
Westenberg
The Westenberg Podcast offers ideas, explainers, book notes, and reflections on technology, philosophy, and the human experience. Hosted by Joan Westenberg, each episode unpacks complex topics with clarity and depth, blending personal insights with thought-provoking analysis. It’s a space for exploring big questions and fresh perspectives in an accessible format.
Latest episodes

Feb 14, 2025 • 3min
Complexity is a Trap
In this episode, I explore a fundamental truth that plays out across every field: simplicity is mastery.We watch the ambitious MBA graduate design an elaborate business strategy while the seasoned entrepreneur focuses on one thing and does it exceptionally well. We see the aspiring chef juggle exotic ingredients while the master chef transforms simple elements—salt, heat, and time—into something extraordinary.This pattern repeats everywhere:The elite athlete masters the fundamentals, while the beginner clings to complexity.The skilled negotiator wins with silence, not argument.The best investors choose focus, not chaos.So why do we keep making things more complicated than they need to be?

Feb 12, 2025 • 5min
On First Steps and False Barriers
I break down the psychology and mathematics behind why we label things "impossible" and how to overcome these false barriers. Through examples from aviation history to Amazon's evolution, I explore how taking that first step – even in the wrong direction – creates valuable information for success.Key Points:Why experts often wrongly label things "impossible"The cognitive bias of viewing complex tasks as monolithic challengesHow bad first steps can provide more valuable information than good onesWhy the path to success never looks like we expectA framework for evaluating potential first stepsQuote: "Nothing is impossible (if you're willing to be wrong repeatedly and publicly while figuring out how to do it)."

Feb 11, 2025 • 2min
The Dark Pattern of Digital Freedom: How Screens Bypass Our Social Wisdom
I explore an unsettling discovery at McDonald's - men order dramatically more food when facing a screen instead of a person. This kicks off a deeper examination of how digital interfaces strip away the social guardrails that evolved to protect us from our worst impulses.Key Points:What McDonald's learned about male ordering patterns through self-service kiosksHow digital interfaces bypass thousands of years of evolved social wisdomWhy that moment of hesitation before ordering a second burger mattersThe hidden costs in dating apps, social media, and digital shoppingWhen friction might actually help us make better choicesNotable Quote: "The screen knows what we want in the moment because it doesn't ask us to consider the future."

Feb 7, 2025 • 3min
You Can't "Win" in Tech Without Cheating
The Dark Side of Tech Giants: Winning by Breaking RulesIn this episode, I get into the controversial strategies employed by tech giants like PayPal, Uber, Airbnb, Facebook, Amazon, and Tesla. These companies are often hailed as innovators, but their success largely stems from breaking existing regulations, misusing user trust, and deploying capital aggressively. Meanwhile, a parallel universe of developers, creators, and entrepreneurs is emerging. These new players are building sustainable businesses through value creation, organic growth, and direct monetization. They are redefining victory by breaking free of the zero-sum game. Discover the contrast between traditional Silicon Valley tactics and the new game-changing approaches in this thought-provoking episode.00:00 The Dark Side of Tech Giants01:41 The New Game: Sustainable Success02:09 The New Breed of Innovators02:29 Choosing Your Path02:37 True Innovation: Breaking Free

Jan 7, 2025 • 4min
What the Left and Right Get Wrong About Free Speech
Free Speech: Finding Balance Beyond ExtremesIn this episode, I get into the complexities of regulating speech in society through a thought experiment. Could you choose between banning all politically controversial speech or allowing complete freedom of expression, without knowing which political faction will rule for the next century? 00:00 Introduction: The Free Speech Dilemma00:25 The Left's Perspective on Free Speech00:42 The Right's Perspective on Free Speech00:57 Critiquing Both Sides01:57 A New Framework for Speech Regulation02:41 The Reality of Modern Speech Control03:16 A Utopian Vision for Free Speech03:50 Conclusion: Building Better Speech Institutions

Dec 29, 2024 • 8min
The Doomscroll Industrial Complex: How Anxiety Powers the Attention Economy
In this episode, I break down the Doomscroll Industrial Complex—a system where bad news fuels the attention economy and anxiety becomes a product. I explore how doom influencers profit from fear, why negativity dominates online spaces, and how this perpetual cycle affects our mental health and ability to focus on real solutions.What I Cover: • How doomer influencers stay vague to never be “wrong.” • Why algorithms reward bad news over constructive solutions. • The rise of paid pessimism through platforms like Substack and Patreon. • How constant doomscrolling creates a collective mental health crisis. • Practical ways we can resist the feedback loop of anxiety.The world’s always been ending in one way or another—but now we’re stuck scrolling through it endlessly. How do we step back, cut through the noise, and focus on what really matters?

