Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz

Guy Raz | Wondery

Business

4.8 • 31.1K Ratings

🗓️ 20 November 2025

⏱️ 50 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 [email protected] 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.

Transcript

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0:00.0	Wonderly Plus subscribers can listen to how I built this early and ad-free right now.
0:05.7	Join Wonderly Plus in the Wondery app or on Apple Podcasts.
0:10.2	Startups move fast, and with AI, they're shipping even faster and attracting enterprise buyers sooner.
0:18.0	But big deals bring even bigger security and compliance requirements.
0:22.9	With AI changing regulations and buyers' expectations, Vanta knows what's needed and when.
0:30.0	And they've built the fastest, easiest path to get you there. That's why serious startups get
0:35.9	secure early with Vanta. My listeners can get $1,000
0:40.7	off at Vanta.com slash hibt. That's V-A-N-T-A dot com slash h-I-B-T for $1,000 off.
0:53.7	The origins of this podcast were once just a dream. That dream did. H-I-B-T for $1,000 off.
0:57.5	The origins of this podcast were once just a dream.
1:02.0	That dream turned into the podcast and business you're listening to today.
1:07.9	Taking your business to the next level is a dream lots of a share, but too often it remains just a dream.
1:09.3	We hold ourselves back thinking, what if I don't have the
1:11.9	skills? What if I can't do it alone? Turn those what ifs into why nots and help your business
1:18.8	soar with Shopify. Turn those what ifs into why nots and keep giving those big dreams the best
1:27.0	shot with Shopify.
1:28.4	Sign up for your one pound per month trial and start selling today at Shopify.co.c.
1:34.0	U.K.
1:35.0	slash built.
1:36.6	Go to shopify.
1:37.4	dot co.
1:38.4	UK slash built.
	...

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