Invest Like the Best with Patrick O'Shaughnessy

Today, we are replaying my conversation with Brad Jacobs. Brad’s resumé is remarkable. He has founded seven companies, all of which are billion-dollar or multibillion-dollar businesses. He has done 500 M&A transactions and raised $30 billion dollars of debt and equity capital. Currently, he is the Executive Chairman of XPO, a commercial trucking company that he started in 2011 and has grown into o...

My guest today is Ernie Garcia. Ernie is the co-founder and CEO of Carvana. Ernie joined me on Founder’s Field Guide in 2021 and despite all that the business has gone through since that conversation, you’ll hear how he has the exact same demeanor and crystal clear vision for the business and its operations today. Carvana is one of the most remarkable business turnaround stories in recent history,...

My guests today are Andrew Homan and Chris Miller. Andrew has spent two decades at Maverick Capital and is a managing partner at Maverick Silicon, where he leads the firm’s technology investments. Chris is a professor at Tufts and the author of the New York Times best-selling book “Chip War,” which details the geopolitical battle to control the semiconductor industry. Together we get into a compre...

My guest today is Boyd Varty. Boyd is a lion tracker, life coach, and storyteller who grew up in the South African wilderness, living amongst and tracking wild leopards. This is his fourth time on Invest Like the Best but the first in six years. Boyd is a perfect follow-up to my episode with Lulu Meservey unpacking the intricacies of storytelling and why it's such an essential for founders. Boyd w...

My guest today is Tobi Lutke, the co-founder and CEO of Shopify. I have spoken to Tobi on this podcast twice before, first in 2020 and then again in 2022. Needless to say, a lot has changed since we last spoke, and we start by talking about the biggest change of all: AI. But I’ll remember this conversation for the next set of ideas we discuss: Founder mode, raising the temperature of an organizati...

My guests today are Matt Perelman and Alex Sloane, Co-founders and Managing Partners of Garnett Station Partners. GSP invests in the trillion-dollar franchise and consumer services industries. Matt and Alex started the firm in 2014 as MBA students when they bought 23 Burger King restaurants. Since then, they've invested in 26 other multi-unit businesses, from gyms to car washes to funeral homes. G...

My guest today is Kareem Zaki. Kareem is a General Partner at Thrive Capital and has been at the firm for a decade. In an episode last year, Thrive's founder, Josh Kushner, told me he is the best healthcare investor in the world. Kareem has co-founded three healthcare businesses worth over one billion dollars. He also has expertise in financial services, where he's led the firm's investments in co...

My guest today is Ray Ozzie, one of the great technologists, software developers, and entrepreneurs of our time. Ray is perhaps best known as the creator of Lotus Notes, a collaboration tool that revolutionized business communication in the 1990s. He later succeeded Bill Gates as Chief Software Architect at Microsoft, where he played a key part in the development of Azure, Microsoft's cloud comput...

My guest today is Ted Seides. Ted is the host of the Capital Allocators podcast and an investment industry expert. It’d been seven years since Ted and I last talked on the record, as he was one of my very first guests on Invest Like the Best. Now that Ted has a full-time focus on all things Capital Allocators and has stepped away from traditional investing roles, he shares with us the wisdom he ha...

My guest today is Lulu Meservey. Lulu is the Founder and CEO of Rostra, a company that partners with founders to level up their communications around all strategic initiatives, from hiring to fundraising. She is also on the board at Shopify. I have been recently fascinated by the challenge of founders telling their story and Lulu is an expert in comms and a believer in creative problem-solving thr...

My guest today is Ric Elias. Ric is the CEO and co-founder of Red Ventures, which has a portfolio of fast-growing digital businesses like Lonely Planet, The Points Guy, Bankrate, and large investments in a variety of other businesses across industries. He began the business in 2000 and has grown it to now a global company with thousands of employees. Ric walks us through the early struggles that h...

This week's episode is special because it marks the launch of a new Colossus show: Glue Guys. My guests this week are the hosts of the new show, Shane Battier, Alex Smith, and Ravi Gupta. Shane, Ravi, and Alex’s stories are remarkable. Each has been at the very top of their profession. Shane as an NCAA and NBA champion. Alex as the first pick in the NFL draft, 3 time-pro bowler, and 16-year NFL ve...

