Dear Ben

Ben Fisher
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Practical AI for CEOs Who Don’t Have Time for BS Hosted on Ausha. See ausha.co/privacy-policy for more information.

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  1. What AI Workflows Are You Sleeping On?

    1월 17일

    What AI Workflows Are You Sleeping On?

    Andrew Warner asked: "Every time I talk to a founder, I hear about some AI workflow I never would have thought to try. What are the non-obvious ones you're seeing?"Most people use AI to make stuff. The overlooked category: using AI to mirror things back to you. Scoring. Flagging. Routing. That's where the leverage is hiding.Ask your own question at DearBen.ai.--# SHOW NOTES- The Make vs Mirror Matrix: you're probably doing Make — but Mirror is where the blind spots live- Jeff Brewer gets rated on clarity, decisiveness, and interruptions after every single meeting- Dan Shipper built a system that flags when he's avoiding confrontation- Wade Foster (Zapier CEO) scores team meetings against Five Dysfunctions and sends individual feedback- Pete Sena's mega prompt analyzed 13 years of my notes and surfaced patterns I'd forgotten- Chris Brownridge routes meeting actions to Linear/calendar automatically via Claude agent- One meeting. One mirror workflow. Ship it. Stack from there.--# TOOLS MENTIONED- Motion AI Exec Coach (meeting scoring)- Granola (local-first meeting notes)- Zapier (automation)- Fireflies (meeting transcription)- Claude Desktop / Claude Code (local file analysis)- Linear (task routing)--# ABOUT DEARBEN.AIPractical AI for CEOs who don't have time to become AI experts.Ben Fisher — 2x CEO, 3x CTO.A founder-to-founder experiment answering real AI questions from operators running real companies.Ask yours at https://DearBen.ai--# CONNECTWebsite: https://DearBen.aiLinkedIn: https://fshr.co/profileX: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy for more information.

    17분
  2. How Do I Turn Conversations Into Actual Work Artifacts?

    2025. 12. 20.

    How Do I Turn Conversations Into Actual Work Artifacts?

    Work happens in conversations. The problem is it stays there.You hash out a product idea, talk through requirements, make decisions — and then somehow you're supposed to recreate all of that in a document later. That's where everything falls apart.I use AI to extract the work that already happened and turn it into artifacts that keep the momentum going. PRDs, user stories, requirements — pulled straight from the conversation.Ask your own question at DearBen.ai.--# SHOW NOTES• Work happens in conversations — but it stays trapped there• The "missing middle" — decisions made verbally rarely become documents• Extract the work, don't recreate it — AI pulls out what you already figured out• Zero-draft artifacts — PRDs, user stories, requirements from the conversation itself• Pressure-test with clarifying questions — surface gaps before you build• 95% of the work already done — you just need to extract it--# TOOLS MENTIONED• Fireflies.ai — Meeting recording and transcription• Claude Desktop — Extraction and synthesis• Claude Code — Workflow automation• claude-code-requirements-builder — Requirements extraction workflow--# ABOUT DEARBEN.AIPractical AI for CEOs who don't have time to become AI experts.Ben Fisher — 2× CEO, 3× CTO.A founder-to-founder experiment answering real AI questions from operators running real companies.Ask yours at https://DearBen.ai--# CONNECTWebsite: https://DearBen.aiLinkedIn: https://fshr.co/profileX: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy for more information.

    11분
  3. Behind the Build: How I Prep Dear Ben Episodes with AI (Part 1)

    2025. 12. 20.

