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Co-Authored and Uploaded by R.I.F.F. — Darby’s AI Chief of Staff
Most people use AI to write emails faster. I use it to run my business.
Not in a “set it and forget it” way. In a “my AI knows my sponsor pipeline has 308 brands, knows which press outlets cover entrepreneurship events in Austin, and can launch a show in a new city with a single command” way.
This is the AI Chief of Staff — and it’s built entirely on Claude’s ecosystem.
I’m going to walk you through the whole thing: the platform, the architecture, the 31 custom skills I’ve built, and how they work together to run SideHustle LIVE (a comedy game show for entrepreneurs — think Shark Tank meets interactive improv), Gen AI University (where I teach this stuff), and a full book production pipeline. By the end, you’ll understand what’s possible when you stop treating AI as a chatbot and start treating it as your most capable team member.
Before we get into the skills, you need to understand the foundation. Claude isn’t one product — it’s an ecosystem with three layers that stack on top of each other.
Claude Cowork is the desktop experience where you interact with your AI Chief of Staff. Think of it as the command center. You talk to Claude in natural language, and it has access to your files, your connected tools, and your custom skills. It runs in a secure sandbox on your computer, which means it can actually create documents, build spreadsheets, generate presentations, and write code — not just talk about doing those things.
The key insight: Cowork isn’t just a chat window. It’s an execution environment. When I say “run MarketSauce PRIME for this prospect,” Claude doesn’t just describe what a market analysis would look like. It researches the market, builds a 10-phase diagnostic, generates a professional Word document, and hands me a downloadable file. That’s the difference between a chatbot and a Chief of Staff.
Claude Code is the command-line tool that powers the skill-building side. This is where the magic gets made. Claude Code lets you create skills — reusable instruction sets that give Claude deep expertise in specific domains. Think of skills as specialized training manuals that Claude reads before executing a task.
When I build a new skill, I’m essentially writing a detailed playbook: here’s how to think about this problem, here are the inputs you need, here are the phases of execution, here’s what the output should look like. Claude Code is how those playbooks get created, tested, and refined.
Here’s where it clicks. Claude Cowork is the interface where you work. Skills are the intelligence layer that makes Claude an expert. And MCP connectors (more on those next) are the arms and legs that let Claude reach into your actual business tools.
The result: you sit in Cowork, issue a command in plain English, Claude activates the right skill, pulls data from your connected tools, executes a multi-step workflow, and delivers the output — all without you touching a single spreadsheet, CRM, or project management tool.
A Claude skill is a structured instruction set that transforms Claude from a general-purpose AI into a domain expert. Without skills, Claude is brilliant but generic. With the right skill loaded, Claude becomes a market researcher, a PR agency, a show producer, or a book editor — with deep knowledge of your specific business, your frameworks, and your standards.
Here’s what makes skills different from a regular prompt:
They’re persistent. You install a skill once and it’s always available. You don’t re-explain your process every conversation.
They’re composable. Skills can call other skills. My SideHustle Chief of Staff skill orchestrates eight other skills depending on what the situation demands.
They’re buildable. You don’t need to be a developer. If you can describe how you do something step by step, you can build a skill. (I have a skill that builds other skills — more on that later.)
They have execution modes. Most of my skills have multiple modes. MarketSauce PRIME can run Express (2 phases, quick clarity), Strategic (5 phases, core diagnostic), or Full Diagnostic (all 10 phases with implementation roadmap). You pick the depth based on what you need.
The mental model: skills turn Claude into a team of specialists that all share your context, your standards, and your business knowledge.
Skills give Claude expertise. MCP integrations give Claude access.
MCP stands for Model Context Protocol, and it’s the standard that lets Claude connect to external tools. Without MCPs, Claude is smart but isolated — it can think but it can’t act. With MCPs, Claude can read your email, update your CRM, post to Slack, check your calendar, scrape websites, create Canva designs, and manage your Notion workspace.
