Squarespace: Anthony Casalena

Squarespace: Anthony Casalena

Like many classic technology stories, Squarespace started in a college dorm room. In 2003, 21-year-old Anthony Casalena created a website-building tool for himself. But after hearing some positive feedback from friends, he decided to put the tool online and start a business. For years, Anthony ran Squarespace almost entirely on his own but the stress took a toll and he reached the limits of what he could accomplish by himself. The journey to hiring a staff and scaling the company had its own set of growing pains for Anthony, including difficulty letting go of control, and learning how to manage other people. Today, Squarespace has grown to more than 800 employees, and valued at $1.7 billion. PLUS in our postscript "How You Built That," how Kate Westervelt took an overwhelming experience and turned it into a gift box for new moms – filled with essential items women need to recover from childbirth. See 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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Episoder(855)

Advice Line with Chris Riccobono of UNTUCKit

Advice Line with Chris Riccobono of UNTUCKit

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30 Jul 46min

Sweetwater: Chuck Surack. How a Customer Service Strategy Built a Billion Dollar Online Pro Audio and Music Company.

Sweetwater: Chuck Surack. How a Customer Service Strategy Built a Billion Dollar Online Pro Audio and Music Company.

Chuck Surack never planned to build one of America's largest online retailers. He just wanted to be a musician. So right after high school, he took his sax and drove off in his old VW van to play gigs...

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Advice Line with Curt Richardson of OtterBox

Advice Line with Curt Richardson of OtterBox

Today’s callers: Andy from Sarasota weighs whether the path to scalability for his live game show business is through personality or product. Then, Marissa from Tampa wants to recapture sales for her ...

23 Jul 41min

Toast: Aman Narang. How a Long Wait for the Dinner Check Launched a $2 Billion Business.

Toast: Aman Narang. How a Long Wait for the Dinner Check Launched a $2 Billion Business.

After waiting too long to pay his restaurant bill, Aman Narang thought there had to be a better way. His first idea—a mobile payment app—flopped.But that failure revealed a much bigger opportunity.Res...

20 Jul 51min

Advice Line with Kenneth Cole

Advice Line with Kenneth Cole

Today’s callers: Matt from New York City unpacks the stigma working against his line of foot wellness products. Then Emefa in Toronto seeks a direct relationship with customers of her fashion brand in...

16 Jul 45min

Sun Bum: Tom Rinks. The Secrets of a Master Brand Builder (2023)

Sun Bum: Tom Rinks. The Secrets of a Master Brand Builder (2023)

Tom Rinks got his start in the commission-only "shark tank" of midwestern furniture sales. That’s where he learned what makes customers buy. Decades later, those instincts helped him grow a joke of a ...

13 Jul 1h 15min

Advice Line with Jeni Britton of Jeni's Splendid Ice Creams (2025)

Advice Line with Jeni Britton of Jeni's Splendid Ice Creams (2025)

Jeni’s Splendid Ice Creams founder Jeni Britton joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, how Jeni’s newest venture Floura is tackling one of America...

9 Jul 48min

Catalina Crunch: Krishna Kaliannan. From Homemade Keto Cocoa Puffs to Breakfast Aisle Breakthrough

Catalina Crunch: Krishna Kaliannan. From Homemade Keto Cocoa Puffs to Breakfast Aisle Breakthrough

Krishna Kaliannan wanted to start a tech company but failed at every attempt. On the side, he was teaching himself how to cook with high-protein, low-sugar ingredients. Not just out of interest, but o...

6 Jul 1h 3min

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