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Bootstrapped Giants

Why you don't go to the gym

10 Dec 2025

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⏱ Episode Breakdown00:00 – Andrew’s gym story: fear that it won’t last01:30 – “Are you either a gym person or you’re not?”02:15 – The emotional wound of not achieving your fitness goal03:30 – Jesse challenges Andrew: are you willing to feel it?04:30 – The difference between thinking vs. feeling06:00 – Jesse’s story: the P90X cycles and obsession with goals07:00 – How Jesse finally created a sustainable routine08:00 – “I stopped making it mean something about me”09:00 – Creating routines that don’t rely on motivation10:30 – The power of feeling good after—not during—the workout11:30 – Jesse’s trainer Rock: turning brain-off into a meditative lift13:00 – Using AI (Suno + Claude) to generate emotional songs15:00 – Jesse creates a song about being a dad live on air17:00 – Playing AI-generated songs: “That’s actually good…”19:00 – AI models, memory, and lock-in vs open toolchains21:00 – ChatGPT vs Claude: the future of personalized creativity23:00 – Jesse’s argument: people over-worry about privacy25:00 – The three valid concerns about AI and data26:00 – Jesse’s poli-sci roots: privacy and due process28:00 – Real-world privacy concerns: China, Facebook, global policy30:00 – The irrationality of rich people and neighborhood security31:00 – HOA story: voting against $800/year for better safety32:00 – Direct mail is more dangerous than the internet33:00 – Andrew’s past: tracking data leaks with suite numbers34:00 – Letting go of control and embracing the tradeoff34:30 – 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.

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