Vol 1 · Issue 104 · Sunday, September 6, 2026

Tomorrow is Labor Day, which is a holiday about work that most business owners will spend working.

You'll answer a few emails. You'll think about the invoice that hasn't been paid. Somebody will ask how the business is going and you'll say good, busy, can't complain, and then you'll go stand by the cooler and think about the thing you're actually worried about, which you will not mention to anyone at that barbecue.

That's the part of this job nobody puts in the brochure. Not the hours. The isolation.

Your team can't hear it. If you tell your operations lead you're nervous about the fourth quarter, she updates her resume that night, and she should. Your clients definitely can't hear it. Your spouse hears the emotional version, which they love you enough to absorb, but they usually can't help with the actual decision because they don't live inside the problem.

So it stays in your head. And decisions made entirely inside one person's head, with no friction from anyone who understands the stakes, are how good operators talk themselves into terrible ideas.

You need three people you can call. Not a mastermind you pay four thousand dollars to sit in. Three actual humans, specific roles, specific cadence.

Here's how to build it, because I built mine badly for years before I built it right.

One person isn't enough, because one person gives you one worldview and you'll start mistaking their preferences for the truth. Ten people is a committee, and a committee will average your good instincts into mush.

Three is the number where you get real disagreement without getting paralysis. And they need to be three different kinds of person, or you've just built an echo with extra steps.

The one who's ahead of you. Someone running a business roughly two to five years further down the road than yours. Not twenty years ahead, because a person running a two hundred person company genuinely does not remember what it felt like to have eleven employees and a cash flow problem. Their advice will be technically correct and practically useless to you. Two to five years ahead means they solved your current problem recently enough to remember the details.

The peer. Someone at roughly your stage, ideally in a different industry. Different industry matters. If they're in your market, there's a competitive edge under everything and neither of you will be fully honest. Different industry means they can hear about your pricing problem without wondering what it means for them, and they'll ask the dumb obvious question your industry has trained you not to ask.

The truth-teller. This is the one everybody gets wrong. It's the person who is not impressed by you. Might be a former boss, a friend from before you owned anything, an accountant with a personality, a sibling who works in something unrelated. The qualification is that they will say the thing to your face and they have no incentive to keep you happy. Half the value of this seat is that the other two, over time, start to like you, and people who like you get gentle.

Faster to say who's out.

Anyone who sells to you. Your vendor is not your advisor. Their advice is genuinely useful and also structurally shaped by what they sell, and both of those things are true at the same time.

Anyone who works for you. You cannot get honest counsel from someone whose mortgage you're responsible for. That is not a character flaw in them, it's just physics.

Anyone who has never run anything. Smart is not the same as scarred. There's a specific category of advice that only comes from having made payroll when you weren't sure you could.

Anyone whose response to your bad news is to make you feel better. Comfort is not the product here. You have friends for comfort. This is a different job.

This is where most owners stall out. Asking feels like admitting something.

Two rules that make it easy.

Rule one, ask small. Do not ask anyone to be your mentor. That's a huge open-ended commitment and the polite answer is a slow no. Ask for one specific conversation about one specific thing.

"Hey, you dealt with the jump from eight people to twenty a few years ago. I'm staring at that right now and I'm second-guessing the whole thing. Could I buy you lunch and ask you about four specific things?"

Almost nobody says no to that. It's flattering, it's bounded, and it has a clear end.

Rule two, earn the second one. Show up with actual questions written down. Take notes in front of them. Then, and this is the whole thing, follow up in three weeks and tell them what you did with their advice and what happened.

That follow-up is the entire recruiting mechanism. Almost nobody does it. When you do, you become the person whose calls get taken, because you're demonstrably not wasting their time. The second conversation happens on its own. So does the third. Six months later you have an advisor and you never had to use the word.

Quarterly with each of them. Sixty to ninety minutes. Not monthly, because monthly is too often for meaningful change and you'll end up reporting news instead of thinking. Not annually, because a year is long enough to get deep into a bad decision.

Stagger them so you're talking to one of the three roughly every month. Put the whole year's dates on the calendar in one sitting, right now, and send the invites. Something that isn't scheduled doesn't happen, and this is exactly the kind of thing that gets postponed forever because it's never urgent.

Keep track of who you talked to and when. I keep mine in Clay alongside the notes from the last conversation, so I walk into the next one actually remembering what they told me instead of making them repeat themselves.

An unstructured hour with a smart person produces a pleasant conversation and no change. Use this shape.

Ten minutes. What actually happened. The number, not the story. Revenue, headcount, margin, the one metric you track. Say the real figures. This part is short on purpose.

