SC

Strategy Canon

Squarespace

Squarespace charged every customer for a designed, hosted website, and the creatives who paid kept their sites for years, funding measured podcast ads and a profitable business while Wix won more subscribers by giving its builder away.

How Squarespace won

  1. 1 · 2004–14A designed, hosted site for people whose site is their workOne subscription replaced blog, forum, host and database software; the team pruned weak templates for 'the design crowd'.Product Leadership
  2. 2 · 2005–23Paid-only: a filter for customers who value a finished siteThe free plan went after one year because free users 'were never, ever, ever going to upgrade'.Premium Pricing
  3. 3 · 2004–10Paying customers fund support and growth from the first yearAdWords returns went back into AdWords; six profitable years before the first outside money in 2010.Self-Serve Only
  4. 4 · 2009–15Long subscriptions pay for measured podcast host readsA This Week in Tech read brought a third of new subscribers; offer codes tracked every show after it.Podcast Advertising
  5. 5 · 2016–24The same cash flow on a smaller, paying baseIn 2020 Squarespace matched Wix's operating cash flow on less than two thirds of its revenue.Trade-offs & activity fit

Versus Wix: Wix gave its builder away and bought a larger user base with years of losses SQX-2. Squarespace charged everyone, kept the creatives who valued a designed site, and made as much cash as Wix on less than two thirds of its revenue SQX-4.

Arena: Market Conditions Before Squarespace

People wanting a personal or portfolio website · 2004 · United States and other English-speaking markets

High setup and upkeep costsBarriers to participation

A photographer, designer or small business that wanted a website with a blog, galleries and pages in 2004 had to install publishing software on a rented web server. Movable Type ran on Perl, and WordPress, first released in May 2003, needed PHP and a MySQL database SQ53 SQ52. WordPress gained plugins only in May 2004 and themes in February 2005, so a distinctive look meant editing templates by hand or paying someone who could SQ52. One site meant stitching together separate programs for blogging, pages and hosting, and the hosted services of the time paid little attention to design SQ17 SQ13.

How each step happened

Step 1 of 5 · 2004–14

A designed, hosted site for people whose site is their work

Squarespace's founding choice was to sell a finished website, not software to assemble one. At the end of 2004 one subscription replaced the blog software, forum software, web host and databases a site owner otherwise had to combine, and Squarespace ran all of it SQ64. That removed the hosting, plugin updates and security work that self-hosted WordPress left to the owner SQ54.

The other half of the choice was who the site was for. Casalena said 'it's really the design crowd that we seem to connect with the most' SQ19. The team removed templates it judged substandard SQ17, and Squarespace 7 in 2014 let customers edit beside a live preview SQ24. Design became the reason people whose site was part of their work chose it; a shop owner who later left for Shopify still called it ideal for bloggers and photographers SQ55. The rest of the chain depends on that customer, who judges a site by how it looks.

Rivals Wix started in 2006 as a Flash drag-and-drop builder for people with no knowledge of code SQX-3. By 2021 it offered more than 800 templates to Squarespace's little more than 100 and was known for flexible editing rather than design SQX-4.

Product LeadershipManaged Service

Step 2 of 5 · 2005–23

Paid-only: a filter for customers who value a finished site

Squarespace launched with a free, ad-supported blogging plan beside its paid packages SQ64. After the first year Casalena dropped it: many free users 'were never, ever, ever going to upgrade' and were using servers he paid for himself SQ62. By June 2005 the pricing page listed only paid packages, and a free trial became the way to try the product SQ64 SQ62.

Charging from the start selected customers who valued a finished, designed site, and they stayed; Casalena noticed early that 'they make a website. They're not leaving quickly' SQ62. Squarespace also priced above the cheapest option on purpose, charging $20 a year for a domain that GoDaddy sold from 99 cents SQ16. In 2023 Casalena still called it 'not a free product', built for 'a more serious user' rather than the largest count of websites SQ63.

Rivals Wix has been freemium since its 2006 founding; at the end of 2013 it had 42.1 million registered users and 789,753 premium subscriptions SQX-2. Weebly, another free builder, had 625,000 paying customers when Square bought it for $365 million in 2018 SQ51.

