A client asked me a question over dinner in San Francisco a few weeks back. We were still in disbelief about how his deal had played out.
He’d been three hours from signing a high-pressure “best and final”—coming in at just a hair over a million a year.
Then an eleventh-hour competing offer landed—nearly three million annual. Suddenly the first company’s “best and final” doubled.
Best and finals, it turns out, are only final until someone else bids.
He leaned back and chuckled.
“Where did you learn to do this—and how did you know the second offer would pull through?”
The first question I get all the time.
The second one deserves an honest answer.
The truth is that I didn’t know. Intuition gave me the read.
He meant his questioning as a compliment, and I took it as one. I joked about making a lucky guess—but he didn’t laugh.
Then I did what I always do with the “where did you learn this” question.
“Do you want the BS reason,” I asked him, “or the real reason?”
Nobody orders BS in this industry—but we’re served it anyway.
The real reason always turns a dinner into a different kind of conversation—because the honest answer doesn’t come with a diploma attached.
Here’s the truth.
The Pedigree Most Imagine
When someone asks where I learned this, there’s usually a résumé forming behind their eyes—especially since they can’t dig anything up on me via LinkedIn anymore.
A hostage-negotiator mentor. Some legendary MBA program. An executive father who ran deals at the kitchen table.
There was a kitchen table. But nobody was teaching—at least not intentionally.
I grew up an only child with two parents locked in a competition neither of them ever named—matching each other drink for drink, escalation for escalation, until the drinking turned into abuse and the abuse became its own kind of routine.
There was no safer parent to run to, because there wasn’t one.
The next morning, everyone pretended nothing had happened.
So I spent much of my childhood quietly wondering whether I could trust my own memory of the night before.
Sound like corporate?
A therapist would have names for all of this—hypervigilance, parentification, the gaslighting that makes a kid doubt his own eyes.
I’ve read those chapters and the names are accurate. They just don’t capture what it felt like to live inside it.
What it felt like was measurement.
I knew what kind of night it was going to be by the mile marker on my father’s Bacardi or my mother’s Skyy—how far the line had dropped since I left for school.
The rings of condensation on the counter told me how long they’d been sitting there. The sound of keys hitting the counter told me the rest.
I tracked these things the way my friends tracked Pokémon card prices, because in my house, the data mattered.
Getting the read right was the difference between a quiet night in my room and stepping into the middle of something no kid should stand in the middle of.
I wasn’t a precocious child. I was a scanner. And my scanning never turned off.
What You’re Actually Complimenting
Executives have flattering names for what I do now.
Pattern recognition.
Reading the room.
Presence.
The more honest name is vigilance that never clocked out.
When a board member’s tone drops half a degree, I notice.
When a recruiter’s warmth has a deadline hiding inside it, I notice.
When a CEO tells me “we’re fully aligned” while her hands say otherwise, I notice.
Not because I decide to—because I can’t not.
The wiring that kept my kid self safe in an unpredictable house is the same wiring that reads the neurosis in a boardroom and obsesses over word choice in every email. Sometimes I wonder whether my obsession is healthy.
My nervous system never learned to stop scanning for safety.
That’s also why corporate chaos doesn’t rattle me.
When a deal turns volatile—an exploding offer, a blindside from the board, a bluff somebody didn’t plan to have called—most people spike.
I settle.
Compared to how I learned to read a room, semantics over a few million dollars is not fear—no matter how loudly our bodies insist otherwise.
These are champagne problems. Nobody is going to get hurt jostling over employment contracts and buyout terms.
I See It in My Clients Too
A surprising number of the executives who find their way to me run on some version of the same wiring.
Not usually the same story—but the same signature.
The obsessive focus. The preparation that borders on compulsion. The inability to leave a problem alone until it’s solved, and the low hum of restlessness once it is.
The career built, at least partly, on being so exceptional that nothing bad could reach them.
Sit with enough of these leaders long enough, past the deal mechanics and into the real conversation, and you often find something underneath the drive.
A parent who couldn’t be pleased.
A childhood that demanded performance.
A family rivalry that created acceptance through competition.
A version of the trauma in my house, just with different furniture.
Not all of them—some people are just built ambitious, and I’ve met plenty who grew up loved and calm and still run hard.
But more than you’d guess.
Enough that when a new client’s intensity walks into the room, part of me is already asking where it came from.
The market rewards this wiring lavishly and never once asks about its origin.
That’s the part I find fascinating.
Companies pay premiums for the exact traits that childhood adversity installs—the vigilance, the stamina, the refusal to be caught unprepared—and the executive carrying them often has no idea the two are connected.
It’s one of the reasons I advocate so hard for mental health and substance-abuse programs in this industry.
The Bill
I want to be careful with how I share my story, because this is the point where the story usually gets sold as triumph.
Turned my pain into my superpower. You know what comes next. That’s not this.
The truth comes with a bill.
The same self-reliance that built my practice makes accepting help feel unsafe—like a kid who won’t let anyone else touch his Legos. Perhaps that’s why I struggle with scale and operations and excel at people and energy.
The same scanning that reads a comp committee runs at my own dinner table on nights when nothing is wrong. A restlessness. A feeling of being incomplete—reaching for an attention I don’t even need.
And friendships wane—not from fear, just from time.
My hours get bid on all day, and clients get the best of my energy. To be fair, my friends aren’t calling either. And since I refuse to live on social media, unless someone tells me directly, I have no idea what anyone is up to personally. But I know what every major player in tech is up to.
Tradeoffs I guess.
The result is a strange sentence to write. My closest friends are my clients.
Now—before you read that as a sad story, look around your own life. Because I don’t feel sorry for myself, and this isn’t only my bill.
Everyone calls it lonely at the top, as if altitude were the problem.
It isn’t altitude. It’s intimacy.
And I watch executives arrive at it from two different roads.
Some grew up the way I did, in houses that taught them closeness was dangerous. Others got there honestly—twenty years of giving the career their best hours until everyone outside the org chart learned to stop expecting them.
Here’s the part I’ve only recently been able to admit.
I can tell you my entire story over dinner—calmly, clearly, eye contact the whole way.
For years I mistook that for openness.
It’s a technique I teach my clients to control interviews, and it works. I’ve only recently noticed how the same technique can backfire into hiding.
A story you narrate is a story that can’t ambush you.
Even this article is a version of that. I know.
The Real Answer
I’ve built a career asking executives one question.
Was the outcome predetermined before you walked in?
If you’ve read my work for any length of time, you know the question is a trap. Nothing is predetermined—not the offer, not the range, not the career. Outcomes only behave that way when nobody in the room can see the system writing the script.
My house wrote me a script. The wiring was installed before I could object to it, and the script said I’d repeat what I grew up inside.
The script was wrong. Scripts usually are, once someone reads them out loud.
I’ve written before about the night I finally read mine out loud—the skatepark, the bridge, and the decision to stay.
That’s the real answer to where I learned this.
Every deal I touch is the same move I’ve been making since I was a kid—find the script that was written before my client walked in, and break it. The alternative is accepting someone else’s narrative of your life—and playing smaller than you deserve.
Your Version
Somewhere in your career there’s a skill people compliment you on that you never once practiced.
Maybe it’s unnatural calm under chaos.
Maybe it’s the ability to make anyone feel safe.
Maybe it’s a tenth-of-a-second read on which VP is about to torch the meeting.
Find it and ask what built it.
Then ask what it costs to keep running—and whether it’s still working for you, or you’re still working for it.
The people across the table already benefit from your wiring every day. You should at least know where it came from.
Work with me directly. Every session credits toward representation.
Stay fearless, friends.