My guest today is Graham Duncan. This conversation will make you think about your life in new ways. This is a two-hour segment of a 4.5-hour interview I did with Graham last year. It stands alone as remarkable, but those who subscribe to Colossus Review will gain access to the full conversation. This will be true in future issues, too. In 2006, in his early 30s, Graham convinced Stuart Miller, CEO of home construction company Lennar, to let him manage $50 million of his family's wealth. A year l...
Feb 04, 2025•2 hr 17 min•Transcript available on Metacast My guest today is Blake Hall. Blake is the co-founder and CEO of ID.me, a secure digital identity network with over 100 million members. He was an officer in the United States Army and served our country for four years as a a rifle platoon leader, the battalion reconnaissance platoon leader, and as the battalion logistics officer. We explore his formative years in the military and transition into entrepreneurship. Blake shares powerful stories from his time leading scout sniper missions in Iraq,...
Jan 28, 2025•2 hr 34 min•Transcript available on Metacast My guest today is Dylan Field. Dylan is the co-founder and CEO of Figma and last joined me on Invest Like the Best in 2020. A lot has changed since then and we explore the evolving landscape of design and how Figma has been navigating AI while staying true to its founding vision of eliminating the gap between imagination and reality. Despite Figma's incredible success in becoming the default design platform, Dylan remains deeply motivated by helping users achieve their goals. He shares fascinati...
Jan 21, 2025•45 min•Transcript available on Metacast My guest today is Tal Zaks. Tal is a physician-scientist turned biotech executive and investor who served as Moderna's Chief Medical Officer during their COVID-19 vaccine development, giving him an extraordinary perspective on one of modern medicine's pivotal moments. His combination of medical expertise, platform innovation experience, and investing acumen allows us to explore the interconnected challenges of turning scientific breakthroughs into viable medicines while generating venture-scale ...
Jan 14, 2025•1 hr 22 min•Ep 406•Transcript available on Metacast My guests today are Dwight Churchill and Gaurav Misra, co-founders of Captions, which uses AI to generate and edit talking videos and has grown to significant scale at remarkable speed. We explore a key distinction in AI: tackling bounded problems like video generation versus unbounded problems like general intelligence and what this means for building sustainable businesses. We also explore their unique data flywheel, why video generation could reach Hollywood quality within 18 months, and why ...
Jan 07, 2025•1 hr 5 min•Ep 405•Transcript available on Metacast My guest today is Jack Kokko. Jack is the CEO and Founder of AlphaSense, an AI-powered search engine for market intelligence. He shares how AlphaSense began by aggregating fragmented financial data sources and evolved with the advent of large language models to change the research experience completely. He speaks to their recent acquisition of Tegus earlier this year, reshaping the business and further supporting their expansion to serve all types of companies instead of exclusively investment f...
Dec 31, 2024•49 min•Ep 404•Transcript available on Metacast My guest today is Jared Kushner. Jared has lived more lives than just about anyone I know his age. He ran Kushner companies for years, investing in real estate in and around New York City. He owned the New York Observer. He was a senior advisor to President Trump in his first term. He now runs Affinity Partners, which we discuss in detail, a private equity firm built to find and execute unique investments around the world that stem from Jared's unique set of experiences in business and governmen...
Dec 20, 2024•3 hr 54 min•Ep 403•Transcript available on Metacast My guest today is Scott Wu. Scott is the co-founder and CEO of Cognition, which is an applied AI lab that has created the first AI software engineer, which they call Devin. In just a year since founding Cognition, Devin functions at the level of a junior software engineer, capable of handling complete engineering workflows from bug fixing to submitting pull requests. He is a former competitive programming champion and describes the field as simply “the art of telling the computer what you want i...
Dec 17, 2024•1 hr 13 min•Ep 402•Transcript available on Metacast My guest today is Micky Malka. Micky is the founder of Ribbit Capital, a global venture capital firm that focuses exclusively on financial technology investments. He is a renowned investor for his adaptability and visionary approach and a believer in killing the thing that got you to where you are in pursuit of what’s next. We discuss his perspective on fintech’s evolution and why his firm boldly declares that “fintech is dead.” We dive into his theory of the "grid," which examines how knowledge...
Dec 10, 2024•2 hr 32 min•Ep 401•Transcript available on Metacast My guests today are Chetan Puttagunta and Modest Proposal. Chetan is a General Partner at venture firm Benchmark, while Modest Proposal is an anonymous guest who manages a large pool of capital in the public markets. Both are good friends and frequent guests on the show, but this is the first time they have appeared together. And the timing couldn’t be better - we might be witnessing a pivotal shift in AI development as leading labs hit scaling limits and transition from pre-training to test-tim...