Premium PricingFocus StrategyFree Trial

Step 3 of 5 · 2004–10

Paying customers fund support and growth from the first year

Paid customers financed the company from the first year, which is why this step begins before the free plan was gone. Casalena launched with $30,000 from his father for two servers and for three years handled code, customers and marketing alone, with no sales team SQ62 SQ16. He measured every small AdWords buy: 'You put a couple of hundred bucks into Google AdWords and get three customers and do the math' SQ17. What AdWords returned went back into AdWords SQ62. Revenue passed $1 million in 2007 and reached $2.2 million in 2008 SQ14 SQ15.

Customer revenue also paid for the support a finished site promises. Customer care was the first job Casalena handed to someone else, and support later made up about a third of the company SQ13 SQ20. Squarespace ran profitably for six years before pushing for fast growth SQ13. When Getty Images approached to buy it in 2010, Casalena instead took $38.5 million from Accel and Index Ventures at a value above $100 million SQ14 SQ29.

Rivals Wix lost $22.7 million, $15.0 million and $28.7 million in 2011–13 while spending 67–88% of its revenue on sales and marketing SQX-2.

Self-Serve Only

Step 4 of 5 · 2009–15

Long subscriptions pay for measured podcast host reads

The paying base made a new channel affordable. In 2009 Casalena paid roughly $20,000 to $30,000 for a host-read ad on This Week in Tech, about a month of the AdWords budget, and said it 'immediately worked' SQ8 SQ62. A third of new subscribers told a post-purchase survey they had heard of Squarespace there SQ7. The company then hunted for emerging hosts 'before they're super popular' SQ7 and tracked each show with offer codes and custom URLs SQ5. Smaller shows let hosts read ads in their own words to listeners who trusted them SQ26.

Measurement let the budget grow with results. By 2015 Squarespace bought about 2.5 times as many podcast ads as the next advertiser and supplied about a third of Midroll's revenue SQ8; its head of media said the attribution work might be what 'kept other advertisers at bay' SQ5. The spending made sense because of step 2: website customers have 'huge lifetime values', Ben Thompson argued, because they set up a site once and keep it for years SQ9.

From 2014 it added in-house Super Bowl spots promising a site apart from 'the clutter' of the web SQ23, though the Emmy-winning 2017 spot made none of YouGov's post-game lists for buzz or purchase consideration SQ25.

Rivals Wix bought reach for mostly free signups: a $4.5 million Super Bowl spot in 2015, then influencers and sports sponsorships, with marketing at 56% of collections in 2014 SQX-5 SQX-6.

Podcast AdvertisingBrand Marketing

Step 5 of 5 · 2016–24

The same cash flow on a smaller, paying base

The choices fit together: paid-only chose the customer, and that customer's long subscription paid for measured ads, with no free users to carry. In 2020 Squarespace had $621 million of revenue and $150 million of operating cash flow; Wix had $989 million of revenue, $148 million of operating cash flow and a $216.5 million net loss SQ1 SQX-4 SQ65. Squarespace had net income every year from 2016 to 2021 SQ10; Wix's first annual GAAP profit came in 2023 SQX-1. Wix won more subscribers, 5.5 million premium subscriptions against Squarespace's 3.66 million SQ65 SQ1. Squarespace won the design-led creatives who pay, and the profits.

The cash paid for expansion: commerce inside the same editor in 2013, then Acuity Scheduling in 2019 and Tock, a restaurant reservations platform, in 2021 SQ21 SQ27 SQ1. Revenue per subscription rose from $182 in 2019 to $228 in 2023 SQ1 SQ33. Casalena said its cash flow let it buy Google Domains' roughly 10 million registrations for $180 million in 2023 SQ63 SQ36. The add-ons did not change who chose Squarespace; merchants whose store was the business chose Shopify SQ55.

None of this rested on a barrier. Squarespace kept about 85% of the prior year's subscription bookings in 2020 SQ10, but Wix's customers stayed too: it expected more than $12.9 billion from existing customers over ten years SQ65. A food blogger who moved 500 recipes to WordPress lost 55% of her traffic until she restored her URLs SQ57; Morningstar rates it as having no durable competitive advantage SQ38. After subscription growth slowed to 3% in 2022 SQ35, Permira took it private in 2024 for about $7.2 billion, with Casalena rolling over most of his stake SQ47 SQ48. The paid-only filter from step 2 set both the limit on its subscriber count and the profits the sale was priced on.

