Invest Like the Best with Patrick O'Shaughnessy

Latest Episodes:

James Reinhart – Lessons in Process Power – [Founder’s Field Guide, EP. 32] May 06, 2021

Show notes

My guest today is James Reinhart, founder, and CEO of thredUP, an online thrift marketplace. thredUP’s online store is distinct in the way the company touches every product, processing every piece of clothing at their own facilities instead of focusing solely on being a marketplace connecting buyers and sellers. We talk about the competitive advantages of building processing plants from the ground up, how James turned thredUP from having negative gross margins to very strong unit economics, and the future of retail more broadly. I hope you enjoy this conversation with James Reinhart.

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.

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

[00:02:47] - [First question] - An overview of thredUP

[00:03:44] - Origination of the idea

[00:04:43] - Initial reactions to the concept

[00:05:22] - Early days trying to acquire the first customers

[00:07:32] - The evolution of their margins

[00:11:04] - Providing convenience for the customer

[00:13:01] - Lessons on working capital and inventory

[00:14:27] - How consumers use the money they receive within the platform

[00:15:47] - The evolution of the operations of the business and scaling

[00:20:20] - When it’s time to shift from human capital to automation

[00:22:00] - The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time

[00:22:39] - Competitive Advantage: Creating and Sustaining Superior Performance

[00:23:15] - Removing the hurdles for acquiring more buyers

[00:27:19] - Convincing investors on this concept

[00:30:44] - The most difficult time for him psychologically in creating the business

[00:31:56] - How he thinks about capital allocation

[00:32:12] - The Startup Way: How Modern Companies Use Entrepreneurial Management to Transform Culture and Drive Long-Term Growth

[00:33:51] - Overview of the clothing landscape and what would surprise most people

[00:38:00] - Expanding their business from here

[00:40:36] - Improving how the raw material is sourced for apparel

[00:42:45] - The nature of work

[00:42:56] - Dustin Moskovitz Podcast Episode

[00:49:04] - What he’s most excited about for the future

[00:50:35] - Kindest thing anyone has done for him

Andrew Sugrue - Investing in Paradigm Shifts - [Invest Like the Best, EP. 224] May 04, 2021

Show notes

My guest today is Andrew Sugrue, co-founder, and partner at Avenir Growth Capital. Avenir is a growth equity firm focused on backing category-defining businesses. In our conversation, we cover Andrew’s investing career, what he learned from Julian Robertson, how counter-positioning could drive unique distribution, and the difference between good and bad growth. We also spend time examining the business model of two of Andrew’s portfolio businesses, SavageXFenty and Latch. There are so many great lessons for investors and operators to take away from Andrew. Please enjoy my conversation with Andrew Sugrue.

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 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.

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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

[00:03:31] - [First question] - His journey leading up to his current firm

[00:05:55] - Lessons learned from time spent with Julian Robinson

[00:07:54] - The chip on his shoulder that helped keep him driven

[00:08:40] - Transforming his early motivators into a sustainable career-long fuel

[00:10:46] - The first things in mind when approaching a new business or person

[00:14:00] - Analysis of Savage Lingerie and learning about how that sector operates

[00:20:27] - Amazon producing a one-hour special Savage infomercial

[00:23:16] - Lessons learned from Savage that can be applied to other direct to consumer brands

[00:25:04] - Having a celebrity at the forefront of your brand

[00:26:41] - Levers and overview of apparel company income statements and how they can shape the way you grow and operate the business

[00:30:08] - Apparel companies always being tied to identity

[00:31:03] - Analysis of Latch and learning about the relationship between hardware and software

[00:33:40] - How Latch works and why you might need it

[00:38:56] - Other businesses that may benefit from understanding the events that drive demand and using it as an opportunity for customer acquisition

[00:40:12] - The concept of density of demand and the power behind it

[00:41:33] - Other areas of operations density of demand could be applied

[00:44:11] - Shared components that unite Avenir’s portfolio companies

[00:46:14] - How he thinks about the world of private investment, having lived such a diverse career

