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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Intro Music Credit:
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Intro Video Credit:
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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
—
Links:
• Runnin’ Down a Dream- https://www.amazon.com/Runnin-Down-Dream-Thrive-Actually/dp/0593799666
—
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• Shaan's weekly email - https://www.shaanpuri.com
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• 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/
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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.
Thanks you to Numeral and Flex for supporting this episode.
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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
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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.
This episode is brought to you by:
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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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Is Strategy's Model Unraveling? What is Driving the Recent Rout and Where It Can Go From Here - Ep. 971
Michael Saylor's Strategy has not had the year it hoped for. Amid an explosion of copycats and Bitcoin price weakness, the company has seen its valuation and so-called mNAV crash.
In this special episode of Unchained, Praxos co-founder Vinny Lingham and The Benchmark Company Analyst Mark Palmer join Unchained Executive Editor Steve Ehrlich to debate Strategy's outlook.
They discuss the impact of new preferred stocks on common shareholders, the company's new cash reserve and the potential impacts of MSCI exclusion.
They also delve into what the Bitcoin digital asset treasury ecosystem could look like in the future and whether Strategy could have employed a better acquisition model.
Thank you to our sponsors!
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Host:
Steve Ehrlich, Executive Editor at Unchained
Guests:
Vinny Lingham, Co-founder of Praxos Capital
Mark Palmer, Senior Equity Research Analyst at The Benchmark Company
Links:
Unchained:
Bits + Bips: Vanguard’s Crypto U-Turn, Tether/MSTR FUD & Picking Future Winners
Bits + Bips: Why the Markets Now Have a Bullish Setup
Senate Committee Shares Bipartisan Draft on Crypto Market Structure Bill
Timestamps:
🚀 00:00 Introduction
📈 2:14 Why Mark still expects Strategy to outperform
📉 5:28 Why Vinny says Strategy preferred stocks are “vampiric”
🤔 11:45 Is Strategy's cash reserve a little too late?
👀 17:11 Debating Strategy's preferreds v. common stock
💡 19:44 How preferreds and CLARITY Act could enable Strategy to start buying Bitcoin dips as well
🫠 24:26 What happens if MSCI delists Strategy
🧠 30:34 The implications of Strategy's recent talk of selling and lending Bitcoin
⚠️ 36:25 Why it might be too late when Strategy decides to sell
🔮 39:28 How the Bitcoin DAT ecosystem could evolve as companies differentiate
🤔 44:17 Could Strategy have employed a better Bitcoin acquisition strategy?
💫 45:30 Closing thoughts on Strategy's future
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20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid
Ev Randle is a General Partner @ Benchmark, one of the best funds in venture capital. In their latest fund, they have Mercor ($10BN valuation), Sierra ($10BN valuation), Firework ($4BN valuation), Legora ($2Bn valuation) and Langchain ($1.4Bn valuation). To put this in multiples on invested capital, that is a 60x, two 30x and two 20x. Before Benchmark, Ev was a Partner @ Kleiner Perkins and before Kleiner, Ev was an investor at Founders Fund and Bond.
AGENDA:
05:25 Biggest Investing Lessons from Peter Thiel, Mary Meeker and Mamoon Hamid
14:36 OpenAI Will Be a $TRN Company & OpenAI or Anthropic: Who Wins Coding?
22:27 Why We Should Not Focus on Margin But Gross Dollar Per Customer
30:25 Why AI Labs are the Biggest Threat to AI App Companies
44:26 Do Benchmark Fire Founders? If so… Truly the Best Partner?
54:38 People, Product, Market: Rank 1-3 and Why?
57:36 Why the Mega Funds Have Just Replaced Tiger
01:04:08 GC, Lightspeed and a16z Cannot Do 5x on Their Funds…
01:14:09 Single Biggest Threat to Benchmark
First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege
Jason Droege is the CEO of Scale AI, a company that provides foundational training data to every major AI lab. He previously co-founded Scour with Travis Kalanick and built Uber Eats from idea to $20 billion in revenue. In this conversation, Jason shares lessons from getting sued for $250 billion, discovering restaurant economics by weighing sandwich ingredients, and over 25 years of launching transformative technology businesses.
