My guest today is Max Simkoff, Founder and CEO of Doma. Max founded Doma in 2016 after experiencing the pain and manual process associated with title insurance and real estate transactions. With a background in predictive analytics, Max built Doma to bring a digital-first approach to a historically manual and labor-intensive process. 

In our conversation, we cover the history behind mortgage closings, where title companies fall into that process, and how Doma is using technology to improve the client experience. We also discuss Max’s formative experiences at his previous venture, Evolv, and the lessons he’s learned from taking Doma from an idea to a public company. There are many great lessons in this episode, and Max’s entrepreneurial energy shines throughout. Please enjoy this great conversation with Max Simkoff.

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 SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. To learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick.

-----

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

[00:03:17] - [First question] - What Doma does and what they do for customers

[00:04:38] - What Title is and why it sits at the center of such a large transaction

[00:08:41] - Overview of the business economics of this space 

[00:13:55] - How the ecosystem works writ large

[00:18:05] - The formative business experiences he had that led him to today

[00:23:03] - What it means to be great at this whole process

[00:26:53] - The thing Doma tries to predict and the inputs that allow them to do so

[00:32:50] - Defining his biggest roadblocks and how they’ve changed over time

[00:36:02] - Managing stakeholder expectations and perception

[00:40:22] - Learning to walk to the line of having a large vision and communicating it

[00:42:51] - What his loose screw is as a founder

[00:45:06] - The square-peg-round-hole they encountered during the pandemic

[00:51:20] - What the counterproductive byproduct of his genius is

[00:53:35] - Figuring out where to take the company next 

[00:56:52] - The big lessons learned from interacting with capital markets

[00:59:30] - Other entrepreneurs he feels are maniacs that he respects

[01:00:55] - What will be the biggest contributing factors to their success over the next decade

[01:02:44] - The key ingredients for building a winning team

[01:04:34] - The kindest thing anyone has ever done for him

The intro music you just heard is from my guest today, Suzanne Ciani, an early pioneer of electronic music dating back to the 1970s. As a 5-time Grammy-nominated composer, Suzanne’s music can be heard on her solo albums as well as films, games, and countless commercials. Many have argued her Coca-Cola “pop and pour” changed the sound of advertising forever. 

During our conversation, we discuss what it means to be an artist, how to evolve away from the need for approval and validation, and the importance of mentors during the creative process. While many of our guests strive to be lifelong learners - Suzanne seems to take this a step further as a lifelong learner and a lifelong creator. I hope you enjoy my conversation with Suzanne Ciani.

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. 

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

[00:03:53] - [First question] - One of her proudest moments early in her life

[00:05:18] - What she’s learned about originality and its role in the creative process

[00:07:24] - Advice for breaking out of a derivative impulse and finding your character

[00:09:27] - Going from a classically trained pianist to exploring modular synthesis

[00:13:47] - Performing on David Letterman

[00:17:55] - What the Buchla is and the sounds it can make

[00:23:03] - How much of playing a modular synth is improvisational versus pre-made

[00:24:36] - Ways she would design a creative system for other creatives

[00:27:38] - What her interface allows her to do and the mechanics of it

[00:29:07] - Describing what the core sound elements are that she manipulates

[00:32:30] - The role of women in music and how it’s evolved over time

[00:35:06] - What stands out from her mentorship with Ilse Bing

[00:38:16] - Later career creative freedom and what it unlocks for artists

[00:39:25] - Her thoughts on the creative process writ large and its components

[00:42:10] - Commercial sound design and working with Coca-Cola and Atari

[00:44:46] - Observations from a creative life that other artists could benefit from

[00:46:11] - Unifying factors across her best performances

[00:47:53] - What the future might hold for technology and music

[00:50:18] - Where to start when exploring her discography

[00:51:17] - The kindest thing that anyone has ever done for her

My guest today is Sameer Shariff, co-founder and CEO of Cambly. After starting his career at Google, Sameer founded Cambly in 2013 as an on-demand service to learn English. At the touch of a button, Cambly connects its global user base into a 1-on-1 conversation with an English speaker.