[00:50:22] - Developing relationships growing such a concentrated portfolio

[00:51:35] - Macro thoughts on the state of investing today

[00:52:59] - Defining and identifying characteristics of bad growth

[00:54:05] - The kindest thing anyone has ever done for him

Alyssa Ravasio - Supply, Demand, and the Outdoors - [Founder’s Field Guide, EP. 31] Apr 29, 2021

Show notes

My guest today is Alyssa Ravasio, co-founder and CEO of Hipcamp, a platform to discover and book your next camping trip. I was excited for this conversation as it combines two of my favorite passions – the outdoors and internet marketplaces. In our discussion, we cover how Alyssa bootstrapped demand in the early days of Hipcamp, the importance of creating not just great experiences but magical ones, and the evolution of Hipcamp’s business model. After listening to this episode, I’m sure the first thing you’ll want to do is get outside in nature. Please enjoy my conversation with Alyssa Ravasio.

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

[00:02:57] - [First question] - The original insight that led to founding Hipcamp

[00:06:15] - What she studied in college and primary lessons learned there

[00:08:18] - Specific features of studying the internet that influenced her trajectory

[00:10:14] - Deciding what to attack first when developing Hipcamp’s infrastructure

[00:14:12] - Dimensions and market size of the outdoor industry

[00:15:48] - Organizing fragmented data into a useable schema and data set

[00:18:24] - What customers cared about most in the early days of Hipcamp

[00:20:00] - Managing focus and liquidity of the initial marketplace

[00:22:58] - Helping landowners manage the logistics of their property placements

[00:25:16] - Liability insurance in the outdoor industry

[00:27:35] - The biggest challenge faced in developing an outdoor marketplace

[00:30:03] - Amplifying and accelerating naturally grooved distribution

[00:32:32] - Identifying the top correlates of making magic happen

[00:34:55] - An ideal future for Hipcamp five years from now

[00:38:28] - What bad supply looks like and creating quality standards

[00:42:08] - Their business model and revenue stream

[00:44:45] - Deciding on their take rate and the debate around booking fees

[00:46:14] - Lessons learned along the way as a leader

[00:47:42] - Unit economics from the host’s perspective

[00:52:33] - The most interesting businesses built on top of Hipcamp

[00:53:35] - Why is Hipcamp’s mission so important to her

[00:57:11] - The kindest thing anyone has ever done for her

Josh Buckley - Identifying Legendary Start-ups - [Invest Like the Best, EP. 223] Apr 27, 2021

Show notes

My guest today is Josh Buckley. Josh is the new CEO of Product Hunt and an investor in many breakout companies like Rippling, Lattice, Boom Supersonic, and Relativity Space. In our conversation, we cover how video game companies are at the forefront of new business models, what current companies can learn from video game companies, Josh’s investing philosophy, and the three things he looks for when trying to identify the next legendary startup. Josh’s long experience operating his video game business, Mino Games, gives him such an interesting perspective as an investor, and I really enjoyed exploring that with him. Please enjoy my conversation with Josh Buckley.

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

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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

[00:03:56] - [First question] - His start as an entrepreneur in online game

[00:05:09] - His parent's reaction to selling his first company at fifteen

[00:05:57] - Starting a second video game company

[00:07:40] - The video game industry being ahead of the curve in performance marketing, distribution, and operations

[00:08:49] - Notable two year lag between gaming innovation and other consumer sectors

[00:10:50] - What is happening today in gaming that may be a glimpse into the future

[00:12:41] - Key elements for creating a great gaming experience

[00:15:29] - Building a meta game on top of the game itself to maximize engagement

[00:17:23] - Monetizing free to play games through in-game purchases

[00:20:25] - The most portable idea from fifteen years in gaming that can be applied to business

[00:22:02] - A future shift towards usage-based pricing models

[00:23:03] - His overall investment philosophy and strategy

[00:26:45] - Example of small a market with a high growth rate

[00:27:38] - Key elements of system elements and design when evaluating a business

[00:31:07] - What a flywheel looks like and investing in one such as Next Health

[00:33:24] - Working core actions versus giving credit ones that aren’t yet working but may drive desirable outcomes

[00:34:13] - Why don’t more investing firms have a flywheel?

[00:39:04] - Product Hunt as a standalone business and part of a self-reinforcing ecosystem

[00:40:17] - Emerging systems and ecosystem edges in the digital landscape

[00:42:17] - Potential barriers for crypto becoming widely adopted in a variety of ways

[00:44:29] - New frontiers and platform shifts like crypto that may unlock new doors for companies

[00:45:13] - Which person has rewired his brain in his lifetime the most

[00:47:13] - Weirdness around Stripe and Plaid when he first encountered them

[00:48:37] - Meta games people in the industry are playing or should be playing

[00:51:25] - Controversial ideas around the business world today writ large

[00:54:01] - Implications of shifting primarily towards a digital world

[00:54:14] - The kindest thing anyone has ever done for him

Thomas Tull - New Physics of Business - [Founder’s Field Guide, EP. 30] Apr 22, 2021

Show notes

My guest today is Thomas Tull, the founder of Tulco LLC, an investment holding company that invests in businesses with high growth potential and helps them apply machine learning and data analytics. Thomas is also the founder and former CEO of Legendary Entertainment, the production company behind the Dark Knight, Hangover, Inception, 300, and many more iconic movies which he sold in 2016. In our discussion, we cover the movie industry’s value chain, the recipe for trying to make a successful movie and how Legendary pioneered the use of data analytics to improve those odds, and Thomas’ concept of the new physics of business and why it matters for what he’s now building at Tulco. Please enjoy my conversation with Thomas Tull.

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

[00:03:06] - [First question] - His overarching career philosophy and theme

[00:04:07] - Attacking a previously established industry in a new way

[00:05:20] - The origin story of Legendary and stepping into the film industry

[00:07:56] - Stakeholders involved in producing a movie and pre-existing profit pools when Legendary was founded

[00:12:44] - Topline and downstream revenue distribution of intellectual property from then versus now

[00:19:46] - Lessons learned about intellectual property writ large

[00:19:03] - What makes Chris Nolan such an exceptional storyteller

[00:23:42] - Power and defensibility of cinematic universes and transmedia storytelling

[00:22:21] - Applying quantitative data analysis to film production and marketing

[00:25:55] - Competitive frontiers in movie studios and his advantageous skillset

[00:28:10] - Potential investment opportunities in media or media adjacent businesses

[00:29:26] - Interesting new tools that could be developed in entertainment technology

[00:31:00] - His favorite mind-blowing and awe-inspiring movies

[00:32:41] - Telling Jackie Robinson’s story in the film, 42

[00:35:30] - Jackie Robinson and Chadwick Boseman’s quiet dignity

[00:36:56] - Building the holding company Tulco

[00:39:02] - The new physics of business that can’t be ignored

[00:42:40] - Modern velocity in the current era of business

[00:46:03] - Interweaving an antifragile mindset into the company culture

[00:47:55] - Who Tulco Labs is and what they do

[00:49:12] - What gets him most excited about exploring a new business for the first time

[00:50:48] - Unique characteristics he seeks out in a management team

[00:52:31] - Trends that make him feel worried about the future

[00:57:47] - Trends that make him feel optimistic about the future

[00:58:49] - An important lesson learned from his career on a personal level

[01:00:15] - The kindest thing anyone’s ever done for him

Paul Enright - The Buy Side Primer - [Invest Like the Best, EP. 222] Apr 20, 2021

Show notes

My guest today is Paul Enright, managing partner at Krainos Capital, his family office. Before running his own family office, Paul worked on the buy-side at Viking Global for over a decade managing their consumer and technology portfolios and before that at Morgan Stanley on the sell-side.

I thought Paul would be the perfect person to help me demystify the world of high finance – explaining the difference between the buy-side and sell-side, how long/shorts differ from long onlys, and walking through the various jobs in the investing world. In addition to setting that foundation, we also cover the evolution of the buy-side, what makes someone a great researcher verse a great stock picker, and various portfolio construction methodologies. Paul brings such a wealth of knowledge and experience to the table. I think this episode will be enjoyable for investing novices and professionals alike.

Please enjoy my conversation with Paul Enright.

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

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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

[00:03:39] - [First question] - His history in both the buy and sell side

[00:05:20] - Different types of roles on the buy side and sell side

[00:06:48] - Interest sets that best align with being a buyer or a seller

[00:07:57] - The emotional experience of being on the buy side and exposed to risk

[00:08:53] - How the nature of buying and portfolio construction has changed

[00:10;15] - What Regulation Fair Disclosure (Reg FD) is

[00:12:46] - Key terminology and definitions of long-only and long-short funds

[00:17:40] - Varying clusters of long-short funds and defining each type

[00:21:48] - Differences in exposure between a platform model versus a traditional long-short stock picking sense

[00:25:16] - Skill sets that are most important to have when navigating this space

[00:29:03] - What is good and what is great when it comes to “digging”

[00:31:20] - Why the quality of one’s analysis matters

[00:33:10] - Having a potential edge when deciding based on someone else’s analysis

[00:35:19] - Foundational building blocks of an effective pitch

[00:37:20] - Finding wrongly identified stocks and reaping the rewards

[00:40:49] - Overview of good portfolio construction and lessons learned over the years

[00:44:06] - Why hedge funds tend to traffic heavily in T.M.T. and consumer sectors

[00:45:53] - Elements that strike him as great in a business

[00:48:05] - A business that once seemed great but has since faded away

[00:49:22] - Why hedge-fund managers seem to always make the most money

[00:53:50] - What a well run firm looks like

[00:56:39] - Characteristics that may make you well suited for a career in fund management

[01:00:23] - Why quality mentors and portfolio managers are so important when deciding where you want to work

[01:01:38] - What interests him mosts in markets today

[01:05:20] - Useful frameworks and formulas used when approaching a new business

[01:08:15] - Interesting features about telecom businesses and what defines them

[01:10:45] - The future of the modern world’s internet infrastructure

[01:14:44] - Abundance vs zero-sum and fixed vs growth mindsets

[01:18:12] - The kindest thing anyone’s ever done for him

Trevor McFedries - Building Web 3.0 - [Founder’s Field Guide, EP. 29] Apr 15, 2021

Show notes

My guest today is Trevor McFedries, the founder of technology startup Brud and the creator of virtual pop star Miquela, a Gen Z icon with millions of fans worldwide. Trevor’s background is fascinating - he worked as a DJ and producer, toured with Katy Perry, worked at Spotify, and done just about every interesting thing I can imagine. In our conversation, we discuss the music-industrial complex, the creation of Miquela, and what Web 3.0 will mean for creators and builders in the future. I hope you enjoy this conversation with Trevor McFedries.

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

[00:02:54] - [First question] - What unites the diversity of his career

[00:03:39] - What inspired him to pivot away from football and step into creative arts

[00:05:50] - Lessons learned from being a touring DJ and producer that apply to the creative tech sector

[00:07:40] - A view of the music industrial complex from the inside

[00:08:57] - How the internet deciding who becomes popular affected already established artists

[00:10:57] - Interesting opportunities in the music landscape in 2021

[00:11:40] - Time spent at Spotify and the spark of insight that led to founding Brud

[00:16:02] - The sequence of creating a digital artist like Lil Miquela

[00:19:02] - What it feels like to be “othered”

[00:20:24] - Embracing one's intersections and applying it to a business model

[00:21:18] - The team behind Lil Miquela and her design process

[00:25:49] - Ingredients required for building a great narrative

[00:28:35] - What social media platforms matter today, and the state of the social landscape

[00:32:21] - Expanding Lil Miquela’s world and digital media monetization

[00:36:32] - Differences between web 2.0 and 3.0 that may directly affect creators