Dec 06, 2024•2 hr 35 min•Ep 400•Transcript available on Metacast My guest today is Ronnie Fieg, founder and CEO of Kith. At age 13, Ronnie started working at David Z., an iconic New York shoe store, where he sold Timberland boots to Jay-Z and Wallabies to Wu-Tang Clan. He worked his way up from the stockroom and earned his first collaboration in 2007, when he worked with ASICS on new Gel-Lyte 3s. That collection sold out in a day after being featured in The Wall Street Journal, catching the attention of Adidas's president and launching his reputation as a cul...
Dec 03, 2024•1 hr 26 min•Ep 399•Transcript available on Metacast My guest today is Gabe Whaley, the founder and CEO of MSCHF. What began with viral internet pranks in 2014 has evolved into one of the most singular creative companies in modern culture. MSCHF’s work ranges from microscopic handbags—the size of a grain of salt—to tax software that helps you file your returns by going on virtual dates with anime characters. Every two weeks, they release something new that challenges our assumptions about art, commerce, and culture. MSCHF is hard to define but Gab...
Nov 26, 2024•1 hr 17 min•Ep 398•Transcript available on Metacast 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 one of the largest logistics businesses in the world. He has also written a book that will be out in ...
Nov 22, 2024•1 hr 26 min•Transcript available on Metacast 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, and Ernie gives us a raw and candid explanation of navigating through a 99% stock price decline and...
Nov 12, 2024•1 hr 13 min•Ep 397•Transcript available on Metacast 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 comprehensive discussion on the semiconductor ecosystem and the silicon backbone of our digital age. Andre...
Nov 05, 2024•1 hr 26 min•Ep 396•Transcript available on Metacast 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 walks us through different mechanisms of cultivating storytelling and becoming a meaning-maker. He en...
Oct 29, 2024•1 hr 2 min•Ep 395•Transcript available on Metacast 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 organization, and the importance of building on an island that’s distinct from the mainstream. Tobi embodies t...
Oct 22, 2024•1 hr 7 min•Ep 394•Transcript available on Metacast 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. GSP is now a leader in its field. This discussion is a masterclass in franchise investing. We explore...
Oct 15, 2024•2 hr 41 min•Ep 393•Transcript available on Metacast 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 companies like Ramp and Robinhood. It's a timely moment to have this discussion, with Thrive announcin...
Oct 08, 2024•1 hr 27 min•Ep 392•Transcript available on Metacast 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 computing platform. Ray's work has earned him numerous accolades, including induction into the Computer Hi...
Oct 01, 2024•2 hr 34 min•Ep 391•Transcript available on Metacast 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 has gained from being a neutral third party with in conversations with countless industry experts. We ...
Sep 26, 2024•1 hr 1 min•Ep 390•Transcript available on Metacast 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 through effective communication and compelling storytelling. We discuss the evolution of media and its ...
Sep 24, 2024•1 hr 7 min•Ep 389•Transcript available on Metacast 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 have led to what is now a flourishing investing platform, but mostly this episode is a masterclass on...
Sep 17, 2024•1 hr 25 min•Ep 388•Transcript available on Metacast 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 veteran. Ravi as a leader at KKR, and then as a critical leader turning around & building Instacart, a...
Sep 10, 2024•1 hr 23 min•Ep 387•Transcript available on Metacast 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 of the board at OpenAI. We discuss the past, present, and future of AI agents: new programs that will...
Sep 03, 2024•1 hr 28 min•Ep 386•Transcript available on Metacast 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 so much detail in this discussion and I’m incredibly grateful to Gavin for sharing his wisdom with ...
Aug 27, 2024•2 hr 31 min•Ep 385•Transcript available on Metacast 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. ----- This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern op...
Aug 20, 2024•2 hr 40 min•Transcript available on Metacast 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 to everything he builds. We discuss Robinhood’s new credit card and more products on the horizon, t...
Aug 13, 2024•1 hr 18 min•Ep 384•Transcript available on Metacast 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 her own venture. She shares her unique perspective on the AI landscape and reveals her predictions for...
Aug 06, 2024•1 hr 13 min•Ep 383•Transcript available on Metacast 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 businesses. Hemant discusses how the firm is positioned to respond to the aftermath of crises, inclu...
Jul 31, 2024•1 hr 3 min•Ep 382•Transcript available on Metacast 