What you’ll learn:
What actually happened with Meta’s $14 billion investment in Scale AI
Why AI models still need human experts to improve, and how that relationship is evolving
How AI models learn from experts building websites and debugging code
The business lessons from building Uber Eats from zero to $20 billion
Why most enterprise data is useless for AI models today
Why urgent daily problems beat super-valuable occasional problems when building products
How to think independently when building new products and businesses
—
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—
Transcript: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174979621/my-biggest-takeaways-from-this-conversation
—
Where to find Jason Droege:
• X: https://x.com/jdroege
• LinkedIn: https://www.linkedin.com/in/jasondroege/
—
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) Introduction to Jason Droege
(06:01) Jason’s early career and lessons learned
(10:27) The current state of Scale AI
(12:37) The shift to expert data labeling
(17:02) Challenges and strategies in finding experts
(18:48) Reinforcement learning and AI environments
(28:18) The future of AI and human involvement
(31:21) The role of evals
(35:25) What AI models will look like in the next few years
(41:43) Building Uber Eats and understanding customer needs
(48:19) The importance of independent thinking
(50:45) Setting high standards for new businesses
(53:03) Exploring and selecting business ideas
(57:07) The McDonald’s story
(01:00:13) The role of gross margins in business feasibility
(01:04:49) Why Jason says, “Not losing is a precursor to winning”
(01:09:12) Hiring and building teams
(01:12:11) AI corner
(01:14:47) Lightning round and final thoughts
—
Referenced:
• Travis Kalanick on X: https://x.com/travisk
• Scour: https://en.wikipedia.org/wiki/Scour_Inc.
• Scale: https://scale.com/
• Alexandr Wang on X: https://x.com/alexandr_wang
• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody
• Brendan Foody’s post on X about knowledge work changing: https://x.com/BrendanFoody/status/1970163503702188048
• MIT Finds 95% of GenAI Pilots Fail Because Companies Avoid Friction: https://www.forbes.com/sites/jasonsnyder/2025/08/26/mit-finds-95-of-genai-pilots-fail-because-companies-avoid-friction/
• Uber Eats: https://www.ubereats.com/
• Stephen Chau on X: https://x.com/thestephenchau
• a16z Podcast: https://a16z.com/podcasts/a16z-podcast/
• F1: The Movie: https://www.imdb.com/title/tt16311594/
• V03: https://v03ai.com/
• Careers at Scale: https://scale.com/careers
—
Recommended books:
• The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152
• The Road Less Traveled: A New Psychology of Love, Traditional Values, and Spiritual Growth: https://www.amazon.com/Road-Less-Traveled-Timeless-Traditional/dp/0743243153/
• Good to Great: Why Some Companies Make the Leap . . . And Others Don’t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996
• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/
—
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.
To hear more, visit www.lennysnewsletter.com
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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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.
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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:
Bolt: Help them break a world record for the largest hackathon - up to $1m in prizes. Sign-up here.
Numeral: The end-to-end platform for sales tax and compliance. Try it here.
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
Subscribe to my newsletter to get every episode + the transcript in your inbox every week
Why Twenty One Capital Is More About Volatility Than Bitcoin - Ep. 826
The race for Bitcoin supremacy just got more complicated.
Twenty One Capital, backed by Tether, SoftBank, and Cantor Fitzgerald, plans to stack as much BTC as it possibly can.
But is this new venture really about Bitcoin … or about creating a hyper-volatile stock to play market cycles?
This week on Unchained, Jeff Park of Bitwise and Mark Palmer of Benchmark join to discuss:
Why SoftBank and Tether are a “perfect match”—and why they turned to Bitcoin
How volatility, not bitcoin itself, might be the real asset investors are buying
What Cantor’s involvement says about Wall Street’s readiness for crypto
Why the launch timing matters
Whether Twenty One could repeat MicroStrategy’s mistakes
Whether these new Bitcoin vehicles are better bets than spot bitcoin or ETFs
Plus, is SoftBank getting into crypto a top signal? 👀
Visit our website for breaking news, analysis, op-eds, articles to learn about crypto, and much more: unchainedcrypto.com
Bitwise
Jeff Park, Head of Alpha Strategies at Bitwise
Mark Palmer, Senior Analyst at Benchmark
Recent coverage of Unchained on Twenty One: Twenty One Aims to Buy as Much Bitcoin as Possible. Can It Succeed?
