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Pitch perfect: Why some founders fly and others flop

Pitch perfect: Why some founders fly and others flop

Most founders don’t actually know how to pitch because no one has ever taught them how to.

Apr 08, 2025
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Caffeine Daily
Caffeine Daily
Pitch perfect: Why some founders fly and others flop
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Hana Schofield, General Manager at Insight Investor Relations.

The world of pitching is a high bar, high stakes environment. You have, on average, only a few minutes to ‘hook’ a VC or angel investor - that’s it. And if your capital raise drags out by three months, you’ve potentially lost a year of progress - momentum stalls; key hires slip through your fingers; and the opportunity to scale, expand and dominate your competition diminishes.

“Yet, most founders don’t actually know how to pitch because no one has ever taught them how to. There’s a lot of DIY, a lot of AI-generated decks and a lot of trial and error. But the reality is that few things unlock as much capital, opportunity and growth as a sharp, compelling pitch can,” believes James Schofield of Insight Investor Relations.

James and Hana Schofield have helped successful New Zealand companies with capital raises of over $100M, with a goal to help secure $1B+ of investment into New Zealand’s best businesses. Their new ‘Insight Pitch’ offering has been designed to pull back the curtain on what makes investors clamber to invest - or scramble for the door.

We caught up with them for the insider track, including how to avoid the confidence trap, a handy framework for talking would-be investors through your proposition and some key principles for understanding how investors think.

And as an offer to Caffeine readers, Insight Pitch has offered to review five pitch decks for free. No fluff, no BS - just clear, sharp feedback that will arm you with the clarity, confidence and strategy to unlock millions.

Submit your current pitch deck here, referencing ‘Caffeine comp’ before Friday 18 April. We’ll select the pitches based on their potential.

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