315 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/

    Sam Bankman-Fried - Creating a Perfect Market

    Sam Bankman-Fried - Creating a Perfect Market

    My guest today is Sam Bankman-Fried, founder and CEO of leading cryptocurrency exchange, FTX. In a little over two years, FTX has registered 1.2 million users, grown to facilitate $10.9 billion of daily trading volume, and reached an $18 billion valuation. Prior to FTX, Sam worked at Jane Street Capital before founding a quant trading firm of his own, Alameda Research. At just 29, Sam has packed a lot into a short period of time, and as I’m sure you’ll hear, he has a special ability to harness uncertainty and think deeply across a range of topics.
     
    In our discussion, we cover the building blocks of a perfect market, the key areas of inefficiency in today’s exchanges, and Sam’s north stars of product design and effective altruism. We also talk about fairness in crypto markets, how FTX thinks about user acquisition, and derivatives as key enablers of properly functioning markets.
     
    Please enjoy my great conversation with Sam Bankman-Fried.
     
    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 20,000 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 Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. 



    ------
     
    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
    [00:03:57] - [First question] - What motivates him and what the true north of his vision is
    [00:07:12] - Evaluating the impact of well-functioning markets and philanthropic spending
    [00:11:55] - The key functions and building blocks of a perfect market
    [00:14:59] - Who pays $50 million to access fiat market order books
    [00:21:49] - What is valuable about having access to order book data
    [00:25:41] - Assessing and understanding the state of fairness in crypto markets today
    [00:31:51] - Can crypto only move as fast as the fiat system keeps up
    [00:32:43] - The advantages and disadvantages of stablecoins and USDT
    [00:34:46] - How much fiat inflow there is into crypto markets and exchanges today 
    [00:37:36] - What it is about cryptocurrency exchanges that are so appealing to him 
    [00:42:21] - Building in a dynamic world and deciding the sequence of problems to solve
    [00:45:12] - Whether or not the US is on the wrong side of crypto and countries competing for healthy regulatory environments in this emerging asset class
    [00:47:25] - Thoughts on centralization and what being decentralized unlocks
    [00:50:22] - Why derivatives are such a key function of properly functioning markets
    [00:52:38] - The competitive landscape between derivatives and exchanges
    [00:54:35] - Spending marketing dollars and paid acquisitions for FTX
    [00:57:30] - The growing trend of user-generated content becoming user-generated as

    • 1 hr 14 min
    Nick Neuman - Becoming Your Own Bank

    Nick Neuman - Becoming Your Own Bank

    My guest today is Nick Neuman, CEO and co-founder of Casa. Casa helps bitcoin investors and owners keep their digital assets safe from loss or theft by providing managed self-custody services. In our discussion, we cover the history of asset custody from ancient temples to decentralized ledgers, look at the mechanics of how private keys work, and explore why people are better off holding the keys themselves. We then dive into the future of digital wallets as gateways into our virtual lives, what’s interesting about identity authentication more broadly, and whether these innovations may lead to unintended consequences. Please enjoy this great conversation with Nick Neuman.
     
    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 20,000 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 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".
     
    ------
     
    Invest Like the Best is a property of Colossus, Inc. 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
    [00:03:23] - [First question] - The history of asset custody
    [00:07:56] - What private keys are and their role in financial security 
    [00:12:21] - Overview of storing a token in a wallet and accessing with a private key 
    [00:15:28] - Thoughts on private keys through the lenses of convenience and safety
    [00:18:49] - Solving both self-custody of assets and peace of mind
    [00:21:39] - How the user experience will feel once self-custody is properly developed
    [00:24:11] - Why asset custody is so interesting and what a perfect scenario unlocks
    [00:27:05] - Is the DeFi ecosystem an early manifestation of a self-custody financial system 
    [00:28:57] - Ways Casa is planning to become a convenient and diverse platform for users
    [00:32:16] - The role wallets will play in the future of a digital world
    [00:34:56] - Forms of authentication that are most appealing in creating a seamless user experience
    [00:37:39] - Overview of what hardware wallets are and how they work
    [00:40:17] - Different security options that Casa offers from the simplest to the most secure
    [00:44:51] - How many crypto holders there are and how many use self-custody
    [00:47:31] - The craziest security set up around Bitcoin he’s ever heard of 
    [00:48:49] - What the most ideal outcome for Casa looks like in the coming decade 
    [00:51:26] - Thoughts on the competitive landscape and potential growth challenges 
    [00:53:07] - Important aspects of the crypto ecosystem other than security  
    [00:55:49] - How empowered people feel when they successfully adopt self-custody
    [00:57:13] - Whether or not there are ways that the current centralized system is more secure
    [00:59:5

    • 1 hr 3 min
    Devin Finzer - An Everything Store for Digital Assets - [Founder’s Field Guide, EP. 53]

    Devin Finzer - An Everything Store for Digital Assets - [Founder’s Field Guide, EP. 53]

    My guest today is Devin Finzer, co-founder and CEO of OpenSea, the world’s largest NFT marketplace. In a journey that started like many other founders in the space, Devin went deep down the crypto rabbit hole in 2017 and became particularly fascinated with the potential behind digital assets.
    During our conversation, we touch on the origin story of OpenSea, how Devin differentiates between the spectrum of NFTs in the market, and what he sees as the opportunity in the future for the industry. We also talk about the various risks within a blockchain, from security dynamics to market speculation. I hope you enjoy this great conversation with Devin Finzer.
    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 Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.
     
