Today’s episode represents a new chapter for Invest Like the Best, so requires a longer introduction than normal. Starting today, I’ll be bringing you two episodes per week on the same feed. On Tuesday’s, I’ll focus on investors, and on Thursday’s, I’ll host builders—founders, CEOs, and operators from all different fields. We call this new Thursday series Founder’s Field Guide. There’s nothing more interesting to me than how great businesses get build, and how investors can identify those businesses at the right time. We’ve already recorded with founders build companies in food, technology, infrastructure, shipping, collectibles, and many more categories. The goal each weak will be to have a builder share what they’ve done, how they’ve done it, and what they’ve learned along the way. We view this as a critical next step in furthering our mission: to capture and openly share the world’s best knowledge on business and investing.Onto the kickoff episode with Rahul Vohra. Rahul is the Founder & CEO of Superhuman, an extremely popular product for managing email. Rahul describes himself as a Computer Scientist, Gamer, Entrepreneur, and Designer. You’ll see quickly why it’s the intersection of these areas that sets Superhuman apart. We discuss why emotion matters when building products, and how other entrepreneurs can learn from his experience. Please enjoy the very first episode of Founder’s Field Guide, and stay tuned in future weeks as we host leaders from Nike, Cisco, Twitch, and so many more…listen in as we explore the world of cannabis, baking (not that kind), manufacturing, hardware, software, and more. Let’s dive in. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out.  This episode is also sponsored by Vanta.  Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.  For more episodes go to InvestorFieldGuide.com/podcast.Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.Follow Patrick on Twitter at @patrick_oshag Show Notes(3:56) – (First question) – His interest in game design and emotion in software creation(5:15) – Key elements of game design(6:23) – Toys in digital software creation(8:48) – Finding success in boring software solutions(11:19) – Getting confidence while building when there are no real customers(14:08) – How they landed on their final product(15:40) – The Superhuman Product/Market Fit Engine(20:46) – Determining software price(21:55) – Positioning Your Startup is Vital — Here’s How to Nail It(23:09) – Positioning: The Battle for Your Mind(24:13) – Monetizing Innovation: How Smart Companies Design the Product Around the Price(26:36) – First big break for the business(29:04) – How technology companies actually grow(32:15) – Branding a software(33:57) – How he evaluates a company brand as an investor(36:07) – Questions to ask founders when considering an investment(37:35) – How the distribution of Superhuman worked so well(41:25) – Most common question asked by VC’s about Superhuman(43:00) – Why they do manual onboarding of customers(43:05) – Daniel Ek Podcast Episode(45:10) – Cost structure of a busines looking to reach the billion-dollar valuation(47:18) – Designing for flow in software business(51:21) – His design philosophy and their joy formula (58:03) – His superpower(1:00:46) – The power of therapy(1:02:50) – Why he invests in other companies(1:05:05) – Trends in the technology space that have him excited(1:07:28) – The future for Superhuman(1:10:26) – Kindest thing anyone has done for him  

Before getting to this week’s guest, an announcement: starting Thursday we will be introducing a new series of interviews. Be sure to check this same podcast feed in two days to learn more. My guest this week goes by the pseudonym Modest Proposal. He’s both a close friend, and one of the most respected thinkers on financial twitter. I field more inbound questions about him than just about anyone, and you’ll see why in this episode. We discuss many of the biggest themes in today’s stock market, from consumer to technology to marketplace and local home services. As always, Modest brings specific insight and general frameworks to the discussion. I talk to him as often as I can because I learn something new every time, and this discussion was no exception. Please enjoy my conversation with Modest Proposal.   This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis.  If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.     For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:37) – (First question) – How investing is about underwriting the future (5:42) – Essential tools to underwrite the future             (7:59) – Michael Mauboussin base rate book (9:02) – Increasing returns to scale as the most important tool (11:36) – Example of silly investments (14:00) – Ideas of consumer signal and non-linear beahvior (16:30) – Why he was blown away by ibuyer.com (19:08) – How businesses are targeting facilitating transactions (23:11) – Ecommerce and digital penetration in business             (25:42) – Gavin Baker podcast episode             (26:00) – Modest proposal last podcast appearance (27:56) – His thoughts on the extinction of so many businesses as a result of the pandemic (32:26) – Chart tracking Product to service against homogeneous to heterogenous             (33:41) – The Perfect Store             (33:49) – eBoys (43:51) – Other features of business that fascinate him (46:29) – Ideas that pique his interest right now (51:20) – Case study: IAC/InterActiveCorp (59:36) – Barry Diller’s superpowers (1:01:17) – Why he’s spent so much time exploring IAC/InterActiveCorp (1:02:56) – Related companies to explore Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag  

