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PODCAST · business

Bootstrapped Giants

by Andrew Warner and Jesse Pujji

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

Publisher-supplied feed metadata · PodParley refreshed Jun 5, 2026 · Source feed

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Episodes

  1. 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....

  2. 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…

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  3. 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...

  4. 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...

  5. 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]...

  6. Close - Focused CRM does $50 million a year

    [00:00:00] Intro – Andrew sets up the conversation: sales reluctance, AI, and CRM evolution [00:00:47] Steli explains Close's positioning: high-communication CRM for salespeople [00:01:41] Revenue milestone: Close is on track to hit $50M this year [00:02:36] Bootstrapping vs. fundraising: why…

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  7. He's controlling ChatGPT responses

    [00:00:36] Intro: ChatGPT as a traffic driver and Chirag’s early insight [00:01:48] Revenue Numbers and Profitability of Taco [00:02:24] Personal investment strategy and non-AI assets [00:03:36] How Chirag uses AI agents to replace writers and boost efficiency [00:05:42] What makes Taco a true...

  8. 1440 is a Bootstrapped Giant

    [00:00:00] Quick Montage (Growth, Grit, Vision, Revenue, Meaning of 1440) [00:00:36] Intro: Why 1440 is Different [00:01:48] Revenue Numbers and Profitability [00:02:24] How They Funded Without Venture Capital [00:04:48] How Big Can an Email Newsletter Get? [00:05:15] Why They Ignored Advice to…

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  9. I Built 4 AI Agents in 2 Weeks – No Code!

    [00:00:00] Introduction [00:00:45] Early Adoption of Generative AI & GitHub Copilot [00:01:30] Discovering How Code Comments Improve AI Suggestions [00:02:33] Skepticism About AI Hype & Fear of Being Left Behind [00:04:03] Seeing a YouTube Tutorial That Unlocked Building a RAG Agent [00:05:06]...

  10. I found my zone of genius

    [00:00:00] Intro & Evolving Work Relationship [00:01:03] Balancing Andrew’s Creative Side vs. Business Demands [00:02:06] Integrating Different Approaches from Teammates [00:02:33] Identifying and Staying in Your “Zone of Genius” [00:04:03] Tasks That Energize vs. Tasks That Drain [00:05:06]...

  11. We launched a $40k/month newsletter

    In this episode: how we launched our newsletter, Bootstrapped Giants. Presented by: Superhuman, the email app that gets us to inbox zero fast, helps us sell more and enables us to collaborate. Time stamps: [00:01:03] Why start the Bootstrapped Giants podcast? [00:01:26] Can you introduce yourself...

  12. E00: Why can't Andrew start this podcast?

    We recorded 4 episodes and Andrew hasn't posted 1. Why not?

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ABOUT THIS SHOW

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

HOSTED BY

Andrew Warner and Jesse Pujji

Produced by Andrew Warner

Frequently Asked Questions

How many episodes does Bootstrapped Giants have?

Bootstrapped Giants currently has 12 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Bootstrapped Giants about?

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

How often does Bootstrapped Giants release new episodes?

Bootstrapped Giants has 12 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to Bootstrapped Giants?

You can listen to Bootstrapped Giants on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Bootstrapped Giants?

Bootstrapped Giants is created and hosted by Andrew Warner and Jesse Pujji.
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