduces risk
    [00:15:09] - Reinvestment opportunity and risk and why they’re important for long term returns
    [00:17:14] - Lessons learned owning Google stock options for over a decade
    [00:22:02] - Skill versus luck when it comes to investing psychology
    [00:24:32] - Perspectives on big market cap companies in a portfolio when success often comes from smaller-cap non-linear growth 
    [00:26:47] - Features of the current market landscape that he finds interesting
    [00:31:24] - What buying behavior looks like in the demand side of the business equation
    [00:34:10] - Discovering a company that served the customer and was a delight to discover
    [00:37:58] - Analysing getting one's hands dirty to get a competitive advantage in serving the customer
    [00:39:24] - The hardest episode of his investing career and what he learned from it
    [00:43:03] - Reasons why a company succeeded after doing a deep dive but not buying in
    [00:43:54] - One of the CEOs he finds most remarkable
    [00:47:20] - Examples of businesses where scale isn’t the driver of competitive advantage
    [00:49:50] - A company they owned that did well but didn’t have the strongest company culture
    [00:50:56] - His view on the investment industry today writ large
    [00:52:16] - Ways investors could expand their imagination when analyzing businesses
    [00:53:07] - The kindest thing anyone has ever done for him

    • 59 min
    Florian Hagenbuch and Mate Pencz - Everything Will Be Bought Online – [Founder’s Field Guide, EP. 37]

    Florian Hagenbuch and Mate Pencz - Everything Will Be Bought Online – [Founder’s Field Guide, EP. 37]

    My guests today are Florian Hagenbuch and Mate Pencz, co-founders of Loft. Based in Sao Paulo, Brazil, Loft is a digital platform designed to bring Latin American real estate into the e-commerce age. The 3-year-old startup scaled to over $150mm in annualized revenue in 2020 and is on track for multiples higher this year. We dive into the market opportunity in Brazilian real estate and how that differs from the US market, the value proposition for iBuying across the US and Latin America ecosystems, and touch on the potential for Loft to expand from real estate into adjacent services such as mortgages. Florian and Mate are second-time founders and have some great lessons shared throughout the episode. Please enjoy my conversation with Florian and Mate.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.
     
    See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders.
    -----
    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
    [00:02:52] - [First question] - Why Latin America currently presents such a unique opportunity for modern technology companies
    [00:04:38] - What the market looked like when they started Loft
    [00:07:20] - How they approached gathering data that wasn’t available or accessible in order to develop the company infrastructure
    [00:09:39] - How the process of buying a home used to be in São Paulo versus today
    [00:12:19] - What Loft’s hard work unlocks for consumers and home buyers
    [00:14:06] - What iBuying feels like writ large and more specifically in real estate
    [00:18:07] - Analysis of an iBuying real estate transaction from start to finish
    [00:20:09] - The role machine learning plays in property valuation and building that feature  
    [00:22:50] - Defining their business model and being a fulfillment center aggregator 
    [00:24:47] - Notable characteristics of the iBuying market in the United States 
    [00:27:00] - How they think about the competitive advantage extensions of Loft 
    [00:29:53] - Exciting opportunities for the FinTech broadly in Latin America 
    [00:32:47] - Deciding on what it is they want to tackle next as they grow the company 
    [00:34:13] - Thinking about the value proposition to customers and how they market it 
    [00:35:50] - Lessons learned about building businesses early on that were applied to Loft
    [00:40:12] - What led them to finding their early product-market fit 
    [00:42:48] - Calibrating and defining their ambitions for Loft out of the gate 
    [00:45:05] - Important and interesting trends in the business world today writ large 
    [00:48:43] - Further lessons and key challenges around building and scaling Loft 
    [00:52:24] - The kindest things that anyone has ever done for them

    • 57 min
    Gabriel Leydon - Designing Digital Economies

    Gabriel Leydon - Designing Digital Economies

    My guest is Gabe Leydon, who is the co-founder and former CEO of MZ, also known as Machine Zone, the company behind huge games such as Mobile Strike and Game of War. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I have talked to in a long time. In our conversation, we cover why great design can be a bad sign that we’d run out of ways to innovate, the most important lessons from human psychology for building games and products, and why products which are busted or breaking but still booming can be great investment opportunities. This conversation rewired my brain on many levels, so I’m excited for you to listen. Take the red pill with us, and please enjoy my conversation with Gabe Leydon.
     
    For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.
    ------
    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.
    ------
    This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick.
    ------
    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
    [00:03:59] - [First question] - Thoughts on the importance of design and the role it plays in capitalism writ large
    [00:07:26] - Huxley’s vision of the future versus Orwell’s - Amusing Ourselves to Death
    [00:10:49] - A question about game design in interviews that no one can answer well
    [00:18:27] - What about his early experiences that allowed him to be good at answering that question when others could not
    [00:26:35] - Another example to further explain the nature of meta software design mechanics
    [00:29:44] - Characteristics of what drives players to spend money in games
    [00:34:46] - Defining heroic spending and the group dynamics of spending gamification
    [00:38:18] - Skill set required to design an economy and what makes it so difficult
    [00:41:27] - Cosmetic purchases as a revenue stream in North American video games
    [00:43:56] - What he’s learned about human psychology through his design work
    [00:45:48] - How the technological infrastructure developed in building video games overlap in performance marketing
    [00:48:44] - His experience with the RT platform and some of the technologies he’s built
    [00:55:49] - Celebrity NFTs and a shift to becoming virtual manufacturers in the future
    [00:59:58] - What businesses can do now to prepare for and adapt to NFTs
    [01:01:03] - Why we need AI more than think we might
    [01:04:32] - What he plans to do with his skillset if the world becomes increasingly gamified
    [01:05:40] - Companies with poor design may be indicative of an attractive acquisition
    [01:08:11] - How differing cultural perspectives on video game design permeate into NFTs
    [01:08:46] - Defining the Chinese item box appro