Rivals Wix stayed public and larger, with $1.76 billion of revenue in 2024 SQ50. Shopify took merchants who outgrew a site with a shop SQ55.

Trade-offs & activity fitMulti-ProductM&A Strategy

Key dates

  1. 2004-01Hosted website service launches SQ16 SQ62
  2. 2005-06Free plan gone; only paid packages listed SQ64
  3. 2006Wix founded on a freemium model SQX-2
  4. 2007$1M revenue Full year, first time past $1 million SQ14
  5. 2008$2.2M revenue Full year, +160% year over year SQ15
  6. 2009First podcast ad, on This Week in Tech SQ7 SQ8
  7. 2010-07First outside funding, $38.5M from Accel and Index SQ14
  8. 2013-02Squarespace Commerce SQ21
  9. 2014-02First Super Bowl ad SQ23
  10. 2014-10Squarespace 7 with live-preview editing SQ24
  11. 2015$100M revenue Full year; more than 1 million paid customers SQ16
  12. 2019-04Acuity Scheduling acquired SQ27
  13. 2020$621.1M revenue Full year, +28%; Wix $989M with a net loss SQ1 SQ10 SQX-4 SQ65
  14. 2021-05Direct listing on the NYSE SQ29
  15. 2022$867.0M revenue Full year, +11%; net loss after a Tock impairment SQ32
  16. 2023$1,012.3M revenue Full year, +17% SQ33
  17. 2023-06Google Domains bought for $180M SQ36
  18. 2024-10Permira takes Squarespace private SQ47 SQ48

Sources

Oldest first.

