90-Day Business Buildout

This 90-day plan is for experienced IT professionals who suddenly find themselves without the structure of a traditional employer. The goal is to replace the missing “professional identity” with a new one built from the ground up - deliberately, methodically, and supported by modern tools like ChatGPT.

By the end of this plan, you will have:

• a complete brand identity
• a professional website
• cohesive presence across digital platforms
• a functioning LLC
• a business bank account
• a Stripe account
• a clear set of services or offers
• basic financial hygiene
• a repeatable system for content and communication
• the infrastructure to earn your first dollar
• the confidence that you are a business, not a job seeker

This plan operates on three layers:

1. Identity - who you are as a professional brand
2. Presence - how the world finds and understands you
3. Business Infrastructure - how money flows, how services are delivered, how risk is managed

And ultimately, a final milestone:
Your first sale.

Week 1 - Define Your Brand Identity

Theme

Clarity. Foundation. Direction.

Objectives

• Identify your niche or specialty.
• Define your audience.
• Establish your brand positioning.
• Begin the psychological transition from “job title” to “founder.”

Deliverables

• A clear one-sentence identity statement
• Brand purpose and value proposition
• Draft of your core message
• A ChatGPT Project created specifically for your brand

Checklist

• Define what you help people do.
• Define who you help.
• Identify the skills you want to monetize.
• Start populating your ChatGPT Project with notes and drafts.

Week 2 - Generate a Complete Vision Board

Theme

Turn the abstract into something tangible.

Objectives

• Create a cohesive visual identity using ChatGPT.
• Establish brand colors, fonts, logo concepts, and design direction.
• Build the foundation for your website, graphics, and thumbnails.

Deliverables

• A full vision board generated from the prompt below
• A color palette with hex values
• Typography pairings
• Logo concepts
• Example YouTube thumbnail layout
• Example website hero layout
• Design tokens JSON (optional)

Vision Board Prompt

Use the following high-fidelity prompt:

I want you to act as a professional brand designer and creative director. 
Generate a complete, cohesive **vision board** for a new business.

Here are the business details (fill these in):
- Brand name:
- Tagline or slogan:
- What the business does:
- Target audience:
- Tone/personality (e.g., professional, friendly, bold, minimalist):
- Industry:

Please produce the following:

1. **Brand Identity Summary**
   - One-sentence brand description
   - Three-sentence brand personality profile
   - Tone of voice and communication style

2. **Visual Identity System**
   - Color palette with hex values and how each color should be used
   - Primary and secondary font recommendations with Google Font alternatives
   - Iconography style (line, glyph, rounded, geometric, etc.)
   - Layout recommendations (spacing, rhythm, grid style)
   - Suggested logo concepts (describe at least 3 distinct concepts)

3. **Example Assets**
   - Mock headline examples using the fonts/colors
   - A sample YouTube thumbnail layout (describe composition)
   - A sample website hero section (describe composition and copy)
   - A sample LinkedIn banner concept
   - A sample product card or service listing layout

4. **Brand Guidelines**
   - Do’s and Don’ts for the brand
   - How to use color and typography together
   - Recommended photography or illustration style

5. **Optional: Generate metadata JSON**
   - Provide a JSON structure containing:
       - colors
       - fonts
       - spacing
       - border radii
       - icon style
       - shadow style
     This is for use in components, front-end frameworks, or design tokens.

Please be specific, modern, and opinionated. 
The goal is to deliver something that feels like it came out of a real design studio.

Checklist

• Save results in your ChatGPT Project.
• Export assets to your notes system.
• Decide on your favorite logo direction.

Week 3 - LLMs as Your Co-Founders

Theme

Use AI to fill the leadership team you don’t have.

Objectives

• Create Custom GPTs or role-based personas.
• Load Project docs into ChatGPT.
• Begin long-form strategic conversations with these “roles.”

