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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Zumiez: Tom Campion

Zumiez: Tom Campion

Working as a manager for nine years at JCPenney, Tom Campion learned a critical lesson about how to succeed in retail: you have to keep close track of inventory. Tom’s experience navigating the ebb and flow of style, color, and size—all without the benefit of computers—gave him the confidence to launch his own retail business, aimed at teenagers. In 1978, he and his partner Gary Haakenson opened their first store, Above the Belt, in Seattle, and soon tapped into the hot new “action sports” category and the growing popularity of surf, skateboard, and snowboard culture. Tom placed his stores in shopping malls, and created spaces where teenagers would want to hang out, by leaning into “organized chaos” as a design principle. Today, with roughly 750 stores, Zumiez is the largest action sports retailer in the world.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

6 Helmi 202356min

HIBT Lab! The Sioux Chef: Sean Sherman

HIBT Lab! The Sioux Chef: Sean Sherman

Chef Sean Sherman is on a mission to revitalize and reimagine Native American cuisine. Growing up on a reservation in South Dakota, Sean ate a lot of highly processed foods provided by the U.S. government. It wasn’t until he started working in restaurants as a teenager that he began to learn about fresh ingredients and how to prepare them. But as Sean climbed the kitchen ranks, learning the techniques and recipes of European-style fine dining, he began to wonder what happened to the culinary traditions of his Native American ancestors. This week on How I Built This Lab, Sean talks with Guy about establishing a modern North American indigenous cuisine by cutting out non-native ingredients such as pork, chicken, beef, dairy, wheat and cane sugar. Instead, he cooks with heirloom varieties of corn, wild rice, foraged plants and native animals such as bison, salmon, duck and beaver. Under The Sioux Chef brand, Sean has hosted pop-up dinners, published a cookbook, operated a food truck, and in 2021, he opened Owamni, which won the James Beard Award for Best New Restaurant.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

2 Helmi 202335min

Chomps: Pete Maldonado and Rashid Ali

Chomps: Pete Maldonado and Rashid Ali

When steaks don’t sell you shift to sticks; that’s how Chomps was born. After several failed ventures—one of which left him bankrupt—Pete Maldonado decided to take another chance on launching a business. He partnered with Rashid Ali to start a mail-order service similar to Omaha Steaks, but with grass-fed meat that was more suited to the Paleo diet. When the partners couldn’t get that off the ground, they shifted to individually-wrapped meat sticks; one of the first in a long line of ‘healthier for you’ protein snacks. For several years, each co-founder tried to manage the business as a side-hustle, but the sausage hit the fan in 2016 when a surprise order from Trader Joe’s left them scrambling to produce a million sticks. Today, Chomps is available in major chains across the country and pulls in more than $100 million a year. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

30 Tammi 20231h 25min

HIBT Lab! Osmo Salt: Nick DiGiovanni

HIBT Lab! Osmo Salt: Nick DiGiovanni

Do you know who holds the record for making the world’s largest chicken nugget? How about the world’s largest sushi roll?If you know Nick DiGiovanni, then you know the answer to those questions. Each week, more than 15 million followers across YouTube and TikTok gawk and drool over Nick’s masterful and over-the-top culinary creations. Nick is at the helm of some analog business ventures too, including a DTC salt and seasoning company and his debut cookbook, Knife Drop, which publishes later this year. This week on How I Built This Lab, Nick talks with Guy about overcoming shyness to become an on-camera personality, and his recent decision to forego Harvard Business School to continue on his path as a creator. Nick also opens up about his struggles to set strong work-life boundaries and speculates about his professional future. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

26 Tammi 202342min

Tarte Cosmetics: Maureen Kelly

Tarte Cosmetics: Maureen Kelly

Let’s say you had a passion but thought of it only as a hobby; certainly never the seed of a billion-dollar company. Plus, you are studying for a career in something unrelated to business. That’s Maureen Kelly’s story, CEO of Tarte Cosmetics. She was pursuing a Ph.D. in clinical psychology and already had TWO Master’s degrees when she realized she didn't want that to be her career. What she wanted was to launch a makeup company—despite having no significant start-up money, no experience, and no connections. How she did it is a story of pure moxie. She relentlessly knocked on the doors of chemists, manufacturers, retailers, and the fashion press. She maxed out her credit cards and enlisted the help of friends and family, turning Tarte into a wildly successful brand.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

23 Tammi 20231h 21min

HIBT Lab! Nuro: Dave Ferguson

HIBT Lab! Nuro: Dave Ferguson

When you think about self-driving cars, you might imagine relaxing in the back seat while a vehicle carries you to your destination. But according to Dave Ferguson, nearly half of all car tips that Americans take don’t actually need any passengers at all. That’s because we spend a lot of our time driving around just to pick things up, like groceries and takeout.This week on How I Built This Lab, Dave talks with Guy about his vision of a future where many of these everyday errands could be done by robots. Dave’s company, Nuro, builds autonomous vehicles that are meant to deliver goods rather than carry passengers. Already they’ve run pilot deliveries with big-name partners like Domino’s Pizza, Uber Eats, and Kroger Grocery stores, and in the next few years, they aim to expand their service to cities all across the country. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

19 Tammi 202339min

Complexly: Hank and John Green

Complexly: Hank and John Green

In 2007, brothers Hank and John Green lived thousands of miles apart, so they started posting video blogs to each other on a strange new platform called YouTube. People began tuning in, and the daily Vlogbrothers posts became an early viral hit. Over time, the brothers grew that single channel into a sprawling collection of businesses, including a production studio—Complexly—that makes some of the most entertaining educational content on the internet. They’re also both hugely successful authors; John’s young adult novel The Fault in Our Stars is one of the best-selling books of all time. With every success, Hank says he’s asked himself, “What’s exciting? What’s causing you the most stress? Head in that direction.”See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

16 Tammi 20231h 24min

ICYMI... HIBT Lab! Malala Fund and Our Place: Shiza Shahid

ICYMI... HIBT Lab! Malala Fund and Our Place: Shiza Shahid

On October 9, 2012, Shiza Shahid’s life changed forever. It was on that day that 15-year-old Pakistani activist Malala Yousafzai was shot in the head by a Taliban gunman, capturing the world’s attention. Before long, 22-year-old Shiza found herself leaving her corporate job to join a recovering Malala and her father in launching the Malala Fund, a nonprofit that advocates for girls’ education across the globe. Little did Shiza know, this venture was actually just the beginning of her entrepreneurial journey...This week on How I Built This Lab, Shiza recounts the childhood experiences that forged her commitment to public service and advocacy—ultimately shaping her worldview and leading to her first encounter with Malala. She also discusses her pivot to the for-profit world with Our Place, the cookware company she co-founded in 2019 that’s both profitable and making an impact.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

12 Tammi 202346min

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