Invest Like the Best

By Patrick O'Shaughnessy

Business Investing Careers

What's Invest Like the Best about?

Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at InvestorFieldGuide.com

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Shishir Mehrotra – The Art ...

05.26.2020

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 ...

Invest Like the Best episodes:

06.02.2020 Ben Thompson – Platforms, Ecosystems, and Aggregators - [Invest Like the Best, EP.176] 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 ...
05.26.2020 Shishir Mehrotra – The Art and Science of the Bundle - [Invest Like the Best, EP.175] 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 ...
05.19.2020 Hamilton Helmer – Power + Business - [Invest Like the Best, EP.174] 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.
05.12.2020 Tobi Lutke – Building a Modern Business - [Invest Like the Best, EP.173] My guest today is Tobi Lutke, the co-founder, and CEO of Shopify. This is both a timely and evergreen conversation. Timely, as the world as moved aggressively digital in the past two months, and Shopify powers so much of digital ...
05.05.2020 Ali Hamed – An Update on Private Credit - [Invest Like the Best, EP.172] My guest today is popular past guest Ali Hamed, who joins us for an update on private credit. We discuss what has happened so far, what parts of the market are frozen, and where opportunities may lie. We also talk ...
04.30.2020 Chris Bloomstran - An Update on Public Markets - [Invest Like the Best, EP.171] My guest today for a flash update is Chris Bloomstran, the founder and CIO of Semper Augustus and a popular past guest on the show. We talk about his view on the state of the public equity market, why it ...
04.28.2020 Josh Kopelman - The Past, Present, And Future Of Seed Investing - [Invest Like the Best, EP.170] My guest today is Josh Kopelman, the founder of famed venture capital firm First Round Capital. Prior to starting First Round, which has invested at the earliest stages in companies like Square, Uber, and Roblox, Josh was a three-time entrepreneur, ...
04.21.2020 Manny Stotz - Frontier Markets Investing - [Invest Like the Best, EP.169] My guest today is Manny Stotz, the founder of Kingsway Capital. Manny is one of the leading investors in Frontier Markets, investing in equities in countries like Egypt, Bangladesh, and Pakistan. We discuss the opportunity in these markets from all ...
04.07.2020 Sarah Tavel - Consumer & Marketplace Investing - [Invest Like the Best, EP.168] My guest this week is Sarah Tavel, a general partner at Benchmark, working alongside past guests Bill Gurley and Chetan Puttagunta. Sarah has a long history as both an investor and as an operator. She was an early product leader ...
04.05.2020 [BONUS] Boyd Varty - 40 Days and 40 Nights In the midst of the worldwide quarantine, my friend Boyd Varty decided to begin an adventure he has been considering for a long time: a 40 day and 40 night stay in the African wilderness. I’m releasing this short conversation ...
04.02.2020 Gavin Baker – Investing Through a Bear Market - [Invest Like the Best, EP.167] My guest today is with past guest Gavin Baker, the founder and CIO of Atreides Management, LP. We discuss investing during a bear market and the major ways in which the COVID19 outbreak has dramatically altered the investment landscape. Please ...
03.31.2020 D.A. Wallach – Investing in Healthcare - [Invest Like the Best, EP.166] My guest today is D.A. Wallach, one of the more interesting investors I’ve come across. He is the former lead singer of the group Chester French and the former artist-in-residence at Spotify, where he was also an early investor. While ...
03.25.2020 Chad Cascarilla – Update on Tail Risk - [Invest Like the Best, EP.165] My guest today is Chad Cascarilla, here to discuss some of the tail risks in the economy and markets as of March 24th in the midst of the Coronavirus pandemic. Chad was one of the most successful investors during the ...
03.20.2020 Brent Beshore – Update on Small Business and Private Equity - [Invest Like the Best, EP.164] My conversation today is with my close friend Brent Beshore. Brent is a private equity investor who owns and interacts with many small businesses, which have been hit especially hard by COVID. We discuss the various impacts that COVID has ...
03.16.2020 Dan Rasmussen – Investing Through a Crisis - [Invest Like the Best, EP.163] My guest this morning is Dan Rasmussen of Verdad Capital. Like me, Dan and his firm focus on quantitative research. Just a month before the COVID crisis hit markets, they completely and published a study on investing during periods of ...
03.13.2020 Bill Gurley and Chetan Puttagunta – An Update on Consumer & Enterprise Venture Capital - [Invest Like the Best, EP.162] My guests today are Bill Gurley and Chetan Puttagunta, both partners at benchmark capital. We review the early stage investing world in the face of coronavirus in a very timely conversation, which is one that will remain valuable once this ...
03.13.2020 Bryan Krug – An Update on Corporate Credit - [Invest Like the Best, EP.161] My guest in this flash podcast is Bryan Krug of Artisan partners. We discuss what has happened so far in the corporate high yield and investment-grade credit markets, and the loan market. We compare today’s environment to the financial crisis ...
