# Anthony Casalena

> Anthony Casalena is a Series A investor at Squarespace backing Software. See 15 investments, check sizes, portfolio and contact details. Updated Aug 2026.

- Type: Angel Investor
- Fund: Squarespace
- Location: New York, United States
- Total investments: 15
- Last investment: Jan 2026
- Lead investor: 0%
- Last updated: Aug 2026
- LinkedIn: http://www.linkedin.com/in/acasalena
- X (Twitter): http://twitter.com/acasalena
- Website: https://x.com/acasalena

Anthony Casalena is a Series A investor at Squarespace in New York focused on Software and E-Commerce. Anthony Casalena is based out of New York, New York and is the Founder and CEO of Squarespace. Anthony Casalena attended the University of Maryland.

## Contacts

5 contacts available for Anthony Casalena: work email, personal email, work phone, personal phone and socials. Sign up free to unlock them: https://app.shizune.co/sign-up/investor-profiles/find-email/anthony-casalena?utm_source=investor_profile

## Round sizes

| Stage | Round size |
| --- | --- |
| Seed | $4M–$8M |
| Series A | $5M–$50M |
| Series B | $35M–$100M |

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Software | 5 | 33% |
| E-Commerce | 3 | 20% |
| Artificial Intelligence | 3 | 20% |
| SaaS | 2 | 13% |
| Cyber Security | 2 | 13% |

43 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Series A | 6 | 40% |
| Seed | 3 | 20% |
| Series B | 2 | 13% |
| Series C | 2 | 13% |
| Angel | 1 | 7% |

### Country

| Country | Investments | Share |
| --- | --- | --- |
| United States | 6 | 40% |
| Canada | 3 | 20% |
| Spain | 1 | 7% |
| Denmark | 1 | 7% |
| United Kingdom | 1 | 7% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| Cosmos | Cosmos is a Pinterest alternative for creatives. Save anything on the web, curate into clusters, and share with the world. | $15M | Series A | Jan 20, 2026 |  |
| Tailscale | Tailscale develops a software-defined networking platform that simplifies the creation of secure private networks using the WireGuard protocol. Its solution enables devices to connect directly through peer-to-peer mesh networking, reducing latency and eliminating the need for traditional VPN configurations. The platform integrates with existingidentity providers, allowing for streamlined user authentication and access control. Tailscale supports various operating systems, including Windows, macOS, Linux, Android, and iOS, and offers compatibility with cloud services and Kubernetes environments. The company emphasizes ease of use and scalability, catering to teams and organizations seeking straightforward network security solutions. Tailscale builds on top of WireGuard’s Noise protocol encryption, a peer-reviewed and trusted standard. Their vision is to remove overhead and complexity from this long tail of software and operational problems that people face every day. | $161.4M | Series C | Apr 08, 2025 |  |
| Async | Podcastle is an AI-powered content creation platform that helps podcasters, educators, marketers, and other creators to produce professional-quality audio and video content like podcasts and audiobooks. The company’s goal is to democratize access to content creation by offering an end-to-end suite of tools encompassing creation, editing,transcription, voice duplication, and distribution. | $13.5M | Series A | Feb 01, 2024 |  |
| Venue | Venue turns internal meetings like all hands, town halls, and AMAs into events that engage and inspire. It makes it simple for teams to replicate the production and entertainment value of talk shows, ensuring that employees pay attention, get excited, and achieve more. | $4M | Seed | Aug 17, 2022 |  |
| Medusa | For developers who must customize e-commerce setups, Medusa is a new digital commerce engine that provides extensibility and customizability with low developer effort. Unlike Shopify, BigCommerce and others, we offer an open, modular architecture that removes the need for hacky workarounds and secures maintainability and speed. | $8M | Seed | Jul 15, 2022 |  |
| Lottielab | Easiest animation editor for design and tech teams. | $4M | Seed | Apr 27, 2022 |  |
| Printify | Printify is the world's most famous print-on-demand platform designed to help anyone with an internet connection unlock the freedom that comes with opening your own online business. And because it’s completely risk free, more than 10 million people have signed up to open their stores! We created Printify so that anyone can create greatproducts, drive sales, and unlock their freedom. Printify has been on a steep growth curve since 2015, and now with more than 700 employees, three offices, and an amazing diverse team spread around Europe, we’re continuing to go from strength to strength. The Financial Times has ranked us as a Best Startup Employer for the last 4 years in a row, and we’re headquartered in Riga with investment backing from Richard Branson, Index Ventures, and some of the best angel investors from Silicon Valley and beyond. | $45M | Series A | Dec 01, 2021 |  |
| Printify | Printify is the world's most famous print-on-demand platform designed to help anyone with an internet connection unlock the freedom that comes with opening your own online business. And because it’s completely risk free, more than 10 million people have signed up to open their stores! We created Printify so that anyone can create greatproducts, drive sales, and unlock their freedom. Printify has been on a steep growth curve since 2015, and now with more than 700 employees, three offices, and an amazing diverse team spread around Europe, we’re continuing to go from strength to strength. The Financial Times has ranked us as a Best Startup Employer for the last 4 years in a row, and we’re headquartered in Riga with investment backing from Richard Branson, Index Ventures, and some of the best angel investors from Silicon Valley and beyond. | $5M | Series A | Dec 01, 2021 |  |
| 1Password | 1Password is a secure, convenient password manager, providing businesses and families a safe way to share passwords, credit cards, and documents. It keeps important information secure with AES 256-bit encryption. With 1Password, users can keep all kinds of information easily organized with convenient categories and tags and find what they need witha customizable search.Founded in 2005, 1Password remembers and fills web forms with passwords, credit card information, and addresses—with a single click. It is focused on making security convenient and keeping customers happy. It is headquartered in Toronto, Ontario in Canada. | $100.1M | Series B | Jul 27, 2021 |  |
| Typeform | Typeform is a no-code SaaS platform with thoughtfully-designed tools that help companies grow their business by engaging with their audience. Offering people-friendly forms, quizzes, surveys, and asynchronous video solutions, Typeform turns digital interactions into human connection. Launched in 2012, Typeform drives more than 500 million digitalinteractions per year and integrates with hundreds of other business-critical tools like HubSpot, Calendly, and Slack, to name a few. Typeform is headquartered in Barcelona, Spain with an office in San Francisco, California, and has a globally-distributed workforce of over 450 people. | $35M | Series B | Sep 11, 2017 |  |

