Key takeaways
- In Search Investment Group's 2023 study of self-funded searchers, cold email made first contact in 68% of deals that came from their own outreach, and cold paper mail in 8%.
- Priced at $2.05 a letter, the postal funnel in Stanford's 2014 search-phase guide works out to about $280 per in-person owner meeting.
- When no introduction is possible, Stanford's 2026 primer says a letter sent before the call can be more effective than a pure cold call.
Should a searcher send letters or cold email?#
If you're searching for a company to buy, you're probably emailing owners already, and the survey data says that's where most proprietary deals start. In Search Investment Group's 2023 Self-Funded Search Study (opens in new tab), searchers who bought a company through their own outreach first reached the seller by cold email in 68% of deals, by cold call in 12% and by cold paper mail in 8%. So keep email as your sweep across a sector, and save letters for the owners you've researched and plan to call.
Those are shares of closed deals, not response rates: they show what searchers did, not which channel owners answer. Stanford's 2026 primer on search funds (opens in new tab) adds that owners have been answering fewer emails since the early 2020s, and that when no one can introduce you, a letter before the call can work better than a cold call alone.
This guide covers what the studies report, what an owner conversation costs each way, and a letter, call and email sequence for your next shortlist. It's written for self-funded and investor-backed searchers approaching owners of US businesses, and its figures come from named studies and searchers' own accounts, not a controlled test. If you're weighing the two channels for marketing rather than owner outreach, see direct mail vs email marketing.
Where to start with each owner
Your situation | Start here |
|---|---|
Large qualified list with working emails | Email first; follow up on replies |
Researched shortlist you plan to call | Letter, then a call and an email |
No working email for the owner | Letter, then a call |
Someone you trust knows the owner | Ask for an introduction first |
Bought list; fit and ownership unclear | Research before contacting anyone |
What do the search fund studies say about mail and email?#
Search Investment Group surveyed self-funded searchers from August to October 2022. Of 279 who responded, 109 had bought a business, and most of them didn't find it through outreach: 54% bought through a transaction intermediary such as a business broker or investment banker, 25% through their own outreach, 15% through their personal network and 6% through other intermediaries such as attorneys or accountants. Within the outreach deals, first contact came by cold email 68% of the time, cold call 12%, cold paper mail 8%, other methods 8% and a warm introduction 4%.
Roughly 25 of the 109 deals came through outreach, so the 8% for paper mail is about two deals and the 12% for calls about three. The gap between paper mail and calls is noise; email's lead is the finding. The study's original web address no longer serves the PDF; the copy linked above, hosted by Hadley Family Capital, was online when we checked in October 2026.
Stanford's 2014 guide to the search phase (opens in new tab) states the trade-off from the searcher's side: "E-mail allows a searcher to reach out to thousands of companies per week, while letters to hundreds at most. However, searchers report higher hit rates with personalized letters than with e-mails."
Searchers' own accounts show the range. Joe Wechsler told Acquiring Minds (opens in new tab) in June 2026 that 24 letters led to six phone calls, two offers and one closing.
Joe Springsteen used cold calls and a yellow-letter campaign across about 5,000 contacts in Orlando and got about 150 good conversations, 15 NDAs and no LOIs. "There was really no urgency for them to sell," he told Acquiring Minds (opens in new tab) in March 2026. He later bought his company through a business broker. Neither account is a channel test, but together they suggest that targeting and the seller's timing do more of the work than the channel.
What does an owner conversation cost by letter and by cold email?#
Per conversation, cold email usually comes out cheaper, because each extra email costs almost nothing once you pay for a sequencer. A letter costs more per touch, so it has to earn its place by reaching owners your emails don't.
Start with the cash for a 100-owner shortlist. Stamping letters yourself costs $0.82 each in postage at the USPS rate effective July 12, 2026, plus paper, envelopes, toner and the folding and stuffing. Postmarkr, which publishes this guide, charges $2.05 for a one-page black-and-white letter including printing, postage and processing, so the shortlist costs $205. With its Bulk Send, you upload one letter template and a CSV of up to 100 owners, map columns such as first name, company and your reason for writing to merge variables, and approve a proof of one personalized letter before anything prints.
Entry plans at Smartlead (opens in new tab), Instantly (opens in new tab) and lemlist (opens in new tab) list at $39, $47 and $69 a month on monthly billing (pricing pages checked October 2026). The letters for one shortlist cost about as much as three to five months of one of those plans.
Divide the mailing's cost by the conversations it starts; the counts below are inputs, not forecasts, and the costs are rounded to the dollar.
What one owner conversation costs at $2.05 a letter
Conversations from 100 letters | Cost per conversation |
|---|---|
1 | $205 |
3 | $68 |
5 | $41 |
10 | $21 |
Real campaigns show where a mailing can land on that table. Stanford's 2014 guide reports one searcher's first year of postal outreach: 3,404 initial letters, 256 responses, 25 in-person meetings and 2 signed LOIs. Of the 256 responses, 124 were positive follow-ups, about 3.6 per 100 letters. At $2.05 a letter, that year would cost about $6,980 today: roughly $56 per positive follow-up and $280 per meeting. It's one searcher's year from more than a decade ago, so read it as a sense of scale rather than a forecast.
