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?
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC
4.4 • 637 Ratings
🗓️ 8 October 2021
⏱️ 34 minutes
🧾️ Download transcript
Summary
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
Transcript
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| 0:00.0 | Welcome back. This is 20VC with me, Harry Stebbings, and there's some lovely synchronicity to the shows this week, |
| 0:04.9 | as we had Anton Levy at General Atlantic on the show earlier this week, and Anton led the deal and sat on the board of this incredible company we have on the show today. |
| 0:13.0 | And so with that, I'm very, very excited to welcome Anthony Casalena, found and CEO at Squarespace. |
| 0:17.8 | Now, Squarespace is the company that allows you to create a website and sell |
| 0:21.6 | anything and market your business all online seamlessly. To date, Anthony has raised over $948 million |
| 0:28.1 | for the company from the likes of General Atlantic, Index Ventures, Tiger Global, culminating in |
| 0:33.6 | their IPO in May 2021. Despite the incredible size and scale of Squarespace today though, |
| 0:38.8 | Anthony started the company from his dorm room in 2003 and bootstrapped the business for many years |
| 0:44.0 | to stay where there is now over 1,100 employees around the world within Squarespace. |
| 0:49.2 | I'd also want to say huge thank you to Lisa Landman at NEA and Andrew Bruchier of Excel. |
| 0:53.6 | Some fantastic questions suggestions |
| 0:55.3 | today. They really did make such a difference. But before we dive into the show state, did you know |
| 0:59.6 | that more than 80% of US public stock is owned by just 10% of Americans? This divide is even greater |
| 1:05.3 | in the private markets. Carter makes it as easy to issue equity to your employees as it is to issue |
| 1:10.4 | payroll. And for employees, as easy to accept equity to your employees as it is to issue payroll. |
| 1:11.1 | And for employees, as easy to accept it too. |
| 1:13.7 | More than 16,000 companies issue equity to their employees through Carter, |
| 1:17.8 | whether you're just getting started or getting ready to go public, |
| 1:20.6 | the team that Carter can help. |
| 1:21.9 | Check them out at carter.com. |
| 1:23.7 | And then another incredible product you have to introduce is Secureframe. |
| 1:27.6 | Secureframe helps companies get enterprise ready by streamlining SOC2 and ISO-271 compliance. |
... |
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