- 8
- Episodes
- 2025
- First episode
About Dear Ben
Practical AI for CEOs Who Don’t Have Time for BS Hosted on Ausha. See ausha.co/privacy-policy for more information.
- Publisher
- Ben Fisher
- Category
- business · technology
- Language
- en
- Explicit
- No
- First episode
- 26 Nov 2025
- Latest episode
- 17 Jan 2026
Latest episodes
8 episodes in the feed.
17 Jan 2026
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.AI Practical 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 -- # CONNECT Website: https://DearBen.ai LinkedIn: https://fshr.co/profile X: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy (https://ausha.co/privacy-policy) for more information.
20 Dec 2025
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.AI Practical 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 -- # CONNECT Website: https://DearBen.ai LinkedIn: https://fshr.co/profile X: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy (https://ausha.co/privacy-policy) for more information.
20 Dec 2025
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.AI Practical 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 -- # CONNECT Website: https://DearBen.ai LinkedIn: https://fshr.co/profile X: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy (https://ausha.co/privacy-policy) for more information.
20 Dec 2025
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.AI Practical 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 -- # CONNECT Website: https://DearBen.ai LinkedIn: https://fshr.co/profile X: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy (https://ausha.co/privacy-policy) for more information.
9 Dec 2025
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) -- # FEATURING Chirag 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.AI Practical 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 -- # CONNECT Website: https://DearBen.ai LinkedIn: https://fshr.co/profile X: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy (https://ausha.co/privacy-policy) for more information.
4 Dec 2025
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.AI Practical 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 -- # CONNECT Website: https://DearBen.ai LinkedIn: https://fshr.co/profile X: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy (https://ausha.co/privacy-policy) for more information.
26 Nov 2025
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.AI Practical 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 -- # CONNECT Website: https://DearBen.ai LinkedIn: https://fshr.co/profile X: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy (https://ausha.co/privacy-policy) for more information.
26 Nov 2025
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.AI Practical 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 -- # CONNECT Website: https://DearBen.ai LinkedIn: https://fshr.co/profile X: https://x.com/skinnyandbald Hosted on Ausha. See ausha.co/privacy-policy (https://ausha.co/privacy-policy) for more information.
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