During our conversation, we cover the origin story of the business, what Sameer views as the core functions of the two-sided marketplace, and how the team approached scaling a product that was international from day one. Once you hear Sameer talk, you quickly realize the size of Cambly’s market opportunity and why it may have been easy to overlook this problem. I hope you enjoy this great conversation with Sameer Shariff.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. To learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick.

-----

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

[00:03:05] - [First question] - What led him to the original concept of Cambly

[00:05:21] - Beginning to learn the scope of the problem and what solving it unlocked 

[00:07:58] - What Cambly is and how they started tackling the problem 

[00:09:15] - Lessons learned about the challenges of building an alive marketplace 

[00:11:41] - Technical challenges and the enabling technologies that allowed it to happen 

[00:12:59] - Deciding on what to focus on first when it comes to students 

[00:15:24] - Figuring out the formula for unit economics and the pricing structure

[00:17:02] - Learning what doesn’t work in their business model

[00:18:07] - Setting up quality control measures and moderation

[00:21:01] - Tools and services that will improve their experience in the future

[00:23:18] - What the 11-star version of Cambly would look like in a decade

[00:26:56] - Ways in which their software and concept could be applied elsewhere

[00:28:30] - Setting themselves up for success and fine-tuning the matchmaking component

[00:30:37] - Driving users to the platform and audience building strategies

[00:33:46] - Making the platform feel native to each country it serves

[00:35:59] - Surprising lessons learned around distribution and market penetration

[00:37:13] - The biggest boss battles faced as a business

[00:40:17] - Advice he would give to founders in a similar situation 

[00:41:32] - How he’s personally changed the most across this journey

[00:43:32] - Ways he’s shifted to a state of letting go and trusting his team more

[00:45:14] - Lessons learned from studying Airbnb

[00:47:22] - The kindest thing anyone has ever done for him 

My guest today is Sridhar Ramaswamy, co-founder and CEO of Neeva and Venture Partner at Greylock. After a 15-year career building Google’s ad business, Sridhar launched Neeva as an ad-free search engine with a focus on personalization and privacy. During our conversation, we dive into the early days of search and what led to Google’s dominance. Sridhar shares his view on the potential end state for ad-based search engines, and how all of his experiences led him to found Neeva. Beyond a great deep dive into the origins of search, this discussion is filled with great lessons about data-driven decisions, the value of partnerships, and balancing revenue opportunities against user experience. I hope you enjoy my conversation with Sridhar Ramaswamy.

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 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

[00:03:39] - [First question] - Major chapters of the history of search engine technology 

[00:09:21] - The early days of the page rank revenue model prior to ads 

[00:16:27] - Reputation and quality and how they were applied in Google’s early days

[00:21:10] - Driving variables of Google’s ad model that will drive their business going forward

[00:26:48] - Lessons learned about the importance of partnerships while at Google

[00:33:26] - What is Neeva and what motivated him to start it in the first place

[00:39:11] - Variables in building an ad-free search engine that can compete with Google

[00:44:57] - Thoughts on tracking and privacy in the tech world today writ large

[00:50:09] - Lessons he’s learned about pricing when it comes to software

[00:52:58] - Figuring out finding customers when your addressable market is everyone 

[00:56:20] - What he’s learned about leadership over the course of his career writ large

[00:58:05] - What he’s learned about identifying candidates and winning them over when it comes to recruiting new talent

[01:00:27] - His philosophy on product development in general

[01:02:19] - Framing problems in a way that allows you to reach milestones as you build 

[01:04:43] - His biggest professional mistake and what he learned from it

[01:06:08] - The kindest thing that anyone has ever done for him

[01:07:49] - What Bill Campbell brings to mind when he thinks about him

My guest today is Ernie Garcia, co-founder and CEO of online used car platform, Carvana. Ernie launched Carvana in 2012, and less than a decade later, the business commands a $60 billion valuation while selling a used car every other minute.

