"Will You Marry Me?" and Other Ways to Kill Your Premium Sales in the First DM

Ever had someone ask for your hand in marriage before they even asked for your name? In the world of high-ticket sales, we call that "The Esteban Method." And spoiler alert: it’s a great way to get left on read. Forever.

Today, we’re dissecting the art of the cringe-worthy pitch and why your "A-Game Executive Package™" is currently sitting at a conversion rate of zero.

The "Lamborghini Lifestyle" Trap

Esteban had a coaching business. Well, technically, he had a sleek Wix site, a minimalist logo, and a massive thirst for those $10k months.

After binge-watching three "experts" filming from a rented Lambo in Vegas, Esteban decided his flagship product would be the "Steel Alpha Program™": a 12-session premium grind-fest for $1,200.

Day one of his ad campaign:

"Level up your career. Invest in yourself. DM for info."

Round 1: The "Wall of Text" Special

Enter Paola. She sends a casual: "Hey, can you tell me more about this?"

Instead of acting like a normal human, Esteban went full "Buy Now" bot. He copy-pasted a 20-page PDF, attached a sketchy testimonial from an "Anonymous Fortune 500 CEO," and closed with: — "I can get you on the books today. Do you prefer Visa or Venmo?"

Paola? She didn't just ghost him; she probably blocked him.

Round 2: The "I Know Better Than You" Guy

Then came Rodrigo: "Hey, do you offer single sessions?"

Esteban hit him with that frozen "I’m-a-visionary" smile: — "Look, you don't need a band-aid. You need a total disruptive transformation. Half-baked solutions don't work." (Cue the same massive PDF).

Rodrigo replied with a "👍" and vanished into the digital abyss.

The "Julia Effect" (A.K.A. Actually Being a Human)

The lightbulb finally went off when Esteban met Julia at a networking event. Instead of shoving a pitch down her throat, he did something radical: He shut up and listened.

He asked about her roadblocks. Her goals. Her actual life. They talked for an hour. No PDF. Just vibes and value. Two weeks later, she asked for a trial session. A month later?

She bought the Premium Package without him even asking.

The takeaway: Trying to sell your most expensive service to someone who just met you is like proposing on the first date.

"Hi, I’m Esteban. Want to combine our bank accounts and move in next month?" Yeah... that’s gonna be a no from me, dog.

🔍 The "Don't Be a Creep" Checklist

Before you try to close that high-ticket sale, ask yourself:

• Does this person even know me? Or am I just a random guy in their DMs?

• Have I provided actual value? Or just a sales pitch disguised as "help"?

• Do I have a "Value Ladder"? Or is it just "My most expensive thing or nothing"?

• Am I listening? Or am I just waiting for my turn to talk about the price?

• Where are they in the funnel? (Hint: If they just met you, they aren't ready to "invest in their legacy" yet).

✨ Final Vibe Check:

Selling isn't about "convincing" people to part with their money. It’s about walking them from "Who is this?" to "I need this." If you rush the process, you're going to get ghosted. And honestly? You’d deserve it.