[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?