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Bootstrapped Giants

Bootstrapped Giants

By: Andrew Warner and Jesse Pujji
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Behind the scenes stories of how we're building bootstrapped companies© 2025 Andrew Warner and Jesse Pujji Economics Leadership Management & Leadership Marketing Marketing & Sales
Episodes
  • He's controlling ChatGPT responses
    May 12 2025

    [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 to measure AI visibility and rankings
    [00:09:18] How to rank higher in AI search engines like GPT and Perplexity
    [00:10:30] Paid placement strategies in high-authority sites to boost AI visibility
    [00:11:06] Why AI search traffic converts better than Google
    [00:12:36] Chirag’s backstory: discovering SEO through Neil Patel and Mixergy
    [00:14:15] Cold-emailing Neil Patel and landing a $10K/month contract
    [00:15:27] Lessons from working with Neil and getting exposure to high-performers
    [00:17:06] Transitioning to CMO at Medley and moving into healthcare marketing
    [00:18:36] Failed Facebook campaigns and what really worked to reach doctors
    [00:22:39] Medley’s collapse and fraud charges against executives
    [00:25:21] Leaving Medley to care for his mom during cancer treatment
    [00:26:06] Why Chirag founded Taco based on gaps he saw in SEO agencies
    [00:27:54] Belief that search is changing—not dying—with rise of LLMs
    [00:28:48] Re-embracing SEO as a valuable, evolving skillset
    [00:30:00] Getting first customers through referrals and agency partnerships
    [00:32:06] Using relationships to close deals instead of competing on services
    [00:33:00] Discovering Mutual Intro from Jesse’s post and seeing results
    [00:34:57] Why he needed a repeatable customer acquisition system
    [00:36:00] Cold outreach stories from college and early networking
    [00:37:30] Setting up Mutual Intro infrastructure with just 2 people
    [00:39:27] Becoming systems-oriented and building processes
    [00:41:42] Joining the sales accelerator and breaking down the ROI
    [00:42:54] Generated nearly $1M in run-rate revenue from Mutual Intro alone
    [00:43:03] Future of AI search vs. Google’s market position
    [00:45:09] Why Google can’t rush into full AI interface without risk
    [00:47:06] Search behavior is fragmenting—more room for new players
    [00:48:27] Why now is a land grab moment in AI search optimization
    [00:49:21] SEO history repeating in the age of LLMs
    [00:49:57] Organic optimization matters more than ever in AI-led search
    [00:50:42] Closing thoughts and Taco’s vision moving forward

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    51 mins
  • 1440 is a Bootstrapped Giant
    May 1 2025

    [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’s Previous Startup: When in Rome (Failure Story)

    [00:11:15] Lessons on Unit Economics and Why When in Rome Failed

    [00:15:09] Why Email Newsletters Are Such Great Businesses

    [00:16:03] Inspirations: Sam Parr, Morning Brew, and the Hustle

    [00:18:45] Launching to 78 Friends and Family

    [00:20:06] Early Product Market Fit Signals

    [00:21:45] Feedback: Why They Removed Pictures from the Newsletter

    [00:24:00] Hiring Timeline: When They Brought in Their First Editor

    [00:25:48] Drew’s Grit: Waking Up at 4AM to Write

    [00:26:51] First $100K in Revenue: Growth Strategy and Milestones

    [00:29:15] Current Growth: 300K Subscribers/Month, 50% Retention

    [00:31:39] Economics: Revenue Per Email Open

    [00:32:06] Comparing Broad vs. Niche Newsletter Strategies

    [00:35:33] Why 1440 Focused on One Product (Until Now)

    [00:39:00] Scaling Discipline: Lessons from Private Equity

    [00:42:09] No Layoffs, High Revenue per Employee, Control Through Bootstrapping

    [00:43:30] New Product Launch: Knowledge Platform (Topics)

    [00:46:57] The Vision: Human-Curated Knowledge vs AI

    [00:49:30] Meaning Behind the Name "1440"

    [00:49:48] Closing Thanks

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    50 mins
  • I Built 4 AI Agents in 2 Weeks – No Code!
    Mar 10 2025

    [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 4 Agents, Focusing on Small Single-Purpose Tools
    [00:08:15] Live Business Use Case: The “Mutual Intro” AI Agent
    [00:09:45] Benefits of Ranking Contacts & Saving Significant Human Time
    [00:11:15] Attempt to Build a Large, All-In-One Agent & Its Failures
    [00:14:03] Compounding Error With Multi-Step AI Workflows
    [00:16:57] Conclusion: Why Single-Purpose Agents Work Better
    [00:18:18] Expanding Into LinkedIn Sales Nav & Automated DMs
    [00:19:48] N8n as the Core Platform (Open-Source Alternative to Zapier/Make)
    [00:21:09] Future Vision & “Agent That Builds Agents” Dream
    [00:21:45] Potential for Buying Businesses & Training Their Teams on AI
    [00:22:21] “SaaS Is Dead” – Emphasis on Highly Customized AI Tools
    [00:23:51] Possibility of an AI Course or Accelerator for Nontechnical Builders
    [00:25:12] How Nontechnical People Often Adopt AI Faster Than Engineers
    [00:26:33] Who Should Reach Out About AI (Sales/Support/Small Agencies)
    [00:27:36] Adam’s Email & Looking Toward Future Products/Services
    [00:28:12] Andrew’s Wish for an AI-Generated First Draft from Transcripts
    [00:28:45] Adam’s 4-Step Method for Summarizing Calls & Extracting Stories
    [00:30:27] Closing Remarks & Plan to Continue Updates Based on Audience Feedback

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    31 mins
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