- Nikonomics
- Posts
- Newsletter #0007 - How to Buy Your First Business With AI, in 7 Steps
Newsletter #0007 - How to Buy Your First Business With AI, in 7 Steps
Nikolas Hulewsky
April 19, 2025
If you want to buy a business, PLEASE DON’T SKIP THIS EMAIL!
Today I’m handing you the exact, 7-Step AI playbook I’d use to find, vet, and buy a cash-flowing small business.
This edition is a little different. We moved this week (picture above) so I didn’t have enough time to get to a deal of the week or Week 3 of my AI Series BUT I think you will find this VERY valuable!
Which Kind of Content Do You Want More Of? |
The Ultimate AI Framework for Buying a Business
Today I'm sharing my battle-tested 8-step AI framework for buying businesses that turns you into a one-person deal team, helping you source, analyze, negotiate and close acquisitions faster and smarter than your competition.
I've bought and sold over a dozen businesses.
But if I were starting from scratch today—with limited capital, no team, and no fancy M&A experience—there's no question I'd lean on AI.
Not to replace me.
To give me an edge.
Here's exactly how I'd use AI to find, evaluate, and buy a small business.
The AI Business Buying Framework
STEP 1: Pick Your AI Assistant (Stop Overthinking)
Most people get stuck comparing Chat GPT vs Claude vs Gemini vs Perplexity vs whatever launched yesterday. This is dumb.
Just pick one and start using it.
Recommended Tools:
ChatGPT Plus ($20/month)
Claude Pro ($20/month)
Perplexity Pro ($20/month)
I use ChatGPT because it was first, but it honestly doesn't matter. Pay the $20/month for the premium version to get better performance.
The key is replacing everything you currently Google (except local searches) with AI prompts. This trains your brain to think differently.
STEP 2: Educate Your AI About YOU
AI without context is like a Ferrari without gas.
Tell it who you are. Upload your resume. Copy your LinkedIn. Give it your budget, experience, and risk appetite.
Recommended Tools:
ChatGPT custom instructions
Claude's memory feature
Perplexity profiles
Get-Started Prompt:
"I'd like to create a comprehensive profile to help you understand my background and goals as a business buyer. I'll share my professional experience, financial situation, and acquisition goals. Please ask me 5-7 questions that would help you understand who I am as a potential business owner. After I answer those, I'd like you to summarize what you've learned about me and ask any follow-up questions to fill gaps in my profile."
This feels weird at first. Push through it. You're creating a digital twin that understands your specific situation, not just giving generic advice.
STEP 3: Define Your Acquisition Criteria
After understanding YOU, it's time to get crystal clear on WHAT you're looking for.
Recommended Tools:
ChatGPT custom GPTs
Claude Artifacts
Notion AI
Criteria-Building Prompts (DO THESE IN ORDER):
"Based on my background and skills, what types of businesses would best leverage my experience? Please suggest 3-5 business categories and explain why each might be a good fit."
"For each business type you suggested, what are the key metrics I should evaluate? Include typical revenue ranges, profit margins, growth rates, and customer concentration limits."
"Help me create a prioritized list of 'must-haves' vs 'nice-to-haves' for my business acquisition. Consider geography, size, owner involvement, team structure, and recurring revenue percentage."
PRO TIP: Once you've refined your criteria, save this as your "Acquisition Criteria Document." You'll refer back to it constantly.
STEP 4: Record and Upload EVERYTHING
This changed my life. I wear a recording pendant that captures all my business conversations (with proper consent in two-party states).
Recommended Tools:
Otter.ai for meeting transcriptions
Fireflies.ai for call recordings
Limitless pendant for in-person conversations
Voice Notes app (in a pinch)
PRO TIP: How to Store and Give AI Access to Your Data Create a simple folder structure in your cloud storage (Google Drive, Dropbox) with subfolders for: "Seller Conversations," "Banker Meetings," "Broker Calls," etc. After transcribing conversations, save them as text files with clear naming conventions like "SellerCall_BusinessName_Date.txt" - then you can easily upload relevant files to your AI when asking specific questions.
No more missed details. No more "wait, what did they say again?" Your AI becomes your perfect memory.
The 4 C's Prompt Framework (Best Practice, Not a Step)
Bad prompts = bad answers. I've written extensively about this framework that transforms your AI interactions:
Clarity: Be specific about what you want
Context: Provide relevant background
Constraints: Set clear boundaries
Command: Use direct, actionable instructions
The template looks like this: "[Command] a [format/output] about [topic]. It should be [constraints] with [context]."
Here’s the link to my full article on this for more depth, but keep these principles in mind for all your AI interactions.
STEP 5: Build Your AI Deal Team
This is where things get powerful. Create specialized AI advisors for different aspects of your deal:
Recommended Tools:
ChatGPT custom GPTs
Claude Workspaces
Perplexity Collections
Set up individual projects for each specific aspect of your search. This way, each AI assistant is narrowly focused on its specialty and has all the relevant context:
Deal Finder AI
Upload your acquisition criteria
Feed it business listings from BizBuySell, etc.
Ask: "Which of these 20 businesses best match my criteria and why?"
