How do you balance discipline with intuition when evaluating a deal you want to like?

April 24, 2025

by a searcher in New York, NY, USA

I'm curious how other operators walk the line between trusting their gut and sticking to their numbers. When I first started looking at businesses to acquire, I thought my job was to run the numbers, pressure-test the assumptions, and filter out the noise. But as I’ve dug into more deals—and especially as I’ve started getting serious about submitting offers—I’ve realized that some of the best opportunities don’t always look perfect on paper. A few times now, I’ve caught myself “rooting” for a deal. I’ll justify a customer concentration risk because I like the seller. I’ll soften my standards on margins because I see a path to fixing it post-close. And sometimes I don’t even realize I’m doing it until later. On the other hand, I’ve also passed on businesses that weren’t great by the spreadsheet but were run by deeply ethical owners, had sticky customers, or had some hard-to-quantify asset (like brand trust or a defensible niche). So I’m asking: Where do you personally draw the line between discipline and vision? Have you made an acquisition that didn’t quite meet your model—but still turned out to be a winner? What questions or frameworks do you use when your gut says yes but your spreadsheet says “ehh…”? I’d love to hear your perspectives. Especially from those of you who’ve already closed and are operating—how does your experience owning a business change your view of what’s “acquirable”?

Reply by a professional
from Bentley College in Miami, FL, USA

Many seasoned operators talk about developing a kind of “earned intuition”—gut instincts that are informed by patterns they've seen play out over time. But early on, it’s easy to confuse hope or bias with genuine insight. A few frameworks that might help walk the line: “What would have to be true?” – Ask this when your gut says yes but the spreadsheet is shaky. It forces clarity around key assumptions and what risks you’re implicitly underwriting. Risk concentration scoring – Some buyers assign scores to common risk areas (customer concentration, owner dependency, working capital needs, etc.) to compare deals more objectively—even when gut feel wants to override. Pre-mortem analysis – Picture the deal going badly three years post-close. What caused it? This can surface blind spots that excitement or optimism may obscure. Also, talking through deals with a third party—especially someone who's not emotionally attached—can be hugely grounding. It’s why a lot of buyers lean on buy-side advisors not just for diligence but also as thought partners. Ultimately, experience owning and operating does shift your view of what’s “acquirable.” You start to see that culture, transition risk, and leadership dynamics are often more predictive of success than what the trailing 12-month EBITDA says. If you're ever looking to sense-check a deal with experts across functional areas—financial, operational, commercial—DueDilio can be a helpful way to tap into that kind of perspective quickly. Sometimes just having a second set of eyes can make the difference between intuition and impulse. Would love to hear what’s been most helpful for others in making that call.

Reply by a searcher
from Case Western Reserve University in Cleveland, OH, USA

Thanks ^redacted‌ for the tag. Great question. In my experience you need to first make certain that your deal criteria is well defined. E.g. how much client concentration are you willing to accept...what are the lowest margins etc...". Think through your criteria when you don't have a deal in front of you so that you consider the issues objectively. If a deal doesn't meet those criteria the mitigating factors would have to be overwhelmingly compelling before I would consider a deal (I can't even think of an example right now). Overall, this process is both art and science. Gut matters and so do the numbers, so they should support each other not cancel each other out. One shouldn't trump the other.

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