My guest today is Bret Taylor. His resume is absurd. He built google maps--famously rewriting the whole thing in a weekend. He was the CTO of Facebook in critical years. He founded Quip. He was the chair of the board at Twitter. He was the co-CEO of Salesforce...the incredible list goes on. Now, Bret is the co-founder of Sierra, a conversational AI platform for businesses, and he is the chairman o...

My guest this week is Gavin Baker. Gavin is the managing partner and CIO of Atreides Management, and he has been on the show many times before. He is one of my favorite investors to talk to and this may be my favorite conversation with him. Gavin first started covering Nvidia as an investor at the turn of the millennium, making him the perfect guest to discuss all things AI and investing. There is...

Today, we’re replaying a conversation between John Collison and Charlie Munger that we first aired on 5 December 2023. Charlie said, “The best thing a human being can do is to help another human being know more.” He does just that in this interview. Please enjoy, and may Charlie Rest in Peace. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ---...

My guest today is Vlad Tenev. Vlad is the CEO and co-founder of Robinhood. It was such a treat to sit down with him and discuss the behind-the-scenes of a revolutionary business we all know well. He details Robinhood’s journey to zero-cost trading and what it means to build a consumer-centric financial product. Vlad believes in finding the harmonies across mathematics and art and applies this lens...

My guest today is Sarah Guo. Sarah is the founder and CEO of Conviction, an early-stage venture capital firm built to serve AI companies. She started Conviction in 2022 after 9 years at Greylock because she believes AI is the most important technological advancement of our lifetime. In our conversation, Sarah discusses the challenges and rewards of leaving an established investing firm to start he...

My guest today is Hemant Taneja. Hemant is the CEO and Managing Director of General Catalyst, the global venture capital firm you’ll hear us refer to as GC. GC has set out to build resiliency across critical industries worldwide. The firm leverages technology to retool sectors such as healthcare, energy, defense, and manufacturing and explores innovative capital structures to support founders and...

Today we are replaying one of our most popular episodes from last year with Jeremy Giffon. I spend all my time trying to find people who have some “singularity” to them. People who seem like they can do an N of 1 something. Having spent many days with Jeremy, he strikes me as one of those people. He was the first employee and general partner at private equity firm/holding company Tiny, which buys...

Today, we are replaying what we call a forever episode, which are the few episodes of our show that we think will be as popular a decade from now as they are today. Every time I re-listen to this episode with David Senra, I leave wildly energized and wanting to share that feeling. So we are re-releasing it today for anyone who missed it the first time or hadn't yet discovered Invest Like the Best....

My guest today is Martin Casado. Martin is a partner at Andreessen Horowitz and first joined me on Invest Like the Best in 2022. So much has changed since then, and it was awesome to have Martin back to discuss all of the different implications of this AI revolution. Before joining a16z, Martin pioneered software-defined networking and co-founded Nicira, which was bought by VMware for $1.3 billion...

My guest today is Modest Proposal, joining me for our third conversation and the first in a few years. Modest is anonymous online, but one of the more thoughtful investors I know, overseeing a large pool of capital in public and private markets. He offers insight into many different corners of today’s landscape, covering AI’s frontier models versus open-source models, overcapacity issues in transp...

My guest today is Robert Greene, author of many books but perhaps most famous for his books "48 Laws of Power" and "Mastery." He has spent his life studying why people behave like they do and why some go on to build great things. I love his idea of finding your life's purpose, which we explore in detail. Please enjoy my conversation with Robert Greene. Listen to Founders Podcast For the full show...

My guest today is Pat Grady, a longtime growth investor at Sequoia and one of the firms senior leaders. Pat has been a part of a long list of legendary investments, ranging from Snowflake, Zoom, ServiceNow, Qualtrics, Okta, Hubspot, Notion, and OpenAI, among many others. There aren't many investors who reference as well at Pat, both inside and outside of his firm. We talk about investing, building...

My guest today is Frank Blake. Frank is the former chairman and CEO of Home Depot. I recently interviewed Home Depot co-founder Ken Langone and became fascinated by the business’s impressive lineup of leaders through the decades. Frank led the company from 2007 to 2014 and shares how he carried on the legacy of Ken and the others, upholding their culture of an inverted hierarchy and producing seve...