Navigating Multi-State Business Exits from $1M to $30M

Selling a business is one of the biggest financial decisions an entrepreneur will ever make. But when that business operates across multiple states, owns commercial real estate, employs a large team, or involves millions of dollars in enterprise value, the transaction can quickly become much more complicated than simply finding a buyer and agreeing on a price.

On the Build It to Billions Podcast, Brett Swarts sat down with Gregory Kovsky, President and CEO of IBA Business Brokers, to discuss what business owners should know when preparing for an exit ranging from approximately $1 million to $30 million.

With more than 30 years of experience and over 300 privately held business transactions, Gregory has seen firsthand what separates successful exits from deals that lose value—or never make it to the closing table.

The #1 Secret to a Successful Business Sale: Plan Before You Sell

Gregory’s biggest piece of advice is simple: plan ahead.

Business owners can spend decades building their companies, yet some begin planning one of the largest financial transactions of their lives only when they're ready to sell.

That can be a costly mistake.

A sophisticated business sale can involve multiple areas at once, including:

• Legal structuring
• Accounting and financial reporting
• Tax planning
• Business valuation
• Financing
• Commercial real estate
• Negotiation
• Employee and management considerations
• Psychological and family dynamics

That means an owner shouldn't expect one advisor to solve every problem.

Instead, Gregory recommends surrounding yourself with experienced professionals who understand their respective areas and can work together toward the same objective.

Think of an exit like assembling a championship team. You don't want every player trying to play the same position. You want the right professionals handling the right responsibilities—and coordinating before the transaction gets complicated.

Know Your Market Before Sitting at the Negotiating Table

One of Gregory's strongest points was that sophisticated buyers will come prepared.

Whether someone is buying a $3 million company or a $30 million company, they will likely have advisors helping them evaluate the opportunity, scrutinize the financials, assess risks, and determine what they're willing to pay.

As Gregory put it, there's essentially "no dumb money."

That creates a major risk for an unprepared seller.

If the buyer understands your industry, comparable transactions, financing environment, and business valuation better than you and your advisory team do, you're entering the negotiation at a disadvantage.

Your broker or M&A advisor should therefore be capable of not only establishing an appropriate valuation but also defending that valuation in the marketplace.

The goal isn't simply to put the highest possible asking price on the business. It's to create a credible case for why qualified buyers should pay that price.

Price Isn't the Only Thing That Matters

Business owners naturally focus on the headline sale price.

But a $20 million offer isn't necessarily better than an $18 million offer.

The structure behind the number matters.

Sellers should evaluate factors such as cash at closing, financing contingencies, seller notes, earnouts, working-capital requirements, representations and warranties, transition obligations, and the probability that the transaction will actually close.

The highest theoretical price means very little if the transaction collapses during due diligence.

For owners approaching an exit, the better objective may be to maximize price, terms, and certainty of closing together rather than optimizing one while ignoring the others.

Multi-State Transactions Add Another Layer of Complexity

Things become even more interesting when a company operates in several states or owns real estate alongside the operating business.

Now you're potentially dealing with multiple jurisdictions, different tax considerations, property valuations, entity structures, licensing requirements, and buyers who may value the operating company and real estate differently.

This is where early coordination between your business broker or M&A advisor, CPA, attorney, real estate professionals, financial advisor, and tax-planning team becomes especially important.

Waiting until after a letter of intent is signed—or worse, until shortly before closing can dramatically reduce your available options.

Don't Forget What Happens After the Sale

Selling the company isn't the finish line.

It's the transition from building wealth inside the business to managing wealth outside of it.

An entrepreneur might spend 20 or 30 years creating a successful company and then suddenly experience a massive liquidity event. Without advance planning, a significant portion of those proceeds may immediately be exposed to capital gains taxes, while the remaining capital needs an entirely new investment and wealth-management strategy.

That's why exit planning should ideally include tax planning and wealth planning before the sale occurs.

Strategies such as the Deferred Sales Trust may provide qualifying business and real estate owners an opportunity to defer capital gains taxes while creating greater flexibility for diversification, liquidity, retirement income, and legacy planning.

The key is exploring these strategies early enough to determine whether they fit the owner's circumstances and transaction.

Build the Exit Before You Need It

Gregory Kovsky's message to entrepreneurs is ultimately about preparation.

You've spent years—sometimes decades—building the asset. Don't wait until the buyer arrives to begin thinking about how you're going to exit it.

Build the advisory team early. Understand your market. Strengthen your financials. Know what your company is worth. Think through your real estate. Evaluate the tax consequences. And decide what you want your wealth and life to look like after closing.

Because the best exit isn't simply the one with the biggest check.

It's the one that converts years of entrepreneurship into lasting freedom, wealth, and impact.

We recently discussed this topic in more detail on the Build It to Billions podcast. Here’s the full conversation on YouTube for anyone who wants to dive deeper: