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 - Intro2:14 – “The Era of Doing”6:15 – Startup Capital Intensity in the Age of AI9:14 – The Rise of Trillion Dollar Outcomes15:11 – Silicon Valley as an Idea21:04 – Physics vs Biology-Style Investing25:41 – Business Genetics and Compounding33:04 – Dying of Indigestion and Going Multi-Product35:55 – Co-Pilots, Command Centers, and Defensibility40:07 – Investing Stage Agnostically44:29 – When is VC a Good Capital Instrument?49:18 – Thrive’s Core Beliefs53:57 – A Bet vs a Commitment57:49 – The Few Ideas Miles Takes Seriously59:47 – Doing a Few Big Things vs a Million Little Things1:03:54 – Practicing Scales1:06:22 – 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/adlabossiereLinkedin: https://www.linkedin.com/in/alexlabossiere/
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#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 - Intro04:25 - Kevin's North Star06:27 - The Bottleneck to Entrepreneurship09:20 - The Explosion of Capital in Private Technology Markets11:52 - Monopolies and the Shift in Private Enterprise Value Distribution15:18 - 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 IPOing27:14 - Picking and Magnitude of Outcomes28:41 - Founders and Investors as Personality Types29:56 - Seed and Growth Investing as Distinct Skillsets32:02 - Incubations33:56 - 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 Markets41:51 - Capital Innovation in Venture43:47 - The Endgame of Evaluation44:33 - 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/adlabossiereLinkedin: https://www.linkedin.com/in/alexlabossiere/
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#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/adlabossiereLinkedin: https://www.linkedin.com/in/alexlabossiere/
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#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/
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#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 Metrics1:05:22 - 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/adlabossiereLinkedin: https://www.linkedin.com/in/alexlabossiere/
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