Annafi Wahed The Flip Side
Annafi Wahed founder of The Flip Side. (Credit: Courtesy of The Flip Side)

After graduating from college, Annafi Wahed spent 4 years working in finance. Though her job came with steady pay and security, she sought greater purpose. During the 2016 Presidential Election, Wahed took on work as an organizer, and saw firsthand how polarized those on the “right” and “left” had become. Inspired to help make a difference, Wahed launched a daily political newsletter, The Flip Side, in 2017. Each day, she and her Pittsburgh-based editorial team comb through dozens of news sources – liberal, conservative and centrist – to create thoughtful, well-articulated summaries of an individual issue as viewed from numerous points of view. The success of The Flip Side is in the numbers: Today, Wahed reports nearly a quarter million subscribers. And she expects to see that figure grow. 

Here’s our lightly edited Q&A, from The Story Exchange 1,000+ Stories Project.

How is your business different from others in your industry? 

Our newsletter focuses on one topic per edition, to encourage in-depth discussions, and begins with a summary of liberal and conservative viewpoints. Each issue is prepared by our cross-partisan team. For each topic, we also have conversation prompts that encourage community members to speak from their personal experiences, rather than solely relying upon others’ talking points.

Furthermore, our algorithm prioritizes cross-partisan engagement instead of overall engagement. For example, a post with three “helpful” votes from left-leaning members and five “helpful” votes from right-leaning members will be ranked higher on our end than a post with 10 votes all from left-leaning members. 

Tell us about your biggest success so far. 

I’m most proud of the fact that our audience spans all 50 states – as well as the whole political spectrum. We have everyone from Democratic Socialists, to center-left liberals, to Never Trumpers, to hardcore Trump fans. Plus, we have a growing number of folks who have otherwise disengaged from politics altogether who tell us that we’re the only media outlet they trust – and even look forward to reading!

What is your top challenge and how have you addressed it?

We still only have three full-time employees, including myself. We were told it would be impossible to build a large audience with such a small staff, but we went for it anyway. Over the years, we’ve had dozens of unpaid interns and contributors who have done a great deal of work to make sure our newsletter gets out at 6 a.m. on the dot. To recruit them, I have visited nearly every college in my immediate vicinity, and even engaged some while riding the subway! You must constantly put yourself out there, even when it’s exhausting, so that the right people find you.

What is your biggest tip for other startup entrepreneurs? 

George Bernard Shaw wrote, “The reasonable man adapts himself to the world – the unreasonable one persists in trying to adapt the world to himself. Therefore, all progress depends on the unreasonable man.” Every founder I know is persistent, or stubborn, depending on your view – and certainly beyond what one would call “reasonable.” If you’re not willing to go the distance for what you believe in, you’re probably not going to like being a founder.

How do you find inspiration on your darkest days?

Remember to take care of yourself and invest in things that will make your life easier, whether that’s a meal delivery service, weekly therapy sessions, or a snazzy desk setup.

What is your go to song to get motivated on tough days? 

 “Fight Song” by Rachel Platten.

Who is your most important role model?

It’s hard to pick just one. Right now, it’s Oprah. Her story is incredible, and 25 years on, she’s still able to connect with her guests in a way that’s awe-inspiring. ◼

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Twitter: @theflipside

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