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.

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Chesapeake Bay Candle: Mei Xu (2017)

Chesapeake Bay Candle: Mei Xu (2017)

Twenty-five years ago, after Mei Xu emigrated from China to the U.S., she loved going to Bloomingdale's to gaze at their housewares. She eventually started making candles in her basement with Campbell's Soup cans, an experiment that led to the multi-million dollar company Chesapeake Bay Candle. PLUS in our postscript "How You Built That," we check back with Dan Kurzrock and Jordan Schwartz, who turned up-cycled beer grain into a snack bar called ReGrained. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

17 Kesä 201942min

Allbirds: Tim Brown & Joey Zwillinger

Allbirds: Tim Brown & Joey Zwillinger

Growing up, Tim Brown discovered he was very good at two things: design and soccer. While playing professional soccer in New Zealand, he was turned off by the flashy logos on most athletic gear. He started making simple canvas shoes for his teammates, but soon discovered a better material: soft merino wool from his country's plentiful sheep. Meanwhile, on the other side of the world, his future business partner Joey Zwillinger was frustrated that most companies lacked a genuine commitment to sustainability. In 2015, Tim and Joey teamed up to create Allbirds, a company with two ambitious goals: create the world's most comfortable shoes, and do it in a way that was completely carbon-neutral. Today, just three years after launch, Allbirds is worth $1.4 billion. PLUS, for our postscript "How You Built That," how Kirby Erdely saw a problem with flying beach umbrellas and developed a new kind of tent stake—with a twist. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

10 Kesä 20191h 9min

Live Episode! Tofurky: Seth Tibbott

Live Episode! Tofurky: Seth Tibbott

Seth Tibbott may be the only founder in the world who grew his business while living in a barn, a teepee, and a treehouse. His off-the-grid lifestyle helped him save money as he started to sell tempeh, a protein made of fermented soybeans. Throughout the 1980s he barely scraped by, but things took a turn in 1995, when he discovered a stuffed tofu roast made in Portland, Oregon. Knowing vegetarians had few options at Thanksgiving, Seth named the roast Tofurky and started selling it at co-ops in the Pacific Northwest. Nearly 25 years later, Tofurky sells plant-based protein around the world, and has estimated sales of $40 million a year. Recorded live in Portland, Oregon. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

3 Kesä 201946min

Stacy's Pita Chips: Stacy Madison

Stacy's Pita Chips: Stacy Madison

In the 1990's, Stacy Madison and her boyfriend Mark Andrus were selling pita sandwiches from a converted hot dog cart in Boston. They decided to bake the leftover pita into chips, adding a dash of parmesan or cinnamon-sugar. At first they handed them out for free, but soon discovered that people were happy to pay for them. So they eventually decided to leave the sandwich cart behind and launch Stacy's Pita Chips. They hoped the brand might grow into a modest regional business—but it kept growing. Roughly ten years after the launch, Stacy's sold to PepsiCo for $250 million. PLUS in our postscript "How You Built That," how Prerak Juthani and some friends from college took organic chemistry to the next level with REACT!, a board game that aims to demystify the stigma of molecular science. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

27 Touko 20191h 3min

Zappos: Tony Hsieh (2017)

Zappos: Tony Hsieh (2017)

Computer scientist Tony Hsieh made millions off the dot-com boom. But he didn't make his mark until he built Zappos — a customer service company that "happens to sell shoes." Now Zappos is worth over a billion dollars and known for its completely unorthodox management style. PLUS in our postscript "How You Built That," we check back with Mike Bolos and Jason Grohowski, who brought the office desk closer to the light by creating Deskview, a portable desk that attaches to a sheer window with a suction cup. (Original broadcast date: January 23, 2017). See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

20 Touko 201932min

Belkin International: Chet Pipkin

Belkin International: Chet Pipkin

Chet Pipkin was the kind of kid who loved to take things apart and put them back together. As a young man in the early 1980s, he started hanging out in mom-and-pop computer shops, where he realized he could meet a growing need by selling the cables that connect computers to printers. That simple idea became the main ingredient in Chet's secret sauce: instead of making his own computers, he would make the accessories needed to make them work. Belkin International eventually grew into a massive manufacturer of electronic goods — last year, it sold to a subsidiary of Foxconn for more than $800 million. PLUS in our postscript "How You Built That," how Clay McCabe decided to rebrand his dad's zipper repair business into Zipper Rescue, a repair kit that helps people fix their broken zippers at home. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

13 Touko 201952min

Framebridge: Susan Tynan (2017)

Framebridge: Susan Tynan (2017)

Susan Tynan's experience in the ephemeral e-market of LivingSocial made her want to start a business that she could touch and feel. After being charged $1600 to frame four posters at her local framing store, she decided to create a mail-order framing company that offers fewer designs at lower prices. Framebridge is now five years old and still feeling growing pains, but is slowly reshaping the rules of a rigid industry. PLUS in our postscript "How You Built That," we check back with Len Testa, who created an app that uses real-time data to help people avoid long lines at Orlando area theme parks. (Original broadcast date: November 27, 2017) See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

6 Touko 201958min

Live Episode! Peloton: John Foley

Live Episode! Peloton: John Foley

John Foley started climbing the rungs of the corporate ladder at a young age, first as a fast food server and eventually as an e-commerce executive. Still, at 40, he couldn't climb out of bed fast enough to make it to his favorite spin class. John couldn't understand why there wasn't a way to bring the intensity and motivation of a boutique fitness class into the home. Having never worked in the exercise industry, he teamed up with a few friends to create a high-tech stationary bicycle called the Peloton Bike. Today, Peloton has sold close to half a million bikes, with a valuation as high as 4 billion dollars. Recorded live in New York City. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

29 Huhti 201953min

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