Here’s what I have connected right now:
Communication & Collaboration: Gmail (read, draft, send), Slack (search, post, create canvases), iMessages (read and send)
CRM & Sales: HubSpot (full CRM access — contacts, companies, deals, tickets, pipelines), Stripe (customers, subscriptions, invoices, payments), Clay (contact enrichment, prospect research)
Content & Design: Canva (generate designs, manage brand kits, export assets), Webflow (manage site content, CMS, pages, components), Gamma (AI-powered presentation generation)
Productivity: Google Calendar (events, scheduling, free time), Google Drive (files, folders, documents, sheets), Google Docs (create, edit, format), Google Sheets (full spreadsheet operations), Notion (pages, databases, comments), Apple Notes (read, write, search)
Research & Intelligence: Firecrawl (web scraping, site mapping, content extraction), web search and fetch capabilities
Automation: Make.com (scenarios, webhooks, data stores — the automation backbone)
Meeting Intelligence: Granola (meeting transcripts and notes)
Deployment: Vercel (deploy sites, check build logs, manage projects), Netlify (deploy services, project management)
Community: Skool (invite members, unlock courses)
The power isn’t in any single connection. It’s in the combinations. When my Content Distribution Engine skill runs, it can pull show details from Notion, generate YouTube metadata, create social posts, draft email campaigns through Gmail, and schedule content — all in one execution. That’s what “Chief of Staff” actually means in practice.
Here’s the part that makes this practical for real life: Claude Dispatch lets you manage your AI Chief of Staff from your phone.
You’re at a coffee meeting and a potential sponsor comes up. You pull out your phone, tell Claude to run a Web Recon on their website, and by the time you’re back at your desk, you have a full intelligence report — company overview, partnerships, strategic observations, and recommended angles for outreach.
You’re driving to a venue and remember you need to check the show cycle status. You ask Claude, and it tells you exactly which production milestones are on track, which are overdue, and what needs to happen this week.
Dispatch turns the AI Chief of Staff from a desktop tool into an always-available executive partner. The skills, the connectors, the intelligence — it’s all accessible from a text message-style interface on your phone.
Beyond on-demand skills, the AI Chief of Staff runs scheduled automations that execute without me lifting a finger.
Daily PR Agency (8:00 AM every morning) — Every morning before I’m even at my desk, Claude scans for podcast guest opportunities, press pitch angles, speaking opportunities, and media mentions across both SideHustle LIVE and Gen AI University. It checks recent coverage, identifies new outlets to pitch, and flags time-sensitive opportunities. This isn’t a digest — it’s an active PR agent identifying the highest-leverage media moves for the day and drafting outreach when it finds something worth pursuing.
Weekly Pipeline Cadence (Mondays at 9:00 AM) — Every Monday, Claude sweeps the entire Notion pipeline and flags follow-ups based on a tiered cadence: 3 days after initial contact, then weekly, then monthly, then every 6 months, then annually, with a 90-day re-engagement trigger for cold leads. It knows who’s overdue, who needs a touch, and who’s gone cold. No lead falls through the cracks because the system is always watching.
These scheduled automations are the difference between “I have an AI tool” and “I have an AI team member.” They run in the background, surface what matters, and keep the operation moving even when I’m focused on something else entirely.
This is the part everyone asks about. Let me walk you through every skill I’ve built, what it does, and why it exists. These aren’t theoretical — every single one is in production, handling real work, every week.
SideHustle Chief of Staff — The master orchestrator that sits above all SideHustle operations. Think of it as the CEO brain of the operation. It assesses current state across every dimension — shows, sponsors, content, press, talent — determines what needs to happen next, and executes the right skills in the right sequence. When I say “what should we be doing?” this is what answers. It knows every skill, understands dependencies between them, and routes work to the right specialist automatically.
MarketSauce PRIME — The flagship. A 10-phase market diagnostic that combines deep buyer psychology, competitive intelligence, Blue Ocean strategy simulation, and implementation roadmapping. It starts with “The Question Before The Question” — most entrepreneurs optimize for speed without direction. PRIME forces clarity on what you’re actually building toward. It runs in four modes (Express, Strategic, Full Diagnostic, Interactive) and outputs a professional Word document plus a standalone system prompt for ongoing AI-powered marketing execution. The core philosophy: find the small hinge — the 2-3 opportunities where minimal input creates maximum movement.
MarketSauce PRIME Legacy — The original recipe diagnostic, maintained alongside the current version. Some clients prefer the classic 10-phase format with the original SWOT-to-Blue-Ocean flow. Having both versions means I can match the diagnostic style to the client’s thinking preference rather than forcing everyone through the same pipeline.
