The Days That Break Us: What 17 Years of Selling Taught Me About Grief, Growth, and Getting Back Up

By 23, I'd helped telecom companies generate fifty million dollars in revenue. Trained almost a hundred salespeople. On paper, I had it figured out.

Then I got the call that my best friend in Brazil had died by suicide. He'd gone blind, and the people closest to him made him feel useless instead of loved. I was thousands of miles away, an immigrant with no family in the room, and I did what a lot of us do with pain that big — I numbed it. Heavy drugs. Drinking every night. I nearly walked away from everything I'd built.

Here's what nobody tells you about "making it": the training never stops. New levels, new devils. I have friends who are billionaires. I asked one of them once what it actually feels like to have that kind of money. He told me it's just another zero in the account. The insecurity doesn't leave. The comparison doesn't leave. You just get better at managing it.

I'm telling this story because it's the frame for everything else I've learned about selling — and about staying whole while you climb.

Most sales training teaches you to pitch harder. Tighter script, better objection handling, more energy on the call. I did that for years, and it worked just well enough to keep me in the game — not well enough to make me great. What actually changed my numbers wasn't a better pitch. It was fewer pitches and sharper questions — a method called NEPQ, neuro-emotional persuasion questions. The idea humbled me the first time I heard it: people don't want to be sold, they want to feel understood, so the best thing you can do is stop talking and ask the question that lets them talk themselves into the decision.

A few truths from years of doing this the hard way. Nobody buys your product — they buy the version of themselves they become after they own it, and that decision is made before you ever open your mouth. Rapport doesn't close deals; trust does, and you can like someone plenty and still not trust them with their money. Silence, real silence after a trial close, is one of the most underused closing tools there is — most reps talk straight through their own yes because they can't sit in the quiet for three seconds.

Underneath all of it are the same six reasons anyone buys anything — love, gain, duty, pride, self-indulgence, self-preservation. Cavemen had them. Pharaohs had them. Your prospect has them right now, whether you're selling insurance, a coaching program, or yourself in a job interview.

And here's the part of this business changing fastest, the part nobody wants to say out loud: AI can write you a better pitch than most reps could write themselves — tonight, in thirty seconds. What it can't do is sit across from a scared prospect and hold the silence after the trial close. It can't look someone in the eye and tell them the truth when the truth is uncomfortable. People aren't buying your slide deck. They're buying you, standing behind it.

I lived a version of "starting over" too. Early twenties, sleeping in my car after a blown telecom deal — they took the office, the apartment, my whole team. I started over anyway. Asked one question: what are these companies struggling with, and what are their competitors getting wrong? Pitched commission-only, hired a few guys, took them into the field, showed them exactly how I did it. One month later: $75,000 in revenue for that company, $25,000 of it mine in commission. From there I moved into Fortune 50 accounts — Comcast Xfinity. Eight years, zero missed quotas, over a billion dollars in revenue driven. Still the same guy. I just learned to ask better questions.

I unpack all of this — the grief, the six buying motives, the chemistry behind every yes, why questions beat pitches, and what I'd tell the 23-year-old version of me — in the new episode, "17 Brutal Truths About Sales I Wish I Knew at 23," on The Carlos Inspire Show. Go listen wherever you get your podcasts.

If this episode brings up anything heavy for you, the 988 Suicide & Crisis Lifeline is free, confidential, and available 24/7 — call or text 988.