Owners Decide at the Holiday Table

Picture an owner at a holiday dinner. Twenty-two years into a business they started with one truck. Their daughter has a career in another city and is not coming back to run it. Their spouse has asked, more than once this year, when they plan to slow down. A year-end P&L will land on their desk in a few weeks.

For a searcher, this is the most important month of the year to understand, even though it’s a quiet one for outreach. The thinking owners do in December shapes who they are willing to talk to in January.

Why the End of the Year Hits Differently

Owners spend most of the year inside the business. The end of the year pulls them out of it. The books close and they see the full-year number, with family in the same room asking the questions family asks. Then the calendar flips, and “one more year” stops being a vague idea and becomes a real commitment they’re about to make again.

None of that turns into a decision overnight. In our 2025 outreach data, owners in their 60s and 70s showed the most interest, and most of them were still in the thinking phase rather than an active process. The holiday table is where a lot of that thinking happens.

What Owners Are Weighing

The kids probably are not taking over

Many owners have assumed for years that a child or a longtime employee will carry the business forward. The odds say otherwise.

Family Business Institute, via Conway Center for Family Business.

Around the holiday table, that assumption tends to get tested out loud.

They haven’t made a plan yet

According to the Exit Planning Institute, 80% of owners have no written transition plan, and half have done no exit planning at all. Planning to leave a business you built can feel like planning a loss, so it gets put off. Year-end is often the first time the gap becomes hard to ignore.

They’re tired

A 2023 Ramsey Solutions survey of more than 1,000 small business owners found that 42% had experienced burnout in the past year. An owner who has carried a business through another full year may be more open to a conversation in January than they were in June.

They worry about their people more than the price

In the reply threads we’ve analyzed, owners worried far more about what would happen to their employees and customers than about missing out on a deal. A business is a team they hired and a reputation they built over decades. Any conversation about the future has to start there.

They’re already doing their own math

When an owner eventually names a number, it is usually tied to something real: a retirement target, or what they need to walk away debt-free. Much of that math gets done privately at the end of the year, with the new P&L in hand.

What That Means for Your January Outreach

Most owners leave the holiday table still thinking. They are more open than they were, but a long way from calling a broker. Deals that start from a first email often take 9 to 18 months to close. The searchers who win those deals are the ones an owner already trusts when the thought becomes a plan.

Here’s how to show up as that person.

Lead with what they built, not what it is worth

In our analysis of more than 250 owner reply threads, emails that led with legacy language, such as reputation and taking care of the team, hit positive reply rates of 30% or higher. Emails that opened with comparables and valuations landed at roughly 5 to 10%.

Positive reply rate by opening approach. DealBuff analysis of 250+ owner reply threads.

An owner coming off the holidays is thinking about legacy. Meet them there.

Talk about their people

Say what happens to the team. A plain sentence about keeping employees and serving the same customers answers the question an owner is most likely to be carrying, and most outreach never addresses it.

Make “not yet” a perfectly good answer

An owner in the thinking phase will not say yes to a call about selling. They might say yes to a conversation with someone who clearly is not in a hurry. Make it easy to reply without committing to anything, and when they say “not now,” treat it as the start of the relationship. A short, no-ask note every few months keeps you in the picture until their timing changes.

Sound like someone from their part of the world

Owners respond to outreach that reads like it came from a real person who knows where they operate. In our subject line analysis, local and regional framing replied at 6.4% against a 4.7% baseline.

Reply rate by subject line framing. DealBuff outreach data.

After a season spent with family and community, local beats generic.

Be patient about their number

If an owner names a price that seems high, don’t argue with it. Ask what it is built on. The answer tells you what they need from the deal, and it is usually something you can work with.

The Owner Who Replies in January

The owner at that holiday table is not going to pick up the phone and call a stranger. Sometime in the new year, though, an email might arrive from someone who talks about the business the way they do and doesn’t rush them. That’s often the first reply that turns into a deal a year later.