Bootstrapped Giants

⏱ 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...

 🎧 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...

 ⏱ 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...

🎧 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...

[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...

[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 Close chose profitability over VC [00:04:01] Why staying small and focused is their competitive advantage...

[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 AI-powered agency [00:07:03] Tracking brand rankings inside ChatGPT and Perplexity [00:08:33] Tools used...

[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 “Go Niche” [00:06:09] 1440’s Thesis: Inch-Deep, Mile-Wide for the Intellectually Curious [00:08:24] Tim’...

 [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] Building His First Agent in One Week (and Feeling “Bad at AI”)  [00:07:03] From 1 Agent to...

[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] Struggle With First Drafts & Delegation [00:06:09] Committing to Genius vs. Excellence [00:07:12] “...

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 briefly?   [00:04:03] Should we use clickbait titles?   [00:05:06] How do you handle self-doubt?  ...

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