Our conversation covered a lot of ground. We discussed effective decision-making, what it means to be a long-term thinker, and what Ernie sees as the defining features of attractive markets. We then went deep on Carvana itself, covering the original insight, logistics operations, and counter-intuitive decisions Carvana took as they set about building the brand. I think you’ll find Ernie’s insights and energy infectious. I hope you enjoy this great conversation with Carvana CEO, Ernie Garcia.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. To learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick.

-----

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

[00:03:10] - [First question] - Defining average decision quality and he weaves it into his business

[00:05:40] - How he would assess average decision quality in another company

[00:07:04] - What company culture means to him and building it at Carvana

[00:08:45] - Key features of a market that is desirable to step into as an entrepreneur

[00:10:06] - Various levels of complexity faced in automotive retail

[00:13:51] - Reality Has A Surprising Amount Of Detail; The genesis idea that led to Carvana

[00:17:52] - Critically new things delivered to customers when buying a used car

[00:20:43] - Dealership unit economics vs logistics platform economics and what drives gross profit per unit

[00:24:47] - What is an IRC center, the hub and spoke model, and the skeleton of Carvana

[00:28:44] - The size and scope of one of their fulfillment centers and cost savings involved

[00:30:29] - How the spoke component works and ways it will be improved over time

[00:32:39] - Defining what being a long term thinker means to him

[00:35:50] - The story behind the Carvana car vending machine

[00:39:49] - His thinking on the dual-layer nature of customer experience and communication

[00:41:59] - Mistakes and failures made while learning to become good communicators

[00:44:21] - Great companies get a lot done very fast

[00:48:56] - Infrastructure set in place to maintain their pace as they scale 

[00:51:50] - The embedded formula used for teams to communicate what they want to do

[00:52:50] - What it felt like as a leader going through the pandemic

[00:58:24] - Whether or not COVID-19 has permanently impacted the consumer landscape

[01:00:03] - Businesses, leaders, and things he’s studied that others could learn from

[01:01:55] - Surprising new things arising in the automotive and transport industries

[01:05:23] - The kindest thing anyone has ever done for him

My guest today is Karen Karniol-Tambour, Partner and Co-CIO for Sustainability at Bridgewater Associates. You will quickly understand why Ray Dalio described Karen as a “vacuum cleaner of learning” - our conversation covered a variety of market themes, and Karen goes deep on each of them. We touch on inflation, monetary policy, currencies, retail investors, ESG, and how each of these levers has become more important for investors to understand. Karen has a rare skill for making complex ideas seem simple, and I love the frameworks she uses to deconstruct big, important issues. She does such a good job of explaining what’s changed, why it matters, and what to do about it. I hope you enjoy my great conversation with Karen Karniol-Tambour.

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 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

[00:03:39] - [First question] - How Bridgewater invests and the experiences that led her there

[00:06:47] - What working with Daniel Kahneman felt like and learning his perspective

[00:08:09] - An example of holding herself to accumulating and stress testing data

[00:10:17] - Important variables to consider when seeking returns in large-scale bets

[00:14:18] - What we should be thinking about in terms of inflation as we look to the future

[00:20:07] - How she thinks about inflation and how she defines it

[00:22:57] - Relevant asset classes that can protect or help diversify against inflation

[00:26:14] - What still largely confuses her about inflation and its many facets

[00:28:05] - Her philosophy and model for understanding the system of currency

[00:33:21] - How investors should think about the US dollar 

[00:35:50] - Whether or not owning an unhedged global equity index gives you currency exposure

[00:37:07] - The fundamental nature of equity markets and household balance sheets

[00:41:37] - Ways the growing wave of retail investors will impact prices and returns 

[00:43:53] - How she’s evolved her valuation approach given our new investor landscape