  1. SQ64 Squarespace pricing and home pages, 2004-2006 (Internet Archive snapshots). Squarespace (archived by the Wayback Machine) · 2004-12-30 Archived company page
  2. SQ15 Interview with Squarespace CEO Anthony Casalena. Oliver Lindberg / .net magazine (reposted on Medium 2016) · 2010 Founder interview
  3. SQ14 Squarespace Raises $38.5 Million From Accel, Index Ventures. TechCrunch · 2010-07-13 Reporting
  4. SQ19 Interview: Squarespace Founder/CEO Anthony Casalena On Designing a Great Web Platform. Stated Magazine · 2012 Founder interview
  5. SQX-3 HTML5 With 'Zero Knowledge Of Coding': DIY Flash Site Builder Wix Launches HTML5 Version. TechCrunch (Ingrid Lunden) · 2012-03-26 Contemporaneous trade press with founder quote
  6. SQ54 8 Reasons Why We Switched From WordPress to Squarespace. Marcus dePaula / Mixtus Media · 2013 Customer account
  7. SQ21 Squarespace Launches Powerful, Integrated Commerce Service. Squarespace / PR Newswire · 2013-02-14 Company announcement
  8. SQ23 Squarespace Debuts New Ad Campaign During Super Bowl XLVIII. Squarespace · 2014-01-27 Company announcement
  9. SQ22 Commerce For All. Squarespace newsroom · 2014-01-30 Company announcement
  10. SQX-2 Wix.com Ltd. Form F-1 registration statement. Wix.com / SEC EDGAR · 2014-03-20 Regulatory filing
  11. SQ18 Squarespace Raises $40M in Series B Funding from General Atlantic. Squarespace / PR Newswire · 2014-04-15 Company announcement
  12. SQ17 How a dorm blog snared $79 million in VC funding. CNBC · 2014-05-08 Reporting
  13. SQ24 This Is The New Squarespace. Jordan Crook / TechCrunch · 2014-10-07 Reporting
  14. SQ26 Are Podcasts the Next Big Thing for Sponsored Content?. Contently, The Content Strategist · 2015-01-05 Reporting
  15. SQ13 How Squarespace's CEO Pivoted to Scale for Millions. First Round Review · 2015-01-22 Founder interview
  16. SQX-5 Wix makes Super Bowl ad with Brett Favre, Terrell Owens and Lloyd from 'Entourage'. GeekWire (Molly Brown) · 2015-01-27 Contemporaneous trade press
  17. SQ5 How Squarespace Got Into Podcast Advertising And Why It Stuck. Liz Rowley / AdExchanger · 2015-07-02 Reporting
  18. SQ16 How Squarespace Went From a Dorm-Room Project to a $100 Million Web Publishing Platform. Catherine Clifford / Entrepreneur (republished by Fox News) · 2016-04-22 Reporting
  19. SQX-6 Why Wix opted out of Super Bowl advertising despite a bigger marketing budget. Marketing Dive (Dianna Christe) · 2018-01-22 Trade press with executive quotes
  20. SQ25 How Squarespace Created a Killer Super Bowl Spot That Scored an Emmy. Katie Richards / Adweek · 2018-01-28 Reporting
  21. SQ51 Square Acquires Website Builder Weebly. Crunchbase News · 2018-04-26 Reporting
  22. SQ62 How I Built This: Squarespace, Anthony Casalena (transcript). Guy Raz / NPR How I Built This (auto-transcript on podscripts.co) · 2019-03-04 Founder interview
  23. SQ27 Squarespace makes its first acquisition with Acuity Scheduling. Anthony Ha / TechCrunch · 2019-04-23 Reporting
  24. SQ9 Dithering and Open Versus Free. Ben Thompson / Stratechery · 2020-05-12 Outside analysis
  25. SQ55 Why I switched from Squarespace to Shopify. Lisa / HELLOhappy · 2020-08-11 Customer account
  26. SQ65 Wix Reports Fourth Quarter and Full Year 2020 Results (Form 6-K Exhibit 99.1). Wix.com / SEC EDGAR · 2021-02-17 Company disclosure (rival)
  27. SQ28 Squarespace raises $300M at a staggering $10B valuation. Mary Ann Azevedo / TechCrunch · 2021-03-16 Reporting
  28. SQ1 Squarespace, Inc. Form S-1 registration statement. Squarespace / SEC EDGAR · 2021-04-16 SEC filing
  29. SQ10 Squarespace IPO | S-1 Breakdown. Alex Clayton / Meritech Capital · 2021-05 Investor analysis
  30. SQ2 Squarespace, Inc. Form S-1/A. Squarespace / SEC EDGAR · 2021-05-13 SEC filing
  31. SQX-4 Wix vs. Squarespace: Which Will Be the Better Buy?. The Motley Fool (Ryan Henderson) · 2021-05-13 Outside analysis
  32. SQ11 SQSP S-1 Teardown. Joseph Perez / airCFO · 2021-05-18 Outside analysis
  33. SQ29 Squarespace CEO is worth $2.4 billion after web company he built in college debuts on NYSE. CNBC · 2021-05-19 Reporting
  34. SQ30 Squarespace goes public but Anthony Casalena is still focused on his customers. Sarah Wright / Product Hunt · 2021-05-19 Reporting
  35. SQ31 Squarespace founder Anthony Casalena learnt from hard work, stumbles. The Standard (Hong Kong, wire copy) · 2021-05-20 Reporting
