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.

NYC Startup Funding, Month-end Wrap-up: February 2019

February continued a solid start to the year for NYC-based startup funding. Below are five of the largest rounds of funding closed by NYC-based startups over the course of February 2019.

Aetion - $27M
Date: 2/5/19
Round: Series B
Industry: Healthcare, Enterprise Software
Lead Investor: N/A
Company: Founded in 2013, Aetion is a healthcare technology company that provides analytics and evidence for the improvement of patient care. The company's patented rapid-cycle analytics™ and the Aetion Evidence Platform™ deliver real-world evidence for life sciences companies, payers, and at-risk providers. To date, Aetion has raised over $74.6 million after three rounds of funding.

Chainalysis - $30M
Date: 2/12/19
Round: Series B
Industry: Fintech, Cryptocurrency, Financial Exchange
Lead Investor: Accel
Company: Founded in 2014, Chainalysis is a company designing and developing anti-money laundering software for Bitcoin businesses. According to Chainalysis, its products include, 'REACTOR, an interactive and investigation tool that identifies offenders, visualizes data, and shares results with people and organizations, and API, a transaction based risk scoring solution that contains source and destination of funds to measure risk.' To date, Chainalysis has raised more than $47.6 million after four rounds of funding.

VAST Data - $40M
Date: 2/26/19
Round: Series B
Industry: Data Storage, Software
Lead Investor: N/A
Company: Founded in 2016, VAST Data is an enterprise data storage infrastructure provider. According to VAST Data, their mission is to, 'bring an end to decades of complexity and application bottlenecks that have been caused by mechanical media and by the complex tiering of data across different types of storage systems.' To date, VAST Data has raised more than $80 million after three rounds of funding.  

HiberCell - $60.8M
Date: 2/7/19
Round: Series A
Industry: Biotechnology
Lead Investor: ARCH Venture Partners
Company: Founded in 2016, HiberCell is a biotechnology company specializing in the development of novel therapeutics to prevent relapse and metastasis. According to HiberCell, 'We are the first company exclusively focused on therapeutically modulating the biology and mechanisms of tumor dormancy.' To date, HiberCell has raised $60.8 million after one round of funding.

YieldStreet - $62M
Date: 2/26/19
Round: Series B
Industry: Fintech, Financial Services, Wealth Management
Lead Investor: Edison Partners
Company: Founded in 2015, YieldStreet is an investment platform allowing investors to effortlessly participate in curated investments with low market correlation and high yield, across litigation finance, real estate, and other alternative asset classes. To date, YieldStreet has raised more than $178.5 million after five rounds of funding.

DoorDash Raising $500 Million at $6 Billion Valuation

The Wall Street Journal reported recently that food delivery startup DoorDash is in the process of raising a $500 million round of funding. 

Terms of the Deal

According to the report, the round would value the company at somewhere between $6 and $7 billion. The news comes just days after one of DoorDash’s main competitors, Postmates, filed confidentially for an IPO. According to the report, the round will be led by Singaporean state investment firm Tamasek Holdings Pte. 

A Solid Track Record

This is not be the only large round of funding closed by DoorDash recently. Last year, DoorDash raised $250 million in Series E funding. At the time that round valued the company at $4 billion and was led by DST Global and Coatue Management. Previous investors in the company have included Kleiner Perkins, SoftBank, Sequoia, and others. To date, DoorDash has raised more than $1 billion after seven rounds of funding. 

Expanding to All 50 States

Earlier this year, DoorDash made news when it
officially entered all fifty states. In a statement regarding the move, company
co-founder and CEO Tony Xu remarked, “In the past year alone we’ve more than
quintupled our geographic footprint from 600 to 3,300 cities across North
America, democratizing access to door-to-door delivery for hundreds of
millions of Americans across the nation.”

A Rising Star in the Food Delivery Space

According to a report by the Wall Street Journal, DoorDash retains an 18% market-share of the food delivery services. GrubHub remains the leader with a 34% market-share. According to the report, DoorDash was also able to grow at a faster rate than any of its competitors over the first-half of last year. Other companies in direct competition in the U.S. food delivery market also include UberEats, and the aforementioned Postmates.

Just how much of the market share the new round of funding will allow DoorDash to gain remains to be seen, but at a $6 billion valuation investors certainly seem willing to let them try.

Trying Shapr Matchmaking for Businesses

I recently downloaded the App shapr (as in shape your life). Shapr is a business born and raised in the NYC startup ecosystem with offices in NYC and Paris. For those not familiar, shapr is an online match making app for people interested in business. The idea is to find a cofounder, friend, investor, employee or maybe more.

In their own words:

Networking should be a joyful experience, because It's about meeting new people. It's not just a trick to generate more sales or find some humdrum job – we see it as a lifestyle.

Think of it as Tinder meets or Linkedin. The concept behind the idea is simple and compelling. Enter your interests, put who you are looking to meet and each day you get matched with roughly 16 people who may be a potential match. According to the Wall Street Journal Shapr currently has 60,000 users in NYC and 300,000 users worldwide.

Image Credit Shapr

In order to start a conversation, both people must match, giving the app a very similar feel to Tinder. When I joined my hope was that I could meet some cool people and engage with some fellow entrepreneurs.

Overall, the experience was better than what I expected. Most people on the app seem to be pretty great. That being said every app designed to connect strangers online has a wide range of people you may meet.

The Good

Most people were friendly, open to talking and passionate about the work that they were doing.

I found that many of the entrepreneurs I met or talked with were in the early stages of starting their businesses. Of the business owners I spoke with many are looking for funding for a seed round and/or looking to bring on early hires. It is always great to get to meet other people chasing their passion and building their businesses.

Outside of entrepreneurs, I had some great interactions with sales representatives from businesses looking to grow and younger people looking for guidance in career or business.

I was pleasantly surprised to find most people were not pushy in their sales roles.

The Bad

Overall, 90% of my experience was positive. However, I did find a few people who I think were trying to run some scams for funding. Although I didn’t dive too deep into the conversations, some “fundraising” plans seemed a bit off. Anything that starts out with the opportunity of investing in a Nigerian business generally throws a red flag up in my book.

I also found a few people who were pushing peer-to-peer marketing programs.

Two people sent almost the exact same text  "My mentor (person name) is developing a business and expanding.... We work with Apple, Coach.... (5 more big name businesses)" Then finishes with "are you business minded/entrepreneurial" with the promise of building passive income in my spare time.

I am personally not a fan of MLM programs but to each their own (I guess).

Shapr Conclusion

I would recommend giving the app a try if you are in the startup world or interested in jumping into the startup community in NYC. I found most people on the App were in the early stages of their business and interested in connecting either by phone or in person. There is a good mix of people from business owners, to people looking for mentorship that you could connect with.

Like any place on the internet where you are meeting strangers use good judgment and if something feels a bit too good to be true it probably is. Then again, I may have missed out on a major investment opportunity from a Nigerian Prince.

Company Background

Shapr is a NYC based business cofounded by Ludovic Huraux CEO & Jonathan Rogez Head of Product. Shapr has raised a total of $7 million in funding in two rounds; $3m in January 2015 and an additional $4 million in October 2016.


Josh Bobrowsky- CoFounder & CEO


7 New York City Startups to Watch Over the Next 12 Months

New York City is one of the best cities in the world for startups. Last year, 421 NYC based startups collectively raised over $9.5 billion.  Many brand-name and billion dollar startups have come from New York.

Some of the most notable are FanDuel, Warby Parker, Blue ApronZocdoc, WeWork, Vice, and Buzzfeed. While their are many large companies that started in NYC, the city is a thriving market for small and midsize startups.


Founded in 2013, Casper is an e-commerce company that ships extremely comfortable mattresses, pillows, sheets and other bedding accessories directly to their customers’ doors.

Why they’re hot: Casper revolutionized the mattress industry by selling directly to consumers via online marketing. Taking the brick and mortar cost out of a NYC startup allows for huge profit per mattress. Prices are high, quality is good, and I happen to sleep on their product every night. Buy it at noon and it will ship today if you live in the city.


Andela—which has raised $41 million to date, the company recruits and trains the most skilled software engineers on the African continent and places them in jobs at big-name tech companies based in the United States (e.g., Microsoft and IBM).

Why they’re hot: The company is also backed by the Chan Zuckerberg Initiative and Google. Having a great cause with an ability to really help companies with coding.



Slice is a company that helps mom-and-pop pizzerias transition to the digital era. Pizza to the People is their motto. The company earns $1.95 on each order placed through its platform recently closed a $15 million Series B round.

Why they’re hot: Over the last few years, Domino’s Pizza has fortified its digital sales channels leaving many mom-and-pop pizzerias in the dust. But Domino’s isn’t the only pizza place in the country. Last year, the pizza industry was quite lucrative, bringing in $45 billion. Slice correctly identified a market need and the company now boasts 6,000 partners across the country.

4. builds technology designed to make video production collaboration a easier. Working remotely on a film editing project can provide a lot of technical difficulties, hopes to help solve this pain point.

Why they’re hot: Last year, closed a $10 million Series A round.  Additionally the product supports over 150 file formats while enabling users to post threaded, time-stamped comments on film—making the video collaboration process that much easier. Since video content is in high demand,

5. Cheddar

Cheddar is a streaming news service that focuses on financial and tech industries. The company targets millennials who are increasingly cutting the cord and abandoning cable due to ever-increasing prices.

Why they’re hot: Cheddar recently secured an additional $19 million in financing. According to company figures, 8% of millennials have already seen Cheddar content in only one year of business.

6. Lemonade

In 2015, Lemonade began its quest to disrupt the insurance industry by offering a more affordable solution for homeowners and renters alike.

Why they’re hot: The insurance industry is an antiquated industry that is ripe for change. Using artificial intelligence, Lemonade crafts customized insurance policies for each user. Starting at $5/month for renters and $25/month for homeowners, new algorithms may allow for more savings and profitability.

Nothing to do with Becky with the Good Hair.

CB Insights

Founded in 2008, CB Insights is a tech market intelligence platform that analyzes venture capital, startups, patents, partnerships and news to help clients make better decisions. The company closed its first round of financing in 2015 when it took in $10 million in a Series A.

Why they’re hot: CB insights uses a hot technology in a hot PE market.


Ignitia Office

A shameless self plug. Founded in 2016 we are bringing amazing designs, exceptional community and great value to the coworking industry. The idea is to craft the best offices, to help build amazing companies and help others follow their dreams.

Why we are hot: Great design, atmosphere & Community. Opening September!


Which startups would you include in a list like this? Let us know in the comments below!



Josh Bobrowsky- CoFounder & CEO