We Study Billionaires - The Investor’s Podcast Network

In this episode, Clay tells the story of Uber. Uber started as a simple idea, and evolved into one of the most disruptive companies of the modern era. Drawing from Brad Stone’s The Upstarts, the episode explores Uber’s early days, its global expansion, and the never-ending battles with regulators, competitors, and the taxi industry.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:01:42 - How Uber went from a simple idea in San Francisco to a global transportation platform in under a decade
00:03:58 - Why the taxi industry was ripe for disruption and how regulation shaped Uber’s early strategy
00:31:08 - The role venture capital, aggressive expansion, and competition played in Uber’s rise
00:39:41 - How network effects, data, and dynamic pricing powered Uber’s growth flywheel
01:00:42 - How Uber’s business model and moat evolved over time
01:15:54 - Why leadership style and company culture became both a strength and a liability as Uber scaled

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

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Brad Stone’s book: The Upstarts.

Stig Brodersen’s Uber pitch.

Shawn O’Malley’s Uber pitch.

Bill Ackman’s 2024 Annual Letter.

Follow Clay on X and LinkedIn. 

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Preston, Trey, and Pablo unpack the evolution of AI from agentic capabilities and decentralized systems to practical open-source tools like Clawdbot.

They examine AI’s potential, security risks, personalized workflows, and its societal impact. With candid stories and real use cases, this episode offers a rare look into AI's current frontier and what lies ahead.

IN THIS EPISODE YOU’LL LEARN:

00:00:00 - Intro

00:06:11 - What agentic AI is and how it differs from traditional chatbots

00:07:27 - Why decentralization matters in AI development

00:10:06 - How open-source AI models like Clawdbot enable innovation

00:10:32 - How running AI locally differs from cloud-based models in security and control

00:11:19 - How persistent memory impacts AI behavior and risk

00:12:39 - Ways AI agents collaborate like teams in an organization

00:14:08 - The role of sovereignty and privacy in AI communications

00:15:42 - How Trey and Pablo initialize and manage specialized AI agents

00:17:15 - The risks of AI with access to personal data and how to mitigate them

00:23:09 - The potential of AI to innovate beyond human expectations

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

Pablo on Nostr.

Trey's newsletter and podcast: Fire BTC.

Related ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠books⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ mentioned in the podcast.

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Stig Brodersen speaks with David Fagan about the case for indexing and what most investors get wrong about performance, financial advisors, and risk. They explore why missing a few percentage points can delay retirement by years, how to think about rebalancing, and what it truly means to be the overseer of your investments.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro

00:01:57 - Why indexing works for almost everyone

00:12:49 - How to properly evaluate investment performance

00:24:58 - How to think about asset allocation and rebalancing using a simple, behaviorally sound framework

00:33:42 - What it really means to be the overseer of your investments, even if you outsource management

00:36:21 - Why missing just a few percentage points in returns can cost you years of your life

00:36:42 - Why missing 3% return means having to work another 6–7 years instead of retiring

00:44:13 - How to use expectations in the best possible way

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

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Listen to our interview with David Fagan about investing like a business owner.

Listen to our interview with David Fagan about Buffett’s favorite business book. 

Stig’s ⁠blog post⁠ on his portfolio and track record since 2014.

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Kyle Grieve discusses a refreshingly different take on wealth inspired by The Five Types of Wealth by Sahil Bloom. Rather than focusing solely on money, the conversation explores a more holistic framework that includes time, relationships, health, purpose, and financial independence.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:02:15 - Why you should reframe wealth beyond asset accumulation
00:04:33 - How wealth is built during life, not after reaching a destination
00:04:49 - The five types of wealth and how they shape a fulfilling life
00:07:02 - How defining personal identity clarifies long-term decisions
00:07:57 - Why goals and anti-goals protect success and relationships
00:10:40 - How time wealth depends on awareness, attention, and control
00:17:45 - Why relationships are the strongest predictor of happiness and health
00:36:01 - How curiosity and purpose can drive mental wealth
00:51:27 - Why physical wealth is easy to overlook
00:57:00 - How defining enough creates financial wealth

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

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Seb and Preston explore the rapid evolution of AI, its role in reshaping work, communication, and biology. They discuss tools like Claude Co-Work, delve into the implications of AI relationships, blockchain integration, and breakthroughs in longevity science. With insights from personal experiments and global trends, they paint a vivid picture of the AI-powered future.

IN THIS EPISODE YOU’LL LEARN:

00:00:00 - Intro

00:01:58 - What Elon Musk and tech leaders are saying about AI and the future

00:04:33 - Why time feels like it’s accelerating in today’s tech-driven society

00:05:09 - How AI tools like CoWork outperform others in coding and organization tasks

00:16:15 - How note-taking AI is transforming productivity and book writing

00:17:36 - How AI could power one-person billion-dollar startups

00:18:19 - The significance of Claude’s ethical framework in guiding AI decisions

00:19:27 - The ethical concerns of forming relationships with AI

00:37:03 - How energy-efficient communication protocols can reshape AI infrastructure

00:45:26 - Why legal recognition is essential for real blockchain-based equities

00:54:36 - How stem cell therapies may move medicine toward curing rather than managing disease

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

Official Website: ⁠Seb Bunney⁠.

Seb’s book: ⁠The Hidden Cost of Money⁠.

Related ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠books⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ mentioned in the podcast.

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