Selling to rich people is a cheat code, 6k to 26k while working less

I had a client sit across from me who used to spend an hour and a half just to get a deposit. Now he closes six figure deals in one call and works less than he ever did. His name is Nathan, and his story is the cleanest proof I've got that who you sell to matters more than how good you are at selling.

We've worked together for a year and a half. Last month he hit $26,500 in commissions. This month he's on pace to clear $30k. But that's not even the crazy part. The crazy part is where he started.

Selling to broke people will wreck you

When Nathan first came to me, he was selling marketing services to med spa owners. Sounds decent on paper, right? It wasn't.

"They're kind of broke cuz they weren't getting any people coming through to their business."

These guys were logistical, numbers only, get to the point type people. No emotion, no vision, just "show me the numbers and don't waste my time." That's a hard way to sell. Then the offer went sideways because of stuff totally outside his control, some FTC thing tanked the GLP-1 market. Not his fault. Just bad luck with a bad offer.

So he moved to an e-com offer. This is where it gets painful to even read.

"I would be doing objection handling, not even trolling you, probably for at least an hour, hour and a half, just to maybe collect a deposit."

And then they'd dispute the charge after. He was closing 40 to 60% of his calls on a $3k package and his best month was $12k. Read that again. Closing 60%, grinding for ninety minutes a call, and topping out at $12k a month. That's not a sales problem. That's an offer problem and an audience problem.

Comfortable is a trap

Here's the part every closer stuck at $10k to $20k a month needs to hear. I told Nathan two months into working together that he needed to get off that offer. He didn't listen.

"Well, it's like I'm doing good. Like I'm comfortable here, etc. And I just stuck with the offer."

He admits it now. Staying comfortable cost him real money for months. If you're sitting at a number that feels fine, that's usually the sign you need to move, not stay. Comfortable is where closers go to stall out.

What actually got him to move was a mental shift, not a tactic. He started feeling bad about only making $7k to $12k a month once he understood what was actually possible. That discomfort is what pushed him to finally take the leap.

Your relationship with money has to change fast

This is something I tell every closer I work with. Your relationship with money has to evolve as fast as your income does, or you'll sabotage yourself right back down to where you started.

"You have to allow your relationship with money to change quickly. Like at first you're going to be like, dude, $20,000 will change my life. But then once you hit it, you got to understand it's not actually that much money."

I told Nathan, the same day we recorded this, I'd already made $10.5k in commissions before lunch, on a totally different offer than the sales training I teach. If my relationship with money stayed the same as it was years ago, I'd never be able to hit numbers like that today. You have to let the goalposts move or you'll cap yourself on purpose without realizing it.

The offer switch that changed everything

I got Nathan onto a new offer selling AI automation. People come to this company to start an agency and the company partners on the business and scales it. Ticket prices run from $20k on the low end up to $120k.

He closed a $120k deal. One single deal. That's more than his best month ever on the old offer, where he was grinding 60% close rates for $12k.

"I have more time. Like you would not believe, I'm working less and I'm making so much more. It's insane."

Why selling to rich people is actually easier

This is the part people don't expect. Selling to people who actually have money is not harder. It's easier.

"It's pretty easy breezy. I don't even have to get them to feel all these emotions. With these guys I barely even do any of that. I just walk through everything, get a couple pieces of criteria, and pitch. That's it."

No twisting them into emotional knots just to get a deposit. No future pacing for forty five minutes to convince someone making minimum wage that they can afford your offer. Rich buyers already know what they want. You're not dealing with the same garbage, excuses, disputes, and fake urgency that comes with selling to broke people.

Here's my honest take on it:

"You're always surrounded with people who have abundance. You're not dealing with bullshit. You're still going to have to overcome concerns, still handle objections, still learn to sell well. But the amount of bullshit you have to deal with is nothing."

I lived this myself. Early in my career I was on a sales training offer taking somebody's last $100. Three hours of fighting for that. Compare that to the deals I close now. No contest.

Stop making yourself small

One thing that stuck with both of us, there's a clip of Jeremy Haynes asking a guy how much he makes a month. The guy says $180k. Jeremy asks how it feels. The guy says he's barely scraping by.

"He goes, you are barely scraping by."

That hit Nathan hard. Another one that got him, Jeremy talking about a tree on his property that cost $120k, telling a room of guys just hitting six figures that none of them are bigger than a tree. Nathan's line after hearing that:

"Bro, I'm probably like a bush or some shit."

It's funny, but it's the point. The second you think $25k a month is a ceiling, you've already capped yourself. Somebody paid Nathan $120k in a single deal. That means there are people out there who see that number as pocket change. Your job is to stop making yourself feel big for hitting numbers that are actually still small.

The bottom line

If you're stuck at $7k to $25k a month feeling comfortable, that comfort is the problem, not the achievement. Nathan went from 90 minute objection handling marathons for a $3k package to closing $120k deals with way less friction, because he changed who he was selling to, not just how he was selling.

Stop selling broke people. Get around people with money, get on a bigger offer, and let your relationship with money grow as fast as your income does. As Nathan put it, stop being broke. That's the whole lesson.