Valuation AI
Upload industry reports, comparable sales
Feed it the target's financials
Ask: "What's a fair multiple for this business given its growth rate and customer concentration?"
Due Diligence AI
Upload all seller-provided documents
Ask: "What's missing from these materials that I should request?"
Ask: "What inconsistencies do you notice in these financial statements?"
Legal Review AI
Upload all contracts and legal documents
Ask: "Where could I get screwed in this purchase agreement?"
Ask: "What unusual terms exist in these customer contracts that might affect valuation?"
Negotiation Strategy AI
Upload all correspondence with the seller
Ask: "Based on these emails, what are the seller's primary motivations beyond price?"
Ask: "Draft a response addressing their concern about legacy while still reducing my risk"
By keeping these as separate projects, each AI assistant maintains focus and doesn't get confused by irrelevant information.
STEP 6: Create Your Acquisition Playbook
As you go through deals, successful or not, have your AI create an evolving playbook.
Recommended Tools:
Notion AI
ChatGPT with custom instructions
Ask: "Based on all my deal notes, what patterns of successful negotiations can you identify?"
Ask: "What questions consistently reveal the most important information from sellers?"
Ask: "What red flags did I miss in the deals that fell through?"
This becomes your competitive advantage – a living document that makes each acquisition attempt smarter than the last.
Step 7: Post-Close Playbooks & SOPs
AI doesn’t stop at the LOI.
After you buy the business, use it to:
Draft your 30/60/90 onboarding plan
Write team job descriptions
Turn call transcripts into SOPs
Prompt:
“I’m the new owner of a 10-person HVAC company. Create a 60-day transition plan that balances team trust, customer retention, and operational continuity.”
Real-World Examples
A friend of mine is buying out partners in a $500M business. He uploads all legal documents to his AI before every meeting and asks, "Where could I get screwed in this deal?"
He told me he's consistently the most prepared person in the room – even with teams of lawyers on both sides.
Another colleague used AI to analyze 200+ businesses for sale, quickly narrowing to the 12 that met his specific criteria. He then had his AI draft initial outreach emails customized to each seller's likely motivations based on the listing language.
He closed a deal in 90 days that would have taken 6+ months the old way.
Important Limitations
IMPORTANT!!! You’re NOT replacing lawyers, advisors, CPAs or anyone else you NEED on these deals. This will help you show up to meetings more prepared than anyone else in the room.
AI won't:
Buy the business for you
Write your PSA
Perform your QoE
Make your final decisions
Replace lawyers, accountants, or industry experts
Guarantee success
AI will:
Make you significantly more prepared
Help you avoid common mistakes
Spot opportunities others miss
Give you a critical competitive advantage for the next 2-3 years
My AI Tool Stack
Must-Haves (one of these):
ChatGPT Plus ($20/mo)
Claude Pro (great for long docs)
Otter.ai or Fireflies (call recording)
Custom GPTs or Claude Workspaces
Optional Power-Ups:
Getting Started Today
Sign up for Chat GPT Plus, Claude, or any other AI assistant
Upload your professional background
Start a conversation with: "I'm looking to buy a business. Given my background, what questions should I be asking myself to narrow down the right type of business for me?"
Follow the trail of breadcrumbs it gives you
You’re not behind.
But 6 months from now, you will be if you’re not using this.
This Week’s Nikonomics Podcast Summaries
🎙️ Guest: Dan Thompson
Business: JMAC, a 50-year-old silicone manufacturer in Texas
Insight: Dan built internal AI tools (with zero coding background) to slash reporting time and empower employees—saving $$ and boosting efficiency.
Model: Custom compounding + molding for critical industrial silicone parts.
🎙️ Guest: Matthew Mellinger
Business: Local SEO Partners + SEO Gits + Cookville Buzz
Insight: Matt slashes design costs and dev time using AI tools like MidJourney and Lovable—building client-ready websites with unique, SEO-friendly imagery in minutes.
Model: Full-service local SEO agency + SEO analytics SaaS + newsletter monetization.
🎙️ Guest: Liz Knopf
Highlight: ChatGPT’s new image editing + carousel generator is a game-changer. Nik turned a Twitter thread into a LinkedIn-ready PDF—with slick slides, math, maps, and visuals—no design skills needed.
Insight: AI tools are replacing full creative teams. From turning transcripts into summaries, to remixing retro ads with modern products, Liz shows how prompting + Claude = endless content.
Model: AI-powered content creation stack—Grok for summaries, Claude for visuals, ChatGPT for carousels, and Make.com for automation.
🎙️ Guest: Pranav Ghatraju
Business: AI automation agency + voice-based content generation tools
Insight: Pranav uses AI voice bots to interview users, auto-generate transcripts, and turn them into LinkedIn/Twitter posts—no keyboard needed.
Model: Custom AI workflows via Make.com + Bubble.io, turning calls into content for busy professionals.
🎙️ HoldCo Bros with Chris Koerner
Topic: What AI tools are worth using and which ones can you DITCH?!
How'd I Do Today? |
Every week, I try to answer questions sent to me via Twitter, Speakpipe or [email protected].
Thank you for reading, please share with a friend!
Nik Hulewsky