by Dave Godwin, Executive Business Broker, CBI Team NWA

Selling a Business: Are You Playing Trivial Pursuit… or Risk?

Years ago, two board games dominated living rooms across America: Trivial Pursuit and Risk.

One rewarded knowledge. The other rewarded strategy.

And in many ways, those two games describe exactly how buyers and sellers approach the sale of a business.

The trouble is, they often don’t realize they’re playing different games.

Many Sellers Approach the Sale Like Trivial Pursuit

When founders think about selling their business, they often approach the conversation the way someone approaches Trivial Pursuit.

The goal in that game is simple: answer enough questions correctly to collect all the pie pieces.

If you know the answers, you win.

Business owners feel the same way about their company.

They know every major customer, the history behind key decisions, the challenges the company survived, and the relationships that make things work.

From their perspective, the value of the business is obvious—because they know the answers.

But in Trivial Pursuit, knowing the answers only helps if the dice roll lands you on the right space.

You might know the answer to a geography question… but if the dice sends you to entertainment, your knowledge doesn’t help much.

That’s often what happens in a sale process.

The seller explains why the business is valuable, but the buyer is asking a completely different set of questions.

Buyers Are Playing Risk

Most buyers approach an acquisition more like a game of Risk.

Risk isn’t about trivia. It’s about position on the board.

A good Risk player doesn’t worry about knowing everything. They focus on moves that improve their position.

For example, a strong player might fortify Alaska before attacking Asia because controlling Alaska gives you a defendable entry point into the continent.

Another classic move is building up armies in Ukraine or Central America—not because those territories are glamorous, but because they control the flow between regions.

In other words, Risk players constantly ask: where should I position my armies to control the board later?

That’s exactly how buyers evaluate businesses.

They’re asking questions like: does this acquisition strengthen my market position? Does it expand my territory? Does it give me a defendable customer base? Does it create leverage for future growth?

They’re not just buying a business. They’re making a strategic move on the board.

Where Deals Start to Break Down

This difference in perspective is where many deals stall.

Sellers sit down and begin explaining the business like a Trivial Pursuit champion.

“Let me tell you why this company works.”

Meanwhile, the buyer is studying the board like a Risk general.

“Let me see if this territory strengthens my position.”

Both sides are intelligent. Both sides are rational.

They’re just solving different puzzles.

The Smartest Sellers Start Playing Risk

The founders who achieve the best exits eventually begin thinking like Risk players.

Instead of focusing only on what they know about the business, they start strengthening their position on the board.

They work to ensure revenue isn’t concentrated in one territory, the management team can hold the line without them, systems and processes reinforce the business, and customers are diversified and defensible.

In Risk terms, they’re not just answering questions. They’re reinforcing key territories before the attack begins.

And when that happens, buyers see something very different.

They stop seeing risk and start seeing strategic advantage.

A Simple Way to Think About It

If you’re a business owner, remember this: knowledge helped you build the company, but positioning is what sells it.

And if you’re a buyer, it’s worth remembering something too.

Behind every territory you’re considering acquiring is a founder who spent years building it—sometimes one hard move at a time.

The best deals happen when both sides realize they’re not playing different games anymore.

They’re simply deciding whether the next move on the board makes sense for everyone.

Final Thought

I help business owners think a few moves ahead, designing acquisition and exit strategies that build real, long-term value. From defining your growth objectives to identifying the right targets and navigating due diligence, we’re not just making moves—we’re positioning for advantage.

We’ll assess where you stand today, map out your strategic options, and decide whether it’s time to expand your territory—or begin planning a disciplined, profitable exit.

Because in this game, the best outcomes don’t come from knowing the answers… they come from playing the board the right way.

Call or text me directly at 479-263-7330, or click here to schedule a confidential conversation.