⏱ Episode Breakdown
00:00 – Andrew’s gym story: fear that it won’t last
01:30 – “Are you either a gym person or you’re not?”
02:15 – The emotional wound of not achieving your fitness goal
03:30 – Jesse challenges Andrew: are you willing to feel it?
04:30 – The difference between thinking vs. feeling
06:00 – Jesse’s story: the P90X cycles and obsession with goals
07:00 – How Jesse finally created a sustainable routine
08:00 – “I stopped making it mean something about me”
09:00 – Creating routines that don’t rely on motivation
10:30 – The power of feeling good after—not during—the workout
11:30 – Jesse’s trainer Rock: turning brain-off into a meditative lift
13:00 – Using AI (Suno + Claude) to generate emotional songs
15:00 – Jesse creates a song about being a dad live on air
17:00 – Playing AI-generated songs: “That’s actually good…”
19:00 – AI models, memory, and lock-in vs open toolchains
21:00 – ChatGPT vs Claude: the future of personalized creativity
23:00 – Jesse’s argument: people over-worry about privacy
25:00 – The three valid concerns about AI and data
26:00 – Jesse’s poli-sci roots: privacy and due process
28:00 – Real-world privacy concerns: China, Facebook, global policy
30:00 – The irrationality of rich people and neighborhood security
31:00 – HOA story: voting against $800/year for better safety
32:00 – Direct mail is more dangerous than the internet
33:00 – Andrew’s past: tracking data leaks with suite numbers
34:00 – Letting go of control and embracing the tradeoff
34:30 – Quick sign-off: “That was a 15-minute touch and go”

This episode starts with Andrew’s personal story: he finally finds a gym that feels like it could work for him—but immediately feels the fear that it won’t last. Why? Because for years, he’s believed that some goals (like getting fit) are simply out of reach.

Jesse and Andrew unpack the emotional baggage behind self-improvement: the inner voices, the identity stakes, and why some efforts feel so personal—and so loaded—that failure cuts deeper than we expect.

They explore how redefining the meaning of action can shift your relationship with goals, and why “not enjoying the gym” isn’t actually the issue—it’s the story you attach to it.

The conversation expands into AI creativity (yes, Jesse makes a rap about being a dad), the future of privacy and memory in AI tools like Suno and ChatGPT, and what it really means to use AI as a creative partner vs. just a tool.