How to Source Off-Market Deals in the Age of AI

Many buyers find deals the same way — refresh deal sites, scan broker listings, submit LOIs alongside 20 other people, and hope for the best.

Some buyers build systems.

Here's what a system looks like today. You define your acquisition criteria once. AI tools build a list of 300 business owners who match — enriched with names, addresses, phone numbers, years in business, and succession signals.

Claude writes a unique, personal letter to each one. A robotic handwriting service produces and mails them with real pen and ink. An AI voice clone of your actual voice drops a personalized voicemail to every owner's phone — without it ever ringing.

Your CRM tracks every response. A desktop AI agent organizes your follow-ups, researches your best prospects in depth, and drafts your LOI documents.

Total cost — roughly $1,000 a month. For context, most deal sourcing firms charge $3,000–5,000 per month for a similar service with less personalization. And unlike a brokered deal — where 5–10% of the purchase price goes to the broker's commission — going direct means the seller's net is higher even if you pay a lower purchase price.

Both sides win. That's the whole point of going off-market.

This article is the full stack. Every tool, every workflow, every cost. We're calling it The EBIT Off-Market Sourcing Stack — and we'll be updating it in future editions as new tools emerge and readers share results.

Whether you use one layer or all seven, the core idea is the same — build a repeatable system for finding off-market deals instead of competing in someone else's auction.

When a business is publicly listed with a broker, the seller has leverage. Multiple LOIs compress your ability to negotiate on price, structure, and terms. Multiples inflate by 0.5–1x. Seller financing becomes harder to negotiate. Earnout structures get rejected because the broker is pushing for a clean close.

When you find a seller directly — before they've listed, before they've hired a broker — the dynamic flips. You're not buyer #23 on a spreadsheet. You're the person who took the time to find them, learn about their business, and reach out personally. That relationship changes everything — the price, the structure, and the seller's willingness to stay involved through the transition.

The commission math is simple. On a $2M brokered deal, the seller pays $100–200K in commissions. Go direct and that money stays in the deal — you pay less, they net more.

Going direct gives lenders a clean story — you found the owner, built the relationship, and earned the deal. A succession approach where you've operated alongside the owner before closing directly reduces key-man risk, which is one of the fastest ways to kill an SBA approval. Seller financing is also easier to negotiate off-market, which strengthens your equity injection and overall deal structure. The trade-off is real though — brokered deals come with recasted financials and a polished CIM. Going direct means you own the diligence from scratch — and don't skip the quality of earnings report.

A note on tools vs. judgment. Every tool in this article amplifies strategy — it doesn't replace it. The best AI-generated letter in the world won't close a deal if you can't read a room, build trust over a handshake, or walk away from bad terms. Deal sourcing is still emotional and relational work. The stack handles the manual labor so you can focus on the human side — which is where deals actually close.

So how do you find these deals consistently? You build a stack. Here's each layer.

You need a list of business owners who match your acquisition criteria. What used to take weeks of manual research now takes an afternoon.

This is where most buyers go wrong. They build a big list instead of a right list. AI amplifies your search — but if your criteria are sloppy, you'll generate 500 leads and close zero deals.

The filters that matter for acquisitions:

Start with the right list. Then use AI to make it big.

Leadbay (free tier to $145/mo) is purpose-built for finding SMB leads in fragmented, data-scarce markets — which is exactly what the small business acquisition space is. Upload your past targets or closed deals and their AI learns your ICP, then discovers businesses you didn't know existed. Where LinkedIn and ZoomInfo are optimized for enterprise, Leadbay focuses on the small businesses that fall through those cracks. Free 50-lead trial to test quality.

Clay ($149–349/mo) is the enrichment engine. Feed it your prospect list from any source — Leadbay, Secretary of State filings, licensing databases — and Clay enriches every row automatically using 100+ data providers. Its "Claygent" AI agent crawls websites, news, LinkedIn, and reviews to surface personalization details you'd never find manually.

For additional contact data — verified emails, phone numbers, direct dials — Fiber AI (free tier available) is a strong supplement. 40M+ companies, 850M+ professionals. Waterfall enrichment across 16+ providers delivers sub-1% bounce rates.

For deep research that no database captures, use Claude ($20–200/mo). Feed it a list of business names and ask it to research owner bios, years in business, succession signals, and recent reviews suggesting operational fatigue. It synthesizes unstructured information that structured databases miss.

Use Leadbay's built-in scoring and Clay's AI enrichment to rank your prospects by acquisition likelihood. Weight the signals — owner age, years in business, succession indicators, and growth trajectory (declining growth often correlates with willingness to sell). Your top 100 get the full outreach treatment. The next 200 get a lighter touch.