    -----
     
    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
    [00:02:56] - [First question] - When he first thought up the genesis of OpenSea
    [00:06:00] - What is listed on OpenSea, assets and volume, and the scope of the platform
    [00:07:26] - Thoughts on potentially becoming the current era “everything store”
    [00:09:22] - How they managed to become the main NFT trading platform
    [00:12:28] - What NFTs are, their various classes, and ways they’re stored on the blockchain
    [00:15:25] - How much transaction and auction volume happens on-chain
    [00:17:07] - Profile picture style NFTs and what’s exciting about them
    [00:19:24] - ArtBlocks and the mass interest in AI-generated art
    [00:21:22] - What he’s learned and seen about the emerging crypto gaming space
    [00:24:38] - The user experience of buying an NFT on OpenSea
    [00:26:45] - How the ownership transfer works between wallets
    [00:28:04] - Whether or not they have plans to partner with other companies
    [00:30:32] - How they think about what gets placed on OpenSea and why
    [00:32:09] - Thoughts on take rate and their 2.5% take rate of transactions
    [00:33:22] - Why their take rate is so low compared to other sale platforms online
    [00:34:47] - OpenSea’s relationship with the Ethereum blockchain and other integrations
    [00:36:50] - Perspective on wallets both as businesses and products
    [00:39:16] - Potential risks and the dark side of the unregulated NFT space
    [00:40:48] - The massive boom and bust cycles of crypto and the high prices of NFTs
    [00:41:59] - Interesting areas of Web3 that are in development today
    [00:44:19] - The project he’s enjoyed watching grow the most in the crypto world
    [00:46:42] - What OpenSea might look like in the future if the best-case proves true
    [00:48:59] - The kindest thing that anyone has ever done for him

    • 50 min
    Jenny Lefcourt - The Go-to-Market Motion

    Jenny Lefcourt - The Go-to-Market Motion

    My guest today is Jenny Lefcourt, an equal General Partner at seed-stage venture firm Freestyle Capital, where she manages $450 million in seed investments. Jenny has been engrained in the tech world since the early days of the internet. She dropped out of her Stanford MBA program to co-found online wedding registry startup WeddingChannel.com with classmate, Jessica Herrin, which was subsequently acquired by The Knot. During our conversation, we cover Jenny's investment frameworks, why she believes a deep understanding of the customer is key for founder success, and what makes great go-to-market strategies. We also touch on some of Jenny's favorite market themes around technology for the aging population, the future of work, and the growing low-code/no-code market. Please enjoy my conversation with Jenny Lefcourt.
     
    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 20,000 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 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".
     
    ------
     
    Invest Like the Best is a property of Colossus, Inc. 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
    [00:03:24] - [First question] - Her background and some formative experiences that lead her to where she is today
    [00:08:38] - Common patterns of desirable founders when it comes to customer focus
    [00:09:50] - Her investing framework for evaluating and deciding which companies to invest in
    [00:12:32] - Innovation and adoption in the technology sector for the older generation
    [00:15:11] - The biggest jobs to be done in this space currently today
    [00:17:33] - Cultural differences in how the West views and treats their elderly
    [00:21:02] - Business model options for turn-key apartments offered by UpsideHoM
    [00:22:48] - Other categories and potential opportunities in tech geared towards the elderly
    [00:24:59] - What you need to do differently when building products for the elderly
    [00:27:32] - How she learns about a new prospect’s go-to-market approach and reverse engineering an action plan to execute it
    [00:32:03] - Founders, You Want to Sell Viagra
    [00:33:33] - Selling transformation and an overview of this idea with BetterUp
    [00:36:30] - Her thoughts on how the world and the future of work might change 
    [00:41:14] - Interesting approaches to improving the onboarding and recruiting process
    [00:43:24] - The emerging movement of low code/no code tools
    [00:46:58] - How she as an investor adjusts as the world becomes more digitally connected
    [00:49:02] - Ways her life has most dramatically changed over the past few years
    [00:51:33] - Lessons learned from her time at All Raise
    [00:53:40] -

    • 1 hr 1 min
    Dave Girouard - Making Better Loans - [Founder’s Field Guide, EP. 52]

    Dave Girouard - Making Better Loans - [Founder’s Field Guide, EP. 52]

    My guest today is Dave Girouard, co-founder and CEO of Upstart, a lending platform that leverages AI to make loans more accessible and affordable. Dave started in Silicon Valley as a Product Manager at Apple and later spent eight years at Google, where he built their suite of cloud apps. In our discussion, we cover the lessons Dave has learned about building speed into a habit, the intricacies of training an AI model to predict the future, and what it was like to start a fintech business as an outsider. We also discuss the past, present, and future of lending, why Dave and his team have no plans to build a super app and the differences between public and private market investors from a founder’s perspective. One of the tropes you hear these days is that lending has become a customer acquisition tool for FinTechs, but as Dave explains, the market and opportunity set in lending itself should not be underestimated. Please enjoy this great conversation with Dave Girouard.
     
    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 brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders.
     
    -----
     
    This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambitious problem, then Versett is the firm to call. To check them out, visit versett.com/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
    [00:02:54] - [First question] - Lessons learned about adopting speed as a habit
    [00:05:39] - Knowing which decisions require your attention and are worth it as a CEO
    [00:07:00] - What slows down decision-making execution and overcoming it
    [00:09:34] - Ways to persuade partners to move as fast as you do
    [00:10:44] - One of his most valuable lessons learned from his time at Google
    [00:12:20] - The key insight that first lead him to the idea of creating Upstart
    [00:15:10] - The early days of learning about the financial lending space
    [00:16:49] - Figuring out how to improve on an age-old rigid and regulated system 
    [00:18:42] - Credits scores, what drives them, and why they’re suboptimal
    [00:20:57] - Overview of building an AI learning model and applying it to loans
    [00:23:24] - Surprising findings on predictions and evaluating loan applicants
    [00:25:16] - Machine learning algorithms and interwoven programmer bias
    [00:26:49] - The role interest rates play in their business model
    [00:28:34] - Revenue model and transactions that fund Upstart 
    [00:31:43] - Who the typical customer is and their user experience
    [00:33:09] - Ways in which they can compound their AI models for other services
    [00:35:10] - The biggest hurdle encountered when building Upstart
    [00:36:55] - How he’s seen the FinTech space in his area change over time
    [00:38:39] - A pie chart on revenue for financial services today
    [00:40:24] - Why there are more profits in lending than payments 
    [00:41:25] - Major loans types and how they might change in the future
    [00:44:12] - Disruptive aspects of the buy now pay later consumer movement
    [00:46:09] - How much Upstart could change the future of lending over a decade
    [00:48:17] -

    • 1 hr 7 min
    Jay Hoag - Calibrating Market Adoption

    Jay Hoag - Calibrating Market Adoption

    My guest today is Jay Hoag, co-founder of TCV. If you look at Jay’s investment track record, it’s a “who’s who” of tech giants with Airbnb, Netflix, Peloton, Zillow, and a list that does not stop there. Needless to say, Jay has a Hall of Fame career. During our conversation, we talk about his own journey founding TCV, what advice he has for visionaries, and why he sees advantages for private to public crossover investors. Jay has such a wealth of experience that is on display throughout this episode. Please enjoy my conversation with Jay Hoag.  
    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 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 Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.
     
    ------
     
    This episode is brought to you by Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. 
     
    ------
     
    Invest Like the Best is a property of Colossus, Inc. 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
    [00:03:13] - [First question] - Some of his early key formative experiences that shaped his worldview as an investor
    [00:06:29] - How much software businesses have changed since he started investing in them
    [00:08:28] - The key insight that led him to create TCV
    [00:11:36] - Generating returns by swinging less and raising your average
    [00:15:06] - Understanding and evaluating a value proposition in its early stages
    [00:22:08] - What slightly crazy founders look like and why it’s important for a company
    [00:25:47] - Whether or not we’re in the golden age of content already 
    [00:28:27] - Why Peloton was rejected so many times before TCV invested in them
    [00:32:32] - Things founders often need from him and how he helps them succeed
    [00:36:15] - Lessons learned from investing in public markets versus private ones
    [00:41:35] - Advice for founders when it comes to conveying their ideas to investors
    [00:44:55] - The social dimension of interactive and network building content
    [00:46:18] - How important maintaining a focus in the early days is for a new company
    [00:48:07] - The most challenging aspect of executing his strategy today
    [00:50:48] - One of the most emotionally stressful episodes while launching TCV
    [00:53:44] - Supporting your founders during the good and tough times
    [00:55:16] - New potential headwinds and tailwinds in the tech space writ large
    [00:59:14] - Things people might be overlooking today that could be great opportunities later
    [01:02:58] - Whether or not internet companies are threatened by the crypto boom
    [01:04:32] - What most has him most excited about the world today
    [01:06:20] - Advice for company building in the investing world in general 
    [01:09:48] - The kindest thing anyone has ever done for him

    • 1 hr 15 min

Customer Reviews

4.8 out of 5
1.9K Ratings

1.9K Ratings

JoshCrist ,

Empowering, insightful and actionable! 🙌

Truly one of the best podcasts you can listen to. Patrick and the entire Colossus team do an incredible job leading conversations that push you past your preconceived decision making frameworks, values and reference points to arrive at a depth of understanding that separates the average investor from someone who can build a coherent thesis - and stand behind that thesis while integrating the constant stream of new information coming their way! Can’t recommend this show enough!

Sulyvan Robinson ,

Very interesting guests, when not peddling cryptos

Great podcasts most of the time, with outstanding investment personalities and veterans. Disappointed at the recent disproportional amount of crypto-focused episodes.

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!

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