[00:45:43] - The good and bad roles ESG might play for investors going forward

[00:50:36] - Potential concerns around the growing trend of ESG writ large

[00:53:51] - Thoughts on the 60/40 portfolio and whether or not it’s still worth using

[00:55:32] - Designing a default diversified portfolio in light of markets today

[00:57:45] - Aspects of the global market economy today people should be talking about more

[01:01:15] - Ways she investigates a new topic and how it has evolved over time

[01:04:14] - Variables that matter in investment teams and company cultures

[01:06:53] - How she would approach cryptocurrency and what’s interesting about them

[01:09:08] - A rosey and gloomy take of what the world could look like in a decade

[01:12:37] - The kindest thing that anyone has ever done for her

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.

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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.

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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. 

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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

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.

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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'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

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 for investors and builders that he’s learned from building Slack

[01:03:07] - The kindest thing that anyone has ever done for him 

[01:04:27] - Why a philosophy primer would be beneficial for virtually everyone

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.

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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'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.

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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.

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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 or not all markets becoming 24/7 will be a good thing

[00:51:59] - Big iconic business stories that newcomers should study

[00:56:06] - Whether or not business building is an art form

[00:57:38] - Key levers that typically always matter for a business

[00:59:53] - Other major aspects of the world that are important to consider

[01:01:13] - How his personal motivations morphed over the years and what has changed

[01:02:55] - Valuable lessons learned about the inputs and outputs of education

[01:04:15] - Advice for would-be future investment analysts

[01:05:46] - The kindest thing anyone has ever done for him

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.

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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.

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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. 

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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

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.

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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'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.

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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".

------

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 and how we can apply that to business

[00:55:25] - The kindest thing anyone has ever done for him

My guest today is David Vélez, founder and CEO of Nubank, the world’s largest digital bank with over 40 million customers. In our conversation, David talks about his venture capital background at Sequoia and how that led him down an entrepreneurial path in Latin America. We also talk about the pros and cons of building a digitally native business and what gets him most excited about innovation and technology in emerging markets.

Before we start the episode, I would also like to highlight our newest Colossus show, Business Breakdowns. Since launching in early April, we have published over 15 Breakdowns and continue to release a new episode weekly. To learn more, check out joincolossus.com. I hope you enjoy my conversation with David Vélez.

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 by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. 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

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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

[00:02:55] - [First question] - Why Berkshire Hathaway took such an interest in Nubank

[00:04:46] - Key differentiators between Nubank and other incumbent banks

[00:07:11] - Onboarding user experience and overview of customer acquisition

[00:10:38] - The original problem Nubank wanted to solve and how they approached it

[00:15:32] - Lessons from working at Sequoia about great FinTech businesses

[00:19:18] - What parts of his personality and life experience worked its way into NuBank

[00:23:18] - Obstacles that needed to be overcome in order to serve the Brazilian public

[00:27:52] - Transparency and patience needed to overcome a complicated problem

[00:31:11] - Nubank’s business economics compared to other banks

[00:34:46] - Overview of rewards programs and why customers like them so much

[00:37:27] - Best questions asked that explained Nubank’s market opportunity

[00:42:02] - Second layer unit economics of the company and where to look for them

[00:45:51] - How far we are into the Latin American technological ecosystem’s development

[00:47:24] - Lessons learned from some of the worst decisions he’s made as a founder

[00:51:30] - What he’s most excited about for the future

[00:54:19] - The kindest thing anyone has ever done for him

My guest today is Balaji Srinivasan, a serial entrepreneur and angel investor. Balaji is known to challenge conventional wisdom, and he lives up to his reputation in this conversation. We discuss a wide variety of topics, including advancements in health tracking, ways to evaluate your own information diet, and how technology is driving decentralization and what that could mean for countries, corporations, and individuals.

Before we transition to the episode, if you enjoy this conversation with Balaji, I’d recommend the Ethereum episode on our newest show, Business Breakdowns. You can find that episode and more on your favorite podcast player or at joincolossus.com. Please enjoy my conversation with Balaji Srinivasan.

