How to Approach Owners About an Off-Market Deal.

Good morning Buyers!

Some of the best businesses? You’ll never find them on a listing site.

They’re not on BizBuySell. They’re not working with a broker. They’re quietly operating, often owned by people nearing retirement and open to selling if the right person asks.

This week, we’re breaking down How to Approach Owners About an Off-Market Deal without sounding spammy or getting ignored.

“If you don’t ask, the answer is always no.” — Nora Roberts

💡 Deal Tip of the Week: The Best Deals Aren’t Always for Sale

Off-market deals take effort, but they come with less competition, better pricing, and more flexible terms. The key? Respectful outreach and real conversations, not a pushy pitch.

✉️ How to Approach Business Owners (Without Burning Bridges)

1. Start with Curiosity, Not a Sales Pitch
Your first message should sound like:

Simple. Personal. No pressure.

2. Keep It About Them, Not You
Talk about their business and their legacy. Avoid launching into your resume or a full acquisition plan. That comes later.

3. Be Prepared for Silence—or Surprise
Some owners won’t respond. Others might say, “Funny you reached out. I’ve been thinking about retiring.” You’re planting seeds.

🧠 Who Should You Reach Out To?

• Longtime Owners – Especially those who’ve been running the business 20+ years

• No Online Presence – Often behind the times, but full of value

• High-Review, Low-Marketing – Solid operations but no scaling efforts

• Businesses with Owner Names in the Title – Signals an owner-dependent setup and potential burnout

Look for businesses with solid reputations and aging infrastructure—they often just need a fresh operator.

🛠️ Tools & Tactics for Outreach

• Cold Email & Direct Mail – Personalized letters or emails can stand out more than generic calls

• LinkedIn – Connect before you pitch

• Google Maps – Identify targets in your area or niche and research the owners

• Chamber of Commerce & Trade Groups – Great for local leads and warm intros

And yes—walking in and striking up a conversation still works.

🗯Expert Soundbite 

“When you approach with humility and genuine curiosity, most business owners appreciate it—even if they’re not ready to sell right now.”
— Codie Sanchez, Investor & Founder of Contrarian Thinking

🔍 Signs an Owner Might Be Ready to Sell

• They’re older and have no clear succession plan

• They complain about “kids not wanting to take over”

• Business has flatlined but they’re not trying to grow

• You hear “I’m tired” more than once

All of these are green lights to keep the conversation going.

📉 Mini Market Watch

• Baby Boomer Boom: Nearly 50% of small business owners in the U.S. are over age 55. Many haven’t listed their businesses but would sell for the right offer.

• Broker Shortage: A lack of brokers in rural and specialty industries means many deals never hit the market.

• Private Deals = Private Terms: Off-market deals tend to be more flexible—with more creative financing options and fewer bidding wars.

🔜 What’s Next?

Next week: “How to Value a Business: Key Methods (SDE, EBITDA, Multiples)”

Forward this to a fellow buyer looking for off-market leads—or hit reply if you want help drafting your first outreach message.

Until next week,

— The Practical Buyer Team 

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