    • 1 hr 17 min
    Assaf Wand - Innovation in Static Industries – [Founder’s Field Guide, EP. 36]

    Assaf Wand - Innovation in Static Industries – [Founder’s Field Guide, EP. 36]

    My guest today is Assaf Wand, CEO, and co-founder of Hippo, a homeowner insurance startup founded in 2015. In March 2021, Hippo announced a SPAC merger, valuing the business at over $5bn. In our discussion, we cover how Hippo approached innovation in the highly regulated insurance industry, unique strategies for building brand trust, and how direct relationships with homeowners has opened up Hippo's business model to a wide range of opportunities. I was excited to speak with Assaf, given his experience as a serial entrepreneur, and he did not disappoint. Please enjoy my conversation with Assaf Wand.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
    This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.
     
    See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders.
    -----
    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
    [00:02:44] - [First question] - His philosophy on business
    [00:04:04] - His first experience in entrepreneurship
    [00:05:03] - Lawyers vs entrepreneurs
    [00:07:03] - Major lessons taking risk in entrepreneurship
    [00:11:14] - Importance of speed in business
    [00:15:02] - Increasing urgency into the business as a leader
    [00:18:59] - What the insurance sector was like at the start of Hippo
    [00:24:49] - Steps he took to bootstrap trust
    [00:27:03] - Convincing partners
    [00:29:04] - Building the products and distribution
    [00:32:49] - Thoughts on innovators dilemma
    [00:35:00] - Flaws within the insurance industry
    [00:34:57] - Vision for the firm 
    [00:37:44] - Importance of culture in company building
    [00:41:19] - Storytelling as an essential piece of company building
    [00:41:50] - Building and managing a roadmap
    [00:43:19] - What does it mean to respect the customer
    [00:46:11] - Defensibility of the insurance industry
    [00:49:34] - Rewards of the trench warfare of entrepreneurship
    [00:53:33] - The feeling of getting wealthy 
    [00:55:29] - Kindest thing anyone has done for him

    • 57 min
    Dennis Lynch - Delivering Alpha in Adapting Markets

    Dennis Lynch - Delivering Alpha in Adapting Markets

    My guest today is Dennis Lynch, Head of Counterpoint Global, where he oversees over $100bn in AUM and boasts one of the strongest track records of any public investor. In our conversation, we cover Dennis's unique approach to building a research team, how misclassification of companies often creates the highest upside opportunities, and how Dennis has adapted his investment process over the past 20 years. I think Dennis defines what it means to be intellectually honest, and you will hear that in his answers throughout our discussion. I hope you enjoy my conversation with Dennis Lynch.
     
    For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.
     
    (for me-  )
     
    ------
    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.
     
    ------
    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
    [00:03:47] - [First question] - How he would teach potential students to be investors
    [00:04:26] - The Money Game
    [00:04:40] - Moneyball
    [00:05:59] - Pros and cons of volatility when investing
    [00:08:55] - Emotional response to volatility
    [00:12:44] - Training to have a better temperament
    [00:14:20] - What is his investing game
    [00:15:17] - The Ethical Algorithm
    [00:16:44] - How time horizon impacts their investment strategy
    [00:20:53] - Assessing a company’s earnings power
    [00:26:12] - Shifting business models vs. evolving within a business model
    [00:32:32] - Understanding how to invest in disruptive businesses
    [00:35:26] - Why he’s skeptical on Growth and Value investing strategies
    [00:38:42] - Expectations Investing
    [00:38:55] - How his view of assessing businesses has changed
    [00:43:56] - Defining unit economics
    [00:45:41] - Taking on uncertainty risk in the portfolio 
    [00:50:38] - The business that taught him the most; Amazon
    [00:53:32] - Dealing with massive amounts of change
    [00:56:01] - The Big Short
    [00:59:46] - Interest in psychedelic research
    [01:01:02] - What has changed the most in investing from when he started
    [01:04:19] - Kindest thing anyone has done for him

    • 1 hr 10 min

Customer Reviews

4.8 out of 5
1.9K Ratings

1.9K Ratings

malfoxley ,

Great Show!

Patrick, host of the Invest Like The Best podcast, highlights all aspects of investing and more in this can’t miss podcast! The host and expert guests offer insightful advice and information that is helpful to anyone that listens!

Carl from chicago ,

Great podcast for learning about SAAS

I listen to a wide variety of podcasts and this is one of the highest quality ones. I compare it to “how I built this” but with modern and up and coming companies which is a high compliment.

GosiaMB ,

The Best!

This is high quality content! So much knowledge shared with listeners. Thank you for all your efforts being the best in what you do!

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