    Behind the Build: How I Prep Dear Ben Episodes with AI (Part 1)

    This isn't a Q&A episode — it's for builders who want to see how I actually work.I walk through using Claude Code and Every's skill creator to build the system that helps me prepare for Dear Ben episodes. The process: do it manually first, pay attention to what you repeat, then systematize.Ask your own question at DearBen.ai.--# SHOW NOTES• Do it manually first, then systematize — I did this process by hand several times before building the automation• AI is probabilistic, not deterministic — the agent built the skill but forgot to create the slash command• ChatGPT's Prompt Optimizer genuinely improves prompt efficacy, even for Claude• The LLM asking questions extracts your thinking — it's a brainstorming tool that forces you to articulate what you believe• Four phases: Ideation, Content Development, Proof of Concept, Blind Spots--# TOOLS MENTIONED• Claude Code• ChatGPT Prompt Optimizer• Every's Skill Creator Agent--# ABOUT DEARBEN.AIPractical AI for CEOs who don't have time to become AI experts.Ben Fisher — 2× CEO, 3× CTO.A founder-to-founder experiment answering real AI questions from operators running real companies.Ask yours at https://DearBen.ai--# CONNECTWebsite: https://DearBen.aiLinkedIn: https://fshr.co/profileX: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy for more information.

    24분
  4. How Do I Index Sales Collateral So My Team Can Find It?

    2025. 12. 20.

    How Do I Index Sales Collateral So My Team Can Find It?

    Murali asked: "I run a 600-person software dev agency. How do I index our sales material so my team can actually find what they need?"Before jumping to AI, ask: is this a process problem or a familiarity problem? When the people creating docs aren't the ones searching, semantic search creates real leverage.Ask your own question at DearBen.ai.--# SHOW NOTES• First question: is this a structure problem? At 600 people with creators ≠ searchers, it's not• Lindy gives full visibility into prompts — you can tweak and experiment, not just hope it works• The agent builder gets you 85% there; you course correct the rest• Use a smaller model for retrieval — it's not reasoning, save budget for generation• 5-minute setup: Google Drive → Lindy → Slack integration• Future extension: calendar triggers that auto-fetch docs before meetings--# TOOLS MENTIONED• Lindy AI — automation platform with prompt visibility and agent builder• Fireflies — AI note-taker with real-time knowledge base features (bonus)--# ABOUT DEARBEN.AIPractical AI for CEOs who don't have time to become AI experts.Ben Fisher — 2× CEO, 3× CTO.A founder-to-founder experiment answering real AI questions from operators running real companies.Ask yours at https://DearBen.ai--# CONNECTWebsite: https://DearBen.aiLinkedIn: https://fshr.co/profileX: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy for more information.

    8분
  5. How Do I Win at AI Search When Nobody Really Knows the Rules?

    2025. 12. 09.

    How Do I Win at AI Search When Nobody Really Knows the Rules?

    Henry asked: "What's your best practice advice for winning AI search? Nobody really knows how to game the system."There's a lot of speculation presented as fact in this space. But practitioners who've been deep in SEO are starting to converge on real patterns. I brought in Chirag from Taco to break down what's actually working.Ask your own question at DearBen.ai.---# SHOW NOTES• LLMs run web searches behind the scenes — if you don't rank on Google, you probably won't rank in ChatGPT• Turn keywords into questions: "dandruff shampoo" becomes "what are the best dandruff shampoos for men?"• Identify where LLMs pull citations from — Reddit, listicles, authoritative publications in your vertical• Create content on third-party sites that LLMs already trust (Reddit threads, guest posts, affiliate sites)• Spam tactics get plugged fast — same as traditional SEO• Some startups have leapfrogged traditional SEO for LLM placement (Lenny's podcast goes deeper)--# FEATURINGChirag Kulkarni — Founder & CEO, Taco (AI-powered SEO agency)Forbes 30 Under 30 (Marketing). Former CMO at Medly Pharmacy (scaled 1→50 pharmacies, $100M+ revenue).• Website: https://taco.co/• LinkedIn: https://www.linkedin.com/in/chiragkulkarni/--# TOOLS MENTIONED• Scrunch• Air Ops• Profound--# ABOUT DEARBEN.AIPractical AI for CEOs who don't have time to become AI experts.Ben Fisher — 2× CEO, 3× CTO.A founder-to-founder experiment answering real AI questions from operators running real companies.Ask yours at https://DearBen.ai--# CONNECTWebsite: https://DearBen.aiLinkedIn: https://fshr.co/profileX: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy for more information.