[00:38:27] - Ways innovations like NFTs make spawn new network participants

[00:39:49] - Programmable art and media experiences

[00:41:03] - The most cutting-edge ideas in the digital persona space

[00:43:21] - Technology that wasn’t available that had to be built to enable new experiences

[00:45:49] - One of the hardest decisions he’s had to make in Brud’s history

[00:47:16] - The furthest they’ve ever pushed the envelope

[00:48:06] - What’s the thing that keeps him going every day

[00:50:12] - Finding cultural white space and inventing a character that could speak to investing to inspire new generations

[00:52:01] - Units of media contribution and creative container experimentation

[00:53:27] - What has him the most excited about the future of his industry

[00:54:32] - Missing technological components that could inspire new digital creatives

[00:56:53] - Work ethic through the lens of developing a jump shot

[00:59:00] - One business lesson that he believes in deeply

[01:00:05] - The kindest thing anyone’s ever done for him

Chris Dixon - The Potential of Blockchain Technology - [Invest Like the Best, EP. 221] Apr 13, 2021

Show notes

My guest today is Chris Dixon, a general partner at Andreessen Horowitz. Chris is a prolific investor and thinker, having been an entrepreneur, angel investor, and is now focused on investing in the crypto and blockchain space for Andreessen. Our conversation focuses on Chris's overall thesis for investing in the cryptocurrency space, the opportunities and limitations of blockchain applications, and why this is the most interesting area for investing and building over the next ten years. What's exciting to me is blockchain technology's ability to help us re-imagine old business models and catapult them into the 21st century – and we cover a lot of them. I hope you enjoy my conversation with Chris Dixon.

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

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics and everything in between. Learn more and try Canalyst for yourself at canalyst.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

[00:03:56] - [First question] - His overall crypto investing philosophy

[00:06:37] - New opportunities presented by blockchain technology

[00:15:31] - Permanent limitations and shortcomings of blockchains

[00:18:32] - Evolution of DeFi and crypto currencies

[00:21:11] - Whitepapers: Bitcoin, Ethereum, MakerDAO

[00:22:08] - How to take out a loan using the Maker protocol

[00:23:22] - Utility of Dai and stablecoins

[00:29:14] - How the DeFi network will reinvent the future

[00:39:53] - Uniswap, tokens, and fundamentally redefining leverage

[00:36:29] - The Company: A Short History of a Revolutionary Idea

[00:38:00] - Developer and entrepreneurial incentives for building blockchain technology

[00:39:46] - BitClout, Rally and the early days of social tokens

[00:46:38] - Demand curve and value creation efficiency in a digital creator economy

[00:47:24] - NFTs and a Thousand True Fans

[00:54:49] - Polkadot, Solana, Cosmos and programmable blockchains

[00:58:03] - The most exciting moment for him in the last year

[01:00:19] - Decentralized autonomous organizations

[01:02:46] - The single thing that has him most excited about the future of this space

[01:05:18] - The Next Big Thing Will Start Out Looking Like a Toy

Shopify: The E-commerce On-Ramp - [Business Breakdowns, EP. 01] Apr 09, 2021

Show notes

Welcome to the first episode of our newest show, Business Breakdowns, featuring deep-dive conversations on individual businesses. In each episode, we will dissect a new company with investors and operators that know it best.

We’ve already released the first three episodes on Shopify, Chipotle, and Alibaba. Subscribe to Business Breakdowns through the podcast player of your choice:

Leave us a 5-star rating on Apple Podcasts if you like the show!

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Today we will be diving into Shopify. Shopify was founded in 2004 by Tobi Lütke and Scott Lake around their original problem of why it's so hard to build an online business when they struggled to open an online snowboard equipment store. Today, Shopify's goal is to make commerce better for everyone, and it's used by more than 2 million merchants to run their online businesses. It's essentially an on-ramp for people looking to sell online.

To help us break down Shopify, I'm joined by co-host Zack Fuss and our guest Alex Danco, who works on the Money team at Shopify.

