How to build a career you actually love | Bill Gurley
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.
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Anthropic's Digital God, Pope vs AI, Job Loss Narrative Flips, Open Source Crackdown Coming?
(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
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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
If You Hate Your Job, This is How to Start Over - Bill Gurley - #1071
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
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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
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Bill Gurley: 6 Out of 10 People Are Making This Mistake
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.
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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
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Links:
• Runnin’ Down a Dream- https://www.amazon.com/Runnin-Down-Dream-Thrive-Actually/dp/0593799666
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Benchmark’s Chetan Puttagunta on the Past, Present, & Future of Software
Chetan Puttagunta is a General Partner at Benchmark.
We talk about investing in Manus, the AI company that went from zero to $100M ARR in eight months and was recently acquired by Meta.
We also talk through the full history of application software, from mainframes to client-server, to the internet to cloud, why each wave reduced the barrier to entry and created an explosion in the number of new software, why legacy SaaS companies are making the same mistake on-prem vendors made at the dawn of the cloud, why software companies should be making big AI acquisitions, and how public market investors are begging private AI companies to go public.
We also talk about what Benchmark actually looks for in founders, how they make decisions, and why his last two investments were consumer AI and crypto.
Thanks to Sam Ross and Everett Randle for helping brainstorm topics for this conversation.
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Timestamps:
(0:08) Inside the $2.5B Manus acquisition
(6:24) Manus' three main use cases
(11:08) Taking heat on Twitter
(15:10) Starting to tweet about software in 2018
(22:50) The history of application software
(29:15) Benchmark’s 25x Fund 7
(31:33) SaaS incumbents got too dominant by 2020
(31:48) Going all-in on AI software in 2022
(39:31) Benchmark didn’t invest in the big AI labs
(40:48) How cloud companies beat on-prem competitors
(44:33) Why AI companies will beat legacy cloud competitors
(50:04) Software incumbents should make big AI acquisitions
(57:35) Why incumbents have not bought more AI companies
(1:04:43) Public markets are starving for AI companies
(1:10:14) Inside Benchmark’s fund strategy
(1:14:14) Benchmark’s history of non-traditional VC rounds
(1:17:56) Is the 20% ownership model outdated?
(1:19:20) Chetan’s rebirth as a consumer investor
(1:22:39) What Benchmark looks for in founders
(1:25:01) AI coding and gross margins
Referenced
Benchmark: https://benchmark.com/
Eric Vishria’s podcast episode: https://www.youtube.com/watch?v=I-5IsqFgrZM
Workday S-1: https://www.sec.gov/Archives/edgar/data/1327811/000119312512375787/d385110ds1.htm
Innovator's Dilemma: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Business-Essentials/dp/0060521996
Try FOMO: https://apps.apple.com/us/app/fomo-never-miss-out/id6741115427
Follow Chetan
Twitter: https://x.com/chetanp
LinkedIn: https://www.linkedin.com/in/chetanputtagunta
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Why ‘Playing It Safe’ In Your Career Doesn’t Pay with VC Bill Gurley
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.
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#840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More
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.
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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.
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Bill Gurley - The Gift and The Curse of Staying Private - [Invest Like the Best, EP.427]
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.
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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
Benchmark’s Eric Vishria on Going Zero to $100M ARR in 12 Months, Archetypes of Top AI Founders, Why Storytelling is a Superpower, How Benchmark Makes New Investments
Eric Vishria is a General Partner at Benchmark Capital.
Our conversation goes inside the new class of startups going zero to $100 million ARR in 12 months, the ways AI is changing company building, and how Eric and Benchmark make new investments.
We get into the risk rewards of Series As today, how Benchmark competes to work with founders, and and why the best storytellers win.
We also talk about parallels between the 90’s, 2000’s, and today, and how the archetype of successful founders has changed in the age of AI.
Thanks to Spenser Skates, Sajith Wickramasekara, Bobby DeSimone, and Semil Shah for help brainstorming topics for Eric!
