Bob Sails: Make Your Business AI-Ready (Without Losing Your Mind)
A structured curriculum for solopreneurs and scaling business operators who want to sail into the age of AI with confidence. Baby steps to the boat and strap yourself to the mast.
- Deploy 3 automations within 30 days
- Save $15K+ on avoided tech mistakes in year one
- Build systems your future AI agents can actually use
Built for Solo Sailors and Scrappy Crews
Solopreneurs & Freelancers
Who are the marketing team, ops team, and tech team—all at once
Service and Agency Owners
Who want clean pipelines, cleaner data, and automations that actually reflect reality and accelerate process.
Ops-Minded Founders
Who know their next bottleneck isn't more leads—it's systems, documentation, and smart automation so you can scale with agents.
If you've ever thought, "AI sounds great, but my business is too messy for that right now," this is exactly for you.
Strap Yourself to the Mast. Sail Into the Age of AI.
Most business owners feel the shift: AI is everywhere… but your information is nowhere.
It's in Google Drive, inboxes, text threads, random spreadsheets, and that one Notion page you swore you'd "come back to later."
Bob Sails is a free, practical curriculum that helps you:
- ✓Clarify what your business does and for whom
- ✓Clean up how information flows through your organization
- ✓Design systems and workflows that AI agents can plug into without breaking everything
This isn't "prompt hacks." It's how to architect your business so AI becomes a force multiplier—not another shiny distraction.
Inside the Bob Sails Curriculum
17 modules available

Charting Your Course: Mission & Vision for the Solo Sailor

Find real customer pains, craft a sharp value proposition, and validate fast.

Map your customer journey, design offers that meet intent, and align messaging across every stage.

Turn your value proposition into clear, consistent messages and high-converting copy across pages, emails, and ads.

Turn your message into a high‑clarity landing page, capture leads, and run a simple welcome funnel.

Pick the right channels, build a 30‑day content engine, personalize with your CRM, and measure what matters.

Measure what matters (PMF signals), run small experiments, and make confident persevere/pivot calls.

Design retention loops, measure loyalty (NPS + churn), and build advocacy through community and referral programs.

Design value-based pricing, check unit economics (LTV, CAC, margins), and model runway so you scale with confidence.

Install a simple, ethical sales system: qualification → discovery → demo → proposal → close, plus a lightweight partner/referral motion.

Catalog every core process, assign owners, and publish an Operating Manual index that links all specs.

Define lifecycle stages with entry/exit criteria, a clean data dictionary, enforceable data contracts, automations, dedupe rules, consent basis, and QA checks.

Define clear pipeline stages with observable exit criteria, set stage SLAs (speed-to-lead, follow-up rhythm), select a qualification model, and align stages to forecast categories.

A clear, 30-day onboarding that delivers first value fast: timeline, checklist, welcome pack, ‘Definition of Done’, risks, and metrics.

Publish a simple, auditable delivery process: start/stop, steps, acceptance criteria vs. Definition of Done, QA checklist, change/rework rules, and clean hand-offs.

Retention keeps the boat afloat; referrals and partnerships catch wind. In this module, you’ll design a practical referral system (who asks whom, when, and why), set up a partner playbook, and build tracking that doesn’t require a spreadsheet PhD. You’ll map your referral loop, write scripts you can actually send, set up automation in your CRM, and connect your outcomes to real revenue so you can scale what works.

Referrals and partnerships bring warm introductions—but you still have to convert. In this module, you’ll build a sales operating system: discovery that uncovers real pain, qualification that protects your time, a proposal format that reduces confusion, and a follow-up cadence that feels human (not desperate). You’ll translate it all into a pipeline in your CRM, automate reminders and next steps, and define the metrics that keep you improving week over week.
From Vision → Systems → AI Agents
Set Your Course (Mission, Vision, Offers)
Articulate a mission and vision that actually guide decisions. Use simple frameworks to design offers and value propositions that fit real customer needs.
Know Your People & Your Market
Segment your audience and build buyer personas. Validate demand with lean experiments, surveys, and AI-assisted research. Find and iterate toward product-market fit using simple, repeatable tests.
Design an AI-Ready Business Model
Mix revenue models (subscription, one-time, micro-SaaS, affiliate) without losing operational sanity. Use ERPs or CRMs and similar tools to centralize data so AI can see the whole picture. (We'll show you low cost, affordable, and scalable options.
Blueprint Your Systems & Information Flows
Map your key domains (sales, delivery, support, finance). Turn messy reality into clean process maps and technical diagrams. Create a "source of truth" that your future AI agents can safely act on.
Automate, Then Add Intelligence
Build practical automations with n8n that connect your site, CRM, ERP, and communication channels. Use GoHighLevel as your external brain for leads, follow-ups, and campaigns. Layer in AI + LLMs for content, support, and decision support once the pipes are clean.
Make AI Your Force Multiplier
Learn the basics of generative AI and LLMs in plain English. Practice prompt design as process design—so AI shows up as a useful teammate, not a toy. Build simple exercises where AI generates marketing assets from structured forms and checklists you design.
AI Is Only as Smart as the Systems You Give It
Most people start with, "What prompts should I use?"
Bob Sails starts with, "What does my business need AI to see, understand, and do?"
By the end of the curriculum you'll have:
- ✓Clear mission, offers, and audience definitions for your models to condition on
- ✓Clean(er) processes, pipelines, and data structures that AI agents can plug into
- ✓Automations and workflows that AI can augment instead of accidentally break
You're not just learning AI—you're architecting an AI-ready company.
Short Lessons. Concrete Outputs. No Fluff.
Most core sessions are in the 10–20 minute range, plus walkthroughs and templates.
Every lesson ends in a real artifact: a canvas, a map, a workflow, or a snippet of automation you can actually use.
You don't have to "finish the course" before you get value. Implement as you go: one canvas, one process, one automation at a time.
- Full access to all Bob Sails modules
- Downloadable worksheets, forms, and prompt templates
- Example workflows for n8n, GoHighLevel, and AI tools