For the full show notes, transcript, and links to the best content to learn more, 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've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Marqeta, Oatly, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick.

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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".

------

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] - Thoughts on information diets and how they influence individuals

[00:21:37] - Ways to optimize your diet by reading the source material and consuming less news

[00:26:40] - Understanding the informational supply chain and tracing data back to the origin

[00:41:07] - Modern cities, the nature of a group of individuals, and what sovereignty may mean in the coming years

[00:53:52] - Key ingredients and main components needed for a successful startup city

[01:11:35] - Social impacts from everyone becoming an investor and how it ties into everything

[01:25:49] - Recommendations and a personal prescription for longevity, health, and wealth

[01:37:32] - The kindest thing anyone has ever done for him

My guest today Michael Mayer, is the founder and CEO of Bottomless, a company that automatically replenishes your coffee supply where I am both an excited investor and customer. Today’s conversation is about tactical lessons Michael has learned while building the business. We talk about identifying an addressable problem, how to avoid solving for bottlenecks that don’t yet exist, and how to iterate through problems before scaling. As yet another example of a self-taught entrepreneur, it’s inspiring to hear Michael’s mindset for problem-solving. I hope you enjoy my conversation with Michael Mayer. 

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 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

[00:02:45] - [First question] - How he got into this space in the first place and found the problem Bottomless would eventually solve

[00:08:43] - What he would do better the second time if he had to find a problem and narrow his focus all over again

[00:09:49] - The most notable lessons learned about data legibility beyond the scale

[00:10:15] - Seeing like a State: How Certain Schemes to Improve the Human Condition Have Failed

[00:13:01] - Overview of building the first Bottomless hardware prototype 

[00:14:29] - First steps of physically assembling the first scale and learning fabrication

[00:17:40] - Roughly how long it would take to build scales in the beginning

[00:18:30] - How long the company was bootstrapped 

[00:20:41] - Making the pivot to seeking out investor support

[00:29:03] - The often overlooked role of social capital as a startup founder

[00:31:00] - Importance of following niches and passions

[00:32:15] - His philosophy in successfully scaling the production side of the company

[00:34:45] - Lessons learned from bottlenecks and their utility in founder growth

[00:36:52] - The problem of supplier legibility and improving it

[00:40:14] - Understanding USPS predictability as a product input

[00:43:03] - Always problems to solve and the fractal nature of them

[00:46:13] - Challenges of hiring staff in the tech space

[00:50:15] - Lessons learned about personal bottlenecks and the need to evolve alongside your company

[00:52:21] - Monitoring your informational inputs and their role in shaping your mindset

[00:55:58] - Closing thoughts on the business boss battles founders face

[00:57:38] - Why society writ large should perceive starting a company as status-enhancing

[00:59:44] - What bottlenecks for Bottomless may present themselves in a year from now

My guest today is Silicon Valley icon, Marc Andreessen. Before co-founding the legendary venture capital firm, Andreessen Horowitz, Marc was an early pioneer of the internet. At age 22, he built Mosaic, the first widely adopted web browser and the technology that underpinned Netscape Communications. Marc was an early proponent of cloud computing, social networks, and the software business model. In each case, Marc seemed to be well ahead of the crowd. During our conversation, we explore how software is making the world better, how slow sectors like education, healthcare, and housing are eating the economy, and Marc’s vision of the future for A16Z. Please enjoy my conversation with Marc Andreessen.

Before we transition to the episode, I wanted to highlight our newest series, Business Breakdowns. Each week we do a deep dive into an individual business to understand what makes it great. 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 the best content to learn more, check out the episode page here.

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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.

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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.