MarketSauce Blueprint — The buyer psychology deep dive. Generates detailed Buyer’s Briefs, Creative Briefs, and content strategies with psychosocial insights. If PRIME tells you where the opportunity is, Blueprint tells you exactly how to talk to the humans in that opportunity. Audience segmentation, pain point mapping, objection handling, brand voice, and social content strategy — all in one execution.
Press Chief — A full PR agency in a skill. Generates exhaustive media databases with 100+ outlets across 15+ categories, customized outreach templates for each outlet type, and distribution checklists. Give it an event and a city, and it builds the entire press strategy — from local lifestyle blogs to national entertainment outlets.
Media Relations — The enhanced version that adds automated distribution workflows and coverage tracking. Press releases, customized pitch emails by outlet type, and reports that track what’s been sent, who’s responded, and what coverage you’ve landed. This works hand-in-hand with the daily PR automation — the skill builds the strategy, the automation executes it every morning.
Content Signal Scanner — The research engine. Scans top creators on LinkedIn and Instagram, identifies outlier posts with 1.5x-3x above-average engagement, and extracts the patterns — trending topics, hooks, formats, hashtags, keywords. It also builds curated networks of founder/entrepreneur/creator profiles. This is how you figure out what’s actually working in your niche before you create anything.
Content Distribution Engine — Described internally as “the highest-leverage agent in the SideHustle system.” It transforms every live show into a multi-platform content machine: YouTube episode metadata, clip strategies identifying the 5-10 most clip-worthy moments, Shorts scripts for YouTube/Reels/TikTok, cross-platform posting schedules, and monthly growth reports. The philosophy: every dollar of future revenue traces back to YouTube reach. This skill systematizes the entire pipeline.
Content Ops Architect — The team management layer. Interview preparation for content hires, transcript auditing, performance analysis, and content optimization across omni-channel teams. Built for scaling to 800+ pieces per week. Outputs actionable playbooks with quick wins, long-term initiatives, and implementation roadmaps.
Brand Discovery Enhanced — The sponsor prospecting engine. Runs a systematic 5-phase discovery protocol, scores and qualifies leads, deduplicates against the existing CRM pipeline (308 records and counting), and generates monthly discovery batch reports. It knows what’s already in the pipeline so it never wastes time on duplicates.
Brand Discovery Protocol — The original Austin-focused version. Systematic protocol for discovering local brands and partners aligned with SideHustle LIVE’s entrepreneurial comedy event format. Uses Firecrawl for web research and extracts founder/partnership contact information.
Sponsor Outreach — Moves sponsors from Prospect to Confirmed. Generates personalized outreach messages, follow-up sequences, pre-call briefs for meetings, and pipeline velocity reports. When a lead goes stale, this skill knows how to re-engage them. When a meeting is coming up, it preps you with everything you need.
Vendor Roster Scout — This one is strategically brilliant. Instead of selling to corporate clients directly, SideHustle LIVE gets on vendor rosters at DMCs (Destination Management Companies), corporate retreat planners, and team-building agencies. One strong DMC relationship can generate 5-15 corporate bookings per year with zero outbound sales. This skill finds those companies, identifies the exact person who manages their vendor roster, pulls their contact info, and drafts the personalized outreach to get listed.
Show Production — The logistics brain. Generates production runsheets, payment trackers, sponsor activation checklists, day-of timelines, and post-show financial summaries. Everything from T-30 (30 days before the show) through post-show wrap-up.
Show Cycle Controller — The master orchestrator for show milestones. Maps all operational skills to production timelines, generates cycle checklists, tracks progress across all agents, and tells you exactly what to run and when. This is the skill that answers “where are we on the next show?” with a comprehensive status across every operational dimension.
Talent Scout — Sources, vets, and manages performers and entrepreneurs for shows. Maintains a talent bench with performance ratings, coordinates scheduling, tracks cast diversity, and generates cast recommendations. Currently managing a roster of 26+ performers.
Event Marketing — Fills seats and builds audience between events. Social media campaigns, email sequences, direct outreach messages, ticket velocity tracking, and post-show engagement reports. The full demand generation engine.
SideHustle Launch Cascade — One trigger, three skills, complete event launch package. Chains MarketSauce PRIME (Express mode for local market analysis) → CRIT Session (to refine the campaign approach) → Press Chief (for media outreach database). The philosophy: “One Domino Topples Three.” Each phase feeds the next, and context compounds as it goes.
Brand Asset Generator — Connects directly to Canva MCP and Gamma MCP for on-brand visual asset creation. Takes brand identity inputs — colors, personality, voice, visual style — and enforces brand standards across all generated designs. When you need a social graphic, a presentation, or event collateral, this skill ensures everything looks like it came from the same brand, not from a random AI prompt.
SideHustle Image Style — The visual brand bible in skill form. Generates on-brand image prompts for all SideHustle LIVE visuals — social graphics, event flyers, merch shots, thumbnails, everything. Ensures visual consistency across every AI-generated image. When you’re producing content at scale, brand drift is the silent killer. This skill prevents it.
CRIT Sessions — Based on Geoff Woods’ CRIT framework from The ONE Thing methodology. A structured questioning system: Context (clarify the situation), Role (who’s involved), Interview (surface assumptions and gaps), Task (clarify the action needed). When you don’t know the answer to a refining question, Claude consults expert panels — digital twins of relevant specialists — to fill in the gaps. This is how I make better decisions, not just faster ones.
Web Recon — Autonomous website reconnaissance. Scrapes any website via Firecrawl, maps full site architecture, analyzes key pages, and produces a standardized intelligence report with product/service overview, current events and partnerships, and strategic observations with recommendations. Drop a URL, get a 3-page dossier.
Sales Research Prospect — Pre-outreach intelligence gathering. Research prospects from web, social, and company data before cold outreach, discovery calls, or account planning. Never go into a meeting cold again.
Book Production Conductor — A full 7-phase book production system, from raw idea to published book. Phase 0 (Concept) uses the Book Idea Validator and Purpose Finder. Phase 1 (Outline) uses the Outline Architect. Phase 2 (Research) runs per-chapter research across five tracks — Amazon competitor scan, keyword intelligence, review mining, source curation, and differentiation analysis. Phases continue through Brand, Write, Edit, and Launch. The Conductor orchestrates all of it, assessing where the project is and routing to the right specialist skill automatically.
Book Editor Elite — A 7-pass editorial system operating at Big Five / Hay House publishing standards. Each pass has a specific focus: Developmental editing (structure and argument), Argument & Logic (coherence and evidence), Line Edit (sentence-level craft), Voice & Style (author’s unique sound), Copyedit (grammar and consistency), Fact-Check (verifiable claims), and Proofread (final polish). Produces an edited manuscript, a comprehensive Style Sheet, and an Editorial Report. This is the same editorial rigor you’d get from a top publishing house.
Book Citation Auditor — Autonomous citation research and fact-checking engine. Extracts every citable claim chapter by chapter, fires parallel Firecrawl searches to find peer-reviewed sources, verifies statistics and named studies, flags errors, and compiles a professional Citation Research Dossier with color-coded status and action items. This runs before copy editing to catch factual issues early.
Published Pathway Assessment — Book publishing diagnostic based on Chandler Bolt’s “SPS 90-Day Way” framework from Published. Diagnoses where an author is stuck in the writing-to-published journey and produces a personalized assessment: blocker diagnosis, next 3 moves, 90-day roadmap, and launch strategy recommendation. This is often the first skill fired for someone who says “I want to write a book but I’m stuck.”
SelfPublishing AI Platform — The final mile. Compiles all book pipeline outputs into a single copy/paste-ready document organized by the SelfPublishing.AI platform’s 9-step wizard: Author Info, Book Details, Target Audience, Front Cover, Back Cover, Writing Style, Structure Options, Materials, Outline. When everything else is done, this skill packages it for actual publishing.
Skill Creator — The meta-skill. Creates new skills from scratch, runs evaluations to test them, benchmarks performance with variance analysis, and optimizes skill descriptions for better triggering accuracy. This is how the library grows. It handles the full loop: decide what you want → write a draft → create test prompts → evaluate results → rewrite based on feedback → repeat until quality standards are met.
Expert Method Skill — The skill factory. Feed it any expert’s book, framework, or methodology, and it produces a complete, installable skill package with diagnostic assessment built in. The output isn’t a book summary — it’s an interactive AI agent that meets users where they are and moves them forward. The core insight: “The diagnostic layer is what separates ‘here’s what the book says’ from ‘here’s exactly where you’re stuck and what to do next.’”
Luma Cocktail Bio — Transforms Luma event attendee data into perfectly formatted cocktail party bios using Nick Gray’s 2-Hour Cocktail Party framework. Generates host intro scripts, name tag bios, and attendee profiles for warm introductions. Small skill, massive impact on event quality.
Workshop Breakdown — Transforms workshop recordings and transcripts into comprehensive executive briefs with participant wins, technical demonstrations, cross-pollination opportunities, and actionable insights. Outputs a downloadable Word document ready for participant distribution.
If you’re wondering about the technical side, it’s simpler than you’d think.
A skill is essentially a markdown file (SKILL.md) that lives in a specific folder on your system. Some skills also have reference files — supporting documents, templates, or data that the skill draws on during execution. The skill file contains the instructions, execution modes, required inputs, output formats, and the thinking framework Claude should use.
When Claude starts a session, it sees all available skills and knows when to activate each one based on trigger phrases and context. You say “run MarketSauce PRIME,” and Claude reads the SKILL.md file, follows the protocol, and delivers the output. No API configuration, no coding required for basic skills.
For the connectors (MCPs), each integration gets configured once — authenticate with your Google account, connect your HubSpot, link your Slack workspace — and then it’s available to every skill that needs it. The beauty is that skills and connectors are modular: add a new connector, and every relevant skill immediately gets access to that new capability.
Here’s the thing most people miss: what I’ve described isn’t a novelty project. It’s a production system that handles real operational work every week. The sponsor pipeline gets managed. Shows get produced. Content gets distributed. Books get written. Press gets pitched. And the scheduled automations keep everything moving even when I’m not looking.
But it took hundreds of hours to build, test, and refine. The skills have been through dozens of iterations. The orchestration patterns — how skills call other skills, how outputs feed between phases — that took real architectural thinking.
That’s why I built Gen AI University.
Gen AI University is where I teach entrepreneurs and operators how to build this for their own business. Not in theory. In practice. You’ll build your own custom skills, connect your own tools, and walk away with an AI Chief of Staff that actually knows your business.
The teaching philosophy is experiential. You don’t watch me do it — you build it live, with guidance, and you leave with something that works. The same way I built this system: one skill at a time, each one solving a real problem, each one making the whole system more capable.
The Claude Mastery Series — Deep-dive training on building skills, configuring MCPs, and architecting AI workflows for your specific business. This isn’t “intro to AI” content. This is the builder’s curriculum. Each session covers a specific skill from my production library — how it was built, why it works, and how to adapt it for your business.
VIP Hackathon Days — Two-day intensives where company teams build their AI Chief of Staff from scratch. You come in with your business processes and leave with working automations. The next one features Adelle Archer, CEO of Eterneva (a Shark Tank-backed memorial diamond company), on April 11 — building a complete AI Chief of Staff for her business live, as a case study you can learn from.
1:1 VIP Days — The highest tier. I come in (virtually or in-person) and install your AI Chief of Staff in a single day. We map your operations, identify the highest-leverage automations, build the skills, connect the tools, and hand you a working system before the end of the day.
The Community — Entrepreneurs and operators who are actually implementing, not just talking about AI. Share skills, troubleshoot integrations, and learn from what’s working across different industries.
If there’s one takeaway from this entire system, it’s this: the leverage isn’t in any single skill. It’s in the architecture.
One skill saves you an hour. Thirty-one skills that share context, call each other, and compound their outputs — that replaces a department.
The AI Chief of Staff isn’t coming. It’s here. The question is whether you’ll build yours, or keep writing emails by hand while your competitors automate their operations.
Ready to build your own AI Chief of Staff?
Join Gen AI University and get access to the Claude Mastery series, live build sessions, VIP Hackathon days, and a community of entrepreneurs who are actually shipping AI implementations — not just talking about them.
Next up: Adelle Archer VIP Workshop — April 11. Two days. Your business processes in, working AI automations out.
Darby Rollins is the founder of Gen AI University and SideHustle LIVE (“Shark Tank meets interactive improv for entrepreneurs”). He builds custom Claude skills and MCP integrations that turn AI from a chatbot into an operational partner.
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