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Two years after Apostrophe spun out from P’unk Ave, here’s how its (co)leaders are thinking about place and revenue

The company behind the open-source CMS platform recently launched Apostrophe 3.0 and opted for recurring revenue over fundraising, says co-CEO Geoff DiMasi.

The Apostrophe team in January 2020. (Courtesy photo)
Update: This story has been updated to reflect that Apostrophe has 10 team members.
Since Apostrophe spun out of its parent company P’unk Ave in 2019, the company and its small team has been through some evolution on both the development and organizational sides.

The South Philly webdev firm had worked on the product that became Apostrophe — an open-source CMS platform that allowed clients to build and maintain websites that they could change themselves — for a few years previous. It’s since added enterprise features and recently rolled out Apostrophe Assembly, a multi-site platform that allows companies and universities to “be their own Squarespace or Shopify,” co-CEO Geoff DiMasi told (More on that title in a moment.)

Assembly offers users their own dashboard with options to make a new website, design it with visual tools, and change the layout and content that you might expect in a content management system, but with a no-code option. Customers can also customize the cloud-based platform with their own systems or tools.

“We were trying lots of different things in how we might commercialize Apostrophe,” DiMasi said.

Assembly was the company’s answer to recurring revenue: Customers pay per site, per month. And this model ultimately worked best for the small team, which DiMasi said had looked into fundraising within the last year or so. The company did a convertible note when they spun out in 2019, but they hadn’t done a significant venture capital raise.

DiMasi said he leaned on fellow startup founders like Guru’s Rick Nucci and Crossbeam’s Bob Moore for advice and connections, and found some accessible options for meeting with fundraisers throughout the pandemic that usually would have taken a cross-country trip to form relationships. But each coast was giving them different advice, DiMasi said.

Geoff DiMasi. (Photo via LinkedIn)

“The West Coast folks, from the open source perspective, they really see the value in it, and were interested in that factor more so [than] the revenue,” DiMasi said. “And then we talked to East Coast investors and they were way more focused on revenue.”

After a few months of exploring those options, leadership decided to focus instead on growing its monthly recurring revenue. They put a pause on the fundraising efforts for now.

“We just thought, with the size of our team, and signing a few additional clients, we can do this ourselves for a little while,” the co-CEO added. “We felt like we got pulled in two different directions.”

Earlier this month, the team also launched Apostrophe 3.0, which is powered by RESTful APIs from the ground up, unlike the 2.0 version, which had custom APIs and a separate apostrophe-headless module. They’ve also included new editor interactions with Vue.js and the tiptap rich text editor powered by ProseMirror (The New York Times uses the same). The third version also includes improved module architecture, an async component pattern and an “unopinionated” front end.

Also since the company’s launch, DiMasi and co-CEO Alex Gilbert decided to shed their previous roles of chief of partnerships and CEO, respectfully, and instead share the top leadership role. It clarified for the team and the external world that they were partners, DiMasi said, and it’s been a smooth transition in part because of the pair’s longterm relationship and because they’ve divided up clear areas of responsibility.

While their team was distributed before the pandemic, much of the 10-member team are still in the area. DiMasi isn’t sure how this remote-forward culture will affect local companies moving forward, but for the Ignite Philly co-organizer, it still feels important to be a Philly company right now (and he’s not alone in that).

“We’ve been trying to navigate this from the beginning, but COVID has made place feel to be so disassociated,” he said. “Place has mattered so much to me. I’m still really interested in what it means to be this kind of company in Philadelphia.”

Companies: Apostrophe Technologies, Inc. / P’unk Ave

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