One thing I learned in the syndication world: when a buyer asks a question, it’s rarely for them.
They’re asking on behalf of someone else—an investment committee, LPs, shareholders, or spouse at home.
Every buyer, big or small, has stakeholders.
That’s why when you see 5 to 10 offers hit in a short window, it’s usually not an accident. It’s because of decision-making speed and whether the information the buyer is presented with can survive stakeholder scrutiny.
When you speak tothe stakeholders, rather than just the person in front of you, everything changes.
Conversations sharpen. Behavior shifts. Decisions happen faster.
In order to speak to the stakeholders, you have to avoid AI review.
AI review is the modern-day filing cabinet. If your deal doesn’t hold attention, it gets filed away.
AI can analyze data, but it can’t sell conviction, win over a spouse, or sway an investment committee.
So how do we get the person to read it and stay engaged early?
Nothing makes an OM feel like 1954 quite like a traditional table of contents.
Jokes aside, I prefer removing it—not just because attention spans are shorter today, but because it slows the decision-making process down. It forces you to lead with what actually matters to buyers and their stakeholders.
The most critical information needs to show up immediately, ideally in the first few pages, before anyone has time to lose interest or forward it to ChatGPT with a “can you summarize this?”
I’ve had some of the largest institutions in the world give very positive feedback on a top-heavy, fast approach.
Most brokers prefer tradition.
I prefer results.
Serious capital responds to serious process.
One of the biggest problems I see in larger off-market deals? No deadline.
Institutions are flooded with deals that aren’t real, aren’t serious, and aren’t going anywhere. A clear deadline signals seriousness. It says: this deal matters, there’s a process, and decisions are expected—and stakeholders will need to sign off by this date or miss out.
A deadline like March 31st, 2026 tells the buyers don’t stick this in the AI filing cabinet, review this NOW.
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