Ten minutes. What I said I'd do last time and what I actually did. Including the things you didn't do. Especially those. This is the accountability piece and it is genuinely uncomfortable the first two times, which is how you know it's working.

Twenty five minutes. The one thing. Bring one decision. Not five. One. Frame it as a real question with real options: I'm deciding whether to raise prices twelve percent in January or hold and add a service tier, here's what I know, here's what I'm afraid of, what am I not seeing.

Fifteen minutes. The question I'm avoiding. Ask them what they think you're wrong about. Then shut up. The silence is uncomfortable and the answer usually comes after it.

Five minutes. What I'll do before next time. Two commitments, said out loud, written down, read back to them.

Record it if they're comfortable with that. I run mine through Fathom so I'm actually present in the conversation instead of scribbling, and so that in January I can go back and see that in September somebody told me exactly what was going to happen and I nodded and did nothing about it. That experience is educational.

This will happen within the first year and it throws people, so let me save you the confusion.

Conflicting advice is not a failure of the system. It's the system working. If all three of your people agree on everything, you built the echo chamber you were trying to avoid and you should replace one of them.

When it happens, do not average the advice. Averaging two opposing strategies produces a third strategy that nobody recommended and that has none of the strengths of either.

Instead, do this. Go back to each one and ask what they'd have to see to change their mind. That question is the whole trick. It moves the conversation from opinion to evidence, and it usually surfaces the actual disagreement, which is almost never about the decision. It's about a difference in what they assume about your market, your appetite for risk, or your capacity.

Nine times out of ten one of them is working off a fact you never gave them. Once that fact is on the table, the disagreement resolves itself and you learn something about how you were framing the problem.

The fastest way to get good people to take your calls is to become the person somebody else wants in their three. This is not karma, it's just how the market for attention works.

Practically, that means a few things.

Be specific when you're asked for help. "Happy to help however" is worth nothing. "I'll rewrite your onboarding email and send it back Thursday" is worth something.

Send referrals without being asked and without a scorecard. Three or four a year, deliberately, to people in your circle. Say who it is and why you thought of them.

Answer fast. The person who replies in two hours gets asked again. The person who replies in six days gets asked once.

And be the one who tells the uncomfortable truth when it's your turn. If somebody in your circle is about to do something dumb and you say nothing because you don't want the friction, you've quietly downgraded the whole relationship to social. That's a fine thing to have. It's just not this.

Mild controversy here and I'll stand behind it.

Free advice gets treated like free advice. If someone is giving you two hours a quarter that materially changes how you run a business that feeds your family, find a way to make it worth something to them.

That doesn't have to be a check, though a check is clean and nobody's insulted by one. It can be referrals sent deliberately and often. An introduction they've been trying to get. Real help with something in their business where you're the stronger operator. The point is reciprocity, because a relationship with flow going one direction runs out of gas in about a year, every time.

The peer seat handles this naturally, since you're doing the same thing for each other. The one ahead of you and the truth-teller need you to be intentional about it.

I'll give you the honest version instead of a testimonial.

About four years ago I was two weeks from signing a lease on office space I didn't need, for a version of the business I thought I was supposed to want. Bigger space, bigger sign, all of it. I had the whole justification built, and it was airtight, because it had been assembled entirely inside my own skull with no resistance whatsoever.

I mentioned it to the truth-teller in my three, mostly as a brag. He didn't congratulate me. He asked me one question, which was what the space was going to make possible that I couldn't do already.

I talked for a while. He waited. Then he said it sounded like I wanted to feel like a real business more than I wanted a real business.

That stung for about a week and it saved me somewhere north of a hundred thousand dollars over the term.

He wasn't smarter than me about my business. He knew almost nothing about my business. He was just outside my head, and outside my head was the only place that question could come from.

You've got a holiday. Somewhere between the grill and the traffic, do this.

Write down the names of three people who could fill those three seats. If you can only think of one, that's fine and it's also information. Text one of them tomorrow and ask for one specific conversation about one specific thing.

That's it. That's the whole assignment.

The business you're building is going to demand a hundred decisions between now and New Year's, and you'll make most of them alone, in the truck, at eleven at night, with nobody to push back.

Give yourself three people who will.

Talk Soon,

Dan

Dan Kaufman
Founder, Dead Simple Growth and Pinnacle Masters

P.S. If you don't have anybody who fits the seat of the person who's two to five years ahead of you, that's often the hardest one to fill from a standing start, and it's usually the one worth paying for. Reply with the word CIRCLE and I'll send you the quarterly agenda as a one page doc you can hand to whoever you recruit, plus the exact ask script I use. Enjoy the long weekend. Actually take some of it off.