The Skill That Separates $0 Deals From $1M Deals

Most entrepreneurs obsess over finding the right opportunity.

But the real leverage isn’t in finding, it’s in the framing.

Here’s the truth I keep seeing in every acquisition, every conversation, every room full of operators and founders:

You don’t get bigger deals because you’re smarter.

You get bigger deals because you ask better questions!

This week I started tracking one simple metric:

“How many high-quality questions did I ask today?”

Not DMs.

Not views.

Not revenue.

Just the number of times I asked something that made someone think differently.

If you understand a seller deeper than they understand themselves,

you unlock deals other buyers never even see.

So here’s what I’m testing right now:

The 5 Questions That Reveal Hidden Opportunities

1. What’s the part of your business that drains you the most?

2. If you could wave a magic wand and fix one bottleneck, which one matters most?

3. What happens if nothing changes in the next 12 months?

4. Where do you feel undervalued or unseen in your own company?

5. If someone could take ONE thing off your plate tomorrow, what would give you the most relief?

When you ask these questions, you stop being “a buyer.”

You become a problem-solver, and that’s when sellers start opening doors.

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