Why Smart Biz Buyers Love the Holidays

The information contained here may not be typical and does not guarantee returns. Background, education, effort, and application will affect your experience. Your results will likely vary.

Biz Buyers,

Welcome to Main Street Minute — where we share some of the best stories and ideas from inside our acquisitions community. Whether you’re curious or serious about buying an SMB in 2025, you’re in the right place.

But first…

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Then let’s get down to business.

Today, in 1 minute, you’ll get…

✅ 1 Incredible Biz Buyer Story

✅ 3 Ways the Holidays Are Your Huge Opportunity

✅ Our Top Resources for Main Street Biz Buyers

From 30 Years Fighting Fires to Aspiring Owner

A new member of the community recently shared their story:

His name is Don, and he’s a recently retired fire Captain with 3 decades of service under his belt.

For years, Don balanced the high-stakes demands of the firehouse with running side businesses and working second jobs. Leadership, problem-solving, and decision-making under pressure became second nature.

He dedicated his career to:

• Developing crew members
• Fostering a culture of continuous improvement
• Navigating complex situations with limited information

Expertise in operating under stress, making high-stakes decisions, and rapidly deploying resources to solve problems — these are all critical skills for business ownership.

Now, he’s focused on his next mission: Building wealth, leaving a legacy, supporting the local community, and helping others find success.

After a career of protecting and serving, Don’s ready to lead again — this time, on Main Street.

He’s drawn to industries like healthcare and professional services, where his strategic mindset and operational leadership experience can make the biggest impact.

This is what the Contrarian Community is all about: helping leaders like Don turn a lifetime of experience into ownership and impact.

In a community of 1,000+ current and aspiring business buyers, someone has probably...

• Faced the exact challenge you’re dealing with.
• Cracked the code on a deal structure you're confused about.
• Learned a lesson that can save you months of mistakes.

Leverage the network. Deals are hard — together, they get easier.

3 Ways the Holidays Are Your Huge Opportunity

It’s wild to think about how many life-changing business decisions happen over holiday dinners with family.

Think about it — they form the perfect conditions for business owners to CONSIDER selling…

Here's why the holidays are a goldmine for acquisition opportunity creation:

1. Reflection on Retirement

As the year winds down, business owners take stock of their lives and futures. For aging owners, this reflection naturally leads to questions about succession, legacy, and stepping away.

The emotional weight of another year of grinding through daily operations — especially during the holidays — can tip the scale toward selling.

2. Family Influence

Holiday gatherings bring families together, sparking discussions about the future.

Children may not want to take over the family business, or they might encourage parents to consider retirement for health or lifestyle reasons. These conversations plant the seed for a sale.

3. Clean Slate Mentality

The New Year represents a fresh start. Business owners looking to simplify their lives, reduce stress, or explore new opportunities see January as the ideal time to hand over the reins.

How to Leverage This Timing:

• Direct Outreach: Send personalized letters or emails to local business owners. Position your pitch around this timing and mindset.
  
• Network Proactively: Attend community events, meetings, and even holiday mixers. Owners who might not have listed their business yet are often open to off-market conversations.
  
• Follow Up: Many owners don’t make immediate decisions during the holidays but will revisit the idea in the new year. Reach back out with a gentle nudge.

Folks, some of your next big moves are quietly being born right now in someone else's dining room.