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)

The Lip Bar: Melissa Butler

The Lip Bar: Melissa Butler

While working long hours as a Wall Street analyst, Melissa Butler started making lipstick in her kitchen as a hobby. But it soon turned into an obsession, costing thousands of dollars. She was frustrated by the lack of diversity in the cosmetics industry, and as a Black woman, wanted to create lipstick colors that complimented her complexion and style. So in 2010, she launched The Lip Bar, with bold colors like green and purple, and boozy names like "Cosmo" and "Sour Apple Martini." Undeterred by a disastrous appearance on Shark Tank with her partner Rosco Spears, Melissa was motivated to pitch her lipstick to Target, and in 2016, launched a new color on Target's online store. Today, The Lip Bar has expanded to 500 Target stores, and has continued to grow a following, despite the pain points of the pandemic. 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.

23 Nov 20201h 20min

How I Built Resilience: Father Gregory Boyle of Homeboy Industries

How I Built Resilience: Father Gregory Boyle of Homeboy Industries

Father Gregory Boyle is the founder of Homeboy Industries, one of the largest gang-intervention, rehabilitation and re-entry programs in the world. He speaks with Guy about how the Los Angeles based organization has adapted to continue training and employing people during the pandemic. These conversations are excerpts from our How I Built Resilience series, where Guy talks online with founders and entrepreneurs about how they're navigating turbulent times.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.

19 Nov 202025min

Kenneth Cole: Kenneth Cole

Kenneth Cole: Kenneth Cole

Kenneth Cole launched his shoe business out of a forty-foot truck in midtown Manhattan and quickly became known as an up-and-coming designer with an eye for street fashion. In 1986, he made a bold move by associating his nascent brand with a controversial issue at the time: the AIDS crisis, and the vital need for research. Through the 1990s and 2000s, Kenneth grew the company into a $500M brand, leading it through downturns, department store consolidation, an IPO and a return to private ownership. Throughout, he stayed committed to AIDS research and many other social causes. 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.

16 Nov 20201h 15min

Dropbox: Drew Houston

Dropbox: Drew Houston

In 2006, Drew Houston got on a bus from Boston heading to New York. He planned to use the three-hour ride to get some work done, so he opened his laptop, and realized he had left his thumb drive with all of his work files at home. Drew decided he never wanted to have that problem again. On that bus ride, he started writing the code to build a cloud-based file storage and sharing service he called Dropbox. Fourteen years later, Drew and his co-founder, Arash Ferdowsi, have built Dropbox into a public company worth close to $8 billion. 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.

9 Nov 202047min

How I Built Resilience: Varshini Prakash of Sunrise Movement

How I Built Resilience: Varshini Prakash of Sunrise Movement

Guy talks with Varshini Prakash, co-founder of Sunrise Movement, a grassroots organization that's fighting to make climate change a top priority in the US. The group launched in 2017 and has since grown into one of the largest youth movements in the country. These conversations are excerpts from our How I Built Resilience series, where Guy talks online with founders about how they're navigating these turbulent times.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.

5 Nov 202023min

Famous Dave's: Dave Anderson

Famous Dave's: Dave Anderson

Growing up in 1960's Chicago, Dave Anderson didn't eat much deep dish. Instead, his dad took the family to the South Side for barbecue, and those memories—and aromas—stayed with him. For years, Dave tinkered with his own recipes for sauces and sides while working as a salesman and business advisor to Native American tribes. Finally in 1994, he opened his first barbecue shack in the last place you might expect to find one: the little town of Hayward, Wisconsin. The chain grew quickly—too quickly—and Dave developed a love-hate relationship with the brand he'd created, but never lost his passion for smoked ribs and brisket. Today, Famous Dave's has around 125 restaurants across the U.S., making it one of the largest barbecue chains in the country. 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.

2 Nov 20201h 15min

How I Built Resilience: Justin Gold of Justin's

How I Built Resilience: Justin Gold of Justin's

Justin Gold is the founder of Justin's, known for its nut butters and chocolate peanut butter cups. He talks about how he started by pulverizing peanuts in his home blender, and describes how his customers are shopping differently during the pandemic. These conversations are excerpts from our How I Built Resilience series, where Guy talks online with founders and entrepreneurs about how they're navigating these turbulent times.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.

31 Okt 202021min

How I Built Resilience: Cheryl Contee of Do Big Things

How I Built Resilience: Cheryl Contee of Do Big Things

Do Big Things is a Black woman-led, mission-driven digital agency that works with companies like Google, Etsy, and the NAACP, and has a staff that's 50% people of color. The agency's CEO and founder Cheryl Contee says having a diverse team is a strategy for authentic engagement. These conversations are excerpts from our How I Built Resilience series, where Guy talks online with founders and entrepreneurs about how they're navigating turbulent times. 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.

29 Okt 202019min

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