  36. SQ3 20VC: Anthony Casalena on scaling Squarespace from dorm room to public company. Harry Stebbings / The Twenty Minute VC · 2021-11-17 Founder interview
  37. SQ7 How Did Squarespace Know Podcasts Would Get This Big?. Joel Stein / The New York Times (read via Jordan News republication) · 2022-02-13 Reporting
  38. SQ8 One Big Bet in 2009 Changed Podcast Advertising. Brennan Tapp / Podcast Movement · 2022-02-14 Reporting
  39. SQ6 Why Squarespace went all-in on podcasts. Trung T. Phan / The Hustle · 2022-02-15 Outside analysis
  40. SQ35 Squarespace, Inc. Form 10-K for fiscal 2022. Squarespace / SEC EDGAR · 2023-03 SEC filing
  41. SQ32 Squarespace fourth quarter and full year 2022 results (8-K Exhibit 99.1). Squarespace / SEC EDGAR · 2023-03-07 SEC filing
  42. SQ38 Squarespace: Google Domains Acquisition Is Value Accretive but Cross-Sell Opportunity Is Limited. Emma Williams / Morningstar · 2023-06 Investor analysis
  43. SQ36 Squarespace buys Google Domains for $180 million. Andrew Allemann / Domain Name Wire · 2023-06-15 Reporting
  44. SQ37 My thoughts on Squarespace's acquisition of Google Domains. Andrew Allemann / Domain Name Wire · 2023-06-16 Outside analysis
  45. SQ63 Why Anthony Casalena says Squarespace is ready for the next era of the web (Decoder transcript). Nilay Patel / The Verge · 2023-07-18 Founder interview
  46. SQ20 Interview with Squarespace CEO and Founder, Anthony Casalena. CMS Critic · 2023-08-23 Founder interview
  47. SQ58 Circle Live: interview with Anthony Casalena. Squarespace Circle blog · 2023-09-28 Founder interview
  48. SQ12 Squarespace (SQSP): Solid Capital Productivity. Guy Shanon / Margin of Maybe · 2023-11-26 Investor analysis
  49. SQ34 Squarespace, Inc. Form 10-K for fiscal 2023. Squarespace / SEC EDGAR · 2024-02 SEC filing
  50. SQX-1 Wix ends 2023 with first-ever GAAP net profit. Globes (Shiri Habib-Valdhorn) · 2024-02-21 Trade press
  51. SQ33 Squarespace Announces Fourth Quarter and Full Year 2023 Financial Results. Squarespace / PR Newswire · 2024-02-28 Company announcement
  52. SQ40 Squarespace to Go Private in $6.9bn All-Cash Transaction with Permira. Permira · 2024-05-13 Company announcement
  53. SQ41 Permira is taking Squarespace private in $6.6 billion deal. Paul Sawers / TechCrunch · 2024-05-13 Reporting
  54. SQ42 Squarespace may have left some meat on the bone, says Oppenheimer. The Fly / TipRanks · 2024-05-13 Investor analysis
  55. SQ43 Squarespace preliminary proxy statement (PREM14A). Squarespace / SEC EDGAR · 2024-06 SEC filing
  56. SQ39 Squarespace Agrees to Sell Tock Platform to American Express for $400 Million. Squarespace / PR Newswire · 2024-06-21 Company announcement
  57. SQ56 Why I switched from WordPress to Squarespace. Rhiannon Adler · 2024-06-24 Customer account
  58. SQ4 Glazer Capital Details its Opposition to the Proposed Acquisition of Squarespace by Permira. Glazer Capital / PR Newswire · 2024-08 Investor analysis
  59. SQ61 Squarespace, Inc. Definitive Proxy Statement (DEFM14A / Schedule 13E-3) for the Permira merger. Squarespace / SEC EDGAR · 2024-08-22 Regulatory filing
  60. SQ44 Squarespace and Permira amend merger agreement (8-K Exhibit 99.1). Squarespace / SEC EDGAR · 2024-09-09 SEC filing
  61. SQ46 Squarespace going private in $7.2 billion Permira deal. Craig Hale / TechRadar Pro · 2024-09-10 Reporting
  62. SQ45 For Fairness Sake: Squarespace acquired by Permira for $7.2 billion. Stephen Cussen / For Fairness Sake · 2024-10-01 Outside analysis
  63. SQ47 Permira Completes Acquisition of Squarespace. Squarespace · 2024-10-17 Company announcement
  64. SQ48 Permira completes Squarespace acquisition after upping bid to $7.2B. Paul Sawers / TechCrunch · 2024-10-17 Reporting
  65. SQ57 Why I Switched from Squarespace to WordPress. Vicky Pham · 2024-10-17 Customer account
  66. SQ60 How I Built This Advice Line with Anthony Casalena of Squarespace. Guy Raz / Wondery (podscripts transcript page) · 2025 Founder interview
  67. SQ59 Lessons from Anthony Casalena. Antoine Buteau · 2026-06-26 Outside analysis
  68. SQ49 Squarespace. Wikipedia · 2026-09-24 Reporting
  69. SQ50 Wix.com. Wikipedia · 2026-09-24 Reporting
  70. SQ52 WordPress. Wikipedia · 2026-09-24 Reporting
  71. SQ53 Movable Type. Wikipedia · 2026-09-24 Reporting