    5분
  6. Behind the Build: Building a Sales Collateral Bot with Lindy (Part 2)

    2025. 12. 04.

    Behind the Build: Building a Sales Collateral Bot with Lindy (Part 2)

    Part 2 of the behind-the-scenes series. I take Claude's workflow spec and build it in Lindy — and debug it live when things break.The lesson: check templates first before building from scratch. Lindy has out-of-the-box knowledge base templates I could have started with.Ask your own question at DearBen.ai.--# SHOW NOTES• Check templates first — Lindy has out-of-the-box knowledge base templates I should have used• Debug in public — Google connections drop, folder IDs get lost, agents hang• Multiple approaches exist — agent-built workflow vs. template, different tradeoffs• Token efficiency matters — different workflow structures have different credit consumption• Use Claude to generate test data — I had it create 10 fake sales documents for the demo--# TOOLS MENTIONED• Lindy AI (agent builder, knowledge base templates)• Google Drive integration• Slack integration--# ABOUT DEARBEN.AIPractical AI for CEOs who don't have time to become AI experts.Ben Fisher — 2× CEO, 3× CTO.A founder-to-founder experiment answering real AI questions from operators running real companies.Ask yours at https://DearBen.ai--# CONNECTWebsite: https://DearBen.aiLinkedIn: https://fshr.co/profileX: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy for more information.

    11분
  7. How Do You Manage Junior Devs Using AI to Build Beyond Their Skill Level?

    2025. 11. 26.

    How Do You Manage Junior Devs Using AI to Build Beyond Their Skill Level?

    Jason asked: "How do you manage junior developers when they're using AI to build systems more sophisticated than they understand?"The solution isn't more oversight — it's constraints that force understanding. I share three practices that work together.Ask your own question at DearBen.ai.---# SHOW NOTES• Spec-driven development: write what the system should do in plain language before any code• Opinionated frameworks: use Next.js or T3 stack to prevent AI from inventing architecture• Test-driven validation: understand what each test proves, not just that tests exist• Why these three rules create the same constraint: forced understanding• Bonus: invest in a fractional coach for code reviews and AI workflow guidance--# TOOLS MENTIONED• Next.js• T3 Stack--# ABOUT DEARBEN.AIPractical AI for CEOs who don't have time to become AI experts.Ben Fisher — 2× CEO, 3× CTO.A founder-to-founder experiment answering real AI questions from operators running real companies.Ask yours at https://DearBen.ai--# CONNECTWebsite: https://DearBen.aiLinkedIn: https://fshr.co/profileX: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy for more information.

    5분
  8. Can AI Create My Content, Let Me Approve It, and Post It Everywhere?

    2025. 11. 26.

    Can AI Create My Content, Let Me Approve It, and Post It Everywhere?

    Jeff asked: "Can AI generate my content, let me approve it in Slack, then auto-post to LinkedIn, X, and Reddit?"The orchestration is easy — scheduling, APIs, multi-platform posting. That's solved. The hard part is content quality. Getting AI output that doesn't sound like AI.Ask your own question at DearBen.ai.---# SHOW NOTES• Why orchestration (scheduling, APIs) is the easy part — every platform handles that• The real bottleneck: content quality and voice consistency• AI writing tools vs. automation platforms: black boxes vs. build-it-yourself• Lindy as middle ground: prompt visibility + Slack review + workflow automation• 15-minute proof-of-concept walkthrough with Claude Sonnet 3.5• Year one cost: ~$2,100 (vs. 260 hours of manual content creation)--# TOOLS MENTIONED• Lindy.ai• Zapier.com / Make.com--# ABOUT DEARBEN.AIPractical AI for CEOs who don't have time to become AI experts.Ben Fisher — 2× CEO, 3× CTO.A founder-to-founder experiment answering real AI questions from operators running real companies.Ask yours at https://DearBen.ai--# CONNECTWebsite: https://DearBen.aiLinkedIn: https://fshr.co/profileX: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy for more information.

    13분
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Practical AI for CEOs Who Don’t Have Time for BS Hosted on Ausha. See ausha.co/privacy-policy for more information.

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