What if orange-pilling isn’t persuasion—but marketing, ethics, and timing? In this episode, we sit down with Tad Smith—partner at One Roundtable Partners, former CEO of Madison Square Garden and Sotheby’s, and one of bitcoin’s most articulate educators—to explore the moral case for orange-pilling, and why it’s not a right but a responsibility. Tad shares hard-won lessons from orange-pilling family members across generations and wealth brackets, and explains why alignment—not argument—is the key. We break down how different cohorts—from boomers to creatives—encounter bitcoin, and why effective orange-pilling starts with listening, not preaching. From bitcoin vs. college and homeownership, to AI’s threat to knowledge workers, Tad lays out how bitcoin becomes not speculation, but protection—not rebellion, but insurance—not utopia, but sovereignty.
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TIMESTAMPS:
0:00 – Intro
1:10 – The moral case for orange-pilling
5:47 – Why persuasion fails and alignment works
10:08 – Mistakes made orange-pilling family and friends
15:02 – You need an invitation to orange-pill
18:48 – Cohort-based messaging: it’s not religion, it’s marketing
23:27 – Orange-pilling high-net-worth individuals
28:12 – Retirees, boomers, and fear of complexity
31:40 – Tech-savvy, libertarian, and progressive angles
35:20 – Why creatives matter: expression, ownership, and ordinals
38:47 – College vs bitcoin: a post-AI investment dilemma
44:02 – Should you buy a house or stack more bitcoin?
49:55 – Narrative shapes price: the Marian Antoinette necklace lesson
53:10 – What bitcoin really is: protection, insurance, sovereignty
57:35 – How to orange-pill with respect and precision
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