My guest this week is Lauren Taylor Wolfe. Lauren is the co-founder and Managing Partner of Impactive Capital. Prior to founding Impactive she spent 10 years at Blue Harbour Group, a $3 billion activist investment firm. Our conversation is on the modernization of the activist investor playbook—how investors engage with companies to make them better and improve long term outcomes. We discuss the entire activist toolkit, focuses on what has changed the most in recent years. I’m also very excited to announce a new initiative. After years of building, operating, and investing in software, we are launching Positive Sum, a new early stage equity investing firm. You can read a bit more at positivesumadvisors.com. Now, please enjoy my conversation with Lauren Taylor Wolfe.   This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis.  If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.     For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:31) – (First question) – Her background and how she landed at Impactive Capital (6:25) – Impactive’s strategy vs the stereotype of the activist investor (10:55) – Potential candidates for what they do (13:26) – How they view the small cap tech world as the space is dominated by huge companies (15:24)  - How capital allocation has evolved over her career             (15:30) - The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success (17:38) – Best capital allocation strategies and mistakes that most companies make (18:48) – The levers activists pull: cap structure; capital allocation and operating structure (22:00) – Major lessons from earlier in her career (23:25) – Major changes in Governance as part of the ESG strategy (26:13) – The issue of dual-class in the space (27:35) – Features of a pristine healthy board (28:40) – Board’s role setting incentives and objectives for management (29:55) – How she thinks about the E&S in ESG and how it helps shareholders (32:56) – Applying her strategy in a real-world example (37:40) – What they look for in a business when it comes to sum of the parts (40:29) – Businesses that are misunderstood and what she looks for in that category (41:39) – How she manages relationships with the boards (45:11) – What she has learned transitioning business models (47:08) – The rise of employee activism (50:02) – What she’s seeing in terms of diversity and inclusion in board rooms and C-Suites (53:32) – Best practices and ways to disrupt hiring (57:48) – Something she doesn’t understand well today that she wishes she did (58:59) – Kindest thing anyone has done for her   Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Rory Sutherland. Rory is the Vice Chairman of Ogilvy & Mather Group, which is one of the largest and most renowned advertising agencies in the world. He’s also the author of one of my favorite recent books called Alchemy: The surprising power of ideas that don’t make sense. In this conversation, we explore many of his counterintuitive ideas about business. Rory makes you think as much as anyone, so I hope you enjoy this conversation.   This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis.  If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.     For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:12) – (First question) – Why spreadsheets and logic kill magic (5:42) – What a product/service is vs how it’s delivered and makes people feel (regular moonshot vs psychological moonshot) (13:22) – Psychological anomalies - doing things faster, better, cheaper (Red Bull vs Coke) (19:54) – Swiss army knife that companies should avoid (22:50) – Don’t design for average (24:39) – How do people approach improving their business through marketing (27:30) – Case for direct mail (29:22) – Turning your weaknesses into a strength (34:29) – The seven deadly sins and how useful they are as guideposts (37:38) – Most powerful sin for marketing (39:14) – Reaching intelligent answers from dumb questions (43:25) – Why the opposite of a good idea can sometimes be a good idea (47:30) – Kindest thing anyone has done for him   Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Michael Seibel. Michael is a Partner at Y Combinator, and the CEO of YC's startup accelerator. He was the cofounder and CEO Justin.tv, which eventually became Twitch, and Socialcam. In this conversation, we discuss all Michael has learned reviewing thousands of applications to YC, interviewing countless new entrepreneurs, and watch young companies begin to grow and, occasionally, find product market fit. Listeners will also enjoy when Michael traps me big time in my thinking about AirBnb and his framework for great problems to solve. Enjoy this great conversation with Michael Seibel   This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis.  If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.     For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:22) – (First question) – Emerging trends among founders (6:00) – The long-term impact of Covid on business (7:16) – What an application to YC looks like and what stands out for him (11:46) – What he wants to learn in the interviews (13:54) – Poise in the interviews (15:40) – How the YC experience has evolved and improvements they’ve made (18:38) – How he defines technology             (18:50) – Every Company is Becoming a Software Company (21:12) – His thoughts on non-software companies and how they play into what YC does (23:48) – Why frequency and intensity of the problem matter to him (28:32) – Serving the supplier and building the demand (30:38) – Bravery in founders (36:07) – Partnerships and collaboration in venture capital investing (37:58) – Second time founders focus on distribution (39:23) – Coaching the psychological component of being a founder (44:16) – Learning as a founder vs the education system (46:08) – Customer vs investor focus of founders’ mindset (48:16) – How teams know