Beyond the Deck
#4: Charisma in Fundraising Isn't About Polish — It's About Curiosity
True charisma is warmth, competence — and the courage to ask the right questions
At demo days, you expect to see crisp slides, polished delivery, and confident smiles. And yet most of those founders will never hear from those investors again. Why? Because polish doesn’t build relationships. Curiosity does.
The Founder Who Broke the Script
I was at a demo day recently. The presentations were strong. Each founder spoke with clarity and confidence. Many peppered in humor and personal stories to make their pitches relatable. All of them offered numbers and figures to bolster credibility. The room burst into loud applause when the last founder bowed and said thank you. It was one of the best demo days I’ve attended.
But what impressed me most came during the networking portion. While many founders defaulted back to autopilot — re-pitching the same lines they’d just delivered on stage — one founder did something different. He didn’t re-pitch. Instead, he asked questions of the attending investors: “What would you change in my presentation?” “Where do you see this sector heading?” “What worries you right now that founders might not be thinking about?”
I saw it — the investor leaned in, and a connection of trust was forged. The dynamic flipped. Suddenly, the founder wasn’t auditioning; he was collaborating. He wasn’t performing; he was learning.
That’s charisma. Not the slickness of delivery, but the confidence to turn the spotlight away from yourself and ask smart questions with sincerity and curiosity.
Why Curiosity Wins
Naval Ravikant said, “Play long-term games with long-term people.” Curiosity is how you figure out who those people are.
Most founders treat investors like vending machines — pitch in, money out. But the smart ones use those meetings to test for fit. They ask: “Is this someone who can stay in the trenches with me when things get ugly?”
And here’s what the research says: leaders who ask more questions are perceived as more competent and build stronger trust, according to Harvard Business Review. On the flip side, poor investor alignment is listed among the top reasons why startups falter (CB Insights).
So, curiosity isn’t just charm. It’s strategy.
About the author: Jenny is the co-founder and head creator of Day 2 Coaching.
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