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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

[00:04:10] - [First question] The ways in which software is eating the world

[00:06:25] - The power of transitioning from atoms to bits and its impacts

[00:09:57] - Potential downsides and credible concerns as we shift into an automated world 

[00:16:00] - Major impediments of productive growth over the coming decades  

[00:23:12] - Real change versus false change due to COVID-19 writ large 

[00:30:06] - Thoughts on the rising cost of post-secondary education in light of the internet

[00:37:03] - Why doesn’t Google have their own university and if they might in the future

[00:41:30] - Whether or not an entrepreneurial focus on generally slower sectors may produce excess returns

[00:44:17] - Thoughts on hardware, its unit economics, and its role in shaping society

[00:47:52] - How to think about investing in immensely complicated, large-scale projects

[00:54:10] - What they’re building at A16Z, a new crypto fund, and where their sights are set

[01:03:09] - East coast investing styles and things we can borrow from them

[01:06:01] - Potential plans to step into the public equity space 

[01:11:09] - Defining why it’s time to build and the imperative it sets

[01:15:13] - The kindest thing anyone has ever done for him

My guest today is Will Ahmed, founder of fitness wearable company WHOOP. What started as a business plan in 2011 has evolved into the 24/7 health-tracking device you’ll often see on athletes across professional sports. During our conversation, Will and I discuss how his own backstory ties into the founding of WHOOP, the key design decisions they made in the ultra-competitive wearables market, and how the company grew slowly before inflecting in recent years. Will shares awesome details on health tracking and what it might look like in the future as a preventative tool rather than simply a tracking tool. I hope you enjoy this great conversation with Will Ahmed.

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 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

[00:02:45] - [First question] - The founding story of WHOOP

[00:05:45] - Narrowing in on the problem to focus on solving 

[00:08:58] - Overview of analyzing and quantifying recovery, strain, and sleep

[00:15:52] - Downsizing the problem set to deliver an affordable solution

[00:18:48] - What he’s learned about hardware product road mapping

[00:21:43] - How many people wear their WHOOP all-day

[00:22:05] - Early lessons from taking their wearable tech product to market

[00:26:25] - Ways in which they landed their first high-profile athletic brand ambassadors

[00:27:55] - Interesting methods that proved successful in their marketing tactics

[00:32:06] - Observations of making the switch to a subscription service

[00:34:00] - Why big apparel companies failed where WHOOP didn’t

[00:35:20] - Changes in behavior from users who learn about their habits using WHOOP

[00:40:18] - His philosophy on business partnerships and how he developed it

[00:44:56] - How he ended up with a paddle from the Navy Seals

[00:47:13] - Ways WHOOP stays ahead and upcoming trends in the wearable tech space

[00:50:13] - Data beyond HRV that will become more accessible and affordable to track 

[00:51:09] - The extent that data and software relative to hardware are a key part of WHOOP

[00:53:06] - Lessons learned about effective leadership on a personal level

[00:56:13] - Notable differences in his leadership style from then compared to now

[00:57:34] - Thoughts about business defensibility in such a competitive space

[00:59:44] - Reasons behind why WHOOP products don’t have a screen

[01:02:13] - Valuable lessons for other entrepreneurs when studying WHOOP’s story

[01:05:03] - Systems in place that allow for their speed and pace of growth

[01:06:31] - What makes a day of work fun for him

[01:08:39] - Why we shouldn’t measure our steps

[01:10:01] - What is the kindest thing anyone has ever done for him

My guest today is Howard Marks, co-founder of Oaktree Capital, a leading investment manager, and one of the world’s largest distressed debt investors. In our conversation, we discuss takeaways from the market selloff and rapid recovery in 2020, the importance of assessing both quantitative and qualitative factors in markets, and the benefits Howard has realized from a career of writing. I hope you enjoy this great conversation with Howard Marks. 

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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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.

