LABOSS PODCAST

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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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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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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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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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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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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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.

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

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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

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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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