Longtime general partner at the venture firm Benchmark.
Passion doesn't drive work — fascination does, says venture capitalist and author Bill Gurley. Drawing on years of research into the lives of high achievers, he shows why obsessive, lifelong learning is the real engine of career excellence. Hosted on Acast. See acast.com/privacy for more information.
(0:00) Bill Gurley joins the show! (6:00) Making yourself valuable in the age of AI, first class of "AI Natives" (17:37) Reacting to Pope Leo's AI encyclical: Who guards the guardians? (26:54) Anthropic's Digital God: Do they believe they are creating a superior species? (38:32) AI sovereignty, the next era of privacy, open-source crackdown coming? (59:56) The Great AI Jobs Debate: Dario and Sam Altman flip their rhetoric, Goldman CEO says no AI job apocalypse Follow Bill Gurley: https://x.com/bgurley Apply for Summit 2026: https://allin.com/events Follow the besties: https://x.com/chamath https://x.com/Jason https://x.com/DavidSacks https://x.com/friedberg Follow on X: https://x.com/theallinpod Follow on Instagram: https://www.instagram.com/theallinpod Follow on TikTok: https://www.tiktok.com/@theallinpod Follow on LinkedIn: https://www.linkedin.com/company/allinpod Intro Music Credit: https://rb.gy/tppkzl https://x.com/yung_spielburg Intro Video Credit: https://x.com/TheZachEffect Referenced in the show: https://www.vatican.va/content/leo-xiv/en/encyclicals/documents/20260515-magnifica-humanitas.html https://www.youtube.com/watch?v=ORFrdYSvzuw https://rdad.org https://www-cdn.anthropic.com/9214f02e82c4489fb6cf45441d448a1ecd1a3aca/claudes-constitution.pdf https://www.youtube.com/watch?v=0GaKJ4Fp2x4 https://allpoetry.com/All-Watched-Over-By-Machines-Of-Loving-Grace https://darioamodei.com/essay/machines-of-loving-grace https://x.com/chamath/status/2059850242779136031 https://x.com/vivekgaripalli/status/2059651390784344491 https://x.com/edzitron/status/2059122774401311095 https://p3institute.substack.com/p/from-open-source-software-to-open https://www.theinformation.com/newsletters/the-briefing/anthropic-likely-generating-least-35-revenue-openai https://www.theverge.com/tech/930447/microsoft-claude-code-discontinued-notepad https://x.com/Polymarket/status/2060034216906068131 https://x.com/savipww/status/2060070450785305030 https://www.nytimes.com/2026/05/22/opinion/ai-job-crisis-goldman-sachs.html https://fortune.com/2026/05/26/sam-altman-dario-amodei-walking-back-ai-jobs-apocalypse-prophecies-ipo https://fortune.com/2026/05/05/dario-amodei-jevons-paradox-will-ai-wipe-out-white-collar-jobs https://www.entrepreneur.com/business-news/jack-dorseys-block-cuts-4000-jobs-critics-claim/503108
Bill Gurley is a venture capitalist, general partner at Benchmark, and a former Wall Street analyst. How do you find work you actually enjoy? So many people warn about the jobs they hate and the dreams they never chased. But turning passion into a career is harder than it sounds. So how do you reinvent yourself and build a life where work feels meaningful instead of miserable? Expect to learn why most people end up having careers they regret, how to build a framework for regret minimisation, what people do that achieve success in their dream career, how to know when you’re plateauing versus when you’re just bored, what great mentors actually do that books and podcasts can’t, if someone can learn to love the grind or if it is something that’s innate, how you know if you’re in the wrong field versus just in the hard phase of the right field and much more… Timestamps: (0:00) What Career Regret Really Means (4:44) Why Uncertainty is So Uncomfortable (9:41) Why We Feel Obligated to Stick to One Career (15:05) Is Life Really “Use It or Lose It”? (23:04) How Some Of Us Successfully Pivot Careers (30:14) The Real Risk of Starting Over in Your 30s (38:42) Do Discipline, Motivation and Obsession Work Together? (41:54) Signs It’s Time to Change Your Career (48:30) Plateau or Boredom: How to Tell the Difference (50:12) Can You Upgrade Your Circle Without Losing Yourself? (54:49) Do Mentors Actually Make a Difference? (01:00:53) Can You Learn to Love the Grind? (01:07:37) The Pains and Pleasures of Reinventing Yourself (01:25:21) What Investors Look For in Founders (01:30:34) Founder vs Company: What Matters More? (01:42:01) Why You Should Lean into AI When Honing Your Craft (01:47:13) Which Careers Will AI Replace? (01:49:11) The Best Way to Start Your Career in Your 20s (01:50:56) Why Career Switchers Become Innovators (01:55:43) Where to Find Bill Sponsors: See discounts for all the products I use and recommend: https://chriswillx.com/deals New pricing since recording: Function is now just $365, plus get $25 off at https://functionhealth.com/modernwisdom Get up to $350 off the Pod 5 at https://eightsleep.com/modernwisdom Get 35% off your first subscription on the best supplements from Momentous at https://livemomentous.com/modernwisdom Get up to 20% off the leading longevity and cellular health supplement at https://timeline.com/modernwisdom Extra Stuff: Get my free reading list of 100 books to read before you die: https://chriswillx.com/books Try my productivity energy drink Neutonic: https://neutonic.com/modernwisdom Episodes You Might Enjoy: #577 - David Goggins - This Is How To Master Your Life: lnkfi.re/SN-Goggins #712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: lnkfi.re/SN-Peterson #700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: lnkfi.re/SN-Huberman - Get In Touch: Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx YouTube: https://www.youtube.com/modernwisdompodcast Email: https://chriswillx.com/contact - Learn more about your ad choices. Visit megaphone.fm/adchoices
Run your life like a $100M business. Get Sam's system here: https://clickhubspot.com/fhs Episode 803: Sam Parr ( https://x.com/theSamParr ) sits down with legendary investor Bill Gurley ( https://x.com/bgurley ) about how to avoid the biggest mistake you can make in life. — Show Notes: (0:00) 6 out of 10 people hate their job (11:24) Insane determinism (14:15) Finding your fascination (21:19) Underrated advice: Peer Groups (26:55) Dancing to work (28:44) Learning leadership (33:19) Risk vs uncertainty (42:19) Be fearful when others are greedy — Links: • Runnin’ Down a Dream- https://www.amazon.com/Runnin-Down-Dream-Thrive-Actually/dp/0593799666 — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam’s List - http://samslist.co/ My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /
Bill Gurley, accomplished venture capitalist, longtime Silicon Valley “worrywart,” and early Uber backer, joins Kara Swisher to discuss how to build a career you love and the tech industry’s sharp turn to the right. Gurley’s new book Runnin’ Down a Dream, guides readers on how to find and nurture a truly fulfilling career — and his advice is the polar opposite of Scott Galloway’s “follow your talent, not your passion.” Kara and Bill talk about how to find your fascination, and why the best careers are built through craft, peers, mentors, and a willingness to start at the bottom. They also dig into AI-related job loss anxiety and Gurley’s growing focus on public policy — from regulatory capture to the concentration of power in the Mag 7. Plus: an expert question from Uber CEO Dara Khosrowshahi. Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Bill Gurley (@bgurley) is a general partner at Benchmark, a leading venture capital firm in Silicon Valley. His new book is Runnin’ Down a Dream: How to Thrive in a Career You Actually Love. This episode is brought to you by: Momentous high-quality creatine for cognitive and muscular support Our Place’s Titanium Always Pan® Pro using nonstick technology that’s coating-free and made without PFAS, otherwise known as “Forever Chemicals” Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business Coyote the card game, which I co-created with Exploding Kittens * Timestamps: [00:00:00] Start. [00:01:43] The book that gave Jerry Seinfeld permission to pursue comedy and inspired Runnin’ Down a Dream. [00:03:59] AI bubble or not? [00:06:33] Circular deals and SPV chaos. [00:12:01] Angel investing in the AI era. [00:14:32] Why you should be the most AI-enabled version of yourself, regardless of field. [00:20:47] China deep dive: Ten days, six cities, high-speed trains, and a Xiaomi SU7 factory tour. [00:22:43] Communism misconceptions. [00:25:40] Lei Jun: The Steve Jobs of China. [00:29:17] Jack Ma, ByteDance’s invisible CEO, and the risks of prominence in China. [00:32:11] America vs. China (Lawyers vs. engineers). [00:41:01] Keys for US competitiveness. [00:43:47] Bill is bullish on these countries. [00:47:30] Matthew McConaughey’s “Don’t half ass it” moment. [00:49:45] Runnin’ Down a Dream thesis: Helping people pursue X instead of A, B, or C. [00:51:03] The 80,000-hour question. [00:52:47] The self-learning test. [00:56:58] Bob Dylan as music expeditionary. [01:00:27] Go to the epicenter where the action is. [01:10:56] Danny Meyer’s pivot. [01:13:30] Working for free. [01:19:37] Never too late: Tito Beveridge started Tito’s Vodka at 40. [01:21:51] AI sanity checks. [01:25:59] AI-proof bets. [01:29:13] Sam Hinkie’s Moneyball moment. [01:32:37] Competitive strategy, avoiding false failures, and regret minimalization. [01:43:46] Purpose, Progress, and Prosperity — the P3 Policy Institute. [01:47:18] Regulatory capture explained. [01:51:55] Why the IPO market is broken. [02:01:52] Stablecoins putting Visa and Mastercard on notice. [02:03:40] Hopes for Runnin’ Down a Dream and parting thoughts. * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss Instagram: instagram.com/timferriss YouTube: youtube.com/timferriss Facebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferriss See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
My guest today is Bill Gurley. Bill was the general partner at Benchmark Capital. He joins me for his sixth time on Invest Like the Best with his most comprehensive market analysis yet, examining the realities reshaping venture capital. Bill tackles the uncomfortable math underlying today's venture returns, with companies staying private for far longer. He also walks through why no one—from GPs to LPs to founders—has proper incentives to mark assets accurately, creating a system-wide coordination problem. And, we dig into the investment implications of AI as a platform shift, ranging from evaluating AI revenue quality to international competitive dynamics. Bill offers crucial perspective on playing the game both as it exists today and as it may evolve. Please enjoy my conversation with Bill Gurley. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com to learn more about the platform. – This episode is brought to you by Arcana. Arcana is the world’s most advanced portfolio intelligence platform, trusted by institutional investors managing trillions in AUM — including market neutral, long-short, long-only, and capital allocators. Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and idio, construct optimal portfolios, and decompose performance at incredible granularity. Visit arcana.io to request a demo and learn more. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:23) State of the Union: Venture Capital Edition (00:07:58) The Rise of Mega VC Funds (00:09:38) Zombie Unicorns: The Overvalued Giants (00:17:29) The IPO and M&A Market Stalemate (00:24:08) The AI Wave and Its Impact (00:26:03) Private Markets and LP Liquidity Issues (00:29:57) The Future of Capital Markets (00:37:49) Advice for Founders in a Changing Landscape (00:39:27) The High-Stakes Game of Capital Battles (00:41:35) AI: The New General Purpose Technology (00:42:57) Challenges and Opportunities in AI Revenue Models (00:44:37) The Role of Founders in the AI Revolution (00:46:44) The Impact of Time and Liquidity on Venture Capital (00:50:35) Navigating the Future of Venture Capital (00:58:45) International Dynamics in the AI Race (01:13:58) Advice for Founders in the AI Era
My guests today are Bill Gurley and Michael Mauboussin. Bill is a General Partner at Benchmark, and Michael is the Head of Consilient Research for Counterpoint Global. While they are longtime friends with one another, I’d never heard them appear somewhere together so it was a real treat to be able to do this with the two of them. They are two of the leading minds in their fields, and we combined their decades of expertise into one wide-ranging conversation. We discuss the different kinds of increasing returns to scale, the issue of regulatory capture, AI, and hardware. Please enjoy this great conversation with Bill Gurley and Michael Mauboussin. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:03:38) Dissecting the Dynamics of AI, LLMs, and Market Disruption (00:05:06) The World of AI Investments and Market Trends (00:08:13) Integration of New Technologies in Business (00:15:27) The Power of Increasing Returns and Strategic Investments (00:22:26) Unpacking the Role of Intangibles in Scaling and Innovation (00:28:54) Transformative Potential of Open Source and Idea Recombination (00:34:42) The Complex Landscape of Regulation and Innovation (00:43:17) Today’s Venture Capital Ecosystem (00:47:08) Impact of Fewer IPOs and Private Market Dynamics (00:50:38) Capital Allocation in Zero Interest Rate Environments (00:54:44) The Evolution of Venture Capital and High-Stakes Investment Games (00:57:21) Exploring New Frontiers: AI, Energy, and Physical World Innovations (01:01:14) The Power of Learning by Doing (01:17:49) Working with Genius (01:26:47) The Value of Teaching, Writing, and Sharing Knowledge