Business owners over 60 open physical mail. A personal letter from a real person expressing genuine interest in their life's work lands differently than a LinkedIn InMail from "Acquisition Entrepreneur."

Not one template with mail merge fields. Actually unique letters for each prospect. Here's the prompt framework:

You can generate 100 unique letters in an afternoon. Each one reads like you spent 30 minutes researching and writing it personally.

These services use AI-controlled robots with real pens and ink to produce letters nearly indistinguishable from human handwriting.

LettrLabs — our primary pick. Real pen and ink, CRM integrations with Salesforce and HubSpot, lookalike audience targeting with 4,000+ data points. Scribe Handwritten — no order minimums on their SaaS tier, CRM sync for automated drip campaigns. IgnitePOST — rules-based automation triggers handwritten notes when prospects hit specific CRM stages.

Export your enriched list from Clay. Generate unique letter copy via Claude. Upload to LettrLabs or Scribe for robotic handwriting and mailing. Track responses in your CRM. Second letter at 30 days to non-responders. Third touch at 60 days — switch to phone or voicemail.

Timing matters. Mail in Q4 (tax planning season) or Q1 (New Year's resolution to "finally step back"). Avoid summer.

Set realistic expectations. A 1–3% response rate on your first mailer is excellent. On a list of 300, that's 3–9 conversations with business owners who weren't talking to anyone else.

When they call back — lead with curiosity, not terms. Your only goal on the first call is to earn a second one.

Cost per letter: $2–5 including handwriting and postage. A campaign of 300 letters runs $600–1,500.

This is the most aggressive layer in the stack — and the one that requires the most legal diligence before you scale it.

Ringless voicemail delivers a voice message directly to a recipient's voicemail box without their phone ringing. They see a notification and listen when it's convenient. Platforms report 5–20x higher callback rates compared to cold calling.

Record 60 seconds of your natural voice. AI clones it. Then you generate personalized voicemails where "you" say each prospect's name, reference their business, their city — all dynamically inserted via merge fields. The result sounds like you personally recorded each message.

VoiceDrop.ai — voice cloning from a 60-second sample, dynamic merge fields, AI inbound agent that qualifies callbacks and books meetings. Free trial available. Drop Cowboy — combines ringless voicemail, SMS, and MMS in one platform. Their BYOC option cuts delivery costs 40–60% with a Twilio account.

Keep it under 45 seconds. Warm, not corporate.

Ringless voicemail is regulated under the TCPA. Here's the honest tension: the TCPA requires prior express consent for marketing voicemails, which creates a real conflict with cold acquisition outreach where you don't have a prior relationship. Some states — Florida, Oklahoma, and others — have passed additional RVM-specific legislation with enforcement teeth.

The platforms above include compliance tools (DNC scrubbing, quiet hours, opt-out handling), but tools don't equal legal clearance. Consult an attorney familiar with TCPA and your target states before launching any RVM campaign. This layer has real ROI potential, but also real enforcement risk if you get the compliance wrong. Treat it as an advanced tactic, not a Day 1 default.

This is not legal advice and EBIT doesn't provide legal counsel.

Know someone actively searching for a deal? Forward them this article.

This is the most sophisticated strategy in the stack — and often the one most likely to produce favorable terms.

Most business owners don't want to "sell their baby." But almost all of them worry about what happens when they can't run it anymore. The word "succession" lands very differently than "acquisition."

Identify businesses where the owner is clearly the bottleneck — they're the rainmaker, the manager, and the technician all at once. Then approach with a different frame:

"I'm looking for a business where I can come in as a partner or operator and eventually take over the reins. I'm not looking for a quick flip — I want to build on what you've created."

This works especially well when the owner has no children in the business or their kids don't want it. More than once, operators who've run this approach have heard some version of: "I've been hoping someone like you would come along." That's when you know the structure is working — you're not buying a business, you're solving someone's biggest unspoken problem.

Sellers respond well to this structure because it de-risks the transition. They get to vet you before fully committing. The business doesn't skip a beat during the handoff. And because you've built trust over months of working together, the deal structure often writes itself — seller note, SBA 7(a) for the balance, continued advisory role as a condition both sides actually want.

SBA lenders respond well to it too. A succession plan with demonstrated operational involvement is one of the strongest loan applications you can submit.

Use Claude Cowork (more on this in Step 6) to draft a polished succession proposal — a 2–3 page PDF that outlines your vision, timeline, and how the owner benefits at each phase. Include your background, your values, your commitment to employees and customers.

Use Clay to find the right targets — businesses with strong fundamentals but clear operator fatigue. Declining marketing spend, stale product lines, deferred maintenance, no recent hires.

