Bootstrapped Giants

Behind the scenes stories of how we're building bootstrapped companies

Bootstrapped Giants is a business podcast hosted by Andrew Warner and Jesse Pujji, with 12 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Andrew Warner and Jesse Pujji hosts Bootstrapped Giants, a business show with 12 episodes published.

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  Episode #12

  Why you don't go to the gym

  Dec 10, 202534 minS0

  <p>⏱ Episode Breakdown<br>00:00 – Andrew’s gym story: fear that it won’t last<br>01:30 – “Are you either a gym person or you’re not?”<br>02:15 – The emotional wound of not achieving your fitness goal<br>03:30 – Jesse challenges Andrew: are you willing to feel it?<br>04:30 – The difference between thinking vs. feeling<br>06:00 – Jesse’s story: the P90X cycles and obsession with goals<br>07:00 – How Jesse finally created a sustainable routine<br>08:00 – “I stopped making it mean something about me”<br>09:00 – Creating routines that don’t rely on motivation<br>10:30 – The power of feeling good after—not during—the workout<br>11:30 – Jesse’s trainer Rock: tur...

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  Episode #11

  AI is eating the world

  Dec 8, 202527 minS0

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

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  Episode #10

  How I became a board member of a major supermarket

  Nov 20, 202533 minS0

  <p> ⏱ Episode Breakdown<br> 00:00 – Andrew questions the real value of being on a board<br> 02:00 – Jesse’s framework: people, impact, learning, and comp<br> 04:00 – The unique story of Schnucks: family values and $4B scale<br> 06:00 – What makes a board seat “worth it” for Jesse<br> 08:00 – How he ended up on the Schnucks board<br> 09:00 – The role of impact in Jesse’s decisions<br> 11:00 – Mistaking board work for operational work<br> 12:00 – A pivotal moment: “You think in a way none of us do”<br> 13:00 – Desired Future State (DFS) and shifting legacy companies<br> 14:00 – What Jesse learned from the Festival Foods acquisition<br> 16:00 – The Boomerang Principle...

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  Episode #9

  Why I'm Building an AI Writer

  Nov 13, 202541 minS0

  <p>🎧 Highlights:<br>[00:00:00] Why build your own AI writer instead of using existing tools<br>[00:02:15] The dream of never writing social posts again<br>[00:03:36] “Software is no longer generic — it’s bespoke”<br>[00:06:18] Excel as the original custom-software platform<br>[00:08:42] How Excel models run billion-dollar deals<br>[00:10:39] The rise of low-code and AI-generated workflows<br>[00:13:30] Why generative AI is the missing layer Excel never had<br>[00:14:45] LLMs as amplifiers — the new power stack<br>[00:18:54] The risks and trade-offs of AI-built tools<br>[00:19:57] SaaS vs. services — who wins in the new AI supply chain<br>[00:24:00] The coming shift to voice-first computing<br>[00:26:30] W...

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  Episode #8

  Motorboat Leadership vs. Sailboat Leadership

  Jul 10, 202541 minS0

  <p>[00:00:00] Intro – Jesse hints at a personal and professional transition<br> [00:00:27] Jesse’s life update – spiritual journey and post-Japan reflection<br> [00:01:30] The Motorboat vs Sailboat leadership metaphor explained<br> [00:02:51] Internal conflict: fear of letting go and team dependency<br> [00:04:03] Overwhelm from managing multiple businesses – “a company per day” schedule<br> [00:04:48] Inspiration from a friend who only talks to CEOs – true sailboat mode<br> [00:05:24] Every leader needs both motorboat and sailboat energy<br> [00:06:09] Andrew’s emotional reaction to Jesse pulling back from involvement<br> [00:07:12] Jesse’s evolving role – from fractional president to clearing Slack overload<br> [00:08:15] What Jesse wants to focus on – coaching vs tac...

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