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)

HIBT Lab! Tala: Shivani Siroya

HIBT Lab! Tala: Shivani Siroya

‘This is not our customer...’ That was the common justification banks used to deny loans to the entrepreneurs Shivani Siroya supported through her work with the United Nations. While it’s not unusual for a tech startup to raise millions before ever launching a product, small business owners across the globe are all-too-often deemed unworthy of even just a few hundred dollars by traditional financial institutions. In 2011, Shivani set out to change this at scale. Her company, Tala, has since disbursed more than $3 billion in microloans across India, Kenya, Mexico, and the Philippines. Borrowers simply answer a few questions on a mobile app and — within minutes — they have access to capital. What’s more is that the vast majority of the Tala’s loans are repaid, even with such a frictionless vetting process. This week on How I Built This Lab, Shivani talks with Guy about the lightbulb moments that drove the creation of this vital credit solution and its potential to uplift entire national economies. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

17 Nov 202234min

Chobani: Hamdi Ulukaya

Chobani: Hamdi Ulukaya

As a newly arrived immigrant from Turkey, Hamdi Ulukaya learned to be resourceful, determined, and even stubborn when he needed to be. All those traits would serve him well as he began to navigate the hairpin turns of building a yogurt business from the ground up. In 2005, Hamdi was running a small feta cheese business in upstate New York when he happened upon a piece of junk mail that would change his life: an ad for an abandoned yogurt factory...$700K, as is. He knew if he could get his hands on it, he could bring a new kind of dairy product to the U.S.—the thick, creamy yogurt he’d grown up eating in the mountains of Turkey. With the help of a local bank, Hamdi bought the factory, and sales grew so quickly that he could barely keep up. A few years later, some bad business decisions nearly pushed the company into bankruptcy, but today, Chobani is one of the most popular yogurt brands in the U.S; and Greek-style yogurt has become a staple of the dairy aisle. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

14 Nov 20221h 30min

HIBT Lab! Tomorrow.io: Shimon Elkabetz

HIBT Lab! Tomorrow.io: Shimon Elkabetz

Our planet is warming, and many parts of the world are not equipped to accurately predict the heat waves, hurricanes, tornadoes, wildfires and floods that are becoming more frequent and intense due to the changing climate. Former Israeli Air Force pilot Shimon Elkabetz knows the importance of good weather forecasts — they can literally mean the difference between life and death. In 2016, he co-founded Tomorrow.io to improve the weather data available across the world. This week on How I Built This Lab, Shimon talks with Guy about his company’s work to help businesses, governments and individuals make better decisions in response to increasingly volatile weather. Plus, Shimon recounts some of the challenges he’s faced in fundraising for ‘hard technology’ and stresses the importance of building climate change solutions that generate immediate impact.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

10 Nov 202240min

Ooni Pizza Ovens: Darina Garland and Kristian Tapaninaho

Ooni Pizza Ovens: Darina Garland and Kristian Tapaninaho

When you think of pizza, the first place that comes to mind probably isn’t Finland…or Scotland. But that’s where the two founders of the outdoor pizza oven brand Ooni grew up. In 2012, Kristian Tapaninaho was experimenting with making his own pizza, but he couldn’t get his home oven hot enough to produce an authentic, Neapolitan-style crust. With no background in product design, Kristian decided to design a portable, wood-fired outdoor oven. He used some basic 3D modeling software, enlisted a nearby fence-maker to build a prototype, and raised about $26,000 on Kickstarter. Since launching in 2012, Kristian and his wife Darina have grown Ooni into a $250 million business, accelerated by the home baking boom that happened during COVID. Based in Edinburgh, Scotland, and sold in 90 countries, Ooni has defined a new product category that has helped transform home pizza making.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

7 Nov 20221h 9min

HIBT Lab! MKBHD: Marques Brownlee

HIBT Lab! MKBHD: Marques Brownlee

“Right now I have approximately 70-ish subscribers,” declared a teenage Marques Brownlee at the beginning of his 100th YouTube video back in 2009. Marques recorded his first of many product reviews earlier that year, after buying his first laptop. Quite simply, he wanted others to have more information about this computer than he did when he bought it. Since then, Marques has grown his channel, MKBHD, into a full-fledged business with more than 16 million subscribers and over 3 billion total views. He’s expanded beyond reviews too, posting interviews with well-known public figures like Kobe Bryant, Bill Gates and Elon Musk. This week on How I Built This Lab, Marques reflects on his journey as a content creator and how he turned a love of tech into a lucrative and sustainable business. Plus, he shares his philosophy for building a strong team – which interestingly enough, is inspired by an octopus...See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

3 Nov 202249min

Tripadvisor: Steve Kaufer

Tripadvisor: Steve Kaufer

Steve Kaufer got the idea for Tripadvisor in 1998 after spending way too many hours online, trying to figure out if a resort in Mexico was really as good as its brochure. When he launched a travel guidance site a few years later, his business plan failed spectacularly because he was trying to partner with other websites, rather than engaging directly with travelers. But Steve eventually arrived at a winning formula: make Tripadvisor available to everyone, aggregate tons of information about hotels and attractions, encourage travelers to add their reviews, and earn a fee from travel companies whenever users clicked to their sites. As the company grew, Steve remained at the helm, leading it through a $210 million sale to IAC, followed by a multi-billion dollar IPO in 2011. Today, Tripadvisor gets over 400 million visitors a month; and Steve—who just stepped down after 22 years—is already thinking about his next business. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

31 Okt 20221h 15min

HIBT Lab! Cruise: Kyle Vogt

HIBT Lab! Cruise: Kyle Vogt

Most of us are familiar with rideshare apps at this point. We tap a few buttons on a phone and...voila! A vehicle arrives to take you virtually anywhere you want to go. But what if these vehicles could operate entirely without a human driver? Will we one day live in a world where most cars drive themselves?Kyle Vogt believes that autonomous vehicles will fundamentally change how we get from place to place, and soon! After being part of the team that launched the video game streaming platform Twitch, Kyle charted a new course in 2013 by founding Cruise, which was acquired by General Motors just three years later.This week on How I Built This Lab, Kyle talks with Guy about the process of building a fleet of fully driverless ‘robo taxis’—which are now available for service in San Francisco and coming to more cities across the U.S.. Plus, the two discuss the potential of autonomous vehicles to reduce the alarming number of vehicle-related fatalities and injuries experienced every year.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

27 Okt 202250min

Bluemercury: Marla and Barry Beck

Bluemercury: Marla and Barry Beck

The story of Bluemercury is packed with business lessons—for starters, it’s always good to have a backup plan. That’s what Marla and Barry Beck discovered in 1999, when they realized their startup online cosmetics business was going nowhere fast. They begged the bank for a second loan so they could invest in a brick-and-mortar store in Washington, D.C., and Bluemercury was born. More lessons followed: as they grew, they distinguished themselves by offering high-end brands and personalized service, and by locating stores in fashionable urban neighborhoods, not malls. Today, Bluemercury is owned by Macy’s, with nearly 200 locations across the U.S. And Barry and Marla—who got married somewhere around the launch of store 4—raised three children along the way.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

24 Okt 20221h 11min

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