Invest Like the Best

By Patrick O'Shaughnessy

Technology Business Investing

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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Lauren Taylor Wolfe – The ...

09.22.2020

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 ...

Invest Like the Best episodes:

09.22.2020 Lauren Taylor Wolfe – The Modern Activist Toolkit - [Invest Like the Best, EP.192] 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 ...
09.15.2020 Rory Sutherland – Moonshots and Marketing - [Invest Like the Best, EP.191] 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 ...
09.08.2020 Michael Seibel – Lessons from Thousands of Startups - [Invest Like the Best, EP.190] 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 ...
09.01.2020 Michael Mauboussin – Great Migration Public to Private Equity - [Invest Like the Best, EP.189] 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 ...
08.25.2020 Chetan Puttagunta and Jeremiah Lowin – Open Source Crash Course - [Invest Like the Best, EP.188] 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 ...
08.18.2020 Katrina Lake – The Next Wave of E-Commerce - [Invest Like the Best, EP.187] 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 ...
08.11.2020 Brian Armstrong – The Future of Crypto - [Invest Like the Best, EP.186] 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 ...
08.04.2020 Matt Ball - The Future of Media: Movies, the Metaverse, and More - [Invest Like the Best, EP.185] 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.
07.28.2020 Kat Cole – How to Operate: Lessons in Brand, Distribution, and Leadership - [Invest Like the Best, EP.184] 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 ...
07.21.2020 Eric Vishria – The Past, Present, and Future of SaaS and Software - [Invest Like the Best, EP.183] 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 ...
07.14.2020 Turner Novak – The Past, Present, and Future of Consumer Social Companies - [Invest Like the Best, EP.182] 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 ...
07.07.2020 Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, EP.181] 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 ...
06.30.2020 Blake Robbins – Investing in Gaming - [Invest Like the Best, EP.180] 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 ...
06.23.2020 Brad Gerstner – Public and Private Investing - [Invest Like the Best, EP.179] 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 ...
06.16.2020 John Collison – Growing the Internet Economy - [Invest Like the Best, EP.178] 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, ...
06.09.2020 Jeremy Grantham – An Uncertain Crisis - [Invest Like the Best, EP.177] 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 ...
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, ...

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