Dec 12, 2024 • 2min
All Social Media Sucks
In this episode, I get into the harsh truth about social media platforms and their true nature. No matter where you log in, whether it’s Instagram, BlueSky, Xthreads, TikTok, Warpcast, Reddit, or the latest niche app, you’re always at the mercy of a business-driven machine. These platforms treat you as a product or a customer, not a person. Your content, engagements, and online presence are ultimately irrelevant to the owners' bottom line. It's important to remember that social media is optimized for profit, not humanity, and to not take it too seriously. Log off, touch grass, and reclaim your mind from the digital chaos.00:00 The Harsh Reality of Social Media00:33 The Business Behind the Platforms00:41 The Illusion of Online Validation01:19 The Inevitable Decline of Platforms01:39 Finding Balance and Perspective02:04 Disconnect and Reclaim Your Life

Dec 6, 2024 • 12min
The Rise of Digital Oligarchies
How Tech Giants Control Our LivesIn this episode of the Westenberg Podcast, I explore the concept of digital oligarchies in 2024, where a few tech companies dominate critical infrastructure and influence how we work, socialize, and think. I discuss the power dynamics of platforms like Facebook, Google, and Amazon, emphasizing the role of network effects, data control, and attention capture mechanisms. I also consider the future possibilities of regulation, decentralization, and fragmentation, highlighting the challenges and potential solutions for managing this concentrated power.00:00 Introduction to Digital Oligarchy00:35 The Power of Network Effects01:39 Data Feudalism and Machine Learning02:47 Attention Economy and Psychological Tools03:51 Quasi-Governmental Powers of Tech Giants04:45 The Complexity Tax and Innovation Trap06:29 Digital Identity and Attention Arbitrage08:48 Possible Futures of Digital Oligarchies10:10 Principles for Addressing Digital Oligarchies10:50 Conclusion: Balancing Benefits and Risks

Dec 6, 2024 • 4min
Could You Invest for 100 Years?
The Power of Long-Term ThinkingIn this episode, I explore the concept of long-term thinking and its profound impact on civilization. I challenge viewers with hypothetical bets to illustrate how modern society often prioritizes short-term gains over exponential long-term benefits. Highlighting examples from the Catholic Church to the Dutch flood control systems, I discuss how some organizations successfully think centuries ahead. I propose the creation of a '100 Year Lab' where decisions are made with the future in mind, aimed at benefiting generations to come.00:00 The Bet: $1 Billion vs. Manhattan Real Estate00:15 The Penny vs. The Million: A Lesson in Compounding00:24 Modern Society's Short-Term Thinking00:35 The 10,000 Year Clock: A Symbol of Long-Term Vision00:57 Human Blind Spots in Long-Term Planning01:33 Examples of Long-Term Thinking02:06 The Power of Long-Term Decisions02:31 Imagining a Long-Term Future02:55 Survivorship Bias and Building for Permanence03:38 A Modest Proposal: The 100 Year Lab

Dec 6, 2024 • 3min
You Were Not Born to Censor Yourself for Other People’s Comfort
Stop Self-CensorshipIn this episode, I explore the importance of being true to yourself and rejecting the pressure to self-censor just to fit in. You'll learn why it's crucial to speak your mind, embrace your unique personality, and respect your own voice as much as you do others. Society advances when we challenge the status quo, and it's time to stop diluting our thoughts to make others comfortable. Go long on radical honesty.00:00 Introduction: The Pressure to Conform00:22 The Importance of Authenticity00:28 Respect vs. Self-Censorship01:29 The Consequences of Silence01:54 Embrace Your True Self02:25 Conclusion: Speak Loudly and Honestly