Press Release: Tether, SoftBank Group, and Jack Mallers Launch Twenty One, a Bitcoin-native Company, Through a Business Combination With Cantor Equity Partners
Jeff Park’s post on X
Timestamps:
📰 0:00 Introduction
🚀 2:07 Why Jeff sees the Twenty One Capital launch as a huge development
🧠 6:09 How Twenty One might learn from MicroStrategy’s playbook
🏦 11:59 Risks of turning into the next Celsius, Voyager or Genesis
💸 18:52 Why Bitcoin needs income-generating activities to evolve
📊 21:17 How metrics like bitcoin per share bridge crypto and TradFi
🤝 30:16 Whether Tether’s participation makes sense
💍 34:18 Why Jeff thinks SoftBank and Tether are “a perfect match”
🚩 42:29 Is SoftBank entering crypto a top signal?
🏛️ 46:32 Why Cantor’s involvement shows Wall Street is serious
📈 50:24 Why bitcoin vehicle stocks trade at a premium
🗓️ 55:48 Why timing matters compared to MicroStrategy’s 2020 debut
🧮 1:00:06 How to decide between investing in vehicles, spot bitcoin, or ETFs
🌊 1:08:52 Whether SOL investment vehicles will have the same success as bitcoin ones
Learn more about your ad choices. Visit megaphone.fm/adchoices
20VC: Benchmark's Victor Lazarte on Why Portfolio Construction is BS| Why SaaS Spreadsheet Investing is Dead | Why China is a Stabilising Force for the US | Three Traits All the Best Founders Have & The Lie All Big Tech Companies Have Been Telling
Victor Lazarte is a General Partner @ Benchmark, one of the mot renowned venture firms in the world. At Benchmark, Victor has led deals into the likes of HeyGen and Mercor. As an angel, he was the first investor and board member of Brex, and as a Founder he scaled Wildlife Studios, bootstrapping into the largest gaming company in LatAm, with about 4 billion downloads.
In Today's Episode We Discuss:
04:10 Lessons Scaling Wildlife Studios to 4BN Downloads
04:49 Why Predicting the Future is Wrong When Starting a Company
07:11 Three Different Categories of Company in an AI World: Who Wins & Loses?
09:25 Why You Should Always Ask What a Founder Does in Their Free Time?
17:30 Two Traits That All the Best Founders Have?
23:17 Why If You Start a Company in SF You are 1,000x More Likely to be Successful?
35:30 Why Spreadsheet SaaS Investing is Dead
36:10 Why Replacing Humans is the Most Exciting Opportunity in AI
37:02 Why Knowledge Work Will Be Destroyed and What Happens Then?
37:30 Why China is a Stabilising Force for the US
38:59 China vs. US: The AI Race
42:33 Why All Students Today Should Study Computer Science
44:38 Why Portfolio Construction is BS
47:04 What Makes Peter Fenton One of the Best Ever
51:31 Why Duolingo Will Be One of the Most Valuable Companies in the World
01:00:17 Quick Fire Round: Insights and Predictions
Creativity vs Control: Where AI Fits in the Creative Toolbox
Being a creator in 2025 is tough—but building for creators is even harder. Perhaps no one understands this conundrum better than Scott Belsky. As the founder of Behance, a longtime executive at Adobe, and an advisor to companies like Pinterest and Atlassian, Scott has spent his career at the intersection of technology, design, and creativity.
In this speedrun episode, recorded live in San Francisco during the fourth iteration of our a16z Games Speedrun program, we dive into:
How AI can actually enable creators—and where its toolset should end
The evolution from the "prompt era" to the "controls era" of AI
Whether people really want bespoke, personalized experiences or simply crave familiarity
What happens when creative scarcity disappears and AI-generated content becomes ubiquitous
The future of creative tooling, from generative UI to AI-native interfaces
Plus, Scott shares insights from his time building Behance, leading product strategy at Adobe, and investing in the next generation of creative tools.
