Bootstrapped Giants

[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 

[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[00:04:51] Competing with giants: don’t out-fund, out-focus[00:05:31] The power of saying no and maintaining a narrow product scope[00:06:52] Product-led growth: Close doesn’t rely on integrations to win customers[00:07:48] Focusing on deep communication use cases sets Close apart[00:08:51] Why they resist chasing enterprise customers[00:09:30] Andrew compares this strategy to ClickUp’s broader, less focused model[00:10:10] Saying no to tempting opportunities to stay true to the customer[00:11:35] AI as an accelerant for focused companies with strong opinions[00:13:05] Close’s AI vision: sales inbox automation and no lead left behind[00:14:44] Andrew’s “AI wrapper” idea — simple products that succeed by layering AI[00:16:28] The future of software: niche-focused, AI-powered tools[00:17:23] AI changes what it means to “build” a product[00:18:06] Steli warns against the belief that product alone drives success[00:18:53] Sales is often the missing piece in failed startups[00:20:32] Don’t dismiss simple wrappers — execution matters more than ideas[00:21:18] Close monitors product-market fit actively — it’s always shifting[00:22:24] VoicePen example: AI product evolution from wrapper to workflow[00:23:48] Talking to customers weekly keeps Close grounded[00:24:35] Andrew presses on how to extract value from those calls[00:26:07] The real problem: most people aren’t willing to talk to customers[00:26:52] From agency to SaaS: how Close transitioned from services[00:28:18] Steli’s warning: don’t jump too quickly from services to product[00:30:32] Andrew asks for Close's best sales tactics[00:31:38] Speed matters: follow up within minutes, not days[00:32:57] Long-term follow-up wins deals — even 6 years later[00:34:50] Why Close built high-quality, technical customer support[00:36:00] Trust is built through understanding real customer problems[00:37:01] Steli shares the Close.com domain story — persistence paid off[00:38:33] Final thoughts: $50M revenue and still just getting started

[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

[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

 [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 

[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] “Heroing” & Taking 100% Responsibility[00:09:36] Asking for Help Without Overburdening Others[00:12:18] Intermittent Fasting & Energy Management[00:13:57] Drive to Prove Oneself & Self-Awareness[00:17:06] Pinpointing Andrew’s True Strengths[00:19:03] Jesse’s “Themed” Workdays & Finding Balance[00:24:00] Considering Bigger Moves: M&A vs. New Startups[00:29:18] AI Opportunities & How to Experiment Quickly[00:32:15] Jesse’s Investment Approach & Personal Finances[00:38:00] Shifting Mindset From Scarcity to Abundance[00:40:09] “Die With Zero” & Rethinking Spending[00:44:09] Wrapping Up & Final Reflections 

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?  [00:09:36] Would you refund disappointed sponsors?  [00:13:03] What's the human element in business?  [00:17:33] What's the Bootstrap Giants business model?  [00:20:24] How much revenue from ads?  [00:24:27] What is your growth strategy?  [00:27:45] Why is private equity better?  [00:30:36] Should we explore private equity more?  [00:34:21] How does Gateway X support companies?  [00:44:06] How did GrowthAssistant start?  [00:46:12] Has GrowthAssistant's vision changed?  [00:52:03] How did this Twitter Live work?  [00:52:30] Should we do private meetings publicly?

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