[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