LABOSS PODCAST

Alex LaBossiere
  • 5.0 (6)
  • Business

LABOSS PODCAST

  1. 2d ago

    #59 - Haseeb Qureshi

    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? 🎙️More Episodes🎙️ YouTube: https://bit.ly/3QDLQFt Apple: https://apple.co/478Be6M Spotify: https://spoti.fi/3sfiFiE 📲Socials📲X: https://x.com/laboss Linkedin: https://www.linkedin.com/in/alexlabossiere/

  2. 09/04/2025

    #58 - Miles Grimshaw

    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? 🎙️More Episodes🎙️YouTube: https://bit.ly/3QDLQFtApple: https://apple.co/478Be6MSpotify: https://spoti.fi/3sfiFiE 📲Socials📲 Twitter: https://twitter.com/adlabossiere Linkedin: https://www.linkedin.com/in/alexlabossiere/

  3. 04/10/2025

    #57 - Kevin Hartz

    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? 🎙️More Episodes🎙️ YouTube: https://bit.ly/3QDLQFt Apple: https://apple.co/478Be6M Spotify: https://spoti.fi/3sfiFiE 📲Socials📲 Twitter: https://twitter.com/adlabossiere Linkedin: https://www.linkedin.com/in/alexlabossiere/

  4. 03/20/2025

    #56 - Amjad Masad

    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? 🎙️More Episodes🎙️YouTube: https://bit.ly/3QDLQFtApple: https://apple.co/478Be6MSpotify: https://spoti.fi/3sfiFiE 📲Socials📲 Twitter: https://twitter.com/adlabossiere Linkedin: https://www.linkedin.com/in/alexlabossiere/

  5. 03/06/2025

    #55 - Katherine Boyle

    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? 🎙️More Episodes🎙️YouTube: ⁠https://bit.ly/3QDLQFt⁠Apple: ⁠https://apple.co/478Be6M⁠Spotify: ⁠https://spoti.fi/3sfiFiE⁠ 📲Socials📲Twitter: ⁠https://x.com/adlabossiere⁠Linkedin: https://www.linkedin.com/in/alexlabossiere/

  6. 02/20/2025

    #54 - Keith Rabois

    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? 🎙️More Episodes🎙️ YouTube: https://bit.ly/3QDLQFt Apple: https://apple.co/478Be6M Spotify: https://spoti.fi/3sfiFiE 📲Socials📲 Twitter: https://twitter.com/adlabossiere Linkedin: https://www.linkedin.com/in/alexlabossiere/

  7. 08/08/2024

    #53 - Elad Gil

    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? 🎙️More Episodes🎙️ YouTube: https://bit.ly/3QDLQFt Apple: https://apple.co/478Be6M Spotify: https://spoti.fi/3sfiFiE 📲Socials📲 Twitter: https://x.com/adlabossiere Linkedin: https://www.linkedin.com/in/alexlabossiere/

  8. 05/03/2024

    #52 - Erik Torenberg

    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? 🎙️More Episodes🎙️ YouTube: https://bit.ly/3QDLQFt Apple: https://apple.co/478Be6M Spotify: https://spoti.fi/3sfiFiE 📲Socials📲 Twitter: https://twitter.com/adlabossiere Linkedin: https://www.linkedin.com/in/alexlabossiere/

See All (59)

Ratings & Reviews

5
out of 5
6 Ratings

About

LABOSS PODCAST

Information

  • Creator
    Alex LaBossiere
  • Years Active
    2021 - 2026
  • Episodes
    59
  • Rating
    Explicit
  • Copyright
    © Alex LaBossiere
  • Show Website
    LABOSS PODCAST

You Might Also Like