This Week in Startups is brought to you by… Gusto is easy online payroll, benefits, and HR built for modern small businesses. Get three months free when you run your first payroll at http://www.Gusto.com/twist *Gusto pricing shown in ad is based on pricing prior to March 2025 The Paintbrush Loan is the earliest startup financing on the internet. No pitch deck, no business plan, no minimum time in business, and no warm intros. Plus, you get to keep your equity. Visit http://www.getpaintbrush.com to see if you qualify for a $50K startup loan in less than 2 minutes. Squarespace. Turn your idea into a new website! Go to https://www.Squarespace.com/twist for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain. * Today’s show: Dara Khosrowshahi joins Bill Gurley, Brad Gerstner, and Jason Calacanis to discuss his initial reservations about joining Uber and how he overcame them (14:57), the early magic of Uber that captivated investors (22:36), a deep dive into Uber's future plans (45:50), and much more! * Timestamps: (0:00) Dara Khosrowshahi joins Bill Gurley, Brad Gerstner, & Jason Calacanis to discuss all things Uber (2:41) Setting the stage for Uber entering 2024 (4:52) Untold parts of Uber's story (09:38) Gusto - Get three months free when you run your first payroll at http://www.Gusto.com/twist (11:38) Bill Gurley discusses Dara's selection as CEO (14:57) Dara's initial reservations about joining Uber and how he overcame them (20:57) Dara’s discomfort in the free-money environment of ZIRP (21:43) Paintbrush - Visit http://www.getpaintbrush.com to see if you qualify for a $50K startup loan in less than 2 minutes (22:36) Exploring the early magic of Uber that captivated investors (26:27) How valuations impact founder mindset (30:49) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/twist (32:17) Discussing the relevance of secondaries in the near future (35:02) Breaking down some Uber myths and Dara’s focus on drivers (45:50) A deep dive into Uber's future plans (51:31) Uber’s strategy with upselling as AI enters the conversation (58:04) Bill Gurley on joining Zillow’s board and how innovation is needed in the real estate industry (1:05:27) Brad Gerstner on markets * Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Check out Uber: https://www.uber.com * LINKS: Silicon Valley clip referenced: https://twitter.com/StephNass/status/1745132141652877788 * Thanks to our partners: (09:38) Gusto - Get three months free when you run your first payroll at http://www.Gusto.com/twist *Gusto pricing shown in ad is based on pricing prior to March 2025 (21:43) Paintbrush - Visit http://www.getpaintbrush.com to see if you qualify for a $50K startup loan in less than 2 minutes (30:49) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/twist * X: https://twitter.com/Jason https://twitter.com/dkhos https://twitter.com/altcap https://twitter.com/bgurley LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast
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This Week in Startups is brought to you by… OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop. TWiST listeners can get an extra 20% off any plan for your first 6 months at openphone.com/twist DevSquad. Most dev agencies only offer developers. Why? Because product management is hard. Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist. Squarespace. Turn your idea into a new website! Go to Squarespace.com/TWIST for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain. * Today’s show: Bill Gurley, Brad Gerstner, and Jason Calacanis join David Weisburd to discuss the market downturn's impact on startups, including shutdowns and shifting investment strategies (1:29). They also debate the AI boom (54:50), chatbots' future potential and hype (1:01:11), and which tech giants may perform best or worst in 2024 (1:20:32). * Timestamps: (0:00) David Weisburd hosts Bill Gurley, Brad Gerstner, & Jason Calacanis to discuss the state of tech markets (1:29) Startup shutdowns in 2023 vs dotcom crash (3:52) Perspective on current market from Bill Gurley (7:52) Brad's outlook on startup shutdowns continuing in 2024 (11:48) OpenPhone - Get 20% off your first six months at https://openphone.com/twist (13:16) Different investor perspectives based on investment stage (16:47) Altimeter's recent investing activity (25:32) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist (26:30) Reflecting on past IPOs and paths to building businesses for growth (36:40) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/twist (38:07) State of Series B/C deals in 2023 vs 2021 peak (42:42) Why now is a great time to start a company (47:17) Jason's theories for success in venture (49:42) Abundance of technical talent in Silicon Valley and impact of AI on company size and competition (54:50) AI investments in 2024 (1:01:11) Launguage models raising large rounds quickly and the potential for LLMs to hit a ceiling soon (1:05:18) The best case for Meta being a leader in AI and Apple's position (1:08:55) Importance of voice recognition for AI interfaces, challenges of enabling transactions via AI, and consumers choosing services via AI (1:20:32) Picks for best and worst performing tech giants in 2024 * LINKS: Unicorn Investors article: https://news.crunchbase.com/venture/top-unicorn-investors-eoy-2023/ Bill Gurley's Above the Crowd article: https://abovethecrowd.com/2011/05/24/all-revenue-is-not-created-equal-the-keys-to-the-10x-revenue-club/ * Follow David X: https://twitter.com/DWeisburd David's Podcast: https://limitedpartnerpodcast.com/ * Follow Brad X: https://twitter.com/altcap * Follow Bill X: https://twitter.com/bgurley * Follow Jason: X: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast
This Week in Startups is brought to you by… LinkedIn Marketing. To redeem a $100 LinkedIn ad credit and launch your first campaign, go to linkedin.com/thisweekinstartups Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at vanta.com/twist CLA. Innovation takes balance. CLA's CPAs, consultants, and wealth advisors can help you get from startup to where you want to end up. Get started now at CLAconnect.com/tech * Today’s show: Bill Gurley and Sunny Madra join Jason to discuss open-source AI vs. proprietary AI (1:12), friends and foes of open-source AI (5:42), and strategic choices companies make between open and closed approaches (9:48). Then, Sunny demos more AI tools (22:45), and much more! * Time stamps: (0:00) Sunny Madra joins Jason (1:12) Bill Gurley joins to break down open-source vs. proprietary AI (5:42) Friends and foes of open-source AI (8:17) LinkedIn Marketing - Get a $100 LinkedIn ad credit at https://linkedin.com/thisweekinstartups (9:48) Strategic choices companies make between open and closed approaches (21:37) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist (22:45) Sunny demos LLaVA: Large Language and Vision Assistant (29:56) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech (31:00) Sunny breaks down parameter models (38:56) Companies manufacturing their own chips (42:26) Sunny demos Mistral AI (46:56) Jason and Sunny demo Meta AI on WhatsApp (50:44) FTX and the SBF trial * Follow Bill: https://twitter.com/bgurley Follow Sunny: https://twitter.com/sundeep * Check out LLaVA: https://llava-vl.github.io/ Check out Mistral: https://huggingface.co/spaces/Open-Orca/Mistral-7B-OpenOrca?utm_source=substack&utm_medium=email * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast
(0:00) Bestie intros: Friedberg's bad haircut (1:17) Welcome BG^2! Biography recommendations and film talk (22:27) VC market update: State of Series A's (33:43) Dry powder misconceptions, marking incentives (48:57) IPO window starting to open, IPO down rounds, incentives to go public (1:03:17) Cyclical venture cycles, managing distributions, benchmarking VC performance vs public market (1:22:26) Tragic Maui wildfires, extreme temperatures (1:26:11) Macro picture: inflation cools, deflation risk? Follow the besties: https://twitter.com/chamath https://linktr.ee/calacanis https://twitter.com/DavidSacks https://twitter.com/friedberg https://twitter.com/altcap https://twitter.com/bgurley Follow the pod: https://twitter.com/theallinpod https://linktr.ee/allinpodcast Intro Music Credit: https://rb.gy/tppkzl https://twitter.com/yung_spielburg Intro Video Credit: https://twitter.com/TheZachEffect Referenced in the show: https://youtu.be/xmYekD6-PZ8 https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/0060742755 https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/147770146X https://www.amazon.com/Elon-Musk-Spanish-Walter-Isaacson/dp/B0CBTHK86N https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996 https://www.amazon.com/Man-Arena-Selected-Writings-Roosevelt/dp/0765306700 https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike/dp/1501135910 https://www.amazon.com/Alexander-Hamilton-Ron-Chernow/dp/1594200092 https://www.amazon.com/Something-Autobiography-Vintage-Akira-Kurosawa/dp/B0C3D5NDJX https://www.amazon.com/Born-Standing-Up-Comics-Martin/dp/B017QUU3EO https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1439193630 https://www.amazon.com/Autobiography-Malcolm-told-Alex-Haley/dp/0345379756 https://www.linkedin.com/posts/peterjameswalker_cartadata-seriesa-valuations-activity-7092542118803488768-vOcY https://www.theinformation.com/articles/venture-firms-still-writing-small-checks-despite-271-billion-in-dry-powder https://twitter.com/bgurley/status/1688605654188224512 https://finance.yahoo.com/chart/SN https://www.google.com/finance/quote/CAVA:NYSE https://finance.yahoo.com/quote/SRFM https://twitter.com/altcap/status/1686086247029055489 https://www.wsj.com/articles/university-endowments-mint-billions-in-golden-era-of-venture-capital-11632907802 https://www.youtube.com/watch?v=Hhy7JUinlu0 https://twitter.com/gokulr/status/1680006171149869056 https://www.statista.com/statistics/277501/venture-capital-amount-invested-in-the-united-states-since-1995 https://www.bls.gov/charts/consumer-price-index/consumer-price-index-by-category-line-chart.htm https://www.bloomberg.com/news/newsletters/2023-08-10/disinflation-wave-the-bloomberg-open-americas-edition https://www.nytimes.com/2023/08/09/business/china-economy-inflation.html https://twitter.com/KobeissiLetter/status/1689010884062904320
Brought to you by Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating, Secureframe automated security and privacy compliance platform, and AG1 all-in-one nutritional supplement. Welcome to another episode of The Tim Ferriss Show, where it is usually my job to deconstruct world-class performers to tease out the routines, habits, et cetera that you can apply to your own lives. This is a special episode and a turning of the tables. This time, legendary investor Bill Gurley interviews me, and the recording is from earlier this year at SXSW in Austin, TX. The conversation explores some of my lessons learned and favorite findings over the last two decades in areas like entrepreneurship, tech, and podcasting. I throw in some favorite books and other spice to keep things interesting. Bill Gurley (@bgurley) has spent more than 20 years as a general partner at Benchmark. Before entering the venture-capital business, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at Credit Suisse First Boston. Over his venture career, he has worked with such companies as GrubHub, Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow. For more takeaways from his incredible investing career, you can find my interview with Bill at tim.blog/billgurley. As a side note, my 2007 SXSW speech that I mention in the interview is what started it all, in many senses. It’s what put my first book, The 4-Hour Workweek, on the radar of influential bloggers and bigger media outlets, ultimately landing it on The New York Times Best Sellers list, where it stayed, more or less, for the next seven years. It’s been a wild ride. You can hear that 2007 presentation at tim.blog/sxsw. One last thing: Hugh Forrest, if you’re listening, thank you again for giving me a shot way back in the day! Please enjoy! * This episode is brought to you by Secureframe! Secureframe’s industry-leading compliance automation platform, paired with their in-house compliance experts and former auditors, helps you get audit-ready in weeks, not months, so you can close more deals faster. Secureframe simplifies and streamlines the process of getting and staying compliant to the most rigorous global privacy and security standards. They help thousands of businesses achieve compliance with security and privacy frameworks including SOC 2, ISO 27001, HIPAA, PCI, and GDPR. Schedule a demo today at Secureframe.com, and tell them during the demo that Tim Ferriss sent you to unlock 10% off for your first year. * This episode is also brought to you by AG1! I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1, my all-in-one nutritional insurance. I recommended it in The 4-Hour Body in 2010 and did not get paid to do so. I do my best with nutrient-dense meals, of course, but AG1 further covers my bases with vitamins, minerals, and whole-food-sourced micronutrients that support gut health and the immune system. Right now, you’ll get their Vitamin D Liquid Formula free with your first subscription purchase—a vital nutrient for a strong immune system and strong bones. Visit DrinkAG1.com/Tim to claim this special offer today and receive the free Vitamin D Liquid Formula (and 5 free AG1 travel packs) with your first subscription purchase! That’s up to a one-year supply of Vitamin D as added value when you try their delicious and comprehensive all-in-one daily greens product. * This episode is also brought to you by Eight Sleep! Eight Sleep’s Pod Cover is the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced (and user-friendly) solution on the market. Simply add the Pod Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. It also splits your bed in half, so your partner can choose a totally different temperature. Go to EightSleep.com/Tim and save $250 on the Eight Sleep Pod Cover. Eight Sleep currently ships within the USA, Canada, the UK, select countries in the EU, and Australia. * [06:32] From