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.
Why would anyone make a website in 2023? Squarespace CEO Anthony Casalena has some ideas
Today I’m talking to Anthony Casalena, the founder and CEO of Squarespace, the ubiquitous web hosting and design company. If you’re a podcast listener, you’ve heard a Squarespace ad.
I was excited to talk to Anthony because it really feels like we’re going through a reset moment on the internet, and I wanted to hear how he’s thinking about the web and what websites are even for in 2023.
If you’re a Vergecast listener, you know I’ve been saying it feels a lot like 2011 out there. The big platforms like Facebook and TikTok are very focused on entertainment content. Twitter is going through… let’s call them changes. People are trying out new platforms like Instagram Threads and rethinking their relationships with old standbys like Reddit. And the introduction of AI means that search engines like Google, which was really the last great source of traffic for web pages, just doesn’t seem that reliable anymore as it begins to answer more questions directly. It’s uncertain, and exciting: a lot of things we took for granted just a couple years ago are up for grabs, and I think that might be a good thing.
I love talking to people who’ve been building on the web for this long, and Anthony was no exception – we had fun with this one. Also I think this is the most we have ever talked about pressure washers on Decoder.
Links:
Google sunsets Domains business and shovels it off to Squarespace - The Verge
How Did Squarespace Know Podcasts Would Get This Big? - The New York Times
Watch Squarespace CEO on Leveraging AI Into Website Building - Bloomberg
Transcript:
https://www.theverge.com/e/23559195
Credits:
Decoder is a production of The Verge, and part of the Vox Media Podcast Network.
Today’s episode was produced by Jackie McDermott and Raghu Manavalan, and it was edited by Callie Wright.
The Decoder music is by Breakmaster Cylinder. Our Editorial Director is Brooke Minters, and our Executive Producer is Eleanor Donovan.
Learn more about your ad choices. Visit podcastchoices.com/adchoices
20VC: Squarespace Founder, Anthony Casalena on Scaling Squarespace from Dorm Room To Public Company with over $700M in ARR, The Decision to Direct List over Traditional IPO or SPAC & What Changes When You Go Public?
Anthony Casalena is the Founder & CEO @ Squarespace, the company that allows you to create a website, sell anything and market your business. To date, Anthony has raised over $948M for the company from the likes of General Atlantic, Index Ventures, Tiger Global; culminating in their IPO in May 2021. Despite the incredible size and scale of Squarespace today, Anthony started the company from his dorm room in 2003 and bootstrapped the business for many years to today with over 1,100 employees around the world.
In Today's Episode with Anthony Casalena You Will Learn:
1.) How Anthony came to start Squarespace from a dorm room and turn it into a public company with over 1,200 employees globally?
2.) Why did Anthony decide to bootstrap with Squarespace for over 6 years when the company was scaling fast and profitable? How was Anthony's mindset impacted by the efficiency of bootstrap scaling? How did Anthony's mindset change when Squarespace raised their first large round? How does Anthony advise founders today on raising venture vs bootstrapping?
3.) Why did Anthony decide to do the direct listing over the more traditional IPO or a SPAC? How does Anthony advise other founders contemplating the same exit choices? How does Anthony personally describe this chapter of the company? Does he enjoy being a public company CEO? What are the best elements? What are the worst?
4.) E-Commerce has been a massive driver for growth for Squarespace, how does Anthony feel about the future of e-commerce on Squarespace? Only 1% of Squarespace's $700M ARR comes from enterprise, does enterprise hold a meaningful position in the future of the company? What are the core challenges of moving into enterprise? How does the company need to change?
5.) With the growth of the company, how has Anthony changed his style of leadership? What are his biggest strengths? What are his biggest weaknesses? What are the most obvious breakpoints in the scaling of companies?
Item's Mentioned In Today's Episode with Anthony Casalena
Anthony's Favourite Book: Thinking Fast and Slow
Facebook puts Instagram Kids on pause, Bevy’s high-profile firing + Squarespace’s Anthony Casalena | E1291
Jason covers Instagram's Adam Mosseri announcing the pause of Instagram Kids (2:09), the recent firing of Bevy employee following a hostile interaction in Brooklyn (21:51). Then, Squarespace Founder and CEO Anthony Casalena joins (35:43) to discuss what marketing channels have been best for growing the company, new products offerings and shares stories from scaling and more!
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.