they are really onto something (52:38) – His being a founder trainable or innate (54:08) – Kindest thing anyone has done for him   Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Michael Mauboussin, the head of consilient research at Counterpoint Global. Michael is an all-time favorite guest here on the show, and this is his fourth appearance. We discuss one of the biggest topics in the world of investing: the shift from public to private markets that has taken place over the last several decades. We explore the reasons for this shift, the biggest overall changes in capital markets, and what the future may hold. Along the way we explore other fascinating topics like the rise of intangible asset investments, employee-based compensation as a form of financing, and more. If you enjoy this conversation I urge you to read Michael’s paper on the topic which will be linked in the shownotes. Please enjoy this conversation with Michael Mauboussin.   This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis.  If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.     For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:27) – (First question) – Motivation for writing the book from public to private equity             (2:28) – Public to Private Equity in the US: A Long-Term Look             (3:02) – The Incredible Shrinking Universe of Stocks (4:48) – Size of the public vs private markets (7:20) – History and changes in the public to private markets (12:00) – Public market vs venture capital returns (16:48) – Persistence of returns (20:01) – Role of price and EBIDTA on the returns of a buyout (23:31) – How buyout forms are sourcing the debt (29:31) – Transition to businesses relying on intangibles             (29:42) – Capitalism without Capital: The Rise of the Intangible Economy             (30:13) – Endogenous Technological Change             (30:36) – Should Intangible Investments Be Reported Separately or Commingled with Operating Expenses? New Evidence             (34:18) – Explaining the Recent Failure of Value Investing (36:21) – Superstar firms and increasing returns (42:38) – Role on monopolies in creating network effects (4:52) – The allocators perspective in these investments (49:16) – How does this all impact public market active management (51:54) – Advice to young people getting into the investment industry             (52:30) – Jeremy Grantham Podcast Episode (53:30) – Other areas he is researching/looking into (55:44) – How investment work and Santa Fe research influence eachother (56:54) – Investors to learn from             (57:15) – John Collison Podcast Episode  Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guests this week are Jeremiah Lowin and Chetan Puttagunta. Jeremiah is the founder of Prefect.io, an open-source software company where my family and I are investors, and Chetan is a partner at Benchmark Capital. Both are past guests and good friends. I asked them on to help the audience understand the open source software business model. I’ve been fascinated with this model in which companies give a huge chunk of their work and value away for free to a community of developers, and then make money by building additional tools, functionality, and services on top of their free and open platform. While this may strike you as a wonky discussion on a niche software topic, I think it is valuable for everyone because the ideas can be applied to more than just code. I view much of my own activity as open-sourcing investment research and knowledge. It is also important because much of the world’s technology is built on top of open source projects. I hope you learn something new about this emerging category. Please enjoy.   This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis.  If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.     For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:40) – (First question) – Originator business in open source software; Redhat (5:51) – Why open source is valuable in building a business (7:40) – Examples of the benefits of open source projects (10:27) – Open source business models that produce the best results (17:04) – Defensibility of open source companies (25:02) – Mentoring younger founders on using open-source (30:54) – The benefits of launching open-source (36:41) – Building a digital community (41:31) – Lessons from Open Source that can be applied to other businesses (50:04) – The opportunity sets available in the open source space (53:33) – Future of open source             (56:31) – Tobi Lutke Podcast Episode   Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Katrina Lake, the co-founder and CEO of Stitch Fix. Stitch Fix is a multi-billion-dollar public company which has brought an entirely new model to retail apparel by combining data science, technology, and personal stylists to create a unique shopping experience tailored to the individual consumer. I first met Katrina through past guest Bill Gurley and have been excited to host her since that first meeting. In our conversation, Katrina and I discuss all aspects of Stich Fix—its history, business model, innovations, and its future. Please enjoy this great and thought-provoking conversation with Katrina Lake.   This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically re-orders coffee for you based on your consumption habits.  Bottomless is offering one month and your second bag of coffee for free at bottomless.com/patrick.