Advice Line with Anthony Casalena of Squarespace

Advice Line with Anthony Casalena of Squarespace

Squarespace founder Anthony Casalena joins Guy on the Advice Line, where they answer questions from three early-stage entrepreneurs. Plus, Anthony shares how Squarespace is leveraging AI to help people bolster their sites and digital presence more effectively.

First we meet Bob in Connecticut, who’s wondering how to pump up awareness for his custom-made mattresses. Then Stacy in California asks how her new first aid products can stand out in a category dominated by legacy brands. And Mehek in New York strategizes about how to best launch a new digital companion she’s building: an app that supports people recovering from eating disorders.

Thank you to the founders of Custom Sleep Technology, All Better Co., and Kahani for being a part of our show.


If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298.

And be sure to listen to Squarespace’s founding story as told by Anthony on the show in 2019.


This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was James Willetts.

You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episoder(786)

Author and Podcaster: Tim Ferriss

Author and Podcaster: Tim Ferriss

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Riot Games: Bonus Episode

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Riot Games: Brandon Beck and Marc Merrill

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How I Built Resilience: Emily Powell of Powell's Books

How I Built Resilience: Emily Powell of Powell's Books

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10 Des 202024min

Kodiak Cakes: Joel Clark

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When he was 8 years old, Joel Clark loaded bags of his mom's whole grain pancake mix into a red wagon to sell door-to-door. By the mid-90s, he and his older brother had upgraded to selling the mix out of a Mazda sedan and calling it Kodiak Cakes. As he tried to scale the business, Joel made some risky business decisions and almost went bankrupt, but eventually got the brand into Target—a major turning point. Today, Kodiak Cakes is approaching $200 million in annual revenue as one of the best-selling pancake mixes in America.Order the How I Built This book at: https://smarturl.it/HowIBuiltThisSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Remembering Tony Hsieh of Zappos

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How I Built Resilience: Dr. Iman Abuzeid of Incredible Health

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