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System Audit Report

🧠 1. Business Overview

Doug is a business broker operating under the Website Closers franchise. He works with sellers of businesses between $2M and $50M, and while hundreds of buyers express interest in each listing, only a few convert—Doug is only paid when a deal closes. His process includes managing high buyer volume, handling repetitive inquiries, and doing manual seller outreach.

He’s also developing a Whop course aimed at educating prospective buyers and creating a secondary, recurring revenue stream. Doug is looking to reduce repetitive tasks, improve the scalability of both his brokerage and course, and explore automations that increase leverage without requiring a large team.

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📌 2. Automation Opportunities

📌 2. Automation Opportunities

What to Automate

What It Does

What You Get

Access / Requirements to Kick-Off

Auto-Send Deal Room to Buyers

After a buyer signs an NDA, automatically tag them in CRM and email the correct data-room link.

Saves VA time; buyers get instant access; cleaner CRM.

• CRM access/API key • Sample data-room URL

Answer Buyer Questions with AI Drafts

Generates context-aware replies to common buyer questions; escalates only when needed.

Cuts Doug’s repetitive email load; faster, consistent answers.

• Top 10-20 FAQ Q&A pairs • Example deal memo or listing packet (for context) • Email/SMS sending credentials (SendGrid, Gmail API, etc.) • Slack/Zendesk access and API key

Personalized Seller Outreach Emails

Scrapes/identifies target owners (60+, $1M+ rev) and sends tailored cold emails.

Warmer seller leads without mass spam; higher conversion.

• Firm criteria: age, revenue, industry, geography • List of disqualifiers • Lead database access (Airtable/CRM) for storage • Sample outreach email that’s worked before

Turn Newsletter into Social Posts

Splits newsletter into bite-sized posts for LinkedIn, Facebook, X, etc.

Active social presence; drives traffic to Whop course effortlessly.

• Newsletter platform login/RSS (Substack, Mailchimp, etc.) • Brand tone guidelines • Social media management software access • Preferred posting cadence

Deliver Lead Magnet + Follow-Ups

Sends gated resource and sequences email/SMS follow-ups from sign-ups.

Grows email list and course sign-ups on autopilot.

• Lead-magnet PDF/URL • Landing-page or Whop form access • Email/SMS provider key & approved templates

Monitor Buyer/Seller Conversations (Optional)

Tracks Reddit, LinkedIn, etc. for “thinking of selling/buying” signals.

Surfaces high-intent leads in real time.

• Keywords/phrases to flag

Deal Partner AI Calculator

Lets buyers plug numbers and see DSCR, payments, feasibility tips.

Self-serve analysis; fewer “Can I afford it?” emails.

• Spreadsheet with full formulas & defaults • Whop creator login to embed tool

Newsletter Repurposing & Scheduling

Auto-splits each email into 3-5 platform-optimized posts and schedules them.

More reach from same content; zero manual posting.

• Newsletter feed/API

Internal Research Bot

Slack bot that can receive a link and return research; used for competitive analysis, monitoring trends, etc.

Quick intel without manual searching.

• List of research tasks you commonly have to do (scouting businesses, researching business partners, etc.) • List of known competitors

There are no rows in this table

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📑 2.1 Detailed Breakdown

🔹 1. Deal Partner AI Tool (Core Automation Project)

Goal: Help buyers analyze business deals based on financial inputs and acquisition logic.

Automation Needs:

Logic-based input form (e.g. down payment, loan type).

Backend logic to calculate:

Debt service coverage ratio (DSCR)

Monthly loan payments

Cash flow projections

Deal feasibility suggestions

Dynamic feedback: e.g. “You need to bring more cash,” or “Add an investor at 10% per year.”

Possibly voice/chat-based interaction layer (GPT wrapper).

Tech stack suggestions + simple frontend (Whop, WindSurf, etc.)

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🔹 2. Buyer/Seller Interaction Automation

Problem: Doug handles a high volume of repetitive buyer questions post-NDA.

Automation Needs:

AI-powered FAQ assistant that:

Understands deal-specific data.

Drafts context-aware responses to common buyer inquiries.

Escalates only when necessary.

Slack/Zendesk integration for easy handoff to VA or Doug.

Internal notes or response suggestions to speed up manual replies.

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🔹 3. Personalized Seller Outreach Automation

Goal: Proactively source business owners looking to sell.

Automation Needs:

Scrape and identify:

Owners over 60

Businesses with $1M+ revenue

Signals of interest in selling (Reddit, LinkedIn, websites)

Create a lead database (e.g. Airtable or internal CRM).

Generate and send hyper-personalized cold emails.

Possibly use Perplexity or similar for deep research.

Email tracking and reply handling.

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🔹 4. Content Creation Support for TikTok & Socials

Goal: Drive traffic to his Whop course and build brand.

Automation Needs:

Idea generation (hooks, topics, content formats).

AI-assisted script writing and copywriting for TikTok/shorts.

Auto-generation of social posts from newsletter or long-form content.

Intelligent posting schedule (via Buffer, Hootsuite, etc.).

Notification system for high-value comments or engagement opportunities.

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🔹 5. Newsletter Distribution + Repurposing System

Goal: Grow Whop audience and email list more efficiently.

Automation Needs:

Break newsletter into 3–5 parts automatically.

Repurpose for Twitter, LinkedIn, Facebook using AI trained on Doug’s tone/brand.

Distribute on schedule based on past analytics.

Possibly suggest headlines and CTAs tailored to platform.

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🔹 6. Internal Research Automations

Goal: Streamline Doug’s own deal prep and tool research.

Automation Needs:

Slack-integrated research bot (e.g. finds software, runs due diligence).

Auto-digest content (e.g. software update logs, Reddit trends, competitor moves).

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🔧 3. Recommended Build Plan

Phase 1: Quick Wins (Next 2 Weeks)

Buyer Follow-Up Automation Automatically tag buyers in CRM and send the deal room once NDA is signed.

Automated Support System Set up a system to handle related admin and draft business context aware responses to users and auto reply to frequently asked questions.

Phase 2: High-Leverage Systems (Next 30 Days)

Targeted Seller Outreach Lead scraping/monitoring and personalized outreach system to contact business owners who meet Doug’s seller criteria.

Newsletter Repurposing Automation Repurpose Doug’s newsletter into short-form content for platforms like Facebook, X, Reddit and LinkedIn.

Lead Magnet Delivery & Email Sequences Automate the Whop lead magnet flow, follow-ups, and tagging to nurture new subscribers.

Under Evaluation

Online Lead Monitoring / Social media comment monitoring Monitors Reddit, LinkedIn, or other sources for buyer/seller intent signals.

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✅ 4. Next Steps

✅ Approve Phase 1 build scope and identify what automations you’d like to start with

📂 Share required information and access

Deal Partner AI spreadsheet and product overview

CRM Access

Example data-room link

Whop Course link

Active business listings link

📝 We'll begin with quick wins, show results, and iterate from there

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