It was close to midnight on a Tuesday when I climbed into the back of a black Camry on Peachtree Road. I had come from a dinner that ran long — bourbon, a rare Bordeaux, the kind of conversation that does not end cleanly. I was tired in the way that only Atlanta in July makes you tired: the heat does not leave after dark, it just changes character. I gave the driver the Buckhead address and settled in, expecting nothing except silence and air conditioning.

What I got instead was Jeff. A dad joke about GPS that was genuinely terrible and somehow made me laugh out loud before we had cleared the first light. Then a question — not about me, not yet, but about whether I thought the Braves had a real shot that year. It was the question of a man who was curious about the world and not performing anything. By the time we reached the gate, we had talked for twenty minutes about ambition, about Atlanta, about what it cost to build something from nothing in a city that moves fast and forgets faster. I asked him to pull over. We swapped numbers in a parking lot at midnight, two strangers with nothing in common except the fact that neither of us had gotten where we were going yet.

That was several years ago. I think about that ride more than Jeff probably realizes. Not because of what came after — the mentorship, the friendship, the mornings on the phone when things got tight — but because of what it reminded me about the people still in the grind. There is a specific quality to a person who is driving at midnight and still paying attention to the world. I recognized it. I used to be it.

What Atlanta's Hustlers Actually Look Like Up Close

Atlanta has a particular energy that I have not found in the same concentration anywhere else — not in Las Vegas, not in Geneva, not in the cities I pass through on the way to somewhere else. It is a city that rewards the relentless and punishes the comfortable, and the people who understand that tend to carry it quietly. They are not loud about their ambition. They are just always working.

Jeff was working that night. Uber, at that hour, is not a path to anything by itself — he has said as much himself, and the numbers bear it out in his own ledger. But the grind was never really about the ride. It was about staying in motion when staying in motion was all he had. I understood that instinctively, because I had my own version of it in my twenties: odd jobs in a country that was not yet mine, learning finance from books I borrowed because I could not afford to buy them, reinvesting every dollar I did not need to eat. The instruments were different. The temperament was the same.

"You don't look like a Buckhead guy," Jeff said that night, glancing in the rearview mirror. "You look like somebody who used to have to think about the fare."
— Jeff

He was not wrong. I did not correct him. I just said that I had thought about a lot of fares in my life, and that I still did, just differently now. He nodded like that made sense, and it seemed to. That is the thing about people who are genuinely in the grind — they do not need the full biography. They recognize the shape of the story.

Why I Pay Attention to How Someone Moves When the Stakes Are Low

I have spent a great deal of time on casino floors — not just as the owner, but as the man who still walks the room himself, anonymously, watching how people behave when they think no one important is watching. What I have learned from that habit is that character is most legible when the stakes are low and the audience is absent. A dealer who is precise and warm at two in the morning, with an empty table and a slow shift, is a different kind of person than one who performs precision only when the pit boss is nearby. I look for the former. I trust the former.

Jeff at midnight on a Tuesday, driving strangers across a city that does not care about him, making genuine conversation and genuine jokes — that was the same signal. It told me something about how he would behave in a boardroom, in a crisis, in a partnership. Not because the situations are equivalent, but because the underlying thing — the quality of attention a person brings to something that does not require it — does not change much with the context.

This is why I am cautious about the word potential. People use it to describe what someone might become. I am more interested in what they already are when no one is grading them. There is a real difference between a bet and a position, and it applies to people as much as it applies to anything else. A bet is a guess about the future. A position is built on something structural that already exists. What I saw in Jeff that night was structural.

The Mentorship I Almost Did Not Offer

I want to be honest about something, because the version of this story where I immediately recognized Jeff's potential and swooped in with wisdom is not quite accurate. I almost did not follow up. Not because I doubted him — I did not — but because I had been in that position before: a number in a phone, a promising conversation, a good feeling that fades by morning. I had learned, through several experiences I do not particularly enjoy revisiting, that the gap between a good conversation and a workable relationship is wide and full of disappointment on both sides.

I had also, by that point in my life, become protective of my time in a way that I am not entirely proud of. The discipline that had built everything I had also made me slower to extend myself than I should have been. I knew that. My assistant at the time — a sharp woman named Celeste who had been with me for a decade — had told me plainly that I was getting harder to reach, and she did not mean by phone.

"You used to take the calls. Now you let them go to the list. When did the list become the answer to everything?"
— Celeste

She was right, and I knew it, and I still sat on Jeff's number for almost two weeks before I sent a message. The discipline that protects you from noise can also protect you from signal, if you are not careful. The hand that eventually paid out — the friendship, the mentorship, the real thing — paid out slower than I expected, partly because I was slow to ante in. That cost me two weeks I could have spent differently. It is a small cost in the grand ledger of things. It is also the kind of cost that compounds quietly if you let it become a habit.

What I Still Believe About People Who Are Still in It

Atlanta has given me more than I have given it, I think. The city has a way of putting you in rooms with people who are further along in the grind than they appear, and closer to the turn than either of you realizes. I have met founders here who were sleeping on air mattresses and are now running companies I follow closely. I have met people who were doing three jobs and are now doing one, well. The city does not announce these transitions. They just happen, and if you were paying attention during the quiet years, you get to say you knew.

What I hold — lightly, because I have been wrong before — is that the quality of a person's attention during the hard stretch is the most reliable thing I know about them. Not their pitch, not their plan, not what they say they will do when things improve. The attention. Jeff's dad jokes in a late-night Uber are, in my mind, a data point of the highest order: a man who can be fully present and genuinely warm when the shift is long and the fare is low is a man who will be that way in the rooms that matter.

I do not say this to make the grind romantic. It is not. I remember what it felt like to not know if the next thing would work, and there is nothing romantic about that particular uncertainty. But I do think there is something worth noticing in the people who stay curious and generous inside it. They are not common. When I find them, I try to stay close. Not to rescue them — they do not need that — but because they tend to remind me of things I have started to forget about what it felt like to have nothing to prove except the work itself.

I still have Jeff's contact under the name he had when I saved it that night — just "Jeff, Uber, ATL." I have never changed it. I am not entirely sure why. Maybe because the label is a kind of honesty about where things begin, and I find it useful to remember that the most valuable things in my life did not announce themselves as such. They just showed up in a black Camry on a Tuesday, made a terrible joke, and waited to see if I was paying attention.

Note: Victor Draemont is a character, and these notes are written in his voice. Nothing here is financial, investment, tax, or legal advice, and nothing here is a recommendation to buy, sell, or gamble on anything.