Reddit Q&A: “How do I approach a business owner to buy their company—letter, email, or just call them?”

Posted by u/OffMarketOperator:

“What’s the best way to approach a small business owner if I want to buy their company? Do I send a letter? Call and ask to speak with them? Try email? I don’t want to scare them off.”

Answer from the Clearly Acquired Deal Team
Signed by Samson Jagoras, CEO & CIO

This is one of the most common—and most misunderstood—parts of buying a business: how to make the first move without looking like a spammer, sounding like a vulture, or triggering fear in the seller.

The truth? There’s no one-size-fits-all answer. The best outreach strategy depends on the business type, industry norms, the owner's personality, and your tone. But here's how we break it down:

📬 Your 3 Primary Outreach Options (And How to Use Them)

1. Letter (Highly Recommended for First Contact)

• Why it works: Personal, non-threatening, tangible. Business owners—especially baby boomers—respect a well-written letter.
• What to include:
  • Who you are
  • Why you’re reaching out (interested in their business, not just any)
  • That you’re not a broker or mass buyer
  • Reassurance about discretion
  • A soft CTA (e.g., “If you’re ever open to a conversation...”)

This is the gold standard for off-market outreach. We've seen 5–10% response rates from letters—10x better than cold email.

2. Email (Best for Follow-Up)

• Why it works: Efficient, scalable, and easier to reply to.
• When to use: After sending a letter, as a nudge. Or, if the business is digital-native (like SaaS, marketing agencies), email first is more acceptable.
• Tip: Keep it brief. Write like you’re writing to a friend, not pitching a product.

3. Phone Call (High Risk, High Reward)

• Why it works: Direct, hard to ignore.
• When to use: Only if you’re very confident in your pitch and the timing. Works better in industries where cold outreach is common (e.g., sales-heavy businesses, blue-collar trades).
• How to approach:
  • Ask to speak with the owner directly
  • Be warm, not aggressive
  • Position as a quiet inquiry, not a buyout offer
  • If they say “Not interested,” thank them and move on

💡 Pro Tip: Use a Combination Strategy

We recommend the 3-touch approach:

1. Letter first (warm, respectful intro)
2. Follow-up email a week later
3. Phone call only if no response after 2–3 weeks

And always remember: tone matters more than the channel. Be clear, human, and not transactional. You're offering a potential legacy solution, not just a check.

✉️ Example Letter Opening

Hi [Owner Name],

My name is [Your Name], and I’m reaching out because I’ve long admired your business, [Business Name]. I’m a local entrepreneur looking to acquire a business I can run and grow long-term—and yours stood out.

I want to be respectful of your time and privacy. If you’re ever open to a quiet, confidential conversation—whether now or down the road—I’d love to connect.

Warmly,
[Your Name]

🏁 Final Take

Reaching out to a business owner to express interest in buying their company is a mix of art and science. Start with respectful, human messaging, lead with curiosity, and don’t rush the conversation. Many sellers don’t know what they’ll do next—but your approach could open a door they didn’t know was possible.

At Clearly Acquired, we’ve helped thousands of buyers break the ice and build real relationships with business owners—whether they’re listed for sale or not. We can help you craft outreach, analyze deals, and fund your acquisition when the time is right.

—

Onward,

Samson Jagoras
CEO & Chief Investment Officer
Clearly Acquired

P.S. Want outreach templates or access to our verified off-market search tools? Join the platform or talk to our team today.

‍