Deliverables

You should create the following personas:

• CEO GPT - strategy, positioning, niche clarity
• CFO GPT - pricing, budgeting, runway, QuickBooks guidance
• CISO GPT - security posture, policies, SaaS architecture
• Chief Counsel GPT - legal structure, liability, terms
• Creative Director GPT - visuals, thumbnails, brand consistency
• Engineer GPT - architecture, CI/CD, code reviews

LLM Prompts for Cofounders

Below are prompts you can use one-off, or create “Custom GPT’s” in ChatGPT that are dedicated, opinionated, information LLM’s that already know about your organization and think like, and act like these specific personas. LLM’s are absolute masters at impersonating a persona.

CEO Persona Prompt

You are now my CEO-level strategic partner. 
Your job is to help me make high-leverage decisions about:
- market positioning
- product scope
- messaging
- competitive strategy
- customer segmentation
- long-term direction

Use clear reasoning, avoid fluff, and challenge my assumptions.
Always ask:
“What is the simplest possible version of this that delivers value?”

Here is the current state of the business:
[PASTE RELEVANT PROJECT DOCS]

Let’s begin.

CFO Persona Prompt

You are now my CFO and financial strategist.
Your job:
- model runway
- estimate expenses
- advise on pricing strategies
- help me choose accounting tools
- define bookkeeping workflows
- assess risk

Be concrete and conservative.
Explain the simplest financial setup vs the fully protected setup.

Here is my financial context:
[PASTE DETAILS]

Advise me.

Chief Council Persona Prompt

You are now my business attorney and compliance advisor.
Your job:
- explain legal exposure
- outline minimum viable protection
- recommend when to hire real legal help
- help me draft simple, clear policies (privacy, terms)
- advise on LLC, DBA, contracts, and liability

Do NOT produce legal documents without explaining limitations.
Help me understand risk and good practices.

Here is my business:
[PASTE DETAILS]

CISO Persona Prompt

You are now my CISO.
Your job is to ensure my SaaS and business follow best security practices:
- auth patterns
- data handling
- encryption
- RLS best practices
- secrets storage
- vendor risk
- incident readiness

Be practical and specific.
Tailor recommendations to small teams and low-budget founders.

Here is my architecture:
[PASTE DETAILS]

Creative Director Persona Prompt

You are now my Creative Director.
Your job:
- thumbnail design
- brand cohesion
- layouts
- visual consistency
- emotional tone
- graphics that convert viewers into subscribers/customers

Refer to the brand vision board when making suggestions.

Here is my brand direction:
[PASTE VISION BOARD]

Checklist

• Create Project workspace.
• Create 3–6 Custom GPTs.
• Upload brand docs.

Week 4 - Domain, Email, and Professional Identity

Theme

Make the brand “real” - psychologically and operationally.

Objectives

• Buy your domain.
• Create branded email addresses.
• Finalize brand color & typography.
• Set up your LinkedIn organization page.

Deliverables

• Registered domain (e.g., <brandname>.com).
• Professional email (Google Workspace or Fastmail).
• LinkedIn Organization Page with logo, banner, and description.
• Updated personal LinkedIn reflecting that you “work at” your brand.

Why this matters

Brand infrastructure boosts morale.
It replaces the missing identity you lost with your job.

Checklist

• Domain purchased
• Workspace email configured
• Logo placed in favicon + profile + banner
• LinkedIn page created and tied to your work history

Week 5 - Build (or Rebuild) Your Website

Theme

Establish your professional home on the internet.

Objectives

• Create a simple, clean site.
• Build:
  • Home
  • About
  • Services
  • Blog
  • Contact
• Connect your vision board assets.

Deliverables

• Website deployed (Hugo, Jekyll, Gatsby, Next.js - any static site).
• Brand colors and typography applied.
• Basic SEO titles and descriptions.

Checklist

• Website live on Cloudflare Pages
• Contact form functioning
• Analytics enabled (Plausible, PostHog, or GA)

Week 6 - Content Presence Alignment

Theme

Unify the public-facing identity across platforms.

Objectives

• Rebuild LinkedIn profile with new brand voice.
• Update GitHub profile and pin relevant repos.
• Refresh YouTube channel (if applicable).
• Set up newsletter platform.