03.11.2020 Deep Basin – Oil Price War and Its Implications - [Invest Like the Best, EP.160] This week, I’ll be recording and immediately releasing a series of conversations on business and market reactions to the spread of coronavirus. The conversations will be on oil and gas, corporate credit, and the reaction within the venture capital community. ...
03.10.2020 Peter Zeihan - Dis-United Nations - [Invest Like the Best, EP.159] My guest this week is Peter Zeihan, the author of a new book, the Disunited Nations. Peter was an extremely popular guest on the show last year and after reading his new book, I knew we had a lot to ...
03.03.2020 Jeff Lawson – How to Build a Platform - [Invest Like the Best, EP.158] My guest this week is Jeff Lawson, the Founder, and CEO of Twilio. Twilio is a 15-billion-dollar company offering a cloud communications platform to its customers. Twilio is used by customers like Lyft, Twitch, and Yelp to make communications in ...
02.25.2020 Niko Canner – Become a Perfect Instrument - [Invest Like the Best, EP.157] Niko Canner is the founder of Incandescent where he and his team help the leaders of large companies in the areas of strategy and innovation. He was also the founder of Katzenbach Partners and a member of Bridgewater’s management committee. ...
02.04.2020 [REPLAY] What You Learn About Business Deals After: 12,000 Deals Reviewed, 1,500 Deep Dives, 125 Site Visits, and 7 Portfolio Companies with Brent Beshore - [Invest Like the Best, EP.100] For the 100th episode, I’ve brought back my good friend Brent Beshore. Brent was the 10th guest on the podcast, after we met because of a mutual interest in capital allocation. I quickly learned that Brent was one of the ...
01.28.2020 Chetan Puttagunta – Go Slow to Go Fast: Software Building and Investing - [Invest Like the Best, EP.156] My guest this week is a good friend and a business mentor of mine. Chetan Puttagunta is a general partner at Benchmark Capital and has a remarkable track record of investing in early-stage software businesses, including several like Mulesoft, MongoDB, ...
01.21.2020 Rebecca Kaden – Thesis Driven Investing - [Invest Like the Best, EP.155] My guest today is Rebecca Kaden, a partner at famed venture firm union square ventures. USV is known for thesis-driven investing, which is the topic of our conversation. Rebecca walks us through the evolution of USV’s thesis into its third ...
01.14.2020 Matt Clifford – Investing Pre-Company - [Invest Like the Best, EP.154] My guest today is Matt Clifford. He’s the co-founder of Entrepreneur First, the world’s leading talent investor. They invest “pre-company” by helping the best people in cities around the world find a co-founder, develop an idea, and start a company. ...
01.07.2020 Peter Buffett – Finding Your Note - [Invest Like the Best, EP.153] My guest today is Peter Buffett. Peter is a musician, composer, author, and philanthropist. Peter is an Emmy Award winner, New York Times best-selling author and co-chair of the NoVo Foundation. We discuss music, community, philanthropy, and finding one's note ...
12.17.2019 Ben Savage – All Things Fintech Investing - [Invest Like the Best, EP.152] My guest today is Ben Savage, a partner at Clocktower ventures. Ben is focused on financial technology, fintech, investing which is the topic of our conversation. I’ve been making the fintech is rounds of late, and plan on making a ...
12.10.2019 Jeff Ma – Making Decisions with Data - [Invest Like the Best, EP.151] My guest this week is Jeff Ma. Jeff was on the famous MIT Blackjack team from the book Bringing Down the House but has spent his career in an around fields of analytics and data science. He’s studied sports betting ...
12.03.2019 Vaughn Tan – Quality and Innovation - [Invest Like the Best, EP.150] My guest today is Vaughn Tan, who studies quality, innovation, and organizational behavior. His resume is bonkers. He’s a PhD from Harvard, Was an infantry signals logistician in the Republic of Singapore Army, then worked at Google on advertising, Earth, ...
11.26.2019 Gavin Baker – Tech and Consumer Growth Investing - [Invest Like the Best, EP.149] My guest this week is Gavin Baker, the founder, and manager of Atreides Management. I met Gavin in the same way I meet many of the most interesting people, on twitter. His focus is on consumer and technology growth investing, ...
11.19.2019 Kevin Systrom and Mike Krieger – How to Build a Great Product My guests this week are Kevin Systrom and Mike Krieger, the co-founders of Instagram. I met Kevin and Mike a few months ago over a shared interest in business and investing. I have found them both to be extremely good ...
11.12.2019 Daniel Ek – The Future of Audio - [Invest Like the Best, EP.147] My guest this week is Daniel Ek, the founder and CEO of Spotify. In my conversations with Daniel, I’ve found him to be one of the most interesting and thoughtful business leaders in the world. You’ll see what I mean ...
11.05.2019 George Rzepecki – Investing in Africa - [Invest Like the Best, EP.146 My guest this week is George Rzepecki, the found and managing partner Raba, an Africa focused investment firm. George is making investments across Africa in early-stage companies. Africa represents a fascinating opportunity: a huge and diverse population and enormous room ...
10.29.2019 Chad Cascarilla – The Future of Blockchain and Financial Services - [Invest Like the Best, EP.145] My guest today is Chad Cascarilla, the CEO and co-founder of Paxos, which describes itself as a financial technology company “mobilizing assets at the speed of the internet.“ Thanks to more than 20 years of investing and financial services experience, ...