10 of 15 investments shown.

## Co-investors
- [Accel](https://shizune.co/investors/profile/accel) — VC Fund, 4 deals together
- [Point Nine](https://shizune.co/investors/profile/point-nine-capital) — VC Fund, 3 deals together
- [Andreessen Horowitz](https://shizune.co/investors/profile/andreessen-horowitz) — VC Fund, 2 deals together
- [Connect Ventures](https://shizune.co/investors/profile/connect-ventures) — VC Fund, 2 deals together
- [Cooley](https://shizune.co/investors/profile/cooley-llp) — VC Fund, 2 deals together
- [Google Ventures](https://shizune.co/investors/profile/google-ventures) — VC Fund, 2 deals together

## About Squarespace

VC Fund · New York, United States

Squarespace is a website building and e-commerce platform that enables users to build brands and transact with their customers. The company's suite of products helps entrepreneurs, creatives, and professionals manage their projects and businesses through websites, domains, e-commerce, marketing tools, scheduling, and Unfold, tools for managinga social media presence. The firm provides a variety of add-on and independent solutions, including scheduling capabilities, email marketing, member sections for paid content, and design tools for social networking and video content.

5 contacts available at Squarespace.

| Name | Title | Profile |
| --- | --- | --- |
| Abby Larner | Product Team Lead - Growth | — |
| Anthony Casalena | Founder and CEO | https://shizune.co/investors/profile/anthony-casalena |
| Brandon Ferioli | Engineering Team Manager | — |
| David Lee | Chief Brand & Creative Officer | — |
| John Colton | VP, Engineering | — |

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## FAQ

### What does Anthony Casalena invest in?

Anthony Casalena invests primarily in Software, E-Commerce and Artificial Intelligence startups, most often at Series A and Seed stage. Most of the 15 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### What is Anthony Casalena's check size?

Anthony Casalena typically joins rounds of $4M–$8M at Seed, $5M–$50M at Series A and $35M–$100M at Series B. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds Anthony Casalena participates in.

### How do I contact Anthony Casalena?

Public channels for Anthony Casalena include LinkedIn, X (Twitter) and the website linked on this profile. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.

### When did Anthony Casalena last invest?

The most recent investment recorded for Anthony Casalena closed in Jan 2026. Shizune tracks 15 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.

### Is Shizune's investor data accurate?

Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.

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