Oct 24, 2025
Ep 214: Crypto, AI Companions, and the Future of Tech
Special Guests: Reggie James, Avi Schiffmann, Rachel Mayer
Cheryl Douglass
Join us as we explore the latest in crypto, technology, and AI
companions.
Timestamps:
00:00 Introduction
and Setup
00:55 Upgraded
Audio and Learnings
01:38 What
is Boys Club?
03:01 Engaging
with the Audience
03:19 Sponsor
Shoutout and Run of Show
05:10 Draft
Tweets Segment
11:50 Laptop
Time: Exploring Poly Market
16:09 Guest
Segment: Reggie James
23:47 Hardware
and AI Discussion
38:31 Cheryl
Douglass Joins the Show
39:07 Throwback
Sale and Shipping Woes
39:26 Draft
Tweets and Shy Posting
41:55 AI
Companions and Social Media
47:37 CFTC
Roundtable and Market Dynamics
51:05 What's
in the Bag?
53:14 BitKey
Wallet and Self-Custody
54:50 Friend.com
and AI Companionship
01:16:24 Rating
Hate Tweets
01:17:05 Leaked
Seed Phrase Incident
01:17:25 Friend.com
Critique
01:18:25 Successful
Marketing Campaign
01:20:00 Shilling
the Bay Area
01:21:24 Kate's
Whiteboard: Martha Stewart's Morning Routine
01:36:19 Interview
with Rachel Mayer from Circle
01:52:52 Newsletter
Highlights
02:01:21 Wrapping
Up and Announcements
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