Deliverables

• Cohesive banner and avatar on all platforms
• Clear “What I Do / Who I Help” sections
• First long-form “pillar post” on your blog
• Newsletter landing page (Substack or Buttondown)

Checklist

• GitHub README updated
• YouTube channel text + playlists organized
• Newsletter created
• 1–2 pillar posts published

Week 7 - Define Your Offers

Theme

Turn skills into sellable units.

Objectives

Define 1–3 clear, simple offers:

• Consulting Hour
• Troubleshooting Session
• Security Review
• Cloud Setup
• Homelab Build Package
• SaaS Prototype Review
• Resume/Portfolio Overhaul
• Custom Automation
• Website Modernization Review

Deliverables

• Offer descriptions
• Pricing tiers
• Landing pages explaining each service
• Stripe payment links or invoices

Checklist

• Offers published on website
• Stripe product(s) created
• Calendly or SavvyCal scheduling page created

Week 8 - LLC, PO Box, Bank Account

Theme

Form the actual business entity.

Objectives

• Register LLC.
• Get a PO box or virtual mailbox.
• Open a business bank account.
• Set up Stripe properly with EIN and business details.

Deliverables

• Articles of Organization filed
• EIN obtained
• PO Box or business address set
• Bank account opened
• Stripe production mode configured

Checklist

• All business credentials documented
• Receipts stored in bookkeeping system

Week 9 - Financial Hygiene (Minimum vs Fully Protected)

Theme

Understand your financial exposure and obligations.

Objectives

Define two paths:

Minimum Viable Setup (Lean):

• LLC
• PO Box
• Bank account
• QuickBooks Self-Employed or Wave
• No accountant yet
• No attorney yet
• No insurance yet

Fully Protected Setup (Secure):

• Attorney-reviewed operating agreement
• CPA handling bookkeeping & taxes
• Business liability insurance
• Professional liability (E&O)
• Umbrella coverage
• Contracts reviewed by counsel

Deliverables

• Choice of minimum or full setup for your situation
• Bookkeeping system active
• Budget and runway model produced by CFO GPT

Checklist

• Expenses tracked
• Revenue tracked
• First budget and forecast created

Week 10 - Systems, Automation, and Lead Flow

Theme

Operationalize your brand.

Objectives

• Create automations for onboarding leads.
• Build simple CRM tracking (Notion, Airtable, Obsidian, Google Sheets).
• Create email welcome sequence.
• Build a lead magnet.

Deliverables

• Lead magnet PDF or checklist
• Welcome email sequence
• CRM structure for tracking leads, customers, and content
• Website integrated with newsletter

Checklist

• CRM operational
• Auto-reply to contact form
• Email funnel active

Week 11 - Publish, Promote, and Position

Theme

Establish authority through consistent output.

Objectives

• Publish weekly content (blog, YT, newsletter).
• Engage on LinkedIn with thoughtful posts.
• Begin guest content or collaborations.
• Publish your “Signature Long Article” - a deep, authoritative piece that defines your brand.

Deliverables

• 4–6 content pieces published
• First collaboration initiated
• Signature post published

Checklist

• LinkedIn activity daily or near-daily
• Newsletter sent
• Blog maintained

Week 12 - Monetization, Optimization, and Your First Sale

Theme

Cross the line from “preparation” to “execution.”

Objectives

• Launch a low-friction paid offer:
  • one-hour consult, or
  • digital product, or
  • guided review session, or
  • SaaS subscription
• Perform your first marketing push.
• Reach out to your network with a clear offer.
• Announce availability publicly.

Deliverables

• First paying customer
• Public launch announcement
• Website updated with proof of life (testimonials, case studies, screenshots)

Checklist

• Offer live
• Payment link tested
• Outreach complete
• First sale recorded

Milestone Tracker (90 Days)

Conclusion

By the end of these 90 days, you are no longer a displaced engineer trying to reassemble your career. You are the owner of a fully operational micro-business, with:

• identity
• infrastructure
• positioning
• service offerings
• brand presence
• a functioning inbound funnel
• and at least one real customer

From here, growth is a matter of consistency and iteration, not reinvention.

This is how you rebuild your professional identity on your own terms.