⏱ 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.

🎧 Highlights:
[00:00:00] Benedict Evans and “AI Eats the World”
[00:01:30] Will startups unbundle ChatGPT?
[00:05:00] Why vertical specialization wins
[00:07:03] Every startup is now “AI-first”
[00:07:48] The trillion-dollar AI consulting wave
[00:10:57] Is AI a new plateau or the next exponential curve?
[00:12:00] The pyramid of progress: computing → internet → mobile → AI
[00:13:42] Automation, elevators, and the future of jobs
[00:14:30] The “anti-AI” thesis — food, homes, live entertainment
[00:16:00] E-commerce still has 70% left to grow
[00:17:57] ChatGPT as the next shopping catalyst
[00:18:18] Robo-taxis, dating apps, and adoption curves
[00:23:15] How AI expands the creative pie (Suno songs example)
[00:25:03] Final takeaways: hype vs. reality, and why this wave is still early

In this Bootstrapped Giants episode, Jesse Pujji and Andrew Warner break down Benedict Evans’ “AI Eats the World” presentation and explore what it really means for founders, investors, and builders.

They dive deep into the data behind AI adoption, the rise of trillion-dollar service industries, and why this moment in technology might be bigger than the internet itself. From the unbundling of ChatGPT to the explosion of AI-native startups, they discuss where the real opportunities are—and how to spot the ones that last.

⏱ Episode Breakdown
00:00 – Andrew questions the real value of being on a board
02:00 – Jesse’s framework: people, impact, learning, and comp
04:00 – The unique story of Schnucks: family values and $4B scale
06:00 – What makes a board seat “worth it” for Jesse
08:00 – How he ended up on the Schnucks board
09:00 – The role of impact in Jesse’s decisions
11:00 – Mistaking board work for operational work
12:00 – A pivotal moment: “You think in a way none of us do”
13:00 – Desired Future State (DFS) and shifting legacy companies
14:00 – What Jesse learned from the Festival Foods acquisition
16:00 – The Boomerang Principle & culture as a daily habit
18:00 – Why having kids at home is the most finite resource
19:00 – Business never stops—even at 70+
21:00 – Why grocery hasn’t been fully rolled up (yet)
22:30 – What's happening at Gateway X behind the scenes
23:30 – Jesse’s goal: build an AI-focused startup studio in St. Louis
25:00 – The talent challenge: how to attract builders to the Midwest
26:30 – Borrowing ideas from South Park Commons and Brickyard
28:00 – “My only dogma is no dogma”: bootstrapping vs. seed-strapping
29:30 – Why Jesse doesn't feel like a fraud when changing direction
30:30 – The deep commitment to St. Louis and building there
32:00 – Closing: unapologetically building the thing that only you can

In this episode, Jesse and Andrew go deep on something unexpected: what it’s really like to sit on the board of a $4B+ grocery company—and why Jesse said yes.

It turns into a powerful conversation about board dynamics, generational leadership, family legacy, the nature of impact, and Jesse’s renewed mission to attract startup talent back to cities like St. Louis. They also touch on ego, post-exit motivation, and why some founders never stop building.

Whether you're a founder thinking about joining a board, building something meaningful in a smaller city, or wondering what “impact” actually means, this one hits home.