09.24.2019 Bill Gurley – Direct Listing vs. IPO - [Invest Like the Best, EP.144] My guest this week is Bill Gurley, general partner at Benchmark Capital. Our conversation is about one specific issue that has popped up as a topic of interest in the investing community in recent months: the comparison between bringing a ...
09.17.2019 [REPLAY] Albert Wenger - World After Capital - [Invest Like the Best, EP.80] My guest this week is Albert Wenger, a managing partner at Union Square Ventures and the author of the book World After Capital. Albert studied economics at Harvard and earned a PhD in information from technology, but if you’d asked ...
09.11.2019 [REPLAY] Deep Basin – Earning Alpha in Energy - [Invest Like the Best, EP.81] My guest this week are Matt Smith and Ian singer of Deep Basin Capital, a hedge fund specializing in the energy sector. I first met Matt almost 10 years and, in that time, I’ve grown to respect him as much ...
08.27.2019 [REPLAY] Pat Dorsey - Buying Companies With Economic Moats - [Invest Like the Best, EP.51] My guest this week is Pat Dorsey, who was the longtime director of equity research at Morningstar, where he specialized in economic moats: sources of sustained competitive advantage that allow a few companies to deliver huge returns over time. Several ...
08.20.2019 Joe McLean – How to be a Pro’s Pro - [Invest Like the Best, EP.143] My guest this week is Joe McLean, the founder of Intersect Capital, which provides financial advisory services to a variety of clients, including a number of NBA players and other professional athletes. What I loved about this conversation was the ...
08.13.2019 Zack Kanter – All Things Business - [Invest Like the Best, EP.142] This week’s guest is, Zack Kanter, the founder and CEO of the Stedi. Zack and I decided not to talk much about his business on this podcast and opted instead to explore more generally, so a bit of an introduction ...
08.06.2019 Chris Bloomstran – What Makes a Quality Company - [Invest Like the Best, EP.141] My guest this week is Chris Bloomstran, the president and chief investment officer of Semper Augustus Investments Group. He became famous in investing circles a few years back for his incredibly detailed investigations of Berkshire Hathaway. While we do cover ...
07.30.2019 Brian Christian – How to Live with Computers - [Invest Like the Best, EP.140] My guest this week is Brian Christian, the author of two of my favorite recent books: Algorithms to Live By and The Most Human Human. Our conversation covers the present and future of how humans interact with and use computers. ...
07.23.2019 Eric Sorensen - How Quant Evolves - [Invest Like the Best, EP.139] My guest this week is Eric Sorensen, the CEO of Panagora asset management, which manages more than $46B for clients across a variety of strategies. Eric began his career serving in the Air Force as both a pilot and instructor ...
07.16.2019 Jane McGonigal – How Games Make Life Better - [Invest Like the Best, EP.138] Jane McGonigal, PhD is a world-renowned designer of alternate reality games — or, games that are designed to improve real lives and solve real problems. She is the Author of Reality is Broken: Why Games Make Us Better and How ...
07.02.2019 Bill Gurley – All Things Business and Investing - [Invest Like the Best, EP.137] My guest this week is Bill Gurley, a general partner at Benchmark Capital and one my favorite investment thinkers. As you’ll hear, despite enormous success through his career, Bill is clearly still in love with business and investing. Where many ...
06.25.2019 Jesse Livermore – The Search for the Truth with the Anonymous Master - [Invest Like the Best, EP.136] This week I have a very special guest years in the making. Like another favorite episode, with anonymous guest Modest Proposal, this conversation is with one of the stars of the financial twitter universe who writes anonymously and goes by ...
06.18.2019 Chuck Akre – The Three-Legged Stool - [Invest Like the Best, EP.135] My guest today is Chuck Akre, a now widely famous investor who founded Akre Capital Management in 1989, which now manages approximately $10B dollars. We discuss his investing style and his “three-legged stool” for evaluating companies. Please enjoy this great ...
06.11.2019 Jerry Neumann – Why Venture is Hard - [Invest Like the Best, EP.134] My guest this week is Jerry Neumann. Jerry is one of the most thoughtful early stage investors that I’ve encountered, and his writings at reactionwheel.net are my favorite on this topic. He applies an incredibly structured way of thinking to ...
06.04.2019 [REPLAY] Sam Hinkie – Data, Decisions, and Basketball - [Invest Like the Best, EP.88] I came across this week’s guest thanks to the overlap of three passions of mine: data informed investing, value creation, and basketball. Sam Hinkie worked for more than a decade in the NBA with the Houston Rockets, and then most ...
05.28.2019 David Epstein – Wide or Deep? - [Invest Like the Best, EP.133] My guest this week is David Epstein. David is a writer and researcher extraordinaire and the author of two great books. His second, Range, is out today and I highly recommend it. We discuss the pros and cons of both ...

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