Use your professional network (Step 5) for warm introductions. Ask your CPA and attorney contacts: "Who has a great business but is burning out?"

CPAs, wealth managers, estate attorneys, commercial insurance agents, and SBA lenders all sit at the same intersection — "owner wants to exit" and "owner hasn't told anyone yet." This is still the highest-quality deal flow channel because the leads come pre-warmed with trust.

Use Clay or Apollo to build a targeted list of CPAs and business attorneys in your geography who specifically serve small businesses in your target industry. Filter by firm size, specialty, and years in practice. You're looking for the accountant who has 30 small business clients, not the Big Four partner.

Use Claude to draft outreach for each professional. Research their firm, their client focus, their recent blog posts or speaking engagements. Reference specifics. Don't lead with "send me deals." Lead with value — "When your clients ask about succession planning or selling, I'd love to be someone you can refer them to."

Use Claude Cowork to create a polished one-page PDF — your background, what you're looking for, how you handle transitions, and your commitment to keeping the owner's existing professional relationships post-close. That last point is the unspoken incentive — if the CPA introduces buyer and seller, they keep the client through the transition. That's worth more than any referral fee.

Aim for 10–15 professionals who know what you're looking for. Quarterly CRM sequence. Share market updates that position you as the informed buyer they think of first when a client mentions succession. Year one you might get zero leads. Year three it's a consistent pipeline.

Claude Cowork launched in January 2026. Available on Mac and Windows for all paid Claude subscribers ($20–200/mo). It's not a chatbot — it's a desktop AI agent. Point it at a folder, describe what you need in plain English, and it plans and executes multi-step workflows across your files and connected services.

Prospect research:

Due diligence organization:

Anthropic released 11 open-source plugins at launch — sales, legal, finance, marketing, data analysis, and more. You can build custom plugins without writing code.

The manual research, letter writing, data organization, and follow-up tracking that used to require a VA is now handled by an AI agent on your desktop. Monthly cost: $100–200.

Here's the complete EBIT Off-Market Sourcing Stack — every tool, what it does, and what it costs.

Total monthly operating cost: $500–1,000 — roughly a third of what deal sourcing firms charge ($3,000–5,000/month) with more customization and a pipeline you own.

Estimated cost per qualified conversation: $50–200 (varies by niche, geography, and list quality)

Rough benchmarks to aim for: Letters — 1–3% response rate. Voicemail drops — 0.5–1.5% callback rate. Professional referrals — low frequency, highest quality. These will vary by niche and list quality, but they give you a baseline to measure against.

The pipeline you build with this stack is yours. It doesn't reset when a listing expires. It compounds every month you run it. And every strategy in this stack strengthens your SBA loan application — lenders want to see that you found the deal through direct effort, built a relationship with the seller, and understand the business before you sign.

If this stack is useful to you, forward it to one other searcher. If you run any layer of this stack, reply with your numbers — response rates, cost per conversation, channel mix. We'll publish anonymized benchmarks quarterly so every operator in this community gets smarter together. A downloadable version of the full stack — with clickable links and setup guides — will be available in the EBIT Community resource library.

Month 1 response rates will be modest. A 1–3% response rate on your first mailer is a win. The system compounds — Month 3 is where the pipeline starts producing real conversations.

Three months of the EBIT Off-Market Sourcing Stack costs roughly $3,000. The same period with a deal sourcing firm runs $9,000–15,000. The economics work for everyone involved.

The tools in this article are new. Most didn't exist 18 months ago. Most buyers in the acquisition space don't know they exist yet.

That gap is closing fast. Every serious searcher will eventually have access to these same tools — and the advantage of being early will disappear. The window for using AI-powered outreach to reach owners before they're flooded with AI-powered outreach narrows every month.

You don't need a team. You don't need a $50K marketing budget. You need a laptop, $1,000 a month, and the willingness to start while most people are still browsing listings.

Start with one layer this week. Not all seven. Run 100 letters or 100 voicemail drops. See what comes back. Then add the next layer. By the time you've run this for 90 days, you're not a searcher anymore — you're an operator with a pipeline.

This playbook is free. The toolkit that makes it plug-and-play — shared Clay templates, Cowork prompt libraries, voicemail script banks, and weekly intel — that's what this newsletter delivers every week.

Know an operator who should see this? Feel free to forward this email.

One more thing. You just built a system to find deals. Now protect the one signing the guarantee. Personal Guarantee Insurance is the first product designed to cover SBA borrowers' personal exposure — $500K to $5M. Sign up to get notifed.

Disclaimer: Educational content only - not investment advice. Listings from third-party sources, accuracy not guaranteed. Do your own due diligence. Consult professionals before making decisions.