If you want to learn more about A16Z Games Speedrun, visit a16z.com/games/speedrun.
Stay Updated:
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Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.
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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 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. Ramp is the fastest growing FinTech company in history and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. It’s also notable that many best-in-class businesses use Ramp—companies like Airbnb, Anduril, and Shopify, as well as investors like Sequoia Capital and Vista Equity. They use Ramp to manage their spending, automate tedious financial processes, and reinvest saved dollars and hours into growth. At Colossus and Positive Sum, we use Ramp for exactly the same reason. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus.
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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
#210 CEO & Co-Founder Huntress Kyle Hanslovan w/ Ev Randle: Deep Roots
Guest: Kyle Hanslovan, CEO & co-founder of Huntress; and Ev Randle, partner at Kleiner Perkins
Talk is cheap, says Huntress CEO Kyle Hanslovan: “I learned real early on that integrity is like one of the very few things, if not the only thing, you can't buy.” En route to Huntress’ current status as a $1.5 billion firm with $100 million in ARR, he took a long time to hire new execs, or partner with VC firms.
Indeed, Kleiner Perkins partner Ev Randle recalls the deliberation Hanslovan underwent before signing KP’s term sheet. “It's pretty rare for a founder's diligence process on you to increase your conviction on them and the business that they're building,” he says. “You just saw that the effort extended across to so many different places and so many details that it's typically not.”
Chapters:
(01:03) - Learning how things work
(03:31) - Default trusting
(05:07) - Over-sharing
(10:50) - Kyle’s leadership style
(15:44) - Hiring for conflict
(19:24) - Scaling execs
(22:52) - Evaluating VCs
(28:55) - Pattern-matching
(32:13) - Why Huntress is worth $1.5 billion
(38:34) - Kyle’s childhood and early career
(42:00) - The 99 percent
(47:49) - Bootstrapping
(51:14) - Deep roots
(57:47) - Customer love
(01:01:14) - “Nothing will stop us”
(01:05:50) - Who Huntress is hiring
(01:07:22) - What “grit” means to Kyle
Mentioned in this episode: Sony, Sam Altman, Nike, Elad Gil and High Growth Handbook, Kim Scott and Radical Candor, JMI Equity, Vinod Khosla, Todd Park, Capterra, Reddit, FUBU, Rippling, the NSA, QuickBooks, Amazon AWS, and South Park.
Links:
Connect with Kyle
Twitter
LinkedIn
Connect with Ev
Twitter
LinkedIn
Connect with Joubin
Twitter
LinkedIn
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm
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?
AI Avatars & the Future of Video, with HeyGen CEO Joshua Xu and Benchmark's Victor Lazarte
Nathan explores the future of AI-generated video with Joshua Xu, founder of HeyGen, and Victor Lazarte from Benchmark. In this episode of The Cognitive Revolution, we discuss HeyGen's success in practical AI video creation, serving over 40,000 businesses. Learn about the transformative potential of AI in video production, from content translation to personalized experiences, and HeyGen's industry-leading approach to trust and safety.
Apply to join over 400 founders and execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj
RECOMMENDED PODCAST:
Second Opinion
A new podcast for health-tech insiders from Christina Farr of the Second Opinion newsletter. Join Christina Farr, Luba Greenwood, and Ash Zenooz every week as they challenge industry experts with tough questions about the best bets in health-tech.
Apple Podcasts: https://podcasts.apple.com/us/podcast/id1759267211
Spotify: https://open.spotify.com/show/0A8NwQE976s32zdBbZw6bv
-
🎙️ History 102 with WhatifAltHist
Every week, creator of WhatifAltHist Rudyard Lynch and Erik Torenberg cover a major topic in history in depth -- in under an hour. This season will cover classical Greece, early America, the Vikings, medieval Islam, ancient China, the fall of the Roman Empire, and more.
