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Melanie Perkins Collected 100 Rejections Before Canva Was Worth $42 Billion

Melanie Perkins pitched Canva to more than a hundred investors before one said yes. The company is now valued at $42 billion with 240 million monthly users — and the rejection years explain the product better than the valuation does.

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Melanie Perkins, co-founder and CEO of Canva, speaking on Centre Stage at Web Summit 2019 — Melanie Perkins Co-founder & CEO, Canva

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Tope Awotona, founder and CEO of Calendly, on Centre Stage at Collision 2022 in Toronto

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Tope Awotona Bootstrapped Calendly Until He No Longer Needed the Money

Tope Awotona drained his savings and maxed his credit cards to build Calendly, then took $350 million at a $3 billion valuation years later — on his terms. The order of those two events is the whole strategy.

By Future Sharks · Aug 7, 2026