How Squarespace Built a Great Startup


Squarespace is the New York City-based startup that allows clients to easily build their own beautiful websites. Founded in 2003, Squarespace has now grown into one of the hottest startups in NYC.

Squarespace Started in a College Dorm Room

Squarespace was founded by Anthony Casalena in his dorm room at the University of Maryland. The original tool was a way to allow Anthony to easily build his own website. After sharing the tool with his friends and family, Anthony was soon able to raise $30,000 to start the company. For the next four years, Casalena was the only employee at the company. By 2007, the company was generating $1 million in annual revenue. 

From Small Beginnings to a $1.7 Billion Valuation

By 2010, Squarespace had raised $38.5 million in Series A funding and had grown to 30 employees. Four years later, the company closed a second round of Series B funding worth another $40 million. The following year in 2015, the company had reached $100 million in annual revenue and had grown to over 550 employees. Then last year in 2017, Squarespace secured an additional $200 million in secondary market funding in a round that saw the company valued at $1.7 billion.

Simplicity is Key

By simply dragging-and-dropping content into pre-arranged templates, Squarespace allows users to easily make their own beautifully designed websites. For more ambitious users, Squarespeace also allows them to create templates which can then be sold to other users who want to purchase the design. Templates come with tutorials on how to optimize for SEO and even include how-to setup guides for e-commerce. As of 2016, the company was hosting more than 1 million pages.

Expanding and Earning Kudos

Since its founding, Squarespace has grown to over 830 employees. The company has also grown from its NYC-based roots to also having offices in Portland, Oregon and Dublin, Ireland as well. As a vote of confidence, Squarespace also hosts its own website on the platform. Since 2012, the company has been voted one of Crain’s Best Places to Work in NYC and last year was named one of Fortune’s 50 Best Workplaces for Parents.

Furthering the Market Share

As of 2016, the company has also started selling domain names. This put the company on an even more head-on trajectory with rivals like GoDaddy. But Squarespace has fared well. Since then, the company has managed to embrace the e-commerce trend and has also found ways to fully integrate both PayPal and Stripe in order to make online transactions across the platform more seamless.

Today, more-and-more Squarespace is making its presence in the web-hosting industry felt. Few would have guessed the company would ever come so far after starting in that university dorm room all those years ago.

12 Blogs Every Entrepreneur Should Read

The best people in business are lifelong learners of their trade. Below are a few of the best blogs that are organized by category. The numbers are not meant to serve as a ranking of order as they are all great resources for continued education in business.

Large Publications

1. The Wall Street Journal- It’s a pay subscription service but for keeping up with news and business it is some of the best writing on the web for general business and news.

2. Harvard Business Review- HBR is a great blog filled with excellent insight on business and quick reads. A well-known publication that lives up to its namesake.

Startup & VC Advice

3. Y-Combinator Blog Y Combinator is one of the top incubators on the planet. In addition to running one of the top incubators in the world, their blog is top notch. The articles are well written and the bring in amazing guest bloggers who are leaders of industry.


a16z topic matrix


4. A16Z- Created and run by Andreesen Horowotiz, one of the most prestigious venture capital firms. The site focuses on business and startups and includes excellent organization of blog posts by topics. The website is broken down into 3 categories Advice & How To, Tech Topics, Podcasts.

5. Both Sides of the Table- In their own words: "Perspectives of a 2x entrepreneur turned VC at @UpfrontVC, the largest and most active early-stage fund in Southern California." As the name implies the blog gives perspective from the VC and Entrepreneur side of business, and fundraising.

6. Cruncbase- Crunchbase is one of the best resources to research recent funding deals. While this may not be a blog in a traditional sense of written articles by business leaders it is a great tool to keep up with VC funding.

7. 500 Startups Blog, - Similar to Y-Combinator blog, 500 startups is a company that has invested in over 1600 startups and provides a wide range of advice on business and startups throughout their blog. In their own words about their program

Have your act together? We invest $100-250K on market terms and charge a $25-50k fee depending on geography for participation in the 500 Series A Program.

You’ll get all the perks of being in 500 too – like access to our vast network of investors, partners and founders.

8. - Inc Magazine ranks this as the number one blog for entrepreneurs and it ranks as number 2 on Forbes list of best 100 websites for Entrepreneurs. What makes this blog excellent is the in-depth advice from David Skok. David is a lifelong businessman turned VC, who focuses his advice on business, marketing and startups.


9. OnStartups- Run by the founder of Hubspot this is an excellent blog focused on marketing and sales online. An excellent resource for marketing, SAAS and business in general.

10. Rand Fishkin's Blog, Rand is one of the top names in marketing and SEO. Part of the MOZ website (formerly SEO MOZ). This is a great resource for learning expert level SEO tactics and keeping up with the constant changes of how algorithms work. I will also say that I would highly recommend  itself as well.

11. Canva Design School- Canva Design School is a daily blog that focuses on design. This is a great resource for branding, marketing, and building beuatfiul pitch decks. The Canva product itself is an excellent product to use that makes easy work out of graphic design. Guy Kawasaki currently serves as the company's Chief Evangelist.



12. Ted Talks- Some of the most amazing and inspirational presentations. Although many of the presentations are not focused on business, this is an amazing site for great content and inspiration. Video Blog.