Invest Like The Best

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 Can

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

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) –

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 an

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, yo

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

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

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 Inves

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

My guest today is Kat Cole, the COO and president of North America for Focus Brands, which owns famous companies like Cinnabon, Carvel, Jamba, and more. Kat’s story and career trajectory are remarkable, as are the lessons she’s picked up along the way which she shares with us all in this conversation. We discuss negotiation, distribution, brand building, brand extension strategies, and leadership. I always enjoy having a true operator on the show, so I was very excited to discover Kat and her thinking. 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 a

My guest this week is Eric Vishria, a general partner at Benchmark Capital. Eric joined Benchmark after spending the first part of his career as an operator and CEO. The topic of our conversation is the past, present, and future of software businesses. We begin by explaining why public software companies trade at such incredibly high multiples today. We then explore the several different generations of these businesses and why the future remains so bright for companies building software as their primary product. I’d go one step further and suggest that the information in this episode is even more valuable for non-software businesses and investors, because its crucial to understand the impact that these products will have on the overall business landscape. COVID has accelerated the long-running transition to digital across the corporate world, and Eric serves as the perfect guide. Let’s dive in.    This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically r

My guest this week is Turner Novak, a partner at Gelt VC. Many of the largest companies in the world today are consumer social companies, so Turner and I discuss the past, present, and future of those businesses. When executed right, they are often the fastest-growing companies in history, and the rise of TikTok and some other companies we discuss makes it clear that there may always be more room at the top. The network effects that support these companies make them unique beasts to analyze, and Turner’s writing has been among my favorite content on the topic. Please enjoy our detailed conversation on this important are of public and private markets.   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

My guest this week is Charlie Songhurst, the former head of strategy at Microsoft and a prolific investor, having personally invested in nearly 500 companies throughout his career. I met Charlie at an event hosted in New York and you can tell within one minute of meeting him that his mind is sparkling with ideas and curiosity. Its no wonder he’s been among the most commonly requested guests when I asked several top investors and CEOs who I should have on the show. We discuss the lessons he’s learned about business, investing, and people from such a large sample size of companies. I won’t reveal any more here, I highly recommend you just listen to Charlie and learn. Let’s dive in. 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 (1:25) – (First question) –  Stack ranking the vices of power, money and fame (2:41) – Memorable res

My guest today is Blake Robbins, a partner at Ludlow Ventures. We talk about all things video games, including the major companies in the industry, how games monetize, how in-game economies work, how e-sports has evolved, and much more. This is a fast-growing segment of consumer attention and interest, I believe we are in the very early days of gaming going mainstream. I also have a favor to ask. My team and I have built a small survey for Invest Like the Best listeners and if you’ve enjoyed the podcast, I’d deeply appreciate it if you took 5 minutes to fill it out at investorfieldguide.com/survey. It will help shape the future direction of the show, which I intend to keep improving in the years to come. Thank you, and now please enjoy my conversation with Blake Robbins. 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 (1:35)

My guest today is Brad Gerstner, the founder and CIO of Altimeter Capital, a multi-billion dollar technology-focused investment firm. Brad and his team are known for a deep expertise in internet-enabled businesses, including Expedia, Facebook, Uber, and many more. We discuss the evolution of opportunity in this style of investing, including the important shift to private investing, where so much of the value creation now happens. I won’t soon forget our discussion of consumer intent on the internet and how it has shifted, the role that essentialism plays in Brad’s business and life, and the rise of the Chinese internet giants like Bytedance. Please enjoy this great conversation with Brad Gerstner.   This episode is brought to you by the MIT investment management company (MITIMCO) Reach out or learn more:  Email: partner@mitimco.org Website: https://mitimco.org/partner/ MITIMCo 10 year Letter: https://mitimco.org/wp-content/uploads/2017/03/MITIMCo-Alumni-Letter.pdf MITIMCo brochure: https://mitimco.

My guest today is John Collison, the Co-Founder of the digital payments company Stripe. Stripe’s mission is to increase the GDP of the internet, a lofty and deeply interesting pursuit. John is clearly a voracious learner across business and investing, which you’ll hear instantly. He started Stripe with his brother Patrick when he was just 19 years old, and has grown it to, at last valuation, a $36B business. In our conversation, we discuss conglomerates, the internet economy, the power of writing, and why board members are like Pokémon characters, each with different powers. It’s a lively and wide-ranging conversation with one of the entrepreneurs I’ve most enjoyed speaking with. Please enjoy.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (1:30) – (First question) – Interest in industrial cong

My guest today is Jeremy Grantham. Jeremy is the co-founder and chief investment strategist of Grantham, Mayo, & van Otterloo (aka GMO). GMO, which manages more than $60B for clients, was a firm that helped educate me early in my investing career. They’ve long published thought-provoking research, most of which came from Grantham himself. He is regarded as a highly knowledgeable investor in various stock, bond, and commodity markets, but is particularly noted for his prediction of various bubbles. In this conversation we discuss the current crisis, which he calls the fourth major event of his long and storied career as an investor. As he says, this one is the most uncertain. We also discuss unique topics like commodity-based companies, and how opportunity often lies between fields of expertise. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide

My guest today is Ben Thompson. Ben is the author of my favorite business strategy newsletter called Stratechery. He’s also the host of the exponent podcast, and now the Dithering, a podcast he recently launched with John Gruber. I think Ben is among the most interesting business analysts in the world, and I’ve learned from and directly applied many of his ideas. We cover many of the major concepts he’s introduced over the years, including his well know aggregation theory. I think that to understand how the internet has changed the business world for good, you must read Ben and follow his thinking. I’m excited to finally have him as a guest on the show. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (01:26) – (First question) – Companies that are built for the next d

My guest today is Shishir Mehrotra and the topic of our conversation is the bundle: offering access to multiple products, services, or providers for a single bundled price. This topic is full of incorrect pre-conceived notions, and as it turns out, the bundle is one of the most powerful ideas in business. Properly harnessed it is good for everyone involved. Shishir explains the ins and outs of bundles in this conversation. Shishir ran product at YouTube for years and sits on the Spotify board of directors. He founded and now leads Coda (which is “A Doc” spelled backwards) in 2014, to bundle together productivity apps like docs, spreadsheets, databases, and applications. I love this wonky, detailed conversation which has me thinking differently about many businesses and business strategy. Please enjoy.   This episode is brought to by Koyfin.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month

My guest today is Hamilton Helmer, the Co-Founder and Chief Investment Officer of Strategy Capital and the author of one of the best business books in history called 7 Powers, which is the topic of much of our conversation. He has spent his career as a practicing business strategist: advising companies, investing based on strategic insights and teaching strategy.  In the last three decades, he has also utilized his strategy concepts as a public equity investor. In this conversation we cover all seven business powers, from counter-positioning to scale economies, and how companies earn and keep those powers. Any investor or businessperson should understand these concepts, and 7 Powers is the best work I’ve seen that explains them in depth. Please enjoy our conversation.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_o