Subscribe on Spotify: https://open.spotify.com/show/36Kqo3BMMUBGTDo1IEYihm
Apple: https://podcasts.apple.com/us/podcast/history-102-with-whatifalthists-rudyard-lynch-and/id1730633913
YouTube: https://www.youtube.com/@History102-qg5oj
SPONSORS:
Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Join top startups like Vercel, Perplexity, Jasper & Webflow in powering your app with WorkOS. Enjoy a free tier for up to 1M users! Start now at https://bit.ly/WorkOS-TCR
Oracle Cloud Infrastructure (OCI) is a single platform for your infrastructure, database, application development, and AI needs. OCI has four to eight times the bandwidth of other clouds; offers one consistent price, and nobody does data better than Oracle. If you want to do more and spend less, take a free test drive of OCI at https://oracle.com/cognitive
The Brave search API can be used to assemble a data set to train your AI models and help with retrieval augmentation at the time of inference. All while remaining affordable with developer first pricing, integrating the Brave search API into your workflow translates to more ethical data sourcing and more human representative data sets. Try the Brave search API for free for up to 2000 queries per month at https://bit.ly/BraveTCR
Omneky is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/
Head to Squad to access global engineering without the headache and at a fraction of the cost: head to https://choosesquad.com/ and mention “Turpentine” to skip the waitlist.
CHAPTERS:
(00:00:00) About the Show
(00:00:22) Sponsor: WorkOS
(00:01:22) About the Episode
(00:05:25) Introduction
(00:06:15) Joshua's Background
(00:09:47) Video Consumption Trends
(00:10:49) Creating with HeyGen
(00:12:46) Localization Benefits
(00:14:02) Cost of Localization (Part 1)
(00:16:19) Sponsors: Oracle | Brave
(00:18:24) Content Creation
(00:26:33) Engagement vs. Realism
(00:31:44) Future of Content
(00:37:43) Personalization Challenges
(00:42:57) Future of HeyGen
(00:49:13) Creator Experience
(00:59:35) Celebrity Restrictions
(01:03:03) Outro
---
SOCIAL LINKS:
Website : https://www.cognitiverevolution.ai
Youtube : https://www.youtube.com/@CognitiveRevolutionPodcast
Apple : https://podcasts.apple.com/de/podcast/the-cognitive-revolution-ai-builders-researchers-and/id1669813431
Spotify : https://open.spotify.com/show/6yHyok3M3BjqzR0VB5MSyk
Building Enduring Value and Hitting Incremental Gains with Benchmark’s Sarah Tavel | E1983
This Week in Startups is brought to you by…
Squarespace. Turn your idea into a new website! Go to http://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.
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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!
*
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
*
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/
Check out the TWIST500: twist500.com
*
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
*
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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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
*
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:
Oracle Cloud Infrastructure (OCI) is a single platform for your infrastructure, database, application development, and AI needs. OCI has four to eight times the bandwidth of other clouds; offers one consistent price, and nobody does data better than Oracle. If you want to do more and spend less, take a free test drive of OCI at https://oracle.com/cognitive
The Brave search API can be used to assemble a data set to train your AI models and help with retrieval augmentation at the time of inference. All while remaining affordable with developer first pricing, integrating the Brave search API into your workflow translates to more ethical data sourcing and more human representative data sets. Try the Brave search API for free for up to 2000 queries per month at https://bit.ly/BraveTCR
Head to Squad to access global engineering without the headache and at a fraction of the cost: head to https://choosesquad.com/ and mention “Turpentine” to skip the waitlist.
Omneky is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/
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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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
🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1
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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
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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
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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).
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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
Is Generative AI Killing Creativity Or Enhancing It? — With Scott Belsky
Scott Belsky is the chief strategy officer and executive vice president of design and emerging products at Adobe. He joins Big Technology Podcast to examine the impact of generative AI on creativity. In this interview, we discuss whether AI homogenizes creativity or creates more possibilities. We talk about how Adobe is baking it into its products with generative fill. We also discuss creative attribution for images used to train generative AI models and how friction is actually good. Tune in for one of the most fascinating discussions on the podcast in 2023.