Special thanks to this episode’s sponsors:
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Timestamps:
(5:17) What gets Eric excited about a new investment
(7:48) Backing learning machines
(12:34) Backing Cerebras at inception
(16:20) Why the best storytellers win
(21:17) How Eric works with founders
(26:38) Companies going zero to $100m in 12 months
(31:09) Revenue quality of AI products
(32:41) Moats and business models in AI
(38:41) AI margins and runway
(41:14) Parallels between winners of the 90’s and today
(44:54) Archetypes of the best AI founders
(50:43) SaaS companies successfully pivoting to AI
(53:43) LLMs are most comparable to transistors in the 1950s
(56:19) Ways Eric uses AI personally
(58:05) How VC has changed over the past decade
(1:01:40) VC is a hustler’s business
(1:03:20) Backing extraordinary companies is all that matters
(1:09:36) What makes Benchmark unique
(1:17:03) How Benchmark makes investment decisions
(1:18:38) Skipping senior year of high school
(1:20:21) Working with Ben Horowitz and Marc Andreessen ‘00-’08
(1:24:42) Starting RockMelt, selling to Yahoo
(1:26:28) Joining Benchmark in 2014
(1:28:08) Investing in Confluent one month later
(1:28:50) Lessons from Spenser at Amplitude
(1:29:36) Fireworks AI’s hyper growth
(1:30:49) Pricing in AI changing from tokens to outcomes
(1:32:23) Ways Eric’s perception of VCs changed after becoming one
(1:34:07) How to build a management team
(1:38:21 )The best CEOs make new mistakes
(1:39:50) Why there should be more public companies
(1:44:03) “Even great companies can be overvalued”
Referenced
Benchmark
Cerebras
Benchling
Ben Thompson + Mark Zuckerberg Interview
Confluent
Amplitude
Fireworks AI
Andy Price at Artisinal Talent
Follow Eric
X / Twitter
LinkedIn
Follow Turner
X/ Twitter
LinkedIn
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Chetan Puttagunta and Modest Proposal - Capital, Compute & AI Scaling - [Invest Like the Best, EP.400]
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-time compute. Together, we explore how this change could democratize AI development while reshaping the investment landscape across both public and private markets. Please enjoy this discussion with Chetan Puttagunta and Modest Proposal.
My guests today For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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This episode is brought to you by Alphasense. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high-conviction decisions with confidence. AlphaSense provides access to over 300 million premium documents, including company filings, earnings reports, press releases, and more from public and private companies. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest and experience firsthand how AlphaSense and Tegas help you make smarter decisions faster.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
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
(00:05:30) Introduction to LLM Scaling Challenges
(00:07:25) Synthetic Data and Test Time Compute
(00:08:53) Implications of Test Time Compute
(00:11:19) Public Tech Companies and AI Investments
(00:16:58) Small Teams and Open Source Models
(00:29:02) Strategic Positioning of Major AI Players
(00:35:49) AGI and Future Prospects
(00:46:50) AI Application Layer and Investment Opportunities
(00:54:18) The Paradigm Shift in AI Reasoning
(00:55:34) Investing in AI-Powered Solutions
(00:58:46) Economic Impacts of AI Advancements
(01:00:19) The Future of AI and Model Stability
(01:02:52) Private Market Valuations and Compute Costs
(01:05:05) Infrastructure and Utilization in AI
(01:12:50) The Role of Hyperscalers and GPUs
(01:18:02) The Evolution of AI Applications
(01:27:56) Philosophical Questions on AGI and ASI
(01:34:31) The Importance of Innovation Hubs
20VC: Benchmark's Eric Vishria on Where is the Value in AI: Chips, Models or Apps | Why Nvidia Will Not Be The Only Game in Town | The Commoditisation of Foundation Models | Which AI Apps Have Sustaining Value vs Hype and Short Term Revenue
Eric Vishria is a General Partner @ Benchmark Capital, one of the world's leading venture firms. At Benchmark, Eric has served on over 10 boards including Confluent (CFLT), Amplitude (AMPL), Benchling, Contentful, Cerebras and several other private companies. Prior to joining Benchmark, Eric was the Co‐Founder and CEO of RockMelt, acquired by Yahoo in 2013.
In Today's Episode with Eric Vishria We Discuss:
1. How to Make Money Investing in AI Today:
How does Eric think through where value will accrue in the stack between chips, models and applications?
Why does Eric believe foundation models are the fastest commoditising asset in history?
Why does Eric believe that Nvidia will not be the only game in town in the next 3-5 years?
2. How to Invest in AI Application Layer Successfully:
How does Eric analyse between a standalone and deep product vs a product that foundation model will commodities and incorporate into their feature set?
How does Eric differentiate between the 10 different players all going after customer service, or sales tools or data analyst products etc?
How does Eric analyse the quality of revenue of these AI application layer companies? What does he mean when he describes their revenue as "sugar high"?
3. How the Best VC Firm Makes Decisions:
What is the decision-making process for all new deals in Benchmark?
As specifically as possible, how does the voting process inside Benchmark work?
What deal was the most contentious deal that went through? What did the partnership learn?
How has the Benchmark decision-making process changed over 10 years?
4. Does AI Break Venture Capital Models:
Does the price of AI deals and size of their rounds break the Benchmark model?
Will foundation model companies all be acquired by the larger cloud providers?
Unless multiples reflate in the public markets, does venture as an asset class have hope?
Why does AI make paying ludicrously high prices potentially rational?
Building Enduring Value and Hitting Incremental Gains with Benchmark’s Sarah Tavel | E1983
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Todays show:
Benchmark’s Sarah Tavel joins Jason to discuss strategies for competing in a changing venture landscape (9:12), the critical role of governance and accountability in startups (19:39), the relationship between hype, investment decisions, and startup promotion (55:20). and more!
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Timestamps:
(0:00) Sarah Tavel joins Jason.
(1:38) Sarah Tavel, Benchmark Partner, on disciplined fund size and efficiency
(5:06) Benchmark's commitment to founders and investment strategy
(9:12) Strategies for competing in a changing venture landscape
(10:00) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at http://www.Squarespace.com/TWIST
(15:50) Valuations, ownership, and building deep relationships with founders
(18:30) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist
(19:39) The critical role of governance and accountability in startups
(28:36) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist
(30:16) The power of incremental improvements and executive limitations
(34:32) Vanity metrics vs. building enduring value in startups
(43:12) The consequences of choosing status over results in startup success
(46:22) Building trust in leadership and the pressures of maintaining success
(49:03) The importance of non-consensus bets and independent thinking
(55:20) The relationship between hype, investment decisions, and startup promotion
(58:19) In-person work vs. remote work: Impact on startup productivity
(1:02:58) SaaS market challenges: Pricing, AI impact, and future models
(1:07:33) Exciting AI investments and the transformative potential of new technologies
(1:13:01) AI advancements, new use cases, and the competitive landscape
(1:17:16) How incumbents and consumers are benefiting from AI advancements
(1:19:15) Embracing AI in daily tasks and business operations
*
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Check out the TWIST500: twist500.com
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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Check out Benchmark: https://www.benchmark.com/
*
Follow Sarah:
X: https://x.com/sarahtavel
LinkedIn: https://www.linkedin.com/in/sarahtavel/
Sarah’s Substack: https://www.sarahtavel.com/
*
Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
*
Thank you to our partners:
(10:00) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at http://www.Squarespace.com/TWIST
(18:30) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist
(28:36) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist
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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
Investing in AI for Hard Tech, with Eric Vishria of Benchmark and Sergiy Nesterenko of Quilter
Dive into the world of AI investments with Eric Vishria of Benchmark and Sergiy Nesterenko of Quilter. Explore the future of AI in hardware design, the strategies for venture capital investment in the AI era, and the impact on society. Discover why Benchmark has yet to invest in foundation model companies and the significance of solving enduring problems in this dynamic field. Join us for an eye-opening discussion on the intersection of AI technology and business innovation.
🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj
SPONSORS:
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Recommended Podcast - The Riff with Byrne Hobart
Byrne Hobart, the writer of The Diff, is revered in Silicon Valley. You can get an hour with him each week. See for yourself how his thinking can upgrade yours.
Spotify: https://open.spotify.com/show/6rANlV54GCARLgMOtpkzKt
Apple: https://podcasts.apple.com/us/podcast/the-riff-with-byrne-hobart-and-erik-torenberg/id1716646486
CHAPTERS:
(00:00:00) Introduction
(00:10:12) The Idea Maze
(00:12:28) Disruptive Approach
(00:15:47) Sparse reward problem
(00:18:26) Sponsors: Oracle | Brave
(00:20:34) Reliability of the reward signal
(00:28:12) Model size and compute
(00:30:14) Simulation methods
(00:35:48) Superhuman circuit board design
(00:38:53) Sponsors: Squad | Omneky
(00:40:38) What does the future of circuit board design look like?
(00:43:11) How do I make money in AI?
(00:46:18) What is cutting edge?
(00:48:34) Researchers vs. engineers
(00:50:51) Call for startups
20VC: Benchmark's Sarah Tavel on Are Foundation Models Commoditising | Why Frontier Models Will Be Closed Source | Why the Value is in the Application Layer | The Future of AI is "Selling the Work" Not the Tools
Sarah Tavel is a General Partner @ Benchmark, one of the most successful and renowned venture firms in the world. At Benchmark, Sarah has led rounds in Chainalysis, Hipcamp, Medely, Rekki, Glide, Cambly and more. Prior to Benchmark, Sarah was a Partner at Greylock Partners. Before Greylock, Sarah was the first 30 employees at Pinterest. Sarah joined Pinterest in 2012 after co-leading the Series A investment while at Bessemer Venture Partners.
In Today's Episode with Sarah Tavel We Discuss:
1. Becoming a GP at The Most Renowned Firm in Venture:
How did the process of Sarah joining Benchmark start? How did it progress? What was it that convinced her to leave Greylock and join Benchmark?
What does Sarah believe makes Peter Fenton the world-class investor that he is?
What does Sarah know now that she wishes she had known when she started in venture?
2. Foundation Models: Is it All Going to Zero:
Will foundation models be commoditised?
Will 99% of the funding going to foundation models go to 0?
How does Sarah view the future of open vs closed source?
Why does Sarah believe that all frontier models of the future will be closed-source?
Why does the business model of foundation models remind Sarah of the food delivery business?
3. Application Layer: Where $BN Companies Will Be Built:
Why does Sarah believe that sustainable value-creating companies will be in the application layer?
How does Sarah determine between a wrapper on top of ChatGPT and true product value?
Are enterprises opening real budgets for AI today or are we still in experimental budgets?
How does Sarah think about how AI companies differentiate when there are so many in the same space of customer service, sales team support etc etc?
Why does Sarah believe that it is rational to pay more for these companies when investing in them?
What does Sarah mean when she says the future is "selling the work and not the tools"?
4. Inside Benchmark: How the Best Do Venture:
What is the one rule that Benchmark is willing to break when doing a deal?
Why do Benchmark aim to be the best recruitment firm in the world?
Why do Benchmark not agree with the concept of reserves?
In a case where Benchmark have lost, why did they lose? How did they change their approach?
Bill Gurley & Michael Mauboussin - Putting Theory into Practice - [Invest Like the Best, EP.370]
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.
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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.
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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
EP 90: Eric Vishria (General Partner, Benchmark Capital) Behind The Scenes of Benchmark’s Boldest Bets
Eric Vishria and I both got into venture in 2014 and both focus on enterprise software. In episode 90, we discuss Eric’s unique approach to investments and what he looks for in founders and companies.
We go back and forth on his model versus mine, as well as Eric's background, having grown up in Memphis and graduating from Stanford at 19 years old before joining LoudCloud, which became Opsware with Ben Horowitz and Marc Andreessen.
(0:00) Intro
(1:20) The role of venture capitalists
(5:52) Characteristics of Successful Entrepreneurs
(12:00) commonalities in investments that you haven't done
(14:05) The best CEOs
(17:40) The Impact of Artificial Intelligence on Business
(21:16) The role of market trends in investment decisions
(27:46) Reflecting on investment successes
(39:41) Benefits as an investor vs board member
(42:17) From Memphis to Stanford
(44:29) The early days at LoudCloud
(46:49) The Aspiration to be a Great CEO
(49:33) The Journey to Joining Benchmark
(53:20) Bringing new people to Benchmark
(1:01:26) The Evolution of Early Stage Investing
(1:14:07) What career advice would you give?
(1:19:56) The value of Benchmark’s Dinners
Produced: Rashad Assir & Leah Clapper
Mixed and edited: Justin Hrabovsky
Executive Producer: Josh Machiz
🎙 Listen to the show
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.
Executive Producer: Rashad Assir
Producer: Leah Clapper
Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.
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Dara Khosrowshahi, Bill Gurley, Brad Gerstner, & Jason Calacanis on Uber's growth and future | E1878
This Week in Startups is brought to you by…
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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
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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
Bill Gurley, Brad Gerstner, & Jason Calacanis on the state of tech markets, hosted by David Weisburd | E1875
This Week in Startups is brought to you by…
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*
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
The hierarchy of engagement | Sarah Tavel (Benchmark, Greylock, Pinterest)
Sarah Tavel is a General Partner at Benchmark and sits on the boards of Chainalysis, Hipcamp, Rekki, Cambly, and Medely. She is a founding member of All Raise, the nonprofit organization working to accelerate the success of women in the venture-capital and VC-backed startup ecosystem. Before Benchmark, Sarah was a partner at Greylock Partners. She joined Pinterest in 2012 as their first PM and launched their first search and recommendations features. She also led three acquisitions as she helped the company scale through a period of hypergrowth. In this episode, we discuss:
Sarah’s Hierarchy of Engagement framework for growing a consumer startup
• The three levels of the Hierarchy of Engagement: core action, retention, and self-perpetuation
• The importance of measuring cohorts and maintaining focus on the core action
• Examples of core user actions from Pinterest and YouTube
Sarah’s Hierarchy of Marketplaces framework for building a marketplace startup
• The three vectors of growth for dominating a marketplace
• Advice on “tipping the marketplace” and ultimately dominating the market
• The value of focusing on a constrained market
• How to avoid disruption
—
This entire episode is brought to you by Gelt—Redefine your approach to taxes.
—
Find the full transcript at: https://www.lennysnewsletter.com/p/the-hierarchy-of-engagement-sarah
—
Where to find Sarah Tavel:
• X: https://twitter.com/sarahtavel
• LinkedIn: https://www.linkedin.com/in/sarahtavel/
• Substack: https://www.sarahtavel.com/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Sarah’s background
(03:33) Framework 1: The Hierarchy of Engagement
(06:03) Level 1: Core action
(10:33) Level 2: Retention
(14:00) Level 3: Self-perpetuation
(19:32) The importance of focus
(23:54) The challenge of anonymity
(26:04) Advice for founders who want to increase retention
(29:34) What founders often get wrong
(31:43) Examples of core actions
(37:37) Finding your North Star Metric
(38:12) Who should use the Hierarchy of Engagement framework
(38:54) The Hierarchy of Marketplaces framework
(46:09) Level 1: Focus on a constrained opportunity
(50:19) Sarah’s “happy GMV” and “minimum viable happiness” concepts
(54:47) Thumbtack: a counterexample to this approach
(56:36) Signs you’re ready to move to level 2
(58:06) Level 2: Tipping the marketplace
(01:04:15) Tipping loops
(01:10:53) Not all markets are susceptible to tipping
(01:15:55) The challenge of homogeneity in B2B marketplaces
(01:20:29) Signs you’re tipping successfully
(01:21:43) Level 3: Dominating the market
(01:28:29) The opportunity in underestimated markets
(01:30:11) The challenges of chasing GMV and losing focus
(01:36:36) Recognizing currents and momentum in the market
(01:39:20) You can never rest on your laurels
(01:41:03) How to apply these frameworks outside of marketplaces
(01:42:57) Three ways to find marketplace opportunity
(01:45:10 ) Lightning round
—
Referenced:
• Hierarchy of Engagement, Expanded: https://sarahtavel.medium.com/the-hierarchy-of-engagement-expanded-648329d60804
• Pinterest: https://www.pinterest.com/
• Evernote: https://evernote.com/
• Notion: https://www.notion.so/
• Houseparty app: https://en.wikipedia.org/wiki/Houseparty_(app)
• Clubhouse: https://www.clubhouse.com/
• How to price your product | Naomi Ionita (Menlo Ventures): https://www.lennyspodcast.com/how-to-price-your-product-naomi-ionita-menlo-ventures/
• TikTok: https://www.tiktok.com/
• Lessons on building a viral consumer app: The story of Saturn: https://www.lennysnewsletter.com/p/lessons-on-building-a-viral-consumer
• Saturn: https://www.joinsaturn.com/
• What happened to Secret?: https://www.failory.com/cemetery/secret
• How to determine your activation metric: https://www.lennysnewsletter.com/p/how-to-determine-your-activation
• Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/
• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/
• Engagement Hierarchy: Core Actions: https://sarahtavel.medium.com/engagement-hierarchy-core-actions-dd4f72042100
• Choosing Your North Star Metric: https://www.lennysnewsletter.com/p/choosing-your-north-star-metric
• Hierarchy of Marketplaces: https://sarahtavel.medium.com/the-hierarchy-of-marketplaces-introduction-and-level-1-983995aa218e
• Mike Williams on LinkedIn: https://www.linkedin.com/in/yoroomie/
• Everything Marketplaces: https://www.everythingmarketplaces.com/
• Fabrice Grinda on LinkedIn: https://www.linkedin.com/in/fabricegrinda/
• OLX: https://www.olx.com/
• DoorDash Loves the ’Burbs as Much as You Do: https://www.wsj.com/articles/doordash-loves-the-burbs-as-much-as-you-do-11605618001
• Thumbtack: https://www.thumbtack.com/
• NPS: https://en.wikipedia.org/wiki/Net_promoter_score
• Sean Ellis on LinkedIn: https://www.linkedin.com/in/seanellis/
• Rekki: https://rekki.com/
• Ronen Givon on LinkedIn: https://www.linkedin.com/in/ronen-givon-535b2514
• Hipcamp: https://www.hipcamp.com/
• Demand driving supply: The little-understood growth loop behind a surprising number of iconic billion-dollar companies: https://www.lennysnewsletter.com/p/demand-driving-supply-marketplaces
• Inside the Revolution at Etsy: https://www.nytimes.com/2017/11/25/business/etsy-josh-silverman.html
• Faire: https://www.faire.com/
• Bill Gurley on LinkedIn: https://www.linkedin.com/in/billgurley/
• Mechanical Turk: https://www.mturk.com/
• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/
• Rippling: https://www.rippling.com/
• “White Space” for Building a Marketplace: How to Find Your Competition’s Vulnerabilities—and Capitalize: https://sarahtavel.medium.com/white-space-for-building-a-marketplace-how-to-find-your-competitions-vulnerabilities-and-79674aa4d399
• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563935
• The Five Temptations of a CEO: https://www.amazon.com/Five-Temptations-CEO-Anniversary-Leadership/dp/0470267585
• The Five Dysfunctions of a Team: A Leadership Fable: https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756
• Tesla: https://www.tesla.com/
• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/
• What Is A Good Activation Rate: https://www.lennysnewsletter.com/p/what-is-a-good-activation-rate
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Bill Gurley and Sunny Madra talk open-source vs. proprietary AI | E1825
This Week in Startups is brought to you by…
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*
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
Benchmark's Sarah Tavel on the state of VC, AI's impact on startups & more! | E1813
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Banking services provided by Choice Financial Group and Evolve Bank &
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*
Today's show:
Benchmark's Sarah Tavel joins Jason to discuss the state of VC (1:57), her time at Benchmark (13:33), her recent Substack blogs (31:51), AI's impact on startups (44:31), and much more!
*
Time stamps:
(0:00) Benchmark's Sarah Tavel joins Jason
(1:57) The state of VC and the biggest things founders have had to contend with
(12:08) Miro - Sign up for a free account at https://miro.com/startups
(13:33) Benchmark's culture
(21:35) Evolving trends in VC
(24:37) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist
(25:45) Tradeoffs and common VC mistakes
(31:51) Sarah's Substack blogs and the inspiration behind her writing
(35:42) Mercury - Join 100K+ startups banking with Mercury at http://mercury.com
(36:54) Entrepreneurship in 2023 and the importance of a founder's long-term vision
(44:31) Technology catalysts and how AI is impacting startups
(58:36) Business models, the amount of developers needed, and navigating funding rounds
(1:04:42) The complexities of strategic partnerships and corporate VC
(1:14:54) M&A in the era of Lina Kahn and looking at the macro picture as an investor
*
Follow Sarah: https://twitter.com/sarahtavel
Check out Sarah's Substack: https://www.sarahtavel.com
*
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:
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YouTube: https://www.youtube.com/thisweekin
*
Subscribe to the Founder University Podcast: https://www.founder.university/podcast
E141: State of Series A's, VC dry powder, IPO window opens + more with Bill Gurley & Brad Gerstner
(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
#682: Bill Gurley Interviews Tim Ferriss — Reflecting on 20+ Years of Life and Business Experiments
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.
Andy Rachleff on SVB, how to evaluate VCs, market pull indicators, Wealthfront, and more | E1699
Wealthfront Chairman and Co-Founder Andy Rachleff joins Jason for an incredible interview! They start the show by discussing the SVB situation before breaking down different tech mini-crashes throughout Silicon Valley history (2:28). Then, they break down Wealthfront’s business and how to know if a business has market pull (40:49). They finish up the show by covering a range of topics, from AI to stock-based comp (1:13:45).
(0:00) Jason kicks off the show
(2:28) SVB situation
(9:26) The FDIC’s $250K limit
(13:27) MasterClass - Get 15% off an annual membership at https://masterclass.com/startups
(14:49) The bank run
(16:17) The SVB ecosystem
(22:20) Merge - Integrate up to 5 customers for free today at https://merge.dev/twist
(23:45) Cycle changes
(36:15) How to judge a VC
(39:27) Issuu - Get 50% off when you go to https://issuu.com/podcast and use promo code twist
(40:49) Wealthfront’s operation
(48:58) Reactions to the market
(55:00) Modern analysis and stock buybacks
(1:01:24 ) Caring about profitability
(1:02:06) Attaining market pull
(1:13:45) Andy’s thoughts on AI
(1:16:31) The makeup of a great entrepreneur
(1:18:50) Stock-based compensation
(1:25:06) How we avoided inflation
FOLLOW Andy: https://twitter.com/arachleff
FOLLOW Jason: https://linktr.ee/calacanis
#651: Legendary Investor Bill Gurley on Investing Rules, Finding Outliers, Insights from Jeff Bezos and Howard Marks, Must-Read Books, Creating True Competitive Advantages, Open-Source Strategies, Adapting Mental Models to New Realities, and More
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.
20VC: 13 of the Great Investing Minds on When to Pay Up vs When To Remain Disciplined and Walk Because the Price is too High: The Ultimate Guide to Price Sensitivity
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?
20VC: The Memo: Bill Gurley, Doug Leone, Keith Rabois; Investing Lessons from Prior Busts, How Their Investor Psychology Changed, What Can Be Applied To Today's Market
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?
E81: All-In Summit: Bill Gurley & Brad Gerstner on markets, downturns & investment cycles
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
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Bill Gurley and Philip Rosedale - Back to the Future - [Invest Like the Best, EP. 254]
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.
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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.
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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
20VC: Bill Gurley and Michael Eisenberg on The First Signs of an Impending Bust, What Happens with a Market Crash, How Do Public Markets Impact Private Valuations & The Biggest Lessons from 20 Years Investing in Venture
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