Know When to Hold 'Em, Know When to Fold 'Em

After a full day at CES, my brain was buzzing. New tech. Big ideas. Bold promises about what’s next. At night, I found myself sitting next to my son, Carver, watching him gamble.

What struck me wasn’t the losses—that part was expected. What grabbed my attention was what happened when he was up.

He’s drawn to the craps table. He’d have some good rolls. His balance would climb; he was pressing his bets. And instead of stopping, smiling and cashing out… he kept playing. Up. Down. Up again. Then down harder.

At one point, I finally asked him, “Why don’t you just stop while you’re ahead?”

His answer was honest and human: “I feel like I’m on a roll, and when I’m down, it’s time to get even or get even worse.”

That moment stuck with me, because it’s not just gambling psychology—it’s sales psychology.

Behavioral economists tell us that when people are winning, dopamine floods the brain. Confidence rises. Risk tolerance expands. Logic takes a back seat. The same thing that keeps a gambler at the table is the same thing that keeps a seller talking past the close.

In sales, being “up” can look like:

• A buyer nodding along enthusiastically.
• A meeting is going longer than planned because the conversation feels good.
• A prospect saying, “This all makes sense,” or “I really like this idea.”

And instead of stopping and securing the win, we keep going.

We add one more slide.
We introduce one more option.
We pitch one more platform “just in case.”

That’s when momentum turns into risk.

There’s a concept in psychology called overconfidence bias—when success makes us believe the odds are suddenly in our favor. In sales, that bias sounds like: “If this is going well, more must be better.” But experienced sellers know this truth:

More information after the buying signal doesn’t increase confidence—it often creates doubt.

The best closers I know have a rare skill: they recognize the moment when the buyer is emotionally ready, not intellectually overloaded. They know when to stop selling and start confirming.

Here’s the discipline that separates top performers from frustrated ones:

• Listen for buying language (“How would this work?” “What would the next steps look like?”)
• Pause instead of pushing (Silence often does more work than another explanation)
• Ask a closing question sooner than feels comfortable (“What would you like me to do next?”)

Just like gambling, the goal isn’t to stay in the game forever. The goal is to walk away with a win, start executing the strategy and continue building the relationship.

Walking around at CES, it’s easy to become overwhelmed. From a small business perspective, the number of marketing options is overwhelming. They need a steady guide to help them navigate the challenge of building their business. We can be that guide.

Carver eventually cashed out—up, but only after giving some of it back. A small lesson, but a memorable one.

In sales, the same rule applies: Being up doesn’t mean you keep playing. Being up means you’ve earned the right to move forward, and the real work of building a relationship and a business begins.

The best sellers don’t just create momentum—they know exactly when to cash it in and move forward in service to their clients and prospects.

Think Big, Make Big Things Happen!

Jeff Schmidt is the SVP of Professional Development. You can reach him at Jeff.Schmidt@RAB.com. You can also connect with him on X, YouTube, and LinkedIn.