Sales Expert Kayvon Kay Says You're Selling Wrong: Here’s The $375M Playbook That Works

Are You Making Sales Harder Than It Needs To Be?

The host of The Deep Wealth Podcast and post-exit entrepreneur Jeffrey Feldberg speaks with Kayvon Kay.

You Don’t Have a Sales Problem. You Have a Message Problem.

Kayvon Kay has generated over $375 million in sales. That number is real. And he didn’t do it by being slick, pushy, or loud. He did it by getting brutally clear on the message and the offer.

If you’re struggling to close deals or your sales team can’t gain traction, Kayvon says it’s not the team. It’s the story you’re telling. Or worse, the one you’re not.

Most businesses think their sales problem is about closing skills. But according to Kayvon, the biggest issue is upstream. The message doesn’t match the offer. The offer doesn’t match the market. So of course, sales feels like a grind.

Rock Bottom Was the Start of Everything

Kayvon doesn’t come from money. His parents earned below minimum wage. He was labeled in school with every learning issue you can think of. “They said I couldn’t read, write, or communicate. What else was left? Phys Ed?”

By 30, he thought he’d made it. He had the job, the money, the view of the ocean, and the woman. Then in one week, it all disappeared. He lost his job. He was told to move out. His dad’s cancer came back. His sister was abandoned by her husband. And the woman he loved said she couldn’t look at him the same way.

“I was literally on the ground, waiting for someone to save me,” he said. “Then I realized no one was coming. It had to be me.”

That’s when he became an entrepreneur.

Sell It Before You Build It

Most entrepreneurs fall in love with their ideas. So they build the product, obsess over the design, and keep tweaking until it’s “perfect.” Then they launch and wonder why nobody buys.

Kayvon flipped that. He sold the program before creating a single lesson. They told people upfront it was coming and gave them something small while they waited. Not one refund. People were happy to wait.

That program went from zero to $38 million in 18 months.

“Sell it first. If you can’t sell it, don’t build it. You’ll save time, money, and heartbreak.”

Sales Isn't About Closing. It's About Listening.

This one hits hard.

“Most salespeople ask questions just to respond. Great salespeople ask questions to understand.”

Kayvon teaches his team to show up like doctors. Calm. Clear. In control. Not excited. Not robotic. Not trying to impress. Just fully present.

You ask questions to find the pain. You figure out what’s broken. Then you guide them to what’s possible if they fix it. And you don’t push. You don’t pull. You let them arrive at the answer on their own.

By the end of the call, the best prospects aren’t being sold. They’re asking to buy.

Don’t Throw Salespeople at a Broken System

There’s a common mistake founders make. Things aren’t selling, so they hire more salespeople. Then nothing changes.

“You don’t solve a marketing problem with more sales reps,” Kayvon said. “If the offer isn’t clear or the message doesn’t land, your sales team is dead on arrival.”

Marketing has to do the heavy lifting. If people show up to a sales call not knowing what you do, that’s not sales. That’s a funnel problem.

Fix the offer. Fix the message. Then give it to a great salesperson. That’s how you scale.

The Right Salesperson Can’t Save the Wrong Business

You might have the best closer in the game. It won’t matter if the foundation is shaky.

Here’s what needs to be true before you focus on sales:

• The offer solves a real problem

• The message matches what people are feeling

• The marketing brings in leads who are ready to talk

If that’s solid, Kayvon can build the system. His company, The Sales Connection, has done it over and over again. They audit the business, plug the leaks, and install a full sales engine.

They even have an eight-step hiring process that predicts with 98.7 percent accuracy who will succeed. These aren’t guesses. They’ve made the mistakes already so you don’t have to.

Mindset Beats Skill Every Time

This one might surprise you. But it’s probably the most important thing in the whole conversation.

Kayvon said most sales issues aren’t tactical. They’re mental. Sales reps lose conviction. They hear one bad review and forget the 99 wins.

So his team trains daily. They hold morning huddles. They share client wins and remind each other why they do what they do.

If you’re not doing that with your team, performance will dip. It’s not a matter of if. It’s just a matter of when.

More Reps Isn’t Always the Answer

Too many reps and you water down results. Not enough and you miss opportunities.

Kayvon uses a simple benchmark. If it takes longer than 1.5 days for a new lead to get a call, you’re understaffed. Anything under that? You’re in a good place.

He also tracks how many of those leads are actually qualified. If only two out of twenty are good fits, adding more salespeople won’t help. That’s a marketing issue, not a bandwidth problem.

Culture Drives Sales More Than You Think

You might think culture is fluff. Kayvon disagrees.

“Even if you think you don’t have a culture, you do. And it might be hurting you.”

At The Sales Connection, the culture is about winning. Everyone is aligned. No excuses. No drama. Just execution. You can feel it. And it shows up in results.

Sales teams without that kind of clarity and unity struggle. Not because of skills. Because no one’s rowing in the same direction.

Don’t Try to Be a Hero

You don’t have to figure all this out alone. If you’re stuck, if your sales are flat, or if you’re scaling and need systems fast, this episode gives you a roadmap.

Kayvon’s story is powerful. But what matters more are the lessons behind it. The mindset. The systems. The simplicity.

No fluff. No magic bullet. Just what works.

Listen to the full conversation here.

You’ll walk away with a fresh perspective on sales and a few uncomfortable truths. That’s a good thing.

Because what got you here won’t get you there.

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