Motorboat Leadership vs. Sailboat Leadership

Why you don't go to the gym

⏱ 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.

AI is eating the world

🎧 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.

How I became a board member of a major supermarket

⏱ 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.

Why I'm Building an AI Writer

🎧 Highlights: [00:00:00] Why build your own AI writer instead of using existing tools [00:02:15] The dream of never writing social posts again [00:03:36] “Software is no longer generic — it’s bespoke” [00:06:18] Excel as the original custom-software platform [00:08:42] How Excel models run billion-dollar deals [00:10:39] The rise of low-code and AI-generated workflows [00:13:30] Why generative AI is the missing layer Excel never had [00:14:45] LLMs as amplifiers — the new power stack [00:18:54] The risks and trade-offs of AI-built tools [00:19:57] SaaS vs. services — who wins in the new AI supply chain [00:24:00] The coming shift to voice-first computing [00:26:30] Why most AI tools still suck — and how to fix that [00:29:00] The plugin future of AI — small tools that amplify human workflows [00:33:00] “This time it really is different” — the pace of AI adoption [00:35:15] Building AI-first companies in the Midwest [00:36:09] Why AI will redefine marketing and discovery [00:39:00] From websites to zero-click experiences — the new internet economy [00:40:21] The long runway for AI transformation  In this Bootstrapped Giants conversation, Jesse Pujji, Andrew Warner, and Adam Brakhane explore how artificial intelligence is transforming the way companies build and use tools. They discuss why the next wave of billion-dollar companies will focus on custom agents, not generic apps — tools designed for a single person or business — and how this shift will upend everything from marketing to operations.

Motorboat Leadership vs. Sailboat Leadership

[00:00:00] Intro – Jesse hints at a personal and professional transition [00:00:27] Jesse’s life update – spiritual journey and post-Japan reflection [00:01:30] The Motorboat vs Sailboat leadership metaphor explained [00:02:51] Internal conflict: fear of letting go and team dependency [00:04:03] Overwhelm from managing multiple businesses – “a company per day” schedule [00:04:48] Inspiration from a friend who only talks to CEOs – true sailboat mode [00:05:24] Every leader needs both motorboat and sailboat energy [00:06:09] Andrew’s emotional reaction to Jesse pulling back from involvement [00:07:12] Jesse’s evolving role – from fractional president to clearing Slack overload [00:08:15] What Jesse wants to focus on – coaching vs tactical work [00:09:18] “Mommy-daddy” problem in leadership dynamics at GA [00:10:03] Is Jesse not accepting who he’s becoming? [00:10:39] Jesse reflects on the hard realities of running vs starting a business [00:11:06] What Jesse means by “spiritual journey” – internal clarity and awareness [00:13:03] Who are we, really? Jesse and Andrew dig into identity beyond thoughts and the brain [00:15:27] Oneness, awareness, and spirituality as a form of leadership grounding [00:18:09] Life as a game – avoiding suffering over Monopoly money [00:19:48] How spiritual growth translates into business decision-making [00:20:33] Trusting energy and intuition over rigorous logic [00:21:36] Jesse clarifies: it was always about coaching and enabling others [00:23:15] Why being a coach’s coach still leads to high standards and performance [00:24:00] How Jesse arrived at this realization: stripping away attachments (e.g., to money) [00:25:57] Embracing spaciousness and presence over busyness [00:27:18] What sailboat leadership looks like in practice [00:28:39] Letting go of calendar-driven validation – the need for quality over quantity [00:29:42] Andrew tests the sailboat approach – does less structure work? [00:30:27] Jesse: “You're still in motorboat mode” – rethinking performance metrics [00:31:12] Sailboat success story: Growth Assistant took the least time, performed the best [00:32:33] More involvement ≠ more success – Bootstrap Giants vs Growth Assistant [00:33:00] Jesse still applies “more is more” at home, even if not always leading [00:34:03] “I need a software update” – Jesse wants to rewrite his operating model [00:35:06] Build the person in public – mirroring business transparency with personal evolution [00:36:18] Jesse constantly experiments and iterates – calendar overhaul as an example [00:37:30] “Here's my latest experiment” – documenting leadership evolution in real time [00:38:06] Noticing energy loss and making adjustments is key [00:39:00] Trusting that pulling back may help the business more than staying involved [00:39:45] Sailboat experiment with John Oberlander – abdication or setup? [00:40:21] Will Jesse write more about this evolution? Probably – he’s thinking it through [00:40:48] Andrew reflects on how Jesse’s fear prompts clarity in others [00:40:57] Outro – Honest vulnerability, evolving leadership, and thanks