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Why I said no to two meetings this week

Entry
#001
Published
May 2026
Written by
Rajan Nagina
Reading time
3 min read

I met two company leaders this week. Both had real businesses. Both were interested in AI. I said no to both.

The first was a mid-management team at a large bank. Smart people, real problems. But nobody in that room had the authority, or the imagination, to say yes to reimagining something fundamental. They wanted a PoC. We'd have delivered five and converted none.

The second was the founder of a large manufacturer. Decades of building, zero debt, strong margins. When I asked what he wanted from AI, he said: cut 100 frontline workers.

I walked away from both.

Not because the problems weren't real. Windflow only works with people who want to reimagine, not optimize. You can't teach that ambition to someone who doesn't have it.

Writing this down before I forget it: client selection matters as much as client acquisition. Every wrong engagement is the Moonshot you didn't build while you were busy with something smaller.

The right client has three things at once: authority, accountability, ambition. Remove any one and the Moonshot never happens.

Rajan Nagina

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The second-generation founder is the most underserved AI opportunity