100 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 • 2K 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 Englebardt and Richard Kim - Investing in Immersive Worlds

    Sam Englebardt and Richard Kim - Investing in Immersive Worlds

    Today, my guests are Sam Englebardt and Richard Kim, general partners at venture fund, Galaxy Interactive. Having come from the media and finance sectors, respectively, Sam and Richard joined forces in 2018 to invest in their shared thesis that immersive digital experiences would become the dominant way people engage with each other in the future.
     
    Our conversation centers around the evolution of art, finance, and gaming as they proliferate in Web3. Please enjoy my conversation with Sam and Richard.  
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
     
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    This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.
     
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    This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've ever used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. If you want early access to become a Member of their private Beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK
     
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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
    [00:02:50] - [First question] - Their thoughts on the digital art market
    [00:11:33] - What motivates traditional art collectors and what has been carried over into digital art
    [00:17:27] - Is there an attractive beta opportunity in the digital art space?
    [00:24:32] - Why investors should do more work understanding NFTs and ways to consider incorporating them into your portfolio
    [00:27:55] - The history of Galaxy and their thesis writ large 
    [00:33:09] - Exciting and terrifying aspects of the financialization of everything
    [00:37:27] - Places where inserting markets could be beneficial with Web3
    [00:45:27] - Their perspectives on gaming as a subcategory of Web3
    [00:51:38] - Tokenomics and the importance of building great game communities
    [00:59:18] - What we can learn from successful gaming companies and in-game monetization
    [01:04:19] - How Diablo 3’s auction house detracted from the core player experience
    [01:06:36] - Where they disagree with the Web3 investing community
    [01:10:37] - The kindest things anyone has ever done for them

    • 1 hr 20 min
    Ricky Sandler - Building an Investment Compass

    Ricky Sandler - Building an Investment Compass

    My guest today is Ricky Sandler, founder of Eminence Capital. Ricky is a hedge fund veteran managing over $8bn of assets across Eminence's strategies. We cover Ricky's evolution as an active investor, why he thinks this is a stock-picker's environment, and what keeps him competitive after a long and successful career. Please enjoy my conversation with Ricky Sandler.
     
    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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.
     
    -----
     
    This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. Using Levels made me realize how little we understand about what's happening in our bodies - and it was the only product that has ever made me willing to log food. If you want early access to become a member of their private beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK
     
    -----
     
    Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 
     
    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.
     
    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.
     
    Follow us on Twitter: @patrick_oshag | @JoinColossus
     
    Show Notes
    [00:02:42] - [First question] Whether or not great investment firms should be led by a single investor
    [00:03:25] - Episodes where singular investment power has proven effective and powerful
    [00:05:06] - Where he finds joy in the investing process on a regular basis
    [00:06:19] - Ways he’s learned to become better at guiding and helping teams he works with
    [00:08:14] - The most common types of fool's gold he comes across
    [00:11:00] - Evolution of the pricing mechanisms in ever-evolving markets
    [00:16:14] - Common features of a good mispricing opportunity
    [00:18:42] - How he interacts with other hedge funds and long-only investors
    [00:21:14] - An investor he often disagrees with but loves talking to 
    [00:22:13] - The investment he’s most proud of historically
    [00:25:11] - What the healthy draw that keeps him coming back to investing is
    [00:28:31] - His opinion on crossover funds and their growing popularity
    [00:32:09] - What the world in 2022 looks like to him and what both excites and worries him
    [00:38:19] - Key contributors that influence liquidity and how it flows into equity prices
    [00:41:26] - A macro view of the healthcare sector and why it’s so interesting today
    [00:42:59] - Lessons from the Titans
    [00:43:52] - Advice he’d give to younger investors for stepping into the space 
    [00:46:45] - The kindest thing anyone has ever done for him

    • 1 hr 8 min
    Orlando Bravo - The Art of Software Buyouts

    Orlando Bravo - The Art of Software Buyouts

    My guest today is Orlando Bravo, co-founder and Managing Partner of leading private equity firm, Thoma Bravo. Thoma Bravo manages over $90bn of assets and is best known for investing in software and technology businesses. It was Orlando who led the firm’s early entry into software buyouts some twenty years ago, and he has overseen more than 350 software acquisitions since. There are few, if any, people better placed to discuss private equity and software investing. Please enjoy this excellent discussion with Orlando Bravo.
     
    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.
     