We found no published cold email funnel to set beside it, so use your own reply rate. At a few hundred dollars a shortlist, postage rarely limits a search; how many owners you can research well and call back on time does.
How should you sequence a letter, a call and an email?#
Treat the letter as the first of three touches. Stanford's primer says that when no introduction is possible, a letter sent before the call "can be more effective than a pure cold call."
A letter, call and email sequence for one owner
Day 0 — Mail the letter First-Class
USPS states a delivery window of 1–5 days for First-Class Mail. It is an estimate, not a guarantee.
A few business days after arrival — Call and mention the letter
Same day as the call — Email a short version the owner can forward
When the owner replies — Take them out of the sequence
Answer on their channel and timing; honor a request to stop on every channel.
No reply — Park the owner for a later wave
Log what you sent and come back later with a new reason to write.
Expect voicemail: the primer cites private equity callers who often leave 10 to 20 before an owner calls back, though some searchers report better results. It also says the call must come across at once as "useful, credible, or relevant to the business owner," and your letter's reason for writing gives you that opening.
The email covers what a letter can't. Replying to Jim Stein Sharpe's 2015 post Proprietary Prospecting (opens in new tab), Kelly Quann Bianucci wrote that owners forwarded her emails to "a spouse, an advisor, a contract CFO, peers from their Vistage group." She added: "Email lends itself to that more easily than a letter."
What to say on each touch:
- On the call, say that you wrote and why, then ask for 15 minutes. For example: "I wrote to you last week. I'm looking to buy and run one commercial HVAC business, and your school maintenance contracts are why I wrote. Do you have 15 minutes this week?" On voicemail, leave your name, the company you wrote about and your number, twice.
- In the email, name the company and your letter in the subject line, give your reason in two or three sentences and offer one way to reply.
- Say you sent a letter, not that the owner received it; a USPS scan doesn't show they read it.
The personalization guide covers estimating arrival from scan data and tying your follow-up to the letter's opening line.
Where does cold email still win, and what changed for deliverability?#
Email wins whenever reach matters more than depth: testing a thesis across a sector, finding out which owners will talk at all, and staying in touch with the ones who say "not yet."
What changed is the inbox. The primer puts the fall in owner replies down to "lower email deliverability and sellers receiving high volumes of cold outreach." The big mailbox providers have tightened their rules too, but when we checked them in October 2026, those rules reached less of a searcher's outreach than you might expect:
- Gmail: Google's sender guidelines (opens in new tab) apply only to mail sent to personal Gmail accounts, not Google Workspace accounts, and its bulk-sender rules start at about 5,000 messages a day. Gmail stepped up enforcement in November 2025 (Google's FAQ (opens in new tab)).
- Outlook.com: Microsoft's requirements (opens in new tab) cover mail to outlook.com, hotmail.com and live.com addresses from domains sending more than 5,000 emails a day. Microsoft announced that mail failing them would be rejected from May 5, 2025.
- Yahoo: Yahoo's requirements (opens in new tab) cover mail to Yahoo-hosted consumer addresses, with stricter rules for bulk senders, but Yahoo says it "will not specify a volume threshold" for who counts as one (Yahoo's FAQ (opens in new tab)).
A searcher sending a few hundred emails a week won't come near Gmail's or Outlook.com's 5,000-a-day thresholds, and mail to an owner's company address goes through that company's own filters, which these consumer rules don't govern. Either way, meet the baseline: authenticate your sending domain, keep complaints low and stop emailing anyone who asks.
Treat the FTC's CAN-SPAM compliance guide (opens in new tab) as the floor for cold email. It makes "no exception for business-to-business email," requires a valid physical postal address and has you honor opt-outs within 10 business days. CAN-SPAM covers commercial email, not letters.
For choosing a sequencer and keeping every channel's replies in one CRM, see the search fund outreach tools guide.
Which owners should get a letter?#
Give a letter to the owners where it does a job email can't, and where you can show you know their business. For searchers who pick an industry first, Stanford's primer notes that by the outreach stage they have "already completed deep industry analysis, which should increase the searcher's credibility." A letter is where an owner can see that work.
On most shortlists, that means:
- Owners you've researched closely enough to name one true, specific reason for writing.
- Owners with no working email, or who haven't answered your emails.
- The owners you would most regret missing. Sign those letters by hand.
- Owners you can call a few business days after the letter arrives.
Leave the rest of the list to email. A bought list, an owner you haven't verified or a company that only loosely fits your thesis doesn't become a better target on paper.
No letter, email or call makes an owner ready to sell; Springsteen's campaign reached 15 NDAs and still heard "maybe in a few years." What a letter can do is give the owners you care most about something to read in their own time, so your call isn't the first they hear of you.
When the shortlist is ready, the campaign guide covers checking the owner file, proofing the batch and handing replies to your CRM, and the personalization guide covers what to put in the letter.