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:19) – (First question) – Where E-Commerce stands and what the future might hold (4:37) – Why personalization makes Stitch Fix stand out from the others (9:34) – Why data science is foundational to their business (12:15) – What makes for a good augmented human and hiring stylists (14:34) – Stakeholder value and creating a great partnership with suppliers (18:10) – Their emphasis on stakeholder focus and social justice (19:28) – The capital efficiency of their business in the early days (24:46) – Her superpower of recruiting (29:46) – Her strengths in building Stitch Fix (31:56) – Transparency vs authenticity (32:59) – Big break for the business (37:15) – Exclusive brands to Stitch Fix (39:01) – The next act for Stitch Fix (41:43) – Lessons learned in pricing services (44:24) – Future trends in retail apparel (48:02) – Hardest thing to copy about Stitch Fix (49:59) – Lessons for putting data science at the center of your business (53:37) – Moments during her journey she’s felt most alive (55:23) – Kindest thing anyone has done for her Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Brian Armstrong, the co-founder and CEO of Coinbase. The topic of our conversation is the future of cryptocurrency and decentralized finance. Its been a while since I checked in on the world of crypto and while prices are still below the 2017 highs, there’s been a ton of additional work and infrastructure laid. We discuss the major events of the past decade and what might happen in the 2020s. Perhaps most interesting, we cover the potential benefits of a modernized financial system, which Coinbase hopes to help usher in. As I’m trying to do more in conversation with CEOs, we also discuss the lessons he’s learned building a business. Please enjoy my conversation with Brian Armstrong.   This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically re-orders coffee for you based on your consumption habits.    Bottomless is offering one month and your second bag of coffee for free at bottomless.com/patrick.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:23) – (First question) – Most important developments in cryptocurrencies             (3:00) - What happened in crypto over the last decade (3:01) – What will happen to cryptocurrency in the 2020s (4:01) – Long term vision for Coinbase (6:57) – Why should we be aiming towards an open financial system (11:41) – How crypto improves the movement of money (14:22) – Creating sound money and currencies (16:21) – Why economic freedom is an important variable in what he’s trying to do (19:44)  - How economic freedom can happen with various regulators around the world and in different countries (22:49) – How Coinbase attracted its first users (26:33) – The December 2017 madness of cryptocurrencies (29:50) – How he thinks about recruiting teams and motivating them to be productive (33:40) – Mistakes with people he’s learned from (34:56) – Steering a product roadmap and creating a successful business (37:17) – What do the non-Bitcoin currencies offer that Bitcoin doesn’t (41:19) – Innovation in cryptocurrency that excites him: DeFi (43:40) – Interesting geographic locations and their impact on crypto (45:29) – How his thoughts on company building has changed over the years (46:47) – Battling any loss of confidence as a founder (51:01) – Improving decision making as a leader (53:54) – Aspects of the job that he loves the most today (56:25) – Largest impediments to mass adoption of crypto (58:25) – His curiosity for scientific research and bioengineering (59:19) – Advice that helped him that he would offer others (1:01:38) – Kindest thing anyone has done for him   Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today, Matthew Ball, is a long time coming. He’s the former head of strategy at Amazon Studios, an investor, and probably my favorite business essayist writing today. In fact, I can’t think of another author whose work I read as quickly once a new essay drops. Read his latest on the past and future of Nintendo and you’ll see why. Our conversation is all about the past and future of media. We discuss movies, music, television, video games, and the metaverse. When I re-listened to this episode I couldn’t believe how much information was in Matthew's head and how easily he covered so many topics in depth. Please enjoy this great conversation.   This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically re-orders coffee for you based on your consumption habits.    Bottomless is offering one month and your second bag of coffee for free at bottomless.com/patrick.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:20) – (First question) – Compulsive interest of how people entertain themselves (4:19) – Changes of intellectual property and trademark in media (9:12) – Cross media world building and Netflix’s strategy (11:47) – Competing with the major power players at the top (16:54) – Fate of movies in the new media landscape (20:38) – Fate of music in the new media landscape (25:40) – Age and gaming in this media transition             (26:20) – Gavin Baker Podcast Episode (29:50) – Legacy of the Marvel Cinematic Universe (34:48) – How he defines the notion of a metaverse (39:53) – Creating a more interoperable version of our digital world (47:37) – What is not included in the metaverse and investing in one (52:14) – Tim Sweeney’s role in Epic Gaming (58:12) – The unreal engine (1:07:46) – What should investors be thinking about when it comes to gaming worlds (1:12:43) – Opportunities in the gaming space for investors (1:19:59) – Cloud gaming’s impact on the space (1:26:54) – Will other media platforms have to copy the gaming industry (1:30:51) – How interactivity and feedback loops plays into his investment decisions (1:33:07) – Ease of creating a new media business today (1:35:20) – Trends media storytelling (1:38:50) – What makes for good IP in media content (1:42;14) – Why he wants to explore payment platforms and block chain (1:44:56) – Kindest thing anyone has done for him   Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag