
Advertise on podcast: LaBossiere Podcast
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5from
This podcast has
59 episodes
Language
EnglishPublisher
Alex LaBossiereExplicit
No
Date created
2021/05/04
Latest episode
2026/08/24
Average duration
76 min.
Release period
73 days
Description
The New Narrative
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#59 - Haseeb Qureshi
2026/08/24
Haseeb Qureshi is the Managing Partner at Dragonfly, a crypto investment firm with roughly $4 billion under management. Dragonfly recently closed its fourth venture fund at $650 million.
Prior to Dragonfly, Haseeb was a General Partner at MetaStable Capital, the crypto fund co-founded by Naval Ravikant and later acquired by Dragonfly. Before venture, he was a software engineer at Airbnb and Earn.com, and before that a top-10 globally ranked professional poker player.
We spoke about digital dollars, nationalized banks, bubbles and speculation, Iran and BlackRock, jaywalking, and beanie babies.
0:00 – Intro
1:23 – What Happened to Crypto?
3:18 – Stablecoins and Escape Velocity
7:04 – Bitcoin, Gold, and the Generational Trade
10:34 – War and Stores of Value
15:06 – Retail, Nvidia, and Capital Flight
18:23 – Stablecoins 101
20:00 – Eurodollars, Venmo, and AI Agents
23:00 – Dollarization and the Black Market
25:28 – Banks, Airwaves, and the Balance of Power
31:20 – Too Many Currencies
36:11 – Institutions and Cypherpunks
40:08 – Iran and BlackRock
41:00 – Speculation and Bubbles
43:12 – Prediction Markets and the Overton Window
51:04 – Skin in the Game and the Rational Voter
54:06 – Staying in Crypto
57:13 – When Crypto VC Ends
58:57 – What Would Change Haseeb’s Mind on Crypto
1:03:00 – What Should More People Be Thinking About?
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#58 - Miles Grimshaw
2025/09/04
Miles Grimshaw is a Partner at Thrive Capital, an investment firm that builds and invests in internet, software, and technology-enabled companies. Thrive recently closed on $5BN in new funds and also announced Thrive Holdings, a permanent capital vehicle to invest in, acquire, and operate businesses for the long term with the strategic application of technology.
During his time at Thrive, Miles has led investments in companies like Airtable, Monzo, Benchling, Lattice, and more recently Cursor, a code editor built for programming with AI, which you’ll hear us chat about. That team raised a $900 million round at a $9.9B valuation in June.
Prior to Thrive, Miles was a General Partner at Benchmark, where he led seed investments, most notably in LangChain.
We spoke about trillion dollar companies, silicon valley as an idea, business genetics, practicing scales, and Swedish House Mafia.
0:00 - Intro
2:14 – “The Era of Doing”
6:15 – Startup Capital Intensity in the Age of AI
9:14 – The Rise of Trillion Dollar Outcomes
15:11 – Silicon Valley as an Idea
21:04 – Physics vs Biology-Style Investing
25:41 – Business Genetics and Compounding
33:04 – Dying of Indigestion and Going Multi-Product
35:55 – Co-Pilots, Command Centers, and Defensibility
40:07 – Investing Stage Agnostically
44:29 – When is VC a Good Capital Instrument?
49:18 – Thrive’s Core Beliefs
53:57 – A Bet vs a Commitment
57:49 – The Few Ideas Miles Takes Seriously
59:47 – Doing a Few Big Things vs a Million Little Things
1:03:54 – Practicing Scales
1:06:22 – What Should More People Be Thinking About?
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#57 - Kevin Hartz
2025/04/10
Kevin Hartz is Co-Founder and General Partner at A*, a venture capital firm specializing in early-stage investments. Before establishing A*, Kevin co-founded Eventbrite and guided the company as CEO for its first 11 years before it went public. His entrepreneurial journey also includes co-founding Xoom, a digital money transfer service that PayPal acquired in 2015 for over $1 billion. Kevin has established himself as a successful angel investor with seed investments in companies like PayPal, Airbnb, Pinterest, Ramp, Trulia, and Anduril. His investment portfolio also includes early stakes in prominent companies such as Uber, Palantir, SpaceX, Square, Gusto, and numerous others.
00:00 - Intro
04:25 - Kevin's North Star
06:27 - The Bottleneck to Entrepreneurship
09:20 - The Explosion of Capital in Private Technology Markets
11:52 - Monopolies and the Shift in Private Enterprise Value Distribution
15:18 - Do Public Markets Price Themselves In?16:37 - When Is VC a Suitable Capital Instrument?19:09 - Agglomeration and The Future of Venture Capital20:56 - Cost of Capital and Competing in Venture23:09 - Is Value-Add Real?25:33 - On IPOing
27:14 - Picking and Magnitude of Outcomes
28:41 - Founders and Investors as Personality Types
29:56 - Seed and Growth Investing as Distinct Skillsets
32:02 - Incubations
33:56 - Symptoms of Excess Capital35:55 - Can You Kingmake With Capital?
37:17 - When Does It Make Sense to Raise a Huge Round?
38:17 - Capital Efficiency39:39 - The Expansion of Technology Markets
41:51 - Capital Innovation in Venture
43:47 - The Endgame of Evaluation
44:33 - What Should More People Be Thinking About?
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#56 - Amjad Masad
2025/03/20
Amjad Masad is the co-founder and CEO of Replit, a programming environment for everyone that allows anyone to write and deploy code, regardless of experience. Replit has 34 million users globally and is one of the fastest-growing developer communities in the world.
Before Replit, Amjad was a tech lead on the JavaScript infrastructure team (which he helped start) at Facebook, where he contributed to popular open-source developer tools. Additionally, he played a key role as a founding engineer at the online coding school Codecademy.
0:00 - Intro4:31 - Utopia, Dystopia, and Life in a Post-AI World11:28 - Replit and Expressiveness in Computing17:01 - Balancing Accessibility and Control in Products19:53 - Is AI a Sustaining or Disruptive Technology?25:04 - Building With AI and the Future of Company Structure29:32 - The Shape and Defensibility of Software in a World of AI33:37 - The Nation State and Stagnation in the Physical World38:28 - Technology and Resilience41:54 - What Shouldn't Get Automated?43:54 - What Becomes Valuable in a Post-AI World?47:10 - AI Augmenting vs Competing with Humans51:51 - What Should More People Be Thinking About?
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#55 - Katherine Boyle
2025/03/06
Katherine Boyle is a General Partner at Andreessen Horowitz and cofounder of the firm’s American Dynamism practice, which invests in companies supporting the national interest across aerospace, defense, manufacturing, energy, logistics, and critical infrastructure. She sits on the boards of Apex Space and Hadrian Automation and is a board observer for Saronic Technologies and Castelion.
She was previously a partner at General Catalyst, where she co-led the firm’s seed practice and invested in the inception rounds of defense technology companies including Anduril Industries and Vannevar Labs. Prior to General Catalyst, she was a general assignment reporter at The Washington Post. Katherine holds a BA in Government from Georgetown University, an MBA from Stanford and a Masters of Public Advocacy from the National University of Ireland, Galway.
Katherine believes that free speech is essential to promoting American Dynamism. She is a proud champion of new media companies and academic centers that promote free speech and free thought. She serves on the boards of The Free Press and the Mercatus Center at George Mason University.
0:00 - Intro4:48 - The Decline in Public Service7:47 - Making Government Cool Again10:07 - Silicon Valley’s Aversion to National Security13:15 - Positive Sum vs Zero Sum Cultures16:27 - China, Authoritarianism, and Doing Hard Things19:27 - What Makes America Special?23:03 - Silicon Valley and the “Real Economy”26:28 - Investing in Mature Markets29:08 - Vanna White and The Wheel of Fortune30:27 - Journalism and Loneliness32:52 - Time and Suffering38:10 - Seriousness and Purpose41:11 - Is Culture Downstream of Technology?42:48 - Propaganda and Coolness as a Strategic Asset44:40 - Florida, Texas, and Regulatory Arbitrage47:51 - DC, Silicon Valley, and Florida50:20 - What Should More People Be Thinking About?
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#54 - Keith Rabois
2025/02/20
Keith Rabois is a Managing Partner at Khosla Ventures and the CEO of OpenStore, which acquires small direct-to-consumer businesses. Keith co-founded Opendoor and led the first institutional investments in DoorDash and Affirm. He has early stakes in YouTube, Palantir, Lyft, Airbnb, Eventbrite, and Wish, and also led investments in Faire, Ramp, Trade Republic, and Stripe. He’s regarded as one of the greatest early stage investors.
Keith began his career in the industry as a senior executive at PayPal and subsequently served in influential roles at LinkedIn and as chief operating officer of Square. As a board member, Keith guided Yelp and Xoom from inception to IPO, and served on the board of Reddit from 2012-2018.
0:00 - Intro1:56 - Great Founders and the Bottleneck to Innovation4:35 - Vertical Integration6:24 - The Hollywood Model of Startups7:41 - The “Why Now?” in Company-Building9:50 - Multi-Product Companies10:58 - Iteration and Pivots12:52 - Picking Co-Founders14:51 - Identifying Mispriced Talent17:20 - Attracting Talent20:57 - Assessing Talent24:02 - Doing References25:56 - Closing Hires28:28 - Thinking 6 Months Ahead31:36 - How Long Should You Interview For?33:28 - Creating a Monopoly on Talent35:44 - Raising Capital37:40 - Screening Investors41:21 - Building a Board44:11 - Triaging and Identifying Problems47:59 - Writing vs Editing and Consistent Voice49:34 - Creating Transparency50:50 - Barrels and Ammunition54:55 - Task-Relevant Maturity56:40 - On Delegating59:21 - Measuring Inputs vs Outputs1:02:58 - Underrated Metrics
1:05:22 - What Should More People Be Thinking About?
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#53 - Elad Gil
2024/08/08
Elad Gil is a serial entrepreneur, executive, and one of the greatest tech investors of all time, with early stakes in something like 40 billion-plus dollar companies: AirBnB, Anduril, Coinbase, Figma, Flexport, Instacart, Notion, OpenDoor, Pinterest, Square, Stripe… I could really go on. He’s now managing a new billion dollar venture fund, for which he’s the sole investor.
Elad is also the co-founder of 2 companies: Color Genomics, a company providing genetic testing, software and clinical services for large-scale health programs – and before that, Mixer Labs, a company building location infrastructure for mobile devices that was acquired by Twitter. He worked as a VP at Twitter and also started the mobile team at Google.
0:00 - Intro
6:11 - Blank Slates and Decaying Institutions
8:16 - Western Pessimism and Agendas of Abundance vs Scarcity
12:30 - The Long Boom: Is Innovation Speeding Up?
16:26 - Are Startups Founder Limited or Market Limited?
19:26 - EIR Syndrome and Choosing the Right Market
21:41 - What Makes for a Good Investor, Operator and Entrepreneur?
24:05 - Positives and Negatives of Investing and Operating
26:17 - The Brand Value of Individuals vs Institutions
28:05 - Competing with Massive Firms
30:33 - Market-Driven Investing
33:23 - Starting Companies as Surfing Waves
36:09 - Age of Accomplishment and The Deferral of Adulthood
42:15 - What to Say Yes To
44:21 - Defense Tech and Complacency
49:25 - Private Markets and The Future of Venture
52:11 - Discontinuities in AI
53:49 - On Google
55:16 - LLM Oligopoly and Long-Term Scenarios for AI
1:00:41 - AGI and Sleeping 3 Hours a Night
1:03:19 - AI Doomerism
1:06:05 - The Deterioration of Speed
1:09:27 - Bureaucracy and the State of Nuclear
1:12:52 - Generosity and the Culture of Silicon Valley
1:15:19 - What Should More People Be Thinking About?
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#52 - Erik Torenberg
2024/05/03
Erik Torenberg is a technology entrepreneur and investor.
Presently, he’s the founder of Turpentine. Previously, he was the chairman of On Deck, co-founder and general partner at Village Global, and first employee at Product Hunt.
0:00 - Intro
5:08 - On Investing vs Operating and Being a Player
7:34 - Trust and Direct Distribution
10:45 - Legacy Media and the Techlash
17:24 - What is Turpentine
18:41 - Lessons From 1000 Interviews
20:59 - The Printing Press, Barbells, and the Future of Media
25:22 - Pre-Internet Journalism and Survival of the Fittest Ideas
28:44 - Creator Monetization and Price Discrimination
34:55 - Does Media Have a Direction?
41:44 - Tailwinds and Turpentine at Scale
49:37 - Creating More Startups and Understanding Risk
54:24 - Is Entrepreneurship Founder or Market Limited?
59:04 - What Do Most People Get Wrong About Community Building?
1:01:34 - Probabilistic vs Deterministic Mindsets
1:04:29 - On Faith over Logic
1:08:06 - Modernity and God Shaped Holes
1:10:44 - The Hypocrisy of Elites
1:13:30 - Asking Erik Questions He Asks People
1:15:40 - What Should More People be Thinking About?
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#51 - Bryan Johnson
2024/03/21
Bryan Johnson is the world's most measured human. Johnson sold his company, Braintree Venmo, to PayPal for $800m in 2013. Through his Project Blueprint, Johnson has achieved metabolic health equal to the top 1.5% of 18 year olds, inflammation 66% lower than the average 10 year old, and reduced his speed of aging by the equivalent of 31 years.
Johnson freely shares his protocols and data publicly for everyone to use. Project Blueprint, is an endeavor to achieve humanity and earth scale cooperation starting within Self.
In 2023, Johnson launched Rejuvenation Olympics, a leaderboard assessing one's speed of aging using DNA methylation. Of the 1,750 people who have been using this state-of-the-art aging algorithm to track their progress longitudinally, Johnson ranks #1 in speed of age reduction.
Johnson is also the founder & CEO of Kernel, creator of the world’s first mainstream non-invasive neuroimaging system; and OS Fund, where he invested $100M in the predictable engineering of atoms, molecules, and organisms into companies now collectively valued over $6B. He is an outdoor adventure enthusiast, pilot, and author of children’s books, Code 7 and The Proto Project.
00:00 - Intro
3:45 - Biographies
5:03 - Zeroth Principles Thinking and Genius
6:24 - Vision for Blueprint: A 25th Century Perspective
7:50 - Blueprint, Entropy Reduction and Planet Earth
9:23 - Impact of Blueprint
10:47 - Gene Therapy and Breaking Through the Longevity Ceiling
12:06 - Living Longer and Compounding Gains
13:31 - Bryan’s Relationship With Time
14:07 - Measuring Biological vs Chronological Age
15:05 - Encouraging Adoption, Dashboards for Society and Learning How to Swim
17:49 - Enriching vs Degrading Life and the Inevitability of Computational Intelligence
21:03 - Living Forever
22:19 - Knee-Jerk Reactions
26:03 - Free Will
28:12 - Social Drivers and Early Adopters of Blueprint
30:08 - Future of Engineering Atoms, Molecules and Organisms
32:43 - Critical Questions from Longer Lifespans
33:58 - Kernel and the Future of Brain-Computer Interfaces
36:28 - Ketamine
37:47 - Storytelling, Quantifying Reality and the Extent of the Algorithm
40:03 - OS Fund, Foundational Technologies and Architecting Reality
43:38 - Trust and God Shaped Holes
46:55 - Wealth, Effectuating Change and Competing for Legacy
48:23 - What Else Would Bryan Work On?
49:25 - What Should More People be Thinking About?
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#50 - Anthony Pompliano
2024/01/30
Anthony “Pomp” Pompliano is an entrepreneur and technology investor. He runs his family office which makes private investments, along with owning majority stakes in a number of operating businesses.
Additionally, Pomp hosts popular conversations on “The Pomp Podcast,” which has been downloaded more than 50 million times. Pomp also writes a letter that is read by more than 250,000 investors each morning.
Pomp’s interests lie at the intersection of finance, technology, entrepreneurship, and economics, which he tweets about extensively to his more than 1.6 million followers.
0:00 - Intro
3:11 - Incumbents and Competition in the Age of AI
5:12 - Media’s Relationship with Technology
9:48 - Individuals vs Institutions and the Future of Content
11:46 - Consensus, Truth, and Misinformation
15:47 - How to Cut Through the Noise
18:47 - The Decline of Trust in Institutions
24:10 - Balancing Optimism and Cynicism
26:46 - National Debt
33:22 - Bad Legislation, Bad Politicians, and Bad Incentives
37:54 - Growing Our Way Out of the Problem
42:19 - Autonomous Cars, Pig Heart Transplants, and How Innovation Propagates Itself
49:22 - Legislating Technology
55:04 - Increasing the Number of Entrepreneurs in Society
1:03:08 - When Better Technology Doesn’t Mean Better Outcomes
1:05:24 - Talent Allocation
1:10:56 - What Does Pomp Do Every Day?
1:19:52 - Lessons From 1300 Interviews
1:21:56 - On Fame, Audience, and Parasocial Relationships
1:29:23 - The State of Crypto
1:34:14 - Institutional Adoption of Crypto
1:37:20 - Is Slow-Moving Bureaucracy a Bug or a Feature?
1:42:02 - Remote Work and Regulatory Arbitrage
1:46:22 - Promising Cities and the Internet as an Equalizer
1:50:03 - Lessons From War
1:58:07 - What Should More People Be Thinking About?
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#49 - Bryan Caplan
2024/01/09
Bryan Caplan is a Professor of Economics at George Mason University and a New York Times Bestselling author.
He’s the author of 8 books, including The Myth of the Rational Voter, The Case Against Education, and Open Borders: The Science and Ethics of Immigration. His next book, Build, Baby, Build: The Science and Ethics of Housing, will be published by the Cato Institute in 2024.
He’s the editor and chief writer for Bet On It, the blog hosted by the Salem Center for Policy at the University of Texas. He’s published in the New York Times, Washington Post, Wall Street Journal, TIME, Newsweek, Atlantic, American Economic Review, Economic Journal, Journal of Law and Economics, and Intelligence, blogged for EconLog from 2005-2022, and appeared on ABC, BBC, Fox News, MSNBC, and C-SPAN.
0:00 - Intro
2:23 - The Most Irrational Beliefs in Society
3:43 - Why Do People Vote?
5:57 - The Most Net Positive Delusions in Society
7:30 - Bottlenecks in Democracy
9:13 - Idea Traps
13:13 - The Ideological Turing Test
15:16 - Caricatures of Political Parties
17:49 - The Case for Open Borders
21:48 - Tribalism and Social Cohesion
25:33 - Privatization and The Confluence of Cultures
26:56 - What’s the Point of Countries?
28:26 - What Values Are (Mostly) Non-negotiable?
30:27 - The Net Present Value of Immigration
33:43 - The Competition of Cultures
38:15 - Is Globalism Inevitable?
39:30 - Resources and Culture
42:49 - How to Fix Immigration
45:07 - The Case Against Education
48:48 - What is a Degree Actually Worth?
52:05 - Why is Bryan a Professor?
53:13 - The Value of Conformity in Society
55:25 - Is Learning How to Learn Real?
57:51 - Is There Value in the Liberal Arts?
29:27 - Bryan’s Approach to Learning
1:01:49 - Who Does Education Well?
1:02:49 - The Biggest Problems in Academia
1:05:47 - Should we Abolish Tenure?
1:09:32 - Why Parenting is Overrated
1:11:51 - What Kind of Parenting Has an Effect?
1:14:23 - Positive Effects of Having Kids
1:16:03 - The Science and Ethics of Housing Regulation
1:18:50 - Intangible Costs of Deregulation
1:21:39 - How does Ideology Propagate Itself?
1:24:09 - If Everything’s Mimetic are Free Markets Overrated?
1:25:54 - How to Get Ideas Into the Mainstream
1:28:19 - Are Politicians Evil?
1:31:35 - The Future of Labor Markets Under Remote Work
1:34:21 - What Should More People Be Thinking About?
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#48 - Delian Asparouhov
2023/12/12
Delian Asparouhov is the co-founder, President and Chairman of Varda Space Industries, a company building spacecraft to manufacture materials in microgravity that are difficult or impossible to produce on Earth— starting with pharmaceuticals. He’s also a Partner at Founders Fund.
Previously, he was a principal at Khosla Ventures, head of growth at Teespring, and founder of a healthcare company called Nightingale. Delian is Bulgarian, attended MIT, and likes to ski and play soccer.
0:00 - Intro
3:14 - How Does Innovation Happen?
6:23 - Varda and the No Science Allowed Rule
7:52 - A Primer on Solid State Microgravity Manufacturing
18:25 - Space Industrialization, Trading Posts, and the Chinese and Portuguese Navies
21:13 - Economic Incentives and Future Business Models in Space
24:24 - SpaceX and The Costs of Mass to Orbit
27:45 - Demand for Space Manufacturing and Varda at Scale
33:44 - Manufacturing, Servicing, Machining, and Future Markets for Space
36:42 - Incubating Companies
40:33 - When Would Varda Have Been Started Otherwise?
42:19 - The Hollywood Model of Startups
45:20 - Future of Incubations
47:47 - Media’s Role in Technology
50:39 - What Media Inspired Varda’s Founding?
52:38 - Talent, Culture, and Cementing Company Trajectory
53:57 - Narratives and Talent Recruitment
55:28 - Traits Delian Looks for in Founders
57:38 - The ‘Why Now’ When Investing
1:00:08 - Bring Non-Consensus and Right
1:02:53 - Is Varda Consensus Yet?
1:03:24 - Identifying Non-Consensus Opportunities
1:05:12 - Lessons from Founding and Investing
1:07:40 - What Skill Do You Wish You’d Developed Earlier?
1:10:11 - Immigrant Mentality
1:11:24 - Less Obvious Reasons for Success
1:12:55 - On Speed
1:14:23 - What Should More People Be Thinking About?
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#47 - Robin Hanson
2023/11/30
Robin Hanson is a professor at George Mason University and researcher at the Future of Humanity Institute at Oxford.
0:00 - Intro
2:42 - Intelligent Life in the Universe
7:30 - Grabby Aliens: A Primer
15:29 - Elites and the End of Global Coordination
18:59 - 6 Hard Steps for the Emergence of Life
22:11 - The Probability of Aliens
33:05 - Domesticating Humans
38:08 - Signaling and the Elephant in the Brain
42:31 - Conscious and Subconscious Behavior
46:53 - Collective Signaling
49:54 - The Contrarian Economics of Medicine and Lifespan
57:00 - Taste
1:01:18 - Hyper-Rationality and Social Cohesion
1:07:03 - How to Predict the Future
1:12:11 - Brain Emulations
1:21:15 - Artificial General Intelligence
1:27:52 - The Descendants of Humans
1:32:49 - Changing Attitudes Toward Life and Death
1:37:33 - The Future of Inequality
1:42:10 - God and The Sacred
1:57:42 - The Most Surprising Thing Robin’s Learned Recently
1:59:57 - What Should More People be Thinking About?
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#46 - Chris Mason
2023/11/22
Chris Mason is a professor of Genomics, Physiology, and Biophysics at Weill Cornell Medicine. He is also one of the founding Directors of the WorldQuant Initiative for Quantitative Prediction.
He is the author of The Next 500 Years: Engineering Life to Reach New Worlds, and the co-author of The Age of Prediction: Algorithms, AI, and the Shifting Shadows of Risk.
0:00 - Intro
2:29 - How Long Will Humanity Last?
9:01 - On Societal Pessimism and Long-Term Thinking
13:02 - Aliens!
17:36 - The NASA Twins Study
23:17 - Nature vs Nurture
25:56 - Chris’ Dream Experiments
27:45 - Genomics: Ethics, Opportunities, and the Future
37:38 - Space Race 2.0: Colonization, Regulation and Planetary Liberty
40:36 - Colonizing Mars and Achieving Planetary Liberty
45:46 - The Extreme Microbiome Project
47:14 - The Earth Similarity Index, Generation Ships and Leaving the Solar System
53:10 - Why Do Any of This in The First Place?
56:19 - The Age of Prediction
1:01:19 - On Chris, Science, Academia, and Big Questions
1:08:47 - Synthetic Biology, Cyborgs and the Future of Human Life
1:10:10 - Chris’ Biggest Goal
1:11:06 - What Should More People Be Thinking About?
🎙️More Episodes🎙️
YouTube: https://bit.ly/3QDLQFt
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📲Socials📲
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#45 - Keith Rabois
2023/11/15
Keith Rabois is a General Partner at Founders Fund and the CEO of OpenStore, which acquires small direct-to-consumer businesses. Keith co-founded Opendoor and led the first institutional investments in DoorDash and Affirm. He has early stakes in YouTube, Palantir, Lyft, Airbnb, Eventbrite, and Wish, and also led investments in Faire, Ramp, Trade Republic, and Stripe. He’s regarded as one of the greatest early stage investors.
Keith began his career in the industry as a senior executive at PayPal and subsequently served in influential roles at LinkedIn and as chief operating officer of Square. As a board member, Keith guided Yelp and Xoom from inception to IPO, and served on the board of Reddit from 2012-2018.
0:00 - Intro
2:35 - Bomb-Building and the PayPal Mafia
5:10 - Spotting Talent
11:32 - Where Keith is 1000:1
16:14 - PayPal, Regulation, and Law
22:00 - Regulatory Arbitrage
25:03 - AI
27:46 - Keith’s 5 Bosses
31:04 - How to Operate
34:16 - OpenStore
39:33 - Founding vs Investing
42:48 - Requests for Startups
47:39 - Early-Stage Investing
53:46 - Companies as Cults
56:42 - The Future of Venture
1:00:56 - Not Stretching, Engineering Serendipity, and How to Ask Better Questions
1:06:40 - On Keith
1:08:45 - Time Allocation, Self-Grading, Values, Reading and Legacy
1:16:11 - What Should More People be Thinking About?
🎙️More Episodes🎙️
YouTube: https://bit.ly/3QDLQFt
Apple: https://apple.co/478Be6M
Spotify: https://spoti.fi/3sfiFiE
Podcast reviews
Read LaBossiere Podcast podcast reviews
blogofjake.com 2021/11/10
Excellent podcast with interesting people
Alex gets great guests and is a skilled and natural interviewer. His preparation is evident and makes for conversations that are engaging, educational...
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