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From Bootstrapped to Billions

Dozens have tried to reinvent the calendar, and dozens have failed. Tope Awotona built Calendly not as a way to reinvent the wheel, but to add a layer of simplicity to the chaos of human communication and time management. And boy did it work! The once-bootstrapped company is now worth more than $3 billion, serving…

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5 years ago

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Dozens have tried to reinvent the calendar, and dozens have failed. Tope Awotona built Calendly not as a way to reinvent the wheel, but to add a layer of simplicity to the chaos of human communication and time management. And boy did it work! The once-bootstrapped company is now worth more than $3 billion, serving individuals and enterprises alike. Hear from the founder and CEO on how he got Calendly off the ground, why he decided to finally take institutional investment, and how the company has changed as it grows.

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Unboxing: $290 Kindle Paperwhite Signature Edition (2026)

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Kindle’s newest Paperwhite has gotten an upgrade with the Signature Edition which features an aluminum back, an auto adjusting front light, 32GB of storage, dock charging, and more. Let’s unbox it in Seaglass Green. #kindlepaperwhite #kindle #unboxing #BookTok #ereader

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First matcha, now Ube. This new 6-inch Kindle is the company’s most “pocket-sized” Kindle they’ve ever made and is lighter with a new flush-front design. Let’s unbox the $150 e-reader. #unboxing #kindle #ereader #bookstagram #kindlegirlie

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A new cute, pocket-sized Kindle has entered the chat in an Alpine Sky color with a shiny aluminum back. Unbox one of the two colors with us. #unboxing #kindle #kindlealuminum #booktok #ereader

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