Princeton to podcasting. [07:39] How a disenchanted entrepreneur became a reluctant author. [14:22] Angel investing and The 4-Hour Body. [16:40] Investing rulesets and takeaways. [19:09] How a choice location maximizes serendipity. [20:42] Why did I back away from angel investing? [22:28] Entering the blogosphere. [27:02] Why podcasting? [28:33] Early and enduring lessons for improving the craft. [31:37] What makes a successful podcaster? [34:57] The power of direct communication with one's audience. [38:48] Leveraging a lean infrastructure. [40:34] Helpful steps for effective interview prep. [45:08] Respected podcasting peers. [48:00] Spotify's foray into podcasting territory. [50:09] Twitter and LinkedIn. [53:15] Books most gifted. [55:31] Most positively effective purchase of $100 or less. [55:30] Favorite failure. [57:50] Billboard. [58:49] Best investment ever made. [59:30] Most life-improving new belief, behavior, or habit. * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss Instagram: instagram.com/timferriss YouTube: youtube.com/timferriss Facebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferriss Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Brought to you by Protekt's REST sleep supplement, Athletic Greens's AG1 all-in-one nutritional supplement, and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business. Bill Gurley (@bgurley) has spent more than 20 years as a general partner at Benchmark. Before entering the venture capital business, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at Credit Suisse First Boston. Bill also maintains a blog on the evolution and economics of high technology businesses called Above the Crowd. Over his venture career, he has worked with such companies as GrubHub, Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow. Bill has a BS in computer science from the University of Florida and an MBA from the University of Texas. He is also a chartered financial analyst. Bill is a board trustee at the Santa Fe Institute, a research and education center focused on the study and understanding of complex adaptive systems. Please enjoy! * This episode is brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great-looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. No coding or design experience required. Go to shopify.com/tim to sign up for a one dollar per month trial period. It’s a great deal for a great service, so I encourage you to check it out. Take your business to the next level today by visiting shopify.com/tim. * This episode is also brought to you by Protekt’s REST supplement! Protekt's REST is a new take on getting deeper, more restorative sleep. Protekt's REST supplement helps provide consistent, restful sleep without any habit-forming ingredients or groggy side effects. Simply add it to your last glass of water before bed, and it goes to work. REST has no added sugars, artificial sweeteners, or artificial ingredients. Protekt is veteran-owned, and they make all of their products right here in the USA. Protekt is offering you 30% off both flavors of their REST formula! Visit Protekt.com/Tim to claim this special offer today and use code TIM at checkout. * This episode is also brought to you by Athletic Greens. I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1 by Athletic Greens, my all-in-one nutritional insurance. I recommended it in The 4-Hour Body in 2010 and did not get paid to do so. I do my best with nutrient-dense meals, of course, but AG further covers my bases with vitamins, minerals, and whole-food-sourced micronutrients that support gut health and the immune system. Right now, Athletic Greens is offering you their Vitamin D Liquid Formula free with your first subscription purchase—a vital nutrient for a strong immune system and strong bones. Visit AthleticGreens.com/Tim to claim this special offer today and receive the free Vitamin D Liquid Formula (and five free travel packs) with your first subscription purchase! That’s up to a one-year supply of Vitamin D as added value when you try their delicious and comprehensive all-in-one daily greens product. * [05:51] The book Bill calls "the most efficient short-form MBA one can find." [07:31] Sell-side analysts vs. buy-side analysts. [09:45] Financial models, rules of thumb, and making (sometimes wrong) decisions. [17:28] Howard Marks and Stan Druckenmiller. [19:26] Micro vs. macro investing. [20:40] Institutional Investor's All-America Research Team. [24:16] Expanding distribution. [27:04] Return On Invested Capital (ROIC). [33:10] Repurposing good ideas for alternative applications. [37:01] The conviction of network effects. [38:58] SaaS and open source. [42:40] Bet sizing. [44:04] Equal partnership over hierarchy. [50:08] Lessons learned from partners. [52:57] Recommended resources. [58:46] Problems open source can solve. [1:09:28] Building a better network with the interest graph. [1:13:42] Dissecting Bill's Twitter thread about risks and sudden valuation resets. [1:23:50] The Metaverse. [1:29:00] Revenue and earnings quality matter. [1:31:02] Undervalued competitive advantages. [1:35:02] Jeff Bezos: corporate mad scientist? [1:40:42] The counterintuitive condemnation of company camaraderie. [1:45:37] Tobi Lütke. [1:48:51] Books Bill has gifted frequently. [1:52:29] The Santa Fe Institute. [1:54:35] Bill's board. [1:56:32] Cultivating anti-tribalism. [1:58:13] Twitter: what is it good for? [2:01:14] Newsletters and other resources Bill relies on. [2:03:05] Bill's book in progress. [2:04:12] Regulatory capture. [2:09:10] Predicting what America will look like in 10-20 years. [2:10:50] Parting thoughts. * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss Instagram: instagram.com/timferriss YouTube: youtube.com/timferriss Facebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferriss Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Marcelo Claure is an entrepreneur and investor who has founded and led some of the world's most iconic businesses. He is currently the Chairman & CEO of Claure Capital, a newly founded multi-billion-dollar global investment firm. Before this, Marcelo was COO @ Softbank Group, the world's largest technology investment company. Bill Gurley is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including Uber, Twitter, Dropbox, Modern Treasury, Snapchat, StitchFix, and many more. Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade. David Tisch is the Founder and Managing Partner @ Box Group, one of the leading seed focused firms of the last decade with a portfolio including Airtable, Glossier, PillPack, Plaid and many more. Cyan Banister is one of the most successful and renowned early-stage investors in the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital. Luciana Lixandru is a Partner @ Sequoia, one of the world's most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ's total value. Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN. Nick Shalek is a General Partner @ Ribbit Capital, specializing in fintech they are one of the most successful venture firms of the last decade with a portfolio including Robinhood, Coinbase, Revolut, Nubank and more. Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more. Geoff Lewis is the Founder and Managing Partner @ Bedrock, now with over $1BN in AUM, Bedrock invests in breakout technology companies that are incongruent with popular narratives. Justin Fishner-Wolfson is founder and the managing partner of 137 Ventures. Their portfolio includes SpaceX, Wish, Anduril, Flexport, and WorkRise (formerly Rigup) to name a few. David Sze is a General Partner @ Greylock where he has led some of the firms most notable investments including Facebook, LinkedIn and Pandora. In Today's Episode We Discuss Price Sensitivity: 1.) How do you assess your relationship to price and price sensitivity? 2.) When is the time to pay up and have less price discipline? 3.) When should we remain disciplined and not pay up for a deal and walk away because of price? 4.) Of the deals you have paid up for, did their growth rate justify the high entry price? 5.) Knowing all you know now on price, how do you advise younger investors today?
Bill Gurley is a General Partner @ Benchmark Capital, Bill, is widely recognized as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow. Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world's most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more. Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on. Arthur Patterson and Jim Swartz founded Accel in 1983. Under their leadership, they have built Accel into one of the most prominent venture firms of the last 4 decades. Michael Eisenberg is a Co-Founder and Equal Partner @ Aleph, with a portfolio including the likes of Lemonade, Melio and HoneyBook, they are one of the leading early-stage firms of the last decade. Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify and many more incredible companies. Fabrice Grinda is the Founding Partner @ FJ Labs, with over 700 investments, Fabrice has had over 250 exits and built a portfolio including Alibaba, Coupang, Airbnb, Instacart, Flexport, and many more. In Today's Episode You Will Learn: 1.) How does the current environment compare to prior busts? 2.) How will the changing interest rates impact the startup funding climate moving forward? 3.) Why is the rate of inflation the only true metric which reveals the ultimate fate of the economy? 4.) What are the world's leading investors telling their founders? 5.) How are the best investors in the world thinking through reserves management?
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This conversation was recorded LIVE at the All-In Summit in Miami and included slides. To watch on YouTube, check out our All-In Summit playlist: https://bit.ly/aisytplaylist 0:00 Bill Gurley & Brad Gerstner break down the state and historical significance of 2022's market downturn 12:27 How VCs will handle capital commitments from LPs, underwriting startups in the new reality 24:14 Bull run mistakes, why VCs don't underwrite lower valuations, handling distributions 33:52 Gurley's take on WeCrashed & Super Pumped TV series, how sophisticated investors got "gaslit" by the market, influx of capital creating consumer-surplus businesses 47:54 Brad predicts the market for next year, Bill gives post-Benchmark plans Follow the besties: https://twitter.com/chamath https://linktr.ee/calacanis https://twitter.com/DavidSacks https://twitter.com/friedberg Follow the pod: https://twitter.com/theallinpod https://linktr.ee/allinpodcast Intro Music Credit: https://rb.gy/tppkzl https://twitter.com/yung_spielburg Intro Video Credit: https://twitter.com/TheZachEffect
My guests today are Philip Rosedale and Bill Gurley. Philip created Second Life in the early 2000s and helped build it into the largest virtual 3D world ever created at the time. Frequent listeners will recognize Bill, who was an investor in Second Life via Benchmark Capital. During the conversation, we cover the fascinating story of Second Life and the billion-dollar economy that persists through to this day. Bill and Phillip share their key learnings from the experience, including the importance of usability, their views of the current metaverse opportunity, and what excites them most about the current focus on virtual realities. If you’re curious about what the metaverse might become, these two experts have seen much of this already and are kind to share their lessons with us. Please enjoy my conversation with Phillip and Bill. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:22] - [First question] - The origin story of Second Life and why they created it [00:05:38] - How many people were playing Second Life at its peak, the in-game economy and its growth trajectory [00:06:49] - The interface between the in-game currency and its function for players [00:10:53] - An example of early entrepreneurship and user-created IP in Second Life [00:12:13] - Was technology a rate limiter to success in such an early version of the metaverse? [00:14:35] - What was most exciting about creating it and it’s early-stage potential [00:18:23] - Why Unity isn’t more adopted by creators and players like Minecraft [00:24:42] - Defining what the metaverse means to each of them today [00:28:50] - What Discord has taught them about aggregating people digitally [00:33:02] - Simultaneously crossing the digital chasm and the uncanny valley [00:38:16] - Key differences between games and platforms and the role of purpose [00:42:04] - Why cryptocurrencies and blockchains haven’t produced experiences akin to the virtual Travis Scott concert [00:47:13] - Why removing friction and centralizing financial structures can help growth and thoughts on play to earn gaming and user spending [00:53:27] - Digital asset ownership and digital trustless exchanges in the metaverse [00:57:30] - Pros and cons of today’s speculative digital asset valuations [01:01:05] - Interesting pockets of opportunity that could benefit the metaverse ecosystem [01:04:28] - How they’d build and construct an ETF with metaverse exposure [01:07:18] - Thoughts on AR and VR and which holds more promise for public adoption [01:08:02] - Surprising findings about the role audio plays in digital worlds [01:10:23] - What they’re watching most closely in this emergent sector [01:11:29] - Limitations of visual and sonic barriers when recreating real-world interactions [01:12:42] - The kindest things anyone has ever done for them
