After raising more than $250,000 from readers-turned-investors and pledging to launch in 25 cities by 2019, local news parent-startup WhereBy.Us is now doubling its scale. Starting today, Ben DeJarnette (in Portland, the West Coast one) and Katie Johnston (in Orlando) are each spearheading new WhereBy.Us newsletters. CEO Chris Sopher said the company is on track to open six more this year.

“We saw a ton of momentum in dozens of cities around the country in terms of the things we’re interested in: which cities are growing, where there are educated young people shaping and living in the urban core,” Sopher said. “Portland and Orlando stood out to us because they’re near our existing markets” — Miami and Seattle — “and the same kind of energy was in those two cities. They were always at the top of our list. The other big thing we look at is where can we find the right awesome people who are going to build out these projects with us.”

DeJarnette’s Bridgeliner and Johnston’s Pulptown join the original WhereBy.Us brand The New Tropic in Miami and The Evergrey in Seattle. WhereBy.Us’s model focuses on helping the “curious locals” of each city “live like you live here,” a.k.a. engaging with the quirks and questions of the area’s personality and civic life. As DeJarnette explains in one of the alpha-test newsletters: “That means every day this newsletter will catch you up on all things Portland, and it means all our work — whether it’s an Instagram series on badass Portlanders or a deep-dive look at our local transportation systems — will help you connect more deeply with your city and your community.”

“The Oregonian has been shedding reporters left and right just as the city’s growth has been taking off. It’s created the need and the space for something new — and not just something that will fill the gaps, but something that will rethink how journalists engage the public and how they can actively build community through their work,” DeJarnette told me. “I think WhereBy.Us has also tapped into the reality that readers are looking for more than news from local publications. They want help discovering the city, connecting with new people, finding events, and becoming more plugged in.”

WhereBy.Us centralizes backshop operations in Miami, building tools for developing the newsletter, targeting advertisements, and designing campaigns for the local markets through its creative agency. Thirty percent of their revenue now comes directly from the advertising created for the newsletters via WhereBy.Us’s custom self-service platform, Sopher told me, up from 20 percent over the summer. (Half of their revenue still comes from the creative agency.)

“Serving new cities has double effects for us. Part of it is that we’re able to grow our overall base of users to be able to do more work with and get better data and understand how we can serve people better. Moving into more geographies and cities is important way to test that rather than just have a larger audience in one city, because it gives us better data,” he said. “The other piece is that we’ve built a bunch of tools that have helped us get more efficient and effective at the work, that have helped us get to a place where we say, ‘Okay, we’re ready to move on to a new market now with the things we’ve built so far.’ Those things have helped us get to a place where it’s financially feasible to launch in a new market and make sure we get the right return while making something meaningful in those new markets and really being responsible to the opportunity and the users in the city.”

As cofounder and chief operating officer Rebekah Monson put it in July: “We’ve built a lot of tools for us to help do better journalism, but the next phase is understanding our users better and better community participation.” They track their impact with “buckets” such as informed awareness, informed conversations, informed action, and external recognition.

The $1.25 million raised in their latest investment round has been fueling the company’s current growth. Though McClatchy (owner of The Miami Herald, with some ownership in The Seattle Times as well) was a lead investor, $500,000 of that fundraising came from the SeedInvest platform with half of that coming from individual WhereBy.Us followers and supporters, Sopher said. Although it was WhereBy.Us’ second fundraising round, it was their first time inviting community members to chip in their own money, starting at $500.

“You have to be really careful about what you ask people for and how you frame it based on what the offering is. For us, in the case of SeedInvest, we’re asking people to become investors in our parent company,” he explained. “That’s different than asking people to become a member or back us on Kickstarter…It’s worth thinking about what is the ask that you want to make to the community — to back the project or support the brand, or is there some larger endeavor you want people to be a part of.”

Part of that endeavor is building a community in the local market, particularly through storytelling projects and in-person events (which will come in due time to Portland and Orlando), but also, for example, through a Facebook group intentionally celebrating the dismal winter season. This year, The Evergrey created Embracing the Grey, a Facebook group with daily challenges and tips for “how do we help people survive in the winter,” Sopher explained, with posts that highlight and encourage ways to mitigate the effects that the dreary winter days can have on a community. The group grew to over 500 members and just celebrated the end of the season with Greybreak, a holiday party the team dreamt up and put on last week.

Similar ideas, especially when you have cities geographically clustered with similar weather, can also open up the WhereBy.Us network to collaboration or at least co-experimentation. (Though I’m guessing a Facebook group for winter in Miami or Orlando would have a different name.) “We are hopeful that that will be a collaboration in the future,” Sopher said. “There’s a number of places where we saw, in the research, issues that overlapped or where there’s an opportunity to do things together.”

Launching the two publications simultaneously has also allowed for DeJarnette and Johnston to feed off each other’s energy and lessons learned in researching and rehearsing before today’s launch. They joined WhereBy.Us in January and have been deep in market research and experimentation for the past six weeks, with the trial runs of Bridgeliner and Pulptown taking place just last week. They’ll be in beta for a few weeks.

“We met with over 75 people from different backgrounds in the community and we just sat there and listened,” Johnston said in describing the preparation for launch. “We listened to their hopes, their fears, their interests. Their loves and hates about Orlando. Now we’re taking those concerns and observations and creating conversations.

“As a personal goal, I want people to enjoy the newsletter like they would a nice conversation over coffee or a cocktail or while sitting in a wooden swing on a porch. I want them to feel represented and when they don’t, I want them to feel comfortable enough to tell us why,” she added. “And I want it to be their go-to place for staying on the up-and-up of all things Orlando.”