    -----



    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] - His belief about an opportunity/capital mismatch in private equity
    [00:04:26] - Adjusting his own approach to take advantage of seemingly niche opportunities
    [00:06:13] - Differences between software businesses they invest in versus traditional ones
    [00:08:25] - Outline of how he runs their four-hour portfolio meetings
    [00:09:53] - Overview of the very first deal he ever made in the software sector
    [00:14:01] - The dissonance between the average SaaS company and the ones they try to manage
    [00:18:22] - Major contributors that allow for their higher margins
    [00:20:16] - Common mistakes of companies that mis-invest capital for growth only
    [00:22:28] - Defining what market leader means writ large
    [00:23:45] - Why the subsector of cyber security is such a good opportunity set
    [00:26:25] - The evolving nature of the private equity world in general
    [00:28:41] - Where returns will come from going forward
    [00:31:47] - How good the opportunity for returns in this style of investing today is
    [00:35:32] - Lessons learned on knowing when to exit or sell a position
    [00:37:59] - How short their holding periods can be and how much influence they can have in such a short time
    [00:40:04] - Surprising things about deal-making that he’s learned over his career
    [00:41:20] - Difficulties and points of frictions in deals that still exist for him today
    [00:43:11] - What part of the deal-making process he loves the most
    [00:44:30] - If your job title has a C in it you’re not allowed to complain about it
    [00:46:27] - Deeply held beliefs about operating excellence
    [00:47:33] - What the word service means to him given everything we’ve talked about 
    [00:50:27] - How we do a better job of inviting talent into this space
    [00:52:51] - How decentralization will define the 2020s and beyond
    [00:55:48] - What is most interesting about Web3 that might affect cyber security
    [00:57:42] - Where there is a lack in innovation in private equity today
    [01:00:45] - Advice for young talent for building their careers
    [01:03:16] - The kindest thing that anyone has ever done for him

    • 1 hr 5 min
    Nick Saltarelli - One Foot in Front of the Other - [Founder’s Field Guide, EP. 54]

    Nick Saltarelli - One Foot in Front of the Other - [Founder’s Field Guide, EP. 54]

    My guest today is Nick Saltarelli, co-founder of the functional chocolate bar business, Mid-Day Squares. Nick started the company with his wife and brother-in-law a few years ago to build on a simple idea: if the big chocolate bar brands were to start today, what would they look like?
     
    In our conversation, we discuss the importance of Mid-Day Squares’ $100 million revenue target, what’s wrong with the CPG industry today, and how to keep a long-term mindset while making the most of every day. Please enjoy this unique conversation with Nick Saltarelli.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
     
    -----
     
    This episode is brought to you by Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs, so you can focus on what matters most—building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders. 
     
    -----
     
    Founder's Field Guide is a property of Colossus, LLC. 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
    [00:02:01] - [First question] - What Mid-Day Squares is and how he started the business
    [00:04:48] - Why they’re so publicly open about their company’s goals
    [00:09:05] - Major lessons he learned from his father’s early passing and being around very successful entrepreneurs at a young age 
    [00:16:51] - What long term thinking unlocks for him in short term progress
    [00:21:05] - Becoming unexpectedly close and learning from Rory Olson 
    [00:25:44] - What Rory taught him about deal-making
    [00:28:35] - Lessons from Rory about raising capital
    [00:33:25] - Opportunities in a seemingly oversaturated market like chocolate
    [00:42:46] - An example of doing something contrarian that worked out
    [00:47:11] - Their unique approach to marketing Mid-Day Squares
    [00:57:33] - Lessons learned about building a manufacturing operation after years in China
    [01:02:35] - What we can expect from Mid-Day Squares in the near future
    [01:06:59] - The kindest thing anyone has ever done for him
    [01:08:05] - Mid-Day Squares Uncensored Podcast

    • 1 hr 9 min
    Jenny Johnson - Seven Decades of Investing Expertise

    Jenny Johnson - Seven Decades of Investing Expertise

    My guest today is Jenny Johnson, President and CEO of one of the world’s largest asset managers, Franklin Templeton. Jenny joined the business in 1988 and has worked in the organization ever since. In early 2020 she became CEO of Franklin, which now manages some $1.5 trillion. I should, of course, note that I met Jenny as our two firms explored a partnership, which we cemented 3 months ago when we announced that Franklin Templeton would be acquiring O'Shaughnessy Asset Management.
     
    During our conversation, we discuss Jenny’s thoughts on leadership, how she manages the needle-moving problem that afflicts many large companies, and the ways in which she sees private markets becoming more accessible to retail investors in the future. Please enjoy this great conversation with Jenny Johnson.
     
    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.



    -----
     
    At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick
     
    -----



    Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 
     
    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.
     
    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.
     
