How Squarespace Grew to Thousands of Users with Anthony Casalena

As you’ve probably figured out by now, Squarespace has been sponsoring BlogcastFM for the last two months. We absolutely love the product. In fact, we built 500 Business Books in 20 minutes using their product. When I first learned about our partnership, I knew that I wanted to interview their CEO, Anthony Casalena.

Here are few of the highlights from our chat:

  • How Anthony Identified an Opportunity By Solving His Own Problem 
  • Why Looking at the Problems You Have May Present Business Opportunities
  • The Importance of Thinking In Terms of What Your Customers Need
  • A Look at The Three Phases of Squarespace’s Growth
  • Anthony’s Take on How to Make a Career Transition to Entrepreneurship
  • How Squarespace Managed to Be Profitable Since the Day It Started
  • The Importance of Giving Yourself an Entrepreneurial Runway
  • Why Anthony Decided to Raise $38 Million in Venture Funding
  • A Look at How Anthony Used the Funding He Raised
  • Lessons from a Big Company that Apply to Microbusiness
  • Having the Guts to Turn Down a Job at Google
  • How Squarespace Positioned Itself in a Crowded Market

Tweetable Insights Include:

  • We’re in the same boat as our customers, which is a great place to be. (Click to Tweet)
  • Short term thinking is the destruction of a lot of businesses (Click to Tweet)
  • Once you’re profitable you’re very much in control of your own destiny(Click to Tweet)
  • Putting a web site online is going to represent who you are.

Anthony Casalena is the Founder, Chairman, and CEO of Squarespace, which he founded in 2003. As Squarespace’s strategic leader, he is responsible for setting the overall direction and product strategy of the company. He leads product design for all Squarespace services and is an active member of the engineering team. You can follow both him (@acasalena) and Squarespace (@Squarespace) on twitter