What Is the Best Time of Year to List Your Business for Sale

And Why Robbins Pellegrino Helps Sellers Capitalize on This Crucial Window

There’s a rhythm to business—and an even sharper cadence to selling one. If you’re a business owner thinking about an exit, you might be asking, When is the right time to sell? The answer might surprise you. It’s not just about market conditions, valuation multiples, or when you feel ready. Timing is tactical, and few windows are more powerful than the one that opens in Q2.

At Robbins Pellegrino, we’ve helped countless owners navigate the nuances of business sales—and we've found that April through June often provides the ideal launchpad. It’s the sweet spot between performance visibility and calendar-driven urgency, and missing it can mean stalling your deal into next year (or worse, losing momentum entirely).

Let’s break down why Q2 is such a pivotal season to bring your business to market—and how Robbins Pellegrino ensures that sellers capitalize on the opportunities this timing creates.

1. Deals Take Time—And the Clock Starts Ticking in Q2

The average business sale isn’t fast. Whether you're in the small business market or operating in the lower middle market ($2M–$50M), most transactions take 6 to 12 months to complete. That means if you're hoping to close a deal in the current calendar year—for tax efficiency or clean accounting—you need to be on the market now.

At Robbins Pellegrino, we front-load the work to prepare your business for market, so once Q2 hits, you're not scrambling. From our first engagement, we build a runway with clear milestones and contingency planning, recognizing that every week counts when you're chasing a year-end close.

2. Holiday Season Kills Deal Momentum

Momentum is one of the most underrated forces in any transaction. Once an LOI is signed, the speed and consistency of communication between parties can make or break the deal. Unfortunately, Q4 is the Bermuda Triangle for M&A momentum.

During November and December, attorneys go on vacation, CPAs are backlogged, and banks push timelines into the new year. According to Axial’s 2023 M&A Dealmaking Survey, 56% of deal professionals reported losing deals in Q4 due to holiday-related slowdowns.

At Robbins Pellegrino, we’ve seen even well-aligned deals falter when timelines drag. That’s why our process includes maintaining consistent stakeholder engagement and contingency plans for timing disruptions. Our team proactively works with legal and financial professionals to keep everyone aligned—even through the end-of-year noise.

3. Q2 = Stronger Year-to-Date Financials

Listing your business in Q2 allows you to tell a richer, more accurate financial story. By May or June, you’ve got 4–5 months of current-year performance to present, which helps buyers analyze trends and trajectory—not just static year-end figures.

Consider the difference:

• Q1 Listings: Rely mostly on prior-year financials, which may feel stale.

• Q2 Listings: Offer a mix of trailing 12-month performance and fresh, in-year data—making it easier for buyers to understand how your business is performing right now.

Robbins Pellegrino works closely with sellers to present financials in a way that speaks directly to buyer motivations—identifying growth trends, controlling for seasonality, and highlighting earnings stability. We guide you in preparing accurate, compelling seller financial packages that accelerate buyer confidence and shorten due diligence.

4. Buyer Activity Spikes in Spring and Summer

Just like real estate, the business-buying market has its busy season—and it kicks off in Q2. After tax season winds down, and before the summer slowdowns begin, buyers are actively hunting.

BizBuySell’s Q2 Insight Reports confirm that buyer inquiries and closed transactions increase meaningfully between April and June. More buyers in the market means:

• Increased competition for quality businesses

• Faster engagement

• Greater leverage in negotiation

At Robbins Pellegrino, we don't just wait for buyers to come to us. We actively market your business to strategic and financial buyers in our network who are actively deploying capital. Timing your listing with Q2 puts you squarely in front of buyers while they're still working to meet their annual acquisition goals.

5. Tax Strategy Requires Time, Not Just Advisors

Too often, sellers approach tax strategy as an afterthought. But optimizing the tax impact of a business sale is only possible if you plan early. By listing in Q2, you and your advisors have the time to explore:

• Asset vs. stock sale structures

• Tax-deferral vehicles like Qualified Opportunity Zones (QOZs)

• Trust strategies and succession planning

• Reinvestment planning to minimize liability

Robbins Pellegrino collaborates with your CPA and estate planner as part of our holistic advisory model. We flag these conversations early, ensuring you aren’t forced into suboptimal tax outcomes just because time ran out.

6. Buyers Are Flush with Capital—and Clarity

Private equity groups, family offices, and strategic acquirers often begin the year with aggressive acquisition targets. But by Q2, they know exactly how much capital is available and what types of deals they need to complete by year-end.

Being in-market during Q2 ensures you’re top of mind when these firms are still under pressure to deploy capital—not when they’re wrapping things up or slowing down for the holidays.

At Robbins Pellegrino, we maintain ongoing dialogue with active buyers in a variety of sectors. When your business hits the market in Q2, we’re ready to position it in front of the right audience, matching their goals with your company’s strengths.

7. Q2 Gives You a Cushion if Things Go Sideways

Not every deal closes on the first try. Studies from the M&A Source indicate that as many as 50% of deals under LOI don’t close, often due to:

• Buyer financing problems

• Red flags in diligence

• Shifting market sentiment

• Cold feet

When you list in Q2, you give yourself breathing room. If your first LOI falls apart in July or August, you still have time to regroup, re-list, or find a second buyer before the year ends.

At Robbins Pellegrino, our transaction process is built to anticipate the unexpected. We stress-test the deal structure, buyer motivations, and diligence readiness—before a LOI is signed—to improve your odds of closing on the first try. But when Plan A doesn’t work, we always have a Plan B.

Final Thought: Get Ahead of the Calendar

If you're thinking about selling your business in the next 6–12 months, Q2 is not just a good time—it’s the best time. It gives you every advantage: cleaner financials, heightened buyer activity, deal runway, and flexibility to navigate surprises.

At Robbins Pellegrino, we help you get to market fast—but thoughtfully. We manage the complexity, so you stay focused on running your business. And we make sure your transaction is positioned to close before the year is out, not stall out in holiday limbo.

Want a no-cost valuation and market readiness review?Let’s talk now—before time becomes your biggest obstacle.

About Robbins Pellegrino: Robbins Pellegrino is a Florida-based business brokerage firm led by Chandler Robbins and Joe Pellegrino, Jr. that is committed to redefining industry standards. We focus on creating meaningful partnerships and ensuring successful business transitions for both buyers and sellers. For more information, visit us at www.robbinspellegrino.com or call (239) 360-6273