    Follow us on Twitter: @patrick_oshag | @JoinColossus
     
    Show Notes
    [00:03:19] - [First question] - The four P’s of leadership and what she thinks are the most important roles of a CEO 
    [00:06:00] - The difficulty of finding and recruiting great people and keeping them invested 
    [00:07:18] - Things she looks for in her senior leadership team
    [00:07:59] - Knowing when to be more or less involved as a leader
    [00:09:30] - Her takeaways from working in a family-owned business
    [00:11:20] - Advice she’d give to families who are building businesses together
    [00:12:06] - Thoughts on the role technology will play in the asset management industry
    [00:16:13] - Costs and frictions that blockchains could alleviate
    [00:18:17] - General views on disruption and considering ones position when thinking about the future
    [00:20:09] - Knowing when to start a project internally or acquire an existing project
    [00:23:10] - The hardest things about effective M&A decisions
    [00:23:42] - Overseeing a hybrid model of singular focus between multiple investment groups
    [00:28:26] - The pros and cons of active management against passive adoption
    [00:31:15] - Costs and fees in the industry and how they might change in the future 
    [00:33:04] - Talking to clients when they don’t have one specific view on strategy
    [00:34:57] - When consensus is helpful and appropriate for making important decisions
    [00:36:10] - Formative experiences in her career that has shaped her worldview
    [00:38:34] - Managing emotions through seemingly chaotic situations
    [00:39:13] - The impacts on psychology when being a top performer and an average one
    [00:41:15]

    • 1 hr 3 min
    Doug Colkitt - The Evolution of Markets

    Doug Colkitt - The Evolution of Markets

    My guest today is Doug Colkitt. Doug has spent his career searching for and trading inefficient markets, first at Citadel’s high-frequency trading group, then for himself, and then as an operator building CrocSwap - a decentralized exchange or DEX designed to bring modern functionality to crypto markets, which is closer to what large traders have come to expect from a modern electronic market like the NASDAQ. 
     
    My interest in market infrastructure has continued to grow since my great conversation with FTX founder Sam Bankman-Fried. So my conversation with Doug covers the evolution of market and trading infrastructure. We unpack the trading stack as it exists today, dive into DeFi’s innovations, and explore the new category of single contract DEXs that Doug is creating. After learning so much from Doug about how markets function and how crypto markets should function, I became an investor in his new business via my venture capital firm Positive Sum. Please enjoy this great conversation with Doug Colkitt.
     
    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.



    -----
     
    At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick
     
    -----



    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
    [00:03:31] - [First question] - Doug’s career and history working with markets
    [00:08:55] - Defining what a trading stack is 
    [00:13:41] - How HFT firms are such reliable money-making models
    [00:16:27] - What’s at the cutting edge of traditional markets that provides an edge
    [00:18:45] - The mechanical parts of infrastructure involved in building an exchange
    [00:21:00] - Classes of data that matter for operating an exchange
    [00:22:11] - Capacity and what good returns are as an HFT firm
    [00:28:45] - Overview of the mechanics of an AMM
    [00:31:53] - Earning a yield as a liquidity provider
    [00:33:59] - Other ways to think about AMMs and liquidity providers
    [00:36:42] - Key players in the AMM space and the evolution of them
    [00:41:20] - How asset holders can approach DEX tools and be liquidity providers
    [00:42:55] - The function of an exchange’s native token
    [00:45:25] - Token distribution and how to earn them without buying them
    [00:48:31] - How you receive payment for providing liquidity
    [00:51:31] - What CrocSwap will do and what a single contract DEX unlocks
    [00:57:36] - How CrocSwap is able to do this when other exchanges can’t
    [00:59:27] - What single contracts will improve for users 
    [01:00:43] - The impact CrocSwap will have for all participants writ large
    [01:02:28] - Whether or not CrocSwap will cultivate an

    • 1 hr 17 min

Customer Reviews

4.8 out of 5
2K Ratings

2K Ratings

Mariann!! ,

Love it!

It’s definitely worth your time if you are trying to stay informed.

Herd Contrarian ,

A lot of what I’ve learned I learned here

Patrick - you said in episode 46 that a lot of what you’ve learned [in general, in life] you’ve learned here doing this podcast. The same goes for me, right from this podcast. Episode 46 is a great example because I’m so used to learning here that even though the summary description didn’t sound like a sure fire win, I knew the smart thing to do would be to listen. So I am. And I’m already learning more than I thought I would. Again! Thank you!

Shahrak ,

Flirting with Becoming Crypto Scam Shill

I have enjoyed and valued Invest Like the Best for several years. Patrick has great guests and typically produces episodes with interesting conversations.

Recently, however, he has begun hosting various players within the NFT space. No objection there, except that his interviews with these individuals are as entirely credulous as to what they’re pushing. The most recent episode with Eric Golden, owner of the scam known as Bored Ape Yacht Club, was a step too far.

I’ve always liked Patrick’s work, but he’s steering too much content in this direction. Discussing crypto and NFTs is fine. Discussing them as though they’re an unmitigated triumph is not. Starts to feel like an infomercial for junk products.

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