It was a Tuesday night, quieter than most, and Jeff was sitting across from me in the booth I keep near the back of the steakhouse off the main floor. He had his notebook out — he always has his notebook out — and he was asking me about a decision he had been turning over for weeks. A business pivot. Real stakes, real pressure, the kind where the wrong move costs you more than money. He looked at me the way people look at someone they believe has the answer, and I remember the exact moment I understood I was going to disappoint him.

I used to give the answer. Earlier in my life, when someone I trusted asked me what to do, I told them. Directly. I thought that was what mentorship was — the transfer of a conclusion from someone who had been through the fire to someone standing at the edge of it. It felt generous. It felt efficient. It took me longer than I would like to admit to understand that it was neither of those things.

What I gave Jeff that night was not an answer. It was a question, and then another one, and then a long silence over bourbon while he worked out what he already knew. He closed his notebook before we left. He did not need what was in it.

What I Noticed When I Was Still Giving It

For years I watched what happened after I gave someone direct advice. Not always, but often enough to be a pattern: they followed it. And when it worked, they came back faster the next time, with less thinking done beforehand. When it did not work — and sometimes it did not, because my read was incomplete, or the situation was different from the surface — they carried something I had not intended to give them. A small erosion of confidence in their own judgment. A habit of outsourcing the hard question to the nearest person they trusted.

I noticed it most clearly with a young founder I had backed early on. Sharp, genuinely capable, the kind of person who could have built something lasting on her own instincts. But she had learned, somewhere before me, to seek the answer rather than to develop the capacity. Every decision that mattered came to me first. I kept answering. I was flattered, I think, in a way I did not fully examine at the time.

"You're not teaching her to think," my pit boss Marco told me once, after he had overheard a phone call. "You're teaching her to call you." — Marco, floor manager, Las Vegas

Marco has a way of saying the thing I already know but have not yet said to myself. He was right. I had not built a mentee. I had built a dependency, and I had done it with the best intentions, which is the most reliable way to build one.

The Reasoning That Changed How I Show Up

The shift was not philosophical. It was practical. I began to notice that the people who grew fastest were not the ones I had guided most directly — they were the ones I had made uncomfortable most deliberately. The ones I had pushed back into the question instead of handing them the answer. Their judgment sharpened because it had to. Mine had sharpened the same way, decades earlier, when there was nobody to call.

I grew up without a safety net and without a mentor. I have written before about the first company I flipped — how much I got wrong, how long it took to understand what I had actually learned from it. That process was slow and sometimes painful, but it produced something direct advice never could: a tested instinct. A framework that was mine, not borrowed.

When I give someone an answer, I short-circuit that process. I give them a conclusion without the scar tissue that makes a conclusion stick. They can repeat what I said. They cannot yet feel why it was right, and feeling why is the only thing that transfers to the next decision, which will be different in ways neither of us can predict.

There is also this: I am not always right. I think clearly, I have seen a great deal, I have made enough mistakes to have some calibration. But my context is not their context. My risk tolerance is not theirs. My timeline — and I tend to measure in decades even when I talk in weeks — is not the timeline of someone still building the foundation. An answer that fits my life precisely can be exactly wrong for theirs.

What Stopping Cost Me in That Booth

I want to be honest about what it costs to hold back, because it is not nothing, and I would be doing this piece a disservice to make it sound clean.

That Tuesday with Jeff — I watched him sit with the discomfort of not getting the answer. He pushed twice more. He asked it from a different angle, then a third angle, and I kept returning the question to him. At one point he leaned back and said, quietly, not unkindly: "You know, for a guy with all the answers, you sure don't give any of them out."

He was half joking. But only half. And I felt the pull of it — the pull to just tell him, to make the discomfort stop, to be the person he needed me to be in that moment. It would have been easier. It would have felt like friendship. Jeff is one of the few people I have let genuinely close, and sitting there watching him struggle with something I had an opinion on took a kind of restraint that does not get easier with practice.

He got to his answer without me. It took another twenty minutes and a second round. It was, as best I could tell, the right call — better reasoned than anything I would have handed him, because it was built from his understanding of his own situation, not a translation of mine. But I gave up the moment of being the one who knew. I gave up the warmth of being needed in that particular way. That is a real cost, and I think anyone who says otherwise has not tried it.

There is a version of mentorship that is really just the pleasure of being listened to. I have been guilty of it. The discipline of withholding the answer is partly the discipline of managing what it means to be known — the way people project onto you, and the way you can start to play into that projection without noticing.

What I Do Instead, and Why I Hold It Loosely

What I give now, when someone I am mentoring brings me the hard question, is presence and friction. I listen carefully — more carefully than most people expect, because I do not interrupt and I do not rush toward my own experience. I ask what they have already ruled out, and why. I ask what they are afraid to say out loud. I ask what they would tell a friend in the same position.

Sometimes I share a situation from my own past — not as a template, but as texture. Not "here is what you should do" but "here is a thing that happened to me and what I noticed about it." The distinction matters. A story is an invitation to think. An answer is a substitute for it.

I also say, plainly, when something is not mine to weigh in on. Tax structure, legal exposure, specific instruments — those belong to professionals with full context and accountability for their counsel. I am not that, and I say so. Victor Draemont's opinion on your capital structure is not a substitute for the right advisor. I move on quickly when we reach that edge, because lingering there would be a different kind of disservice.

What I hold onto — lightly, because I have been wrong before — is the belief that the most useful thing a mentor can do is make the other person's thinking more rigorous, not shorter. Jeff does not need my conclusions. He has good instincts and a work ethic that I respect without reservation. What he sometimes needs is someone who will not let him skip the part where he earns the answer.

I do not know if this is the right approach for every person or every moment. I have sat across from someone in genuine crisis — not a strategic crossroads but a real emergency — and given a direct answer because the situation required it. There is no rule here that survives every circumstance. That is why I hold it loosely.

Jeff texted me two days after that Tuesday. The decision had landed well. He did not thank me for the advice. He thanked me for the conversation — which, I have come to think, might be the better thing to be known for.

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.