To really understand Shopify, you have to understand its different business units -- Core, Merchant Services, Ecosystem, and the new Shop platform -- and the role they each play in making commerce easier and better for merchants. We begin this breakdown by covering each of those business units and how they compare to Apple's business lines. We then dive deep into how Shopify makes money through the first and second derivative of their merchant success and how Shopify thinks about friction in e-commerce. We close with an incredible analogy of Shopify and StarCraft and the tools that Shopify has built into the still-nascent world of e-commerce.

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

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Business Breakdowns is a property of Colossus, Inc. For more episodes of Business Breakdowns, visit joincolossus.com/episodes.

Show Notes

[00:04:03] - [First question] - What Shopify is as a product

[00:05:58] - Product pillar 1: Core[00:07:58] - Product pillar 2: Merchant services[00:10:02] - Product pillar 3: Ecosystem

[00:12:04] - Product pillar 4: Shop

[00:14:08] - The evolution of commerce with the rise of the internet

[00:21:01] - Differences between high and low trust commerce

[00:25:48] - The role of friction and trust in stakeholder variety

[00:30:18] - Overview of all four product pillars’ business models

[00:33:10] - Shopify App Store

[00:34:16] - How Shopify competes and partners with their competitors

[00:36:53] - Shop Pay expands to Facebook and Instagram

[00:38:49] - Key areas where Shopify will continue to grow across their product pillars

[00:42:52] - Affirm, Klarna, Afterpay

[00:43:56] - Potential pitfalls of having such a high self-imposed quality bar

[00:45:12] - Conway’s law[00:45:12] - Aggregators versus platforms

[00:53:35] - Unique marketing aspects for Shopify’s sales and marketing with their subscription model

[00:56:37] - Shopify: A StarCraft Inspired Business Strategy

Tony Xu - A Human and Math Problem - [Founder’s Field Guide, EP. 28] Apr 08, 2021

Show notes

My guest today is Tony Xu, co-founder, and CEO of DoorDash. Tony started DoorDash 7.5 years ago, and today it is one of the largest food delivery and logistics platforms globally, with operations in the US, Canada, Australia. In our conversation, we discuss the initial problem that DoorDash set out to solve, DoorDash’s counterintuitive approach to building their product, and the surprising benefits of capital constraints in DoorDash’s early days. DoorDash’s business model is an equal parts logistics nightmare and a human coordination problem, or as Tony puts it, a human and math problem. After talking to Tony, I feel his personality makes him a great candidate to solve those problems.

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

[00:03:07] - [First question] - The catalytic moment that inspired Tony to build DoorDash

[00:06:33] - Network density and its role in scalability

[00:09:15] - Solving a math and sales problem simultaneously

[00:11:33] - Becoming aware of multiple problem sets for restaurant owners

[00:14:34] - Designing a team to quantify friction and turn it into useable data

[00:16:49] - How to approach difficult problems and compartmentalize them in a practical way

[00:18:38] - Accounting for high-level variance in long-term goals

[00:21:54] - Factoring in time horizons for variance and planning for the future

[00:23:08] - Slowing down an action process to minimize a high-consequence decision

[00:26:48] - Generating demand after completing their software infrastructure

[00:28:15] - Strategic choices between network health and unit economics

[00:30:32] - Why DoorDash struggled to raise financing in their seed-stage

[00:32:23] - Solving a small fraction of a larger logistics problem

[00:35:00] - Differences between local commerce and distribution centers

[00:36:44] - Creating the DashPass subscription service and how premium experiences influence user behavior

[00:38:34] - Advantages and potential diminishing returns in servant leadership

[00:40:41] - His broader philosophy on leadership and how it’s changed over the years

[00:44:55] - Creating an incentive-aligned culture of ownership at scale

[00:47:02] - The most surprising lessons learned about company building

[00:50:38] - Unexpected positive outcomes that may emerge in other areas due to DoorDash’s growth in the coming years

[00:53:44] - Will DoorDash’s presence change behavioral patterns in where people choose to live or start their business?

[00:55:36] - What has him most excited for the future

[00:56:55] - Kindest thing anyone has ever done for him

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