Jeb's 'Sales Crack' Yearbook Story

Here’s a question that’ll change how you think about this profession forever: What’s the one moment that reveals you’re built for sales success?

For most people, that moment never comes. They stumble into sales, struggle with the stereotypes, and either quit or spend their entire career fighting against what they think selling is supposed to be.

But for those of us who get it, there’s a moment of clarity so powerful it changes everything. Mine happened in high school when I was chasing a girl and ended up on the yearbook staff. Thirty days later, I handed over $3,800 in checks while everyone else struggled to hit their $300 quota.

The Sales Crack Moment

When Mr. Hall at Hall’s Hardware Store wrote me that first check for a yearbook ad after I had done little more than ask outright for the money, something clicked. This wasn’t complicated. Walk in, shake hands, present value, and people give you money.

While my classmates were paralyzed by the same stereotypes you hear today (“I’m not a salesperson”), I was out there having conversations. That’s all prospecting really is. Talking to people.

The gasp in that room when I revealed my numbers? That was better than the money. That was the competitive fire igniting. That was me realizing I could outwork, outsell, and out-earn anyone if I just committed to the process.

The Discipline Problem Most Sellers Miss

Here’s what nobody tells you about sales success: It’s not about talent. It’s not about charisma. It’s about ruthless execution of proven processes.

By the time I was 21 or 22, I was making $300,000 in the early nineties. That’s equivalent to making close to a million today. Not because I was special, but because I understood something fundamental that most people never figure out: The more people you talk with, the more you sell.

And here’s the beautiful part. There are lots of people to go talk with. The pipeline never runs dry if you’re willing to fill it.

The Three Non-Negotiables for Modern Sellers

The future of selling is blending. Not choosing between video and phone and in-person. Blending all of them based on one critical question: What communication channel gives me the highest probability of capturing my desired outcome at the lowest cost of time, energy, and money?

When I started selling, we had two channels. Maybe three if you count snail mail. Phone and in-person. That’s it. Today? You’ve got a dozen ways to connect. WhatsApp lets you text, call, and video chat almost instantly. The options are endless.

But here’s where Gen Z sellers (and honestly, every generation) screw this up: They get single-siloed.

“I’m only good at email.”
“I only do video calls.”
“I hate the phone.”

That mindset is killing your income potential. You need to be good at everything. Master every channel. Because the channel doesn’t matter. The outcome does.

Synchronous Beats Asynchronous Every Single Time

Here’s the second non-negotiable to sales success: Stop hiding behind asynchronous communication.

We do deals in a synchronous world. Real-time conversations. Phone calls. Video meetings. Face-to-face interactions. If you think you can close business through email threads and text messages, you’re delusional.

Why? Because robots can write better emails than you can. AI can craft more persuasive text messages. But sales is the ultimate human career in the age of AI precisely because of the human connection required in synchronous conversations.

Lead with phone calls. Get face-to-face when the deal size justifies it. Use video when it makes sense. But always, always prioritize real-time conversations over digital hide-and-seek.

Ask Questions and Actually Listen

The third non-negotiable is mastering the art of asking great questions and listening to the answers.

People make five decisions before they buy from you: Do I like you? Do you listen to me? Do you make me feel important? Do you get me and my problems? Do I trust and believe you?

Notice what’s not on that list? Your product features. Your company’s awards. Your clever sales pitch.

They’re evaluating you. Your ability to connect. Your capacity to understand. Your commitment to making them feel important.

And the only way to get five affirmative answers to those questions is through synchronous conversations where you ask intelligent questions and actually listen to what they’re telling you.

The Make It Rain Principle

When Mr. Rouse made me editor of the yearbook after I brought in $3,800, I learned something that shaped my entire career: When you can make it rain, you can get anything you want.

That principle holds true whether you’re selling yearbook ads in high school or enterprise software to Fortune 500 companies. Revenue solves problems. Performance opens doors. Results create opportunities.

Most people in sales stumble into it. They take the job because it was available. They stick with it because the money’s decent. But they never commit to mastering the craft.

The question isn’t whether sales chooses you. The question is whether you choose sales. Whether you commit to being good at every communication channel. Whether you prioritize synchronous conversations over digital convenience. Whether you master the art of asking questions and listening.

Those fundamentals never change. The technology evolves. The channels multiply. But the core truth remains: Talk to more people, in real time, with genuine curiosity about their problems, and you’ll make more money than you ever thought possible.

That’s how you achieve sales success. That’s how you go from yearbook ads to seven figures. That’s how you make it rain.

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