Bill Gurley is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including Uber, Twitter, Dropbox, Modern Treasury, Snapchat, StitchFix, and many more. As for Bill, widely recognized as one of the greats in venture having worked with GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade with a portfolio including Lemonade, Melio, and HoneyBook, just to name a couple of Aleph's unicorns. In Today's Episode with Bill Gurley and Michael Eisenberg You Will Learn: 1.) How does the current market activity in venture today compare to the dot com bubble? What elements are different? What elements are the same? What were the ramifications of the dot com bubble? Would Bill and Michael expect to see the same again? Is there anything good that comes from bubbles? How did the prior bubble impact Michael and Bill's investing mindset? 2.) Does Bill Gurley agree that Benchmark are the only firm to have retained price discipline in this crazy market? How do Bill and Michael think about their own relationship to price today? How does Bill try and answer the question, "what could go right?" when he meets entrepreneurs today? On reflection, what have been Michael and Bill's biggest miss? How did it change their approach? 3.) How does one compete in a world of Tiger and crossover funds? When it comes to capital deployment and pacing, do Michael and Bill agree with the suggestion of "playing the game on the field"? What are the nuances to this statement? What companies does Bill believe capital can be a moat for? What companies is capital not a moat and they should be conservative with raising and pre-emptive rounds? 4.) Do Bill and Michael believe that ownership still matters today with outcomes being larger than ever? How do Bill and Michael feel about the importance of temporal diversification today in a world of compressed deployment cycles? What investing lesson learned over 25 years in the business do Bill and Michael wish they had known when they started? Item's Mentioned In Today's Episode with Bill Gurley and Michael Eisenberg Bill's Favourite Book: The Storytelling Animal: How Stories Make Us Human
Howard Marks is co-chairman and co-founder of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, "When I see memos from Howard Marks in my mail, they're the first thing I open and read. I always learn something." Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston. In Today's Episode You Will Learn: 1.) In March Ray Dalio stated we would be entering a "global recession", how do Howard and Bill feel about this statement? How does today's environment remind Howard and Bill of 2010/11? What is similar? What is different? How does Bill think about investing through cycles? 2.) How does Bill think about investing through cycles? What have Bill's lessons been from seeing many venture vintages on LP performance across cycles? How does Howard think about investing through cycles from a distressed debt perspective? What have his lessons been from Oaktree's performance over the years? 3.) Do Howard and Bill agree we will not see interest rates go anywhere for the next 3-5 years? What is the impact of this sustained low-interest rate environment? What could be done that would see interest rates increase in the future? How does Bill believe this will impact the supply of LP dollars in venture? 4.) How do Bill and Howard evaluate the state of the public markets today? Why does Howard believe that FOMO has really taken effect? How does Bill think about network effects and the laws of compounding with regards to public companies? 5.) Do Howard and Bill agree we are seeing a retreat from globalisation? What are the core impacts of this retreat? Why is Bill so concerned about "regulatory capture"? Why does Bill fear that today, "Washington is for sale"? What would he like to see change? Item's Mentioned In Today's Episode Howard's Favourite Book: Across That Bridge: A Vision for Change and the Future of America Bill's Favourite Book: How Innovation Works As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for all things 20VC.
Follow the crew: https://twitter.com/chamath https://linktr.ee/calacanis https://twitter.com/DavidSacks https://twitter.com/friedberg Follow the pod: https://twitter.com/theallinpod https://linktr.ee/allinpodcast Follow the bestie guesties: https://twitter.com/bgurley https://twitter.com/phil_hellmuth https://twitter.com/altcap https://twitter.com/jcpolls
Follow the crew: https://twitter.com/chamath https://linktr.ee/calacanis https://twitter.com/DavidSacks https://twitter.com/friedberg Follow the pod: https://twitter.com/theallinpod https://linktr.ee/allinpodcast Follow the bestie guesties: https://twitter.com/bgurley https://twitter.com/phil_hellmuth https://twitter.com/altcap https://twitter.com/jcpolls Show Notes: 0:00 The besties & Phil Hellmuth on Trump's early lead, live betting odds, the Latinx reversal 10:09 Sacks intros political expert Michael Newman on vote tally timing discrepancies, why some states skew a certain way early & more 20:33 Assessing the 180 in the gambling markets & equity markets towards a pro-Trump outcome 24:18 SurveyMonkey Chief Research Officer Jon Cohen joins the show to talk about polling updates from 2016 to 2020, understanding the race so far, electoral college & more 41:51 Biden losing Florida, tax policy, cultural repudiation of the elites in 2020 50:43 Chamath on the stupidity of the establishment, socialism, Democratic ideology for 2024 if Biden loses 55:40 Mid-show predictions, Jason goes off on Trump 1:07:58 What will happen in the time until we have a clear winner, Trump as a middle finger 1:17:55 Brad Gerstner joins the show to talk about stock futures, what the Democrats keep getting wrong - coastal elites losing touch with normal people, rebuking lockdowns 1:38:24 Reviewing the race swing state by swing state 1:47:28 Bill Gurley joins the show to talk about divisiveness, urban/rural rapture & more 1:55:53 Pete Buttigieg as the future of the Democratic Party, Chamath calls out the democratic leaders 2:00:43 Reconciling middle America & the coastal elites, respecting each other's differences, understanding Prop 22 2:11:34 Diagnosing states that flipped from Biden to Trump, anti-business California state propositions failing, union impact on legislation 2:23:01 Senate races, market talk, which Democratic candidate had the best chance of beating Trump, voting for character over policy 2:34:32 Jason & Sacks debate Russian election interference legitimacy 2:41:34 Sacks unveils his Trump Derangement Score tracker, updated outcome scenarios & more 2:51:51 Trump declaring victory could tank markets, live reaction to Joe Biden's election night address
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 crisis is done. We discuss enterprise and consumer, funding and growth, and the entrepreneurial spirit in the face of a crisis. 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 at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:44 – (First question) – Landscape for venture capital ecosystem 6:47 – The experience in 2009 and the entrepreneurs that tend to rise to the top 8:24 – The relationship between early stage companies and public investors 10:45 – How this crisis impacts enterprise businesses vs the broader corporate sector 14:46 – Advice for early stage companies in a period like this 18:23 – What Chetan was doing during the last downturn and what he learned during it 20:27 – Early stage vs late stage companies in this environment 22:57 – On the Road to Recap 23:00 – Benefits of being small in a period like this 25:22 – How portfolio companies are responding and pivoting during this period 29:33 – Best practices for remote companies 31:39 – Themes that stand out during this period 34:51 – Closing thoughts Learn More 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
Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO. In Today's Episode You Will Learn: 1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world's leading funds in the form of Benchmark? What were Bill's biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill's investment mentality today? 2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, "never turn down a deal based on the valuation it is a mental trap"? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google? 3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays? 4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio? 5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition? Items Mentioned In Today's Show: Bill's Fave Book: Complexity: The Emerging Science at the Edge of Order and Chaos Bill's Most Recent Investment: Good Eggs As always you can follow Harry, The Twenty Minute VC and Bill on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
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 company public through a traditional IPO vs. what’s known as a direct listing. As a third party observer with no real dog in the hunt (as we don’t buy IPOs at O’Shaughnessy Asset Management), I thought this was a small and nuanced issue. I’ve therefore been surprised by the strength of opinions on both sides of this issue as I’ve explored it behind the scenes this past week. It feels almost like I’ve encountered a political third rail, where one side throws a lot of vitriol towards the other. To be clear, this episode is very much in favor of direct listings instead of traditional IPOs. For those that want a good discussion of the IPO process and its upsides, check out episode 173 of the Exponent podcast with Ben Thompson. Now please enjoy my very interesting conversation with Bill Gurley 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 1:22 - (First Question) – His view on the IPO process 5:42 – Will now be the turning point for IPO’s 6:40 – The engagement between a new company going public and their counterparty and the IPO process 13:38 – The math of capital costs 18:18 – Banks that underprice the IPO’s 20:45 – The psychology of IPO’s 23:14 – The pop in the IPO and the media 24:54 – The value that shareholders give vs VC’s 25:37 – The Green Shoots 28:17 – The lock-up 31:40 – Direct listings vs IPO’s 36:07 – Spotify’s CEO Reveals Why He’s Not Doing a Traditional IPO 38:23 – The capital raised in an IPO and diluting the company 40:18 – Privilege access and buy-side firms 43:33 – What will actually lead to changes in the IPO space 44:48 – Why he became so interested in the IPO space Learn More 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
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 might discuss past glories, I’ve been incredibly impressed with how both Bill and his partners emphasize the current portfolio and market landscape. I’m thankful to have had the chance to speak with him in this format. I hope you 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 1:13 - (First Question) – The idea of increasing returns 1:21 – Competiting Technologies, Increasing Returns, and Lock-in By Historical Events 2:07 – Complex Systems Theory – Santa Fe Institute 4:35 – Markers that could be a sign of network effect in a company 6:27 – The opportunities for companies to capture network effect 8:46 – Are there certain teams/leaders that are more conducive to leading a network effect company 11:55 – Liquidity quality 13:35 – How important is the revenue model at the beginning 15:59 – Fascination with Nextdoor 17:56 – Paradox of Choice 18:39 – Finding opportunities 20:17 – Potential marketplaces and assets that could be commoditized 20:20 – All Markets Are Not Created Equal: 10 Factors To Consider When Evaluating Digital Marketplaces 21:39 – Usage yield on the world’s assets 23:50 – Has technology changed the world of value investing 26:28 – Hyper niche marketplaces 27:52 – Challenges of labor marketplaces 30:12 – User generated content businesses 32:44 – People who are capable of building UGC businesses 33:16 – His interest in Discord 34:31 – Factors of a healthy marketplace 37:57 – Fools’ gold in marketplace businesses 39:04 – How influx of cash is impacting the marketplace business landscape 40:43 – All Revenue is Not Created Equal: The Keys to the 10X Revenue Club 43:20 – How does the influx of money into the space impact him 46:44 – Spending money to attack top brands 50:32 – Regulatory capture 53:36 – His thoughts on the IPO market 57:49 – How did he realize this was his passion 1:00:42 – Qualifying his passion 1:01:52 – Favorite thing about working with entrepreneurs 102:48 – Honing your craft 1:04:33 – Making yourself a good mentor 1:05:56 – Kindest thing anyone has done for him Learn More 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
Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO. In Today's Episode You Will Learn: 1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world's leading funds in the form of Benchmark? What were Bill's biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill's investment mentality today? 2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, "never turn down a deal based on the valuation it is a mental trap"? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google? 3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays? 4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio? 5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition? Items Mentioned In Today's Show: Bill's Fave Book: Complexity: The Emerging Science at the Edge of Order and Chaos Bill's Most Recent Investment: Good Eggs As always you can follow Harry, The Twenty Minute VC and Bill on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Benchmark general partner Bill Gurley talks with Recode's Kara Swisher about life as a venture capitalist and why he's still worried about a bubble, a topic he has written about extensively. Great entrepreneurs could raise money at any time, Gurley argues, but when funding is easy to come by, it invites in entitled and less talented startup founders, as well as unwanted government regulation. He also discusses sitting on the board of Uber, challenges faced by its CEO, Travis Kalanick, and why the ridesharing company is unlikely to go public "any time in the near future." Learn more about your ad choices. Visit podcastchoices.com/adchoices
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