TL;DR

People form an opinion in seconds, then spend ages justifying it. I treated a roomful of top‑tier VCs like a practice audience, burned the room, and spent months climbing back. Measure twice, pitch once.

I’ve heard the line since childhood and mostly waved it off: you only get one shot at a first impression. Turns out it’s annoyingly true. Humans decide how they feel almost instantly, invent a reason afterwards, and cling to that story. Those opening moments—product demo, hiring call, deck walk‑through—set the flavour for everything that follows.

Testing new material on the Netflix special

Stand‑up comics road‑test jokes in dingy clubs, notebook in hand. When the Netflix cameras roll, every gag is battle‑tested. During our early fund‑raise at RIFT I did the opposite: I took brand‑new material straight to the Netflix taping.

Instead of warming up with friendly funds or tier‑two investors, I marched straight into my top‑ten list, certain past wins plus a hot AI pitch would carry the day. Call it arrogance, call it naivety—either way, the message was half‑baked and the feedback was brutal. Each meeting tweaked a slide or story, but every tweak happened in front of the very people whose vote really counted. By the tenth meeting they’d already filed us under unclear narrative and moved on.

The innovators’ dilemma in miniature

Our product sits in an awkward middle ground—new category, familiar mechanics. Getting the information hierarchy right is everything: what we are, what we’re not, why it matters now. That clarity emerged only after a dozen conversations… unfortunately the first dozen were with partners we most wanted on the cap table.

Once a VC decides you’re fuzzy, you start every subsequent interaction in a hole. The same is true for candidates, customers, journalists—anyone whose view you care about. Change the frame later and they assume the product changed, not the explanation.

What we learned (and now do)

We treat big‑ticket impressions like code going to prod. Draft privately, test in safe environments, gather the data, thenpush live. The rule of thumb: if you’d cry about losing their support, they’re not your rehearsal audience.

A few tactical habits:

• Tier your targets. Friends‑and‑family first, warm intros second, dream list last.

• Record every practice pitch. Count the questions that hit after slide three; fix until they stop.

• Kill the suspense. Lead with the most valuable truth, not a build‑up.

Measure twice, cut once. Or in fundraising terms: road‑test the set in the pub before you hire the Netflix crew.

Estimated read: 4 minutes
Category: IFUHWIL
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Botched a first impression of your own—or found a hack to nail it? My inbox is open.