Learn more about your ad choices. Visit megaphone.fm/adchoices
20VC Roundtable: Spotify, Adobe & Linkedin CPOs on How AI Changes The Future of Product, Why AI is Now the Product, How TikTok Changed Product, Why Cost is the Biggest Barrier to LLM Usage & Why Incumbents Can Adopt AI Faster Than Any Prior Innovation Cyc
Gustav Söderström is the Co-President, CPO & CTO at Spotify. Gustav has been instrumental in taking Spotify from a 30-person operation in Sweden when he joined to being the global leader of the space.
Scott Belsky is Adobe's Chief Product Officer and Executive Vice President, Creative Cloud. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe.
Tomer Cohen is the Chief Product Officer @ Linkedin where he is responsible for setting and executing the global product strategy at LinkedIn.
In Today's Episode on How AI Changes The Future of Product and Design We Discuss:
1. Why AI Is Now the Product that UI Serves:
Why does Gustav believe that AI is now the product?
How has the importance of UI changed with the rise of AI?
How did TikTok change the product paradigm over the last few years?
2. What Matters More Models or Data:
What is more important the size of the model or the amount of data a company has?
Will companies use many models at the same time?
Why will companies using many models at once create a huge opportunity for startups?
Will every company have their own model? What will be the decision-making framework of whether to have your own model or leverage another?
How does the rise of AI change how companies approach data acquisition, collection and cleaning?
3. The Workforce Needs to Change with AI:
How do product leaders and teams need to change in an AI-first world?
What do designers need to do to stay up to date in an AI-first world?
What does it mean to be good at prompting? How can people get good at prompting?
Why will AI kill companies that charge by the hour?
Why will seat pricing die in a world of AI? What will be the business model for AI?
4. Incumbents vs Startups: Who Wins:
Do incumbents win in a world of AI or do startups?
Why is AI primed for incumbents to win and move fast in a way they could not in prior technology cycles?
What are the biggest hurdles and challenges incumbents have to face that startups do not?
What are the biggest barriers that startups have to win in a world of AI that incumbents do not have?
Peter Fenton & Victor Lazarte - Purpose and Partnership - [Invest Like the Best, EP.354]
My guests this week are Peter Fenton and Victor Lazarte. Peter and Victor are both General Partners at Benchmark. Of the six equal partners at the storied venture firm, Peter is the longest serving and Victor is the newest, having spent the past decade founding and building Wildlife Studios into one of the biggest independent mobile gaming companies in the world.
Peter has been a board member at Wildlife for the past four years and has a remarkable track record of tech investing over his two decades at Benchmark. In our discussion, we talk about the core motivators behind great entrepreneurs, Benchmark's unique operating philosophy, and what it's like to transition from builder to investor. Please enjoy this conversation with Peter Fenton and Victor Lazarte.
Listen to Founders Podcast: #326 Anna Wintour
For the full show notes, transcript, and links to mentioned content, 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.
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
(00:04:10) - (First question) - Victor’s early expectations after being at the company for just three months
(00:05:39) - What Victor misses from the operating life
(00:06:59) - Peter’s opinion on what makes Benchmark a fascinating company
(00:15:00) - Peter and Victor’s perspective on the significance of the phrase “life’s work”
(00:24:19) - The influence of market tailwinds on success in investing
(00:29:42) - How to keep founders’ generative drive at peak levels
(00:32:39) - Balancing aggression, desire and generative drive when building and operating a business
(00:34:22) - Victor’s approach to dealing with pleasure seeking as a successful operator
(00:38:29) - Why Benchmark intentionally raises funds at half the suggested amount
(00:43:13) - Lessons learned from navigating challenging scenarios in venture capital
(00:46:27) - What excites Victor as he starts a new venture at Benchmark
(00:48:19) - Why AI is more akin to the internet than crypto
(00:52:41) - The significance of platform-based businesses in the contemporary landscape
(00:57:45) - The impact tech giants exert on new entrants in the industry
(00:61:00) - Victor’s opinion on what makes great games and great gaming businesses
(01:13:44) - Where Peter and Victor feel they have areas to grow
(01:19:48) - Perspectives on human progress
(01:21:14) - The kindest thing that anyone has done for both Peter and Victor