Most business owners spend decades building the business and give almost no thought to the exit.

They spend years grinding and perfecting a well-oiled machine. They optimize operations, refine services, grow teams, and tighten margins… just to arrive at the endgame, arguably the most consequential moment of their ownership journey, completely unprepared. 

No plan. No playbook. Just the hope that instinct will carry them through.

When they walk into that boardroom, it’s their Super Bowl- their one and only game. The stakes have never been higher. 

But for the private equity team across the table, it’s their fifth deal that week. For them, this is process- just another Tuesday. 

For the business owner, it’s legacy-defining. 

And there’s no second chances for defining a legacy. No dress rehearsals. No do-overs. 

According to recent Forbes projections, over 4 million Baby Boomers will reach retirement age annually through 2027. That’s a flood of business owners heading for the exit, many without a plan, creating a crowded, competitive marketplace for sellers. As a result, many will resort to closing their doors and walking away while  private equity takes full advantage of the rest.

If you’re heading into the fourth quarter of your business ownership journey, the most important question to ask yourself is: 

Are you ready to compete?

Because when it comes to building a business, most write the book, but forget to finish the final chapter.

The smartest move you can make? Build your exit team and your exit plan before the clock runs out.

If you’re heading into your business Super Bowl, here are 7 steps to help you manage the clock, control the field, and protect your legacy.

Don’t Bring a Knife to a Gunfight. Build Your Boardroom.

Selling your business is a massive milestone - financially, emotionally, and personally - but it’s not a DIY project. 

The owners with the best outcomes equip themselves with a team of advisors long before the letter of intent is ever signed. Here’s your A-team:  

Start with a CPA to clean up your books so your numbers speak your value fluently. 

Add a Tax Attorney to minimize your tax burden and help you think through options like equity rollovers, installment sales, and capital gains treatment. 

Then, bring on an Estate Planning Attorney to align the deal with your long-term goals (trusts, gifting, charitable giving).

An Investment Banker brings your business to market, identifies buyers, and negotiates terms. 

In larger deals, an Audit Firm adds credibility, while a Business Attorney protects your interests. 

Finally, a Wealth Advisor structures your financial future post-sale by proactively managing the proceeds to align investments goals.

Valuation and Timing Is the Multiplier YOU CONTROL.

According to The Guardian, "Baby Boomers are selling their small businesses at increasing rates, with sales recovering to pre-pandemic levels and prices rising by 20% from the previous year."  

With over half of business owners reaching retirement age, and 80% lacking succession plans, the market is saturated with businesses for sale, making strategic timing more crucial than ever.

Selling in a burnout moment rarely ends well. 

Another wrench: Global Influence. External economic factors like tariffs, trade policies, and inflation can shift your timeline. Trade tensions and inflation are forcing businesses to rethink pricing, supply chains, and buyer behavior.

In this climate, sometimes the best move is slowing down, not speeding up- a little strategic planning can go a long way.

One of my clients delayed listing for 18 months to streamline operations and reposition from project-based to recurring revenue. They ended up walking away with 2.5× more and a far easier transition. 

Deal Structure Is Where Value Is Gained— or Lost.

One of the biggest regrets post-sale? Not understanding deal structure. 

Too many business owners focus too heavily on “offer price”, overlooking everything else. What determines success: the structure of the deal, the planning that precedes it, and the expectations you carry into the process.

It’s critical to think before you sign. The real pitfalls happen off the balance sheet.

I’ve seen owners accept long-term payouts or performance-based payouts, only to watch the profits disappear under new leadership.

Another surprise? The tax hits that follow. Once the business is gone, so are the write-offs.

Asset sales can bring painful tax bills; stock sales are often better for sellers but harder to land. 

Know your options and understand the differences early. This will help you navigate negotiations so everyone leaves in a limousine.

Think of Modern Tools for Modern Deals.

Today’s exits are becoming increasingly guided by Artificial Intelligence tools, helping owners forecast market timing, model buyer behavior, and pressure-test deal scenarios before they ever enter the room.

Over half of sales professionals now use AI to drive smarter decisions and better outcomes.

Smart tools are just as important as smart advisors!

Protect What You’ve Built— Including Your People.

A valued manager once quit mid-transition after hearing about the sale through a rumor, not the owner. That deal still closed, but the buyer cut staff, morale crumbled, and the culture was never the same.

Exits don’t just transfer ownership. They expose leadership. Protect your people with a plan, communicate early, and lead with integrity.

What Will Life Look Like after the Sale?  You Sell. You Celebrate. Then… Silence.

The rhythm of business, the identity, the team—it’s all gone after the deal closes.

What’s worse? Your financial reality shifts too. 

You're now drawing from investments, not driving income. No more bonuses. No more write-offs. Just taxes and market forces instead of your hustle.

Many struggle here, mentally and financially. True post-sale success starts by aligning your investment strategy with your identity, not just the cash windfall.

The Bottom Line: Mindset Is the Real Multiplier.

What’s the most underestimated, and most regretted, part of selling a business? Not managing expectations.

The real job of every advisor is helping owners recalibrate- sifting through what’s real, what’s reasonable, and what’s worth fighting for.  

Your exit is more than a financial event.  

It’s a personal transformation you can’t afford to improvise. The outcome hinges on preparation, perspective, and people.

So write the final chapter with intention. Surround yourself with experts. Be honest about what you want and what you're afraid of.

This isn’t just a sale. It’s your Super Bowl. Make sure you win.

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Citations:

Gene Goldman, "The Economic Implications Of Aging Boomers And Emerging Millennials," Forbes, September 3, 2024.

Evan Edwards, "As Owners Retire, These Cities Want To Keep Businesses Open," Forbes, May 7, 2024.

Michael Collins, "As Millions Of Boomers Retire, Here’s How To Rethink Skilled Trades As A Path To Job Security," Forbes, April 1, 2025.