295 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 • 121 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/

    Sebastian Mejia - Mastering On-Demand Convenience - [Founder’s Field Guide, EP. 44]

    Sebastian Mejia - Mastering On-Demand Convenience - [Founder’s Field Guide, EP. 44]

    My guest today is Sebastian Mejia, co-founder and president of Rappi. Founded in Bogota, Colombia in 2015, Rappi set out to create an on-demand convenience store and has expanded into nine countries and over 200 cities. In our conversation, Sebastian and I discuss what differentiates Rappi from US-based delivery apps, how the company evolved early by understanding their customers’ behavior, and how the business balances growth vs. unit economics. I loved hearing Sebastian’s views of the value of brands in an increasingly app-based world, the importance of being hyper-local for any delivery-based business, and how fungibility is a key characteristic of any rewards program. I hope you enjoy this great conversation with Sebastian Mejia.
     
    Before we transition to the episode, I also wanted to highlight our newest series, Business Breakdowns. Each week, we do a deep dive into an individual business to understand what makes it tick. Find more information on joincolossus.com or search for and sign up to the Business Breakdowns feed on your preferred podcast player.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
     
    This episode is brought to you by Dell Technologies. When you call a Dell Technologies Advisor, they’re focused on you - ready to give advice on everything from laptops to the cloud to keep your small business ready for what’s next. Call an advisor today at 877 ASK DELL, and do more with modern devices and Windows 10 Pro.
     
    -----
     
    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 ambiguous 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] - What the Rappi is their current scale and user base 
    [00:05:30] - The early-stage problems they encountered when building their platform 
    [00:08:43] - Building the initial network dynamics and unit economics of couriers  
    [00:12:35] - Solving the data collection and integration needed to power Rappi 
    [00:15:22] - Defining what local means  and the difference between units and zones
    [00:17:33] - Other active companies that offer a similar service  
    [00:18:27] - Thoughts on making money in such a diversified supply chain
    [00:22:57] - The moment they realized they were starting to feel scale effects for the first time
    [00:25:11] - Questions they’re asking themselves as they continue to grow
    [00:28:20] - Streaming consumer goods and how they’ll change consumer behavior
    [00:31:45] - Impacts on brands Rappi might have with larger user adoption
    [00:34:34] - Unique attributes and opportunities in Latin American markets today
    [00:38:45] - Observations of early investors and questions investors as him often
    [00:40:17] - The value unlock of having a subscription model akin to Amazon prime
    [00:44:47] - How crypto and blockchain technology might benefit Rappi users
    [00:47:16] - His perspective on crypto in Latin America today compared to the US 
    [00:48:09] - Their work in financial services
    [00:47:30] - Possible reasons why Rappi might not succeed in the future
    [00:50:30] - The kindest thing anyone has ever done for him
     

    • 56 min
    Carl Kawaja - Wisdom from Decades of Investing

    Carl Kawaja - Wisdom from Decades of Investing

    Today’s conversation is one of my all-time favorites, with someone I’ve come to respect deeply in the field of investing. My guest is Carl Kawaja, who has served as a portfolio manager at Capital Group for decades. Capital Group is among the most respected shareholders in the world, with over $2T of assets, and listening to Carl, you’ll hear why.
     
    In our conversation, we cover Carl’s criteria for building conviction around long-term holdings, why he views uncertainty and ambiguity as healthy, and why tolerating failure is key to great investing career. Throughout our discussion, Carl connects his lessons through a variety of direct experiences, personal analogies, and broader frameworks. I love his ability to talk in the weeds about his investments in Vale and TSMC and then quickly shift to his broader thematic views like “The Empire Strikes Back.” I hope you enjoy this great conversation with Carl Kawaja.
     
    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 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. 
     
    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
    [00:03:38] - [First question] - The two companies he has owned the longest and what they’ve taught him as an investor 
    [00:16:37] - Discussing his investment style through the lens of simplicity  
    [00:24:35] - A time where he worked to try and create a simplified equation but couldn’t 
    [00:30:59] - Discussing his investment style through the lens of echolocation and ambiguity 
    [00:36:03] - Thoughts on whether buying well or holding well is more difficult
    [00:40:40] - Capital Group’s history and his river-rafting analogy in regards to the company
    [00:47:48] - What he means by “The Empire Strikes Back” and relevant market themes
    [00:54:50] - A brief summary of “The Empire Strikes Back”
    [00:58:42] - Common reasons that he may have gotten something really wrong 
    [01:03:34] - Impressions made on him by the poet Rilke
    [01:09:00] - The work of Brunello Cucinelli and the nature of quality 
    [01:13:08] - Advice for new investors who want to step into the field and set themselves up for success
    [01:13:54] - The Visual Display of Quantitative Information 
    [01:17:39] - What he’s learned about kindness
    [01:19:54] - The kindest thing that anyone has ever done for him

    • 1 hr 28 min
    Stewart Butterfield - We Don’t Sell Saddles Here - [Founder’s Field Guide, EP. 43]

    Stewart Butterfield - We Don’t Sell Saddles Here - [Founder’s Field Guide, EP. 43]

    My guest today is Stewart Butterfield, founder and CEO of Slack. Stewart’s 2014 essay “Why We Don’t Sell Saddles Here” had a massive impact on my own business journey, which made this discussion extra special. During our conversation, we discuss the concept of owner’s delusion, how to frame the boundaries between product and market, and the challenge of changing people’s mental models and behavior when introducing innovative products. I hope you enjoy my conversation with Stewart.
     
    Before we transition to the episode, I also wanted to highlight our newest series Business Breakdowns. Each week, we do a deep dive into an individual business to understand what makes it tick. For more information go to joincolossus.com or search for and sign up to the Business Breakdowns feed on your preferred podcast player.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
     
    This episode is brought to you by Dell Technologies. When you call a Dell Technologies Advisor, they’re focused on you - ready to give advice on everything from laptops to the cloud to keep your small business ready for what’s next. Call an advisor today at 877 ASK DELL, and do more with modern devices and Windows 10 Pro.
     
    -----
     
    This episode is brought to you by LinkedIn Jobs. With LinkedIn, you get access to an active community of professionals with more than 722 million members worldwide. LinkedIn is the easiest place in the world to post a job and message qualified candidates. Getting started is easier than ever, and now you can do this all from your mobile device.
     
    When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit linkedin.com/fieldguide to post a job for free. Terms and conditions apply.
     
    -----
     
    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
    [00:02:51] - [First question] - Discussing his essay We Don’t Sell Saddles Here  
    [00:06:19] - Important contrast between innovation and the product
    [00:06:46] - Who Do You Want Your Customers to Become? 
    [00:08:07] - His thoughts on marketing from both ends and how he’s gotten better at it
    [00:10:45] - What across Slack’s history has been the most successful market messaging creation strategy
    [00:13:43] - The 5K contest and how it taught him about the design unlock of limitations
    [00:17:44] - How limitations and constraints can power and incentivize innovation 
    [00:21:21] - Why both of his attempts to build videogames ended up as consumer software
    [00:27:55] - Whether or not there is still white space in digital communication software
    [00:30:15] - The dynamic between effective communication and building communication tools
    [00:34:02] - A future of digital-first companies and what that might look like
    [00:40:15] - Leadership and Self-Deception and what self-deception means to him
    [00:43:39] - Examples of self-deception he underwent that he was able to learn from
    [00:46:59] - Mastery and its importance in the world of business
    [00:48:59] - Why hippies and APIs may have a tighter correlation than we think 
    [00:54:01] - Whether or not technology is fundamentally amoral 
    [00:56:10] - Interesting and open questions about the future that remain unanswered 
    [00:58:33] - His current creative outlets that he engages with the most 
    [00:59:24] - Yahoo Resignation Letter and why he wrote it the way he did
    [01:00:31] - Lessons fo

    • 1 hr 6 min
    Steve Mandel - Investing Behind Change

    Steve Mandel - Investing Behind Change

    My guest today is Steve Mandel, founder of Lone Pine Capital, one of the most successful hedge fund and investment firms of this generation. In our conversation, we discuss how the investing business has evolved since Steve’s start in the 1980s, why it’s so difficult to drive alpha by shorting stocks today versus 20 years ago, and why Steve still loves to get into the guts of a business. Steve shares his lessons through a variety of great stories, which made this such a fun experience. Please enjoy my conversation with Steve Mandel.
     
    Before we transition to my interview with Steve, I’d also like to highlight the newest Colossus show, Business Breakdowns. If you like Steve’s idea of getting into the guts of a business, this is the show for you. Please find a list of our episodes at joincolossus.com and subscribe to Business Breakdowns on your preferred podcast player.
     
    I hope you enjoy my conversation with Steve Mandel. 
     
    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. 
     
    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
    [00:03:36] - [First question] - His first encounter with Walmart
    [00:05:51] - What about Sam Walton made him worth idolizing 
    [00:08:14] - The juxtaposition of business to management quality
    [00:10:57] - Why a career in retail influenced the lens he sees the investing world through
    [00:11:23] - What bad company culture in retail looks like
    [00:12:33] - Aspects of Walmart’s culture that could be applied to other companies
    [00:13:54] - Defining the core essence of retail company culture
    [00:15:02] - How long it used to take for a stock to properly reflect new information
    [00:16:40] - The nature of edge and what it looked like back then
    [00:21:09] - Investing behind change and assessing trends
    [00:23:06] - Scars and stories from just how vicious short markets can be
    [00:26:32] - Thoughts on building an enduring firm and how it’s evolved over time 
    [00:32:14] - The process and decision to remove himself from the day-to-day operations
    [00:33:55] - Lessons learned over time about what separates good from bad analysts
    [00:34:42] - Where to start looking when getting into the guts of a business
    [00:36:31] - What is most exciting when you’re inside the guts  
    [00:39:19] - Interesting aspects about payments today writ large
    [00:42:15] - Broad trends around change in consumer trends 
    [00:43:02] - How he views software businesses looking forward as an investor
    [00:45:14] - Great managers and their emphasis on analyzing their competitive advantage
    [00:48:02] - Ways that pace as a variable has changed in importance
    [00:49:27] - What he thinks we’ll look back on as silly in how markets currently operate
    [00:50:33] - Whether

    • 1 hr 10 min
    Spenser Skates - Challenging Big Ideas - [Founder’s Field Guide, EP. 42]

    Spenser Skates - Challenging Big Ideas - [Founder’s Field Guide, EP. 42]

    My guest today is Spenser Skates, CEO and co-founder of Amplitude Analytics. Spenser founded Amplitude in 2012 with a thesis that building the best product requires, deep cross-functional understanding of customer behavior. During our conversation, we discuss Spenser’s long history in programming and how his early experiences tie into his work today. We also explore the nuances of equity compensation, how different VCs can play a role in the success of a startup, and Spenser’s desire to see more direct listings vs. IPOs. While many founders follow the path of others, it is clear Spenser takes time to challenge the status quo.
     
    Before we transition to the episode, I wanted to highlight our newest series, Business Breakdowns. In this episode, you will hear how Spenser’s team worked with the meditation app, Calm, to optimize for customer growth. It was particularly interesting to hear this story after listening to the Calm breakdown. Find episodes of Business Breakdowns on your preferred podcast provider or on joincolossus.com
     
    I hope you enjoy my conversation with Spenser Skates.
     
    For the full show notes, transcript, and links to mentioned content, check out the episode page here.
    -----
     
    This episode is brought to by Dell Technologies. Upgrade your business during Dell Technologies’ Black Friday in July event. Get savings up to 50% off AND take your office with you with Windows 10 Pro. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at https://www.dell.com/en-us/work/shop/deals.
     
    -----
     
    This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.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
    [00:03:15] - [First question] - How he won the Battlecode tournament at MIT twice
    [00:06:43] - A few key insights that helped him win the tournaments
    [00:08:34] - Lessons learned at MIT and the road to starting Amplitude
    [00:13:57] - A typical customer experience when using Amplitude 
    [00:17:17] - How their platform extrapolates key data points in user data that others don’t
    [00:19:03] - His most productive mistakes made while building the company 
    [00:21:10] - The strange history of equity and his thoughts on how it should be used 
    [00:28:08] - The recent changes in the vesting schedule for newly issued equity 
    [00:29:59] - Lessons learned from working with some of the best investors out there
    [00:36:20] - His thoughts on the IPO process and going public writ large
    [00:41:04] - The role the SEC plays and his perspective on SPACs 
    [00:44:01] - Differences in direct listings compared to traditional IPOs 
    [00:48:36] - His thoughts on dual-class structures and corporate governance 
    [00:50:11] - Hopes for Amplitude as he looks five years into the future
    [00:52:03] - The potential value unlock of smart software for end-users  
    [00:55:08] - The kindest thing that anyone has ever done for him

    • 58 min
    David Sacks - How to Operate a SaaS Startup

    David Sacks - How to Operate a SaaS Startup

    My guest today is David Sacks, General Partner at Craft Ventures and founding COO of PayPal. During our conversation, we explore what differentiates Enterprise SaaS from DTC subscriptions, what makes for a magical product launch event, and what key growth metrics David uses to measure success. David has written extensively on his idea of operating cadence, and we explore how that applies to the various functions within an organization. As time goes on, I am more and more impressed at the talent that existed within the original PayPal mafia, and I couldn’t help but ask David to highlight the superpowers for a few of his early partners. This was an incredibly informative conversation with fun threads throughout. Please enjoy my conversation with David Sacks.
     
    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 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. 
     
    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
    [00:03:30] - [First question] - Defining what it means when a company can explode
    [00:05:39] - What it would look like if a company didn’t have what it takes to explode
    [00:06:17] - Key factors that make for a strong product hook
    [00:08:51] - Whether or not there has been a divergence at the early stage of B2B investing compared to B2C
    [00:11:36] - Reasons why products that make people collaborate are always stronger
    [00:14:14] - Nuances between team subscriptions and team product use
    [00:15:37] - Describing the burn multiple metric and how it can be applied to companies
    [00:18:18] - The gross margin problem and issues for businesses in this area writ large
    [00:22:34] - Common practices amongst sales programs that have and haven’t worked
    [00:24:22] - What about new founders makes him most excited
    [00:25:58] - Explaining cadence and why he groups product and marketing as one bucket and sales and finance as another
    [00:30:44] - The anatomy of a great product launch 
    [00:32:17] - Ways in which external dependencies can be landmines for growing companies
    [00:34:06] - Whether or not he’s willingness to invest in a business with regulatory variables
    [00:36:59] - What he’s seen in company culture that breaks a company as they scale
    [00:39:55] - Things a founder actually does in order to reign in and tame their culture
    [00:42:08] - Unique traits of founders who are both investors and operators
    [00:44:12] - Peter Thiel’s superpower 
    [00:44:57] - Max Levchin’s superpower
    [00:45:38] - Elon Musk’s superpower
    [00:46:07] - Roelof Botha’s superpower
    [00:47:15] - Reid Hoffman’s superpower 
    [00:47:43] - Keith Rabois’ superpower 
    [00:48:41] - What zones of change in the world have his attention writ large
    [00:51:43] - Why teams want to be pushed an

    • 1 hr 1 min

Customer Reviews

4.8 out of 5
121 Ratings

121 Ratings

Kishereinoz ,

So so good

Absolutely love this podcast. Fantastic guests - only unimpressed by one or two guests so far and I’ve listened to all but a couple of episodes at this point. o'shaughnessy is hands down the best host in the game. Asks thoughtful questions and has no ego thus avoiding the awful unnecessary interruptions of the “me too” anecdote genre. I listen a lot when driving and have to constantly pull over to write notes down. Highly recommend

jaffass ,

Thought provoking and engaging

Started off with the Gavin Baker interview, now I’m hooked.

Jenova` ,

Something different that works

Amazing content and banter to match, really information series!

Top Podcasts In Business

Listeners Also Subscribed To

More by Colossus