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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

[00:03:40] - [First question] - Ideas he has that he feels will stand the test of time

[00:04:39] - Defining the difference between risk and uncertainty and a frame of mind to have around uncertainty as an investor

[00:05:31] - Equity and debt investing as the businesses of what could go right or wrong

[00:07:01] - How exciting equity up runs can lead to analytical blindspots

[00:09:10] - Ways in which the last 18 months stacked up against his market experience

[00:11:57] - Ways we can change our model of the world going forward to avoid a crisis

[00:15:04] - Why psychology is important to consider over data during market extremes

[00:17:46] - Reflections and lessons from discussing the concept of value with his son

[00:27:33] - Spirited disagreements he and his son continue to have about markets

[00:31:46] - What he’s learned about writing well and the utility of doing so

[00:40:39] - Lessons that are better experienced in investing than reading about them

[00:43:35] - Daring to be great and the willingness to be wrong, alone or different

[00:50:24] - Embracing mystery and the joys it can bring

[00:53:28] - The kindest thing anyone has ever done for him

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.

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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] - 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 based on its current trajectory

[00:54:26] - What her information diet consists of lately 

[00:55:27] - Areas she’s interested in currently but learning more than being proficient 

[00:56:59] - Ways in which she’s become a better leader

[00:57:46] - Unique factors about what makes Vanta tick

[00:58:45] - Negative advice to would-be founders out there

[01:00:22] - The kindest thing anyone has ever done for her

[01:02:44] - Major insights learned from living in Rwanda, Thailand, and Uganda

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.

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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

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.

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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

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.

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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 approach to in-game player rewards

[01:11:24] - The kindest thing that anyone has ever done for him

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

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-  )

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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.

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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.

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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

My guest today is Henrique Dubugras, co-founder and CEO of Brex, an all-in-one finance account for businesses. Brex recently raised funding at a valuation of over 7 billion dollars despite being founded only four years ago. In our conversation, we cover Brex’s transition from a credit card for start-ups to the central account for businesses, why building that central account was orders of magnitude more difficult than expected, and the difference between building a business in Brazil and the US. We also discussed Henrique’s term horizon for building Brex and how that impacts his decision-making for the business. Please enjoy my conversation with Henrique Dubugras.

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 by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at dell.com/en-us/work/shop/deals.

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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

[00:02:53] - [First question] - The state of the B2B financial world before Brex

[00:06:29] - How such a high margin space was generally underserved

[00:08:24] - What the first version of the Brex card looked like

[00:10:48] - How long it took to build and launch their infrastructure

[00:11:13] - Why market penetration is so low for cards in B2B businesses

[00:13:14] - How he thinks about this landscape in Brazil versus the US

[00:14:55] - What interchange and high margins allows him to pass on to the consumer

[00:16:23] - Brex’s first revenue event

[00:17:38] - What the biggest hurdle was to overcome when they launched

[00:19:02] - Key marketing strategy early on and what made it successful

[00:21:16] - Continued distribution lessons they learned from their initial success

[00:22:39] - Building an effective sales force to push their product

[00:24:41] - What makes the current landscape so fertile for fintech businesses

[00:27:12] - Analysis of their unique funding round dynamics

[00:28:42] - Their second product and the insight that lead to that decision

[00:31:05] - Darkest moments while trying to build their central account

[00:31:50] - What their central account allows them to facilitate writ large

[00:35:27] - Notable differences between entrepreneurship in Brazil versus the US

[00:38:55] - Observations on inefficiencies in the US startup space

[00:40:16] - Pros, cons, and costs of being largely remote

[00:41:50] - Keys to building a successful hiring pipeline

[00:44:05] - Lessons learned about decision making and optimization

[00:45:39] - Developing an effective skill set to convince other people of anything

[00:47:35] - What excites him about being a part of Brex lately

[00:49:13] - What excites him about the future in general

[00:50:39] - His business philosophy and the set of principles that guide him 

[00:52:03] - Nuances that make focusing on a single problem so attractive

[00:53:51] - Long term infrastructure decisions that will pay off in the end

[00:55:12] - Thoughts and hi perspective on cash flow in general

[00:58:18] - The kindest thing anyone has ever done for him