Don Connelly's Wit & Wisdom

Don Connelly's Wit & Wisdom

The Kitchen Table Test

Why Gator Believes Clarity Is One of the Greatest Competitive Advantages in the Business

Don Connelly's avatar
Don Connelly
May 13, 2026
∙ Paid

I met Gator for breakfast at the Sun Garden Café in Siesta Key Village.

If you’ve never been there, it’s one of those classic Florida breakfast spots that somehow feels both busy and relaxed at the same time. Locals in golf shirts and sandals. Tourists eating before heading off to the beach. Ceiling fans turning lazily overhead. Coffee cups constantly being refilled. A great place to relax,

Gator loves the place.

Partly because everybody knows him.

And partly because he says you can learn a lot about people over breakfast.

He was already there when I arrived, sitting at an outdoor table wearing a faded blue quarter-zip, wire-rim glasses low on his nose, reading the business section with a yellow highlighter in his hand. He’s one of the few people I know who still reads the newspaper.

I sat down and the waitress walked over.

The waitress didn’t ask Gator what he wanted.

She just smiled and said:

“Same as always, Gator?”

Gator smiled at her.

She laughed.
“So… same as always.”

That’s Gator.

Everywhere we go, people seem comfortable around him within thirty seconds.

Not because he tries hard.
Because he pays attention.

The day before we met, Gator had a meeting with a new client.

A big one.

The kind of client every Advisor wants.

Successful businessman. Sold a company. Significant assets. Sharp guy.

After the coffee was poured, I asked Gator how the meeting went.

He shrugged.

“Good meeting,” he said.

That was it.

No celebration.
No chest pounding.
No dramatic recap.

Just:
“Good meeting.”

I laughed.

“What made it so good?”

Gator took a sip of coffee.

“Basically, because the client was so happy to be there.”

“Happy?”

“Yup. He never got comfortable with his former Advisor.

The Advisor had the habit of talking down to him.

He said it sometimes made him feel both dumb and confused; and he did not like that feeling.”

Gator leaned back in the chair.

“It’s not uncommon for Advisors to make people feel that way.

Not intentionally. Most Advisors are good people. Smart people. But they explain things in ways clients can’t repeat, can’t visualize, and can’t emotionally connect to.”

He paused.

“And when people don’t understand something, they rarely admit it.”

That hit me immediately.

Because he was right.

Most clients won’t interrupt an Advisor and say:

“I have no idea what you’re talking about.”

Instead, they nod politely.

Then they go home confused.

And confused people hesitate.

“Suppose I told you that I was having a problem with my boat. The engine is having intermittent propulsion inefficiencies caused by fuel-delivery inconsistencies within the combustion sequence, what would that mean to you?”

I laughed.

“Not much.”

“Exactly,” he said. “But if I said, ‘The engine sputters and sometimes loses power,’ you’d understand it immediately.”

He smiled.

“Same problem. Different language.”

That’s Gator.

He has this ability to reduce complicated ideas into simple human language without making people feel talked down to.

And that’s a rare skill.

Especially in our business.

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