Invest Like the Best with Patrick O'Shaughnessy

Latest Episodes:

Spenser Skates - Challenging Big Ideas - [Founder’s Field Guide, EP. 42] Jul 15, 2021

Show notes

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.

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

David Sacks - How to Operate a SaaS Startup - [Invest Like the Best, EP. 234] Jul 13, 2021

Show notes

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".

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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.

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

David Vélez - Building the Branchless Bank - [Founder’s Field Guide, EP. 41] Jul 08, 2021

Show notes

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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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

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

Balaji Srinivasan - Optimizing Your Inputs - [Invest Like the Best, EP. 233] Jul 06, 2021

Show notes

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".

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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.

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

Michael Mayer - Business Boss Battles - [Founder’s Field Guide, EP. 40] Jul 01, 2021

Show notes

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 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.

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

Marc Andreessen - Making the Future - [Invest Like the Best, EP. 232] Jun 29, 2021

Show notes

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.

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

Will Ahmed - Optimizing Human Performance – [Founder’s Field Guide, EP. 39] Jun 24, 2021

Show notes

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 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."

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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.

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

Howard Marks - Embracing the Psychology of Investing - [Invest Like the Best, EP. 231] Jun 22, 2021

Show notes

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.

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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.

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

Christina Cacioppo - Building the New Standard in Security – [Founder’s Field Guide, EP. 38] Jun 17, 2021

Show notes

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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Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.

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

John Harris - Resilience and Imagination - [Invest Like the Best, EP. 230] Jun 15, 2021

Show notes

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.

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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.

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

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Invest Like the Best with Patrick O’Shaughnessy

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