Business development / Entrepreneurs / Media / Social media

Why The Flip Side founder traded skyscrapers for the City of Bridges

Annafi Wahed needed a change. Pittsburgh felt like the perfect place to start anew, professionally and personally, as she looks to grow her bipartisan media startup.

The Flip Side founder Annafi Wahed. (Courtesy photo)

This editorial article is a part of How I Got Here Month of's editorial calendar.

Correction: Annafi Wahed launched The Flip Side's new platform, not the company has a whole, a month ago. (11/22/22, 4:55 p.m.)
After 20 years in New York City, Annafi Wahed decided she needed to make a change.

She loved the proximity to her family and friends, but after so many years, the Big Apple was starting to feel small. She was tired of hours-long waits for brunch, walking through the same neighborhoods and sky-high rents, so once she realized her lease was almost up, she decided that Pittsburgh was the place to rediscover herself.

“It just hit all the right boxes,” Wahed told “It’s affordable, it’s walkable [and] there’s plenty of culture and arts. It’s still close enough to New York that I can go home on a day’s notice to see my family, and I must say Pittsburgh has been exceeding my expectations in every way.”

A big part of the draw was simply liking the city, as she learned from the times she’d come to visit a friend before she officially moved this June. Plus, as a Bryn Mawr College graduate, this isn’t the first time Wahed’s lived in Pennsylvania.

Pittsburgh will also serve as her startup’s new HQ. After years working in finance, Wahed is the founder and CEO of The Flip Side, a bipartisan media startup that provides fact checking and curated commentary from both liberal and conservative sources.

Why politics?

The startup, which officially launched its new platform a month ago, publishes a newsletter five days a week, where the content revolves around one topic per day — say, climate change or the recent midterm elections. Wahed’s goal for this year is to develop a platform where subscribers can interact with each other.

“The way we like to phrase it, especially in light of the recent news, is that we’re building the salon to Twitter’s town square,” Wahed said, referring to Twitter’s current turmoil in the aftermath of being purchased by Elon Musk. “Whereas Twitter, Facebook groups or Reddit are kind of these chaotic places where there are actually a lot of really interesting discussions happening, those discussions get hidden in random discussion threads, or are just drowned out by the trolls and the clickbait. We’re building something different.”

One might assume that founding a bipartisan media company wouldn’t be a natural career choice for someone who’d occupied positions such as financial institution specialist — and perhaps it wouldn’t have been if not for the presidential election of 2016. That year, Wahed went to New Hampshire at the height of election season to work as a field organizer for the New Hampshire Democratic Party. The Flip Side emerged as an unexpected passion project and a way to make sense of things after Hillary Clinton’s loss.

“It was just perhaps a way for me to cope after the loss of the presidential cycle,” Wahed said. “Somehow [when] it sort of started to take a life on its own, we realized that we were already having so much impact, even though we weren’t doing anything to grow our readership. It just seemed like there was such a need, and we found ourselves in a position to be able to meet that need.”

Wahed added that a part of the draw to PA is its status as a swing state. Leaving New York City, a mostly progressive city, gives her more exposure to local news orgs and how they may report on conservative candidates differently.

Growing a startup

Now, The Flip Side isn’t just a project: It’s Wahed’s full-time job, with nearly a quarter of a million subscribers, she said. From the founder’s perspective, with so many social media networks in a state of turmoil, now is the right time for a platform focused just on news.

“With the era of Facebook and Twitter ending, we think it’s time for vertical social networks,” Wahed said. “This will not be a place where you learn celebrity gossip, or the sports scores or the weather. This will be a place you go to have a reason to have discussions, unlike Facebook and Twitter, where you don’t know what’s going to come at you when you open the app.”

What’s next for the company? For starters, the company’s looking for funding. With only three full-time employees consisting of Wahed, an editor in chief and a chief technology officer — all of whom work remotely in different cities — The Flip Side is a relatively small operation. Still, Wahed hopes to grow its current readership to 1 million.

As she looks forward, here’s what Wahed would like people to know about her and The Flip Side: She’s always open to feedback about the newsletter. She’s looking for new shows to watch (email her with recommendations). And although starting a business can be rewarding, it can also be hard, so fellow founders, don’t take the small victories for granted.

“It’s a lot harder than even anyone tells you,” Wahed said. “There’s just so many things that need to happen and everything takes longer than you think it will. So don’t measure your progress just by the sort of big goals that you’ve set, right? Also measure the little things — like in my case, a CNN reporter getting back to me.”

Between friendlier people and the lower price tags after five months in the city, Wahed feels like she made the right decision in choosing Pittsburgh as the setting for her next chapter. While she hasn’t had a chance to check out some of the founder-oriented programs in the city’s tech industry yet, she told she’s looking forward to working with the universities because The Flip Side could always use a few interns. Email if you’re looking.

Atiya Irvin-Mitchell is a 2022-2024 corps member for Report for America, an initiative of The Groundtruth Project that pairs young journalists with local newsrooms. This position is supported by the Heinz Endowments.
Series: How I Got Here Month 2022 / How I Got Here

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