The Flip Side Profile

The Flip Side logo.

The Flip Side is a media startup that aims to combat divisiveness in politics through a balanced newsletter and forums for premium members. 

Founder(s): Annafi Wahed

Industry: Media

Founded in: 2017

Interview with Annafi Wahed

Describe your product or service & the problem it’s solving:

“The Flip Side is a free daily newsletter with nearly a quarter million subscribers. Every day, our editorial team combs through dozens of sources – left, right, and center. We focus on one topic and select the most thoughtful and well-articulated pieces to highlight each morning in a 5-minute curated email.

We’ve recently launched a new stage of our venture with an innovative social platform for exchanging ideas with an algorithm that rewards thoughtfulness and bipartisanship for premium (paying) subscribers. Big tech’s algorithms are great when it comes to deciding which TV show to watch next or what recipe to make next weekend for dinner with friends. But when it comes to understanding the war in Ukraine, the Fed’s dual mandate, or new immigration policies… We think you deserve better. We’re building the salon to Twitter’s town square.”

Describe your company values and mission:

“The Flip Side is on a mission to bridge the gap between liberals and conservatives. We hear from readers weekly that our humble newsletter is making a tangible difference in their lives – helping them understand and connect with family, friends, or coworkers with whom they disagree. And we’ve spent the past year researching and speaking with engineers, designers, academics, and community moderators about how best to design an online community where meaningful discussions can take place. Pioneering a new approach to news and user-generated content, we will not be ‘just’ another platform but rather curators of content and conversations.

We’re the nation that defeated the Nazis. We went to the moon in under a decade. We developed a vaccine for a novel virus in less than a year. SURELY we can find a way out of the troll farms. We’re leading the way.”

How did you come up with and validate your startup idea? Tell us the story!

“I spent four years in finance after college. During the summer of 2016, I realized I wanted something different. I wanted to make a positive impact on the world, not help big banks avoid regulations. I wasn’t sure what exactly I wanted to do long term, but the presidential election piqued my interest. I wanted to play my small part in helping elect the first female president, so I traded in my pencil skirt and heels for jeans and converse. I spent the last four months of the 2016 election cycle as a field organizer for the New Hampshire Democratic Party. Walking door to door, I saw firsthand how next-door neighbors could be completely isolated from one another by the media they consume. I launched The Flip Side as a passion project a few months later.”

How big is your team?

“Three full-time employees and five additional contributors.”

Who is your target market? How did you determine this?

“We are a news source for liberals, moderates, independents, conservatives, and even the apolitical. As pollyannaish as it sounds, we really are looking to reach anyone and everyone interested in US politics! And a survey of our current readers suggests we’re well on our way.”

What was the biggest obstacle you encountered while launching your company? How did you overcome 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 yeoman’s work to make sure our newsletter gets out at 6:00 a.m. on the dot. I have visited nearly every college in my immediate vicinity; I even once met a college student and tried to recruit them while on the subway! You must constantly put yourself out there, even when it’s exhausting, so the right people can find you.”

What’s your primary marketing strategy?

“Our first 25,000 readers came via word of mouth and earned media. Since then, it’s been a mix of targeted paid ads, cross-promotions, and our referral program to reach the 250,000 subscribers we have now.”

How did you acquire your first 100 customers?

“Our first 100 premium (paying) subscribers came from our existing audience.”

What are the key customer metrics / unit economics / KPIs you pay attention to to monitor the health of your business?

“We look at subscriber growth (free and premium), open rates, churn rates, and now the level and quality of engagement on our new platform.”

What is something that surprised you about entrepreneurship?

“I think it’s hard for people to appreciate just how much of your identity becomes wrapped up in your company. We’re a bipartisan media startup that fact-checks and curates commentary from liberal and conservative media in a five-minute digest each morning. No matter how hard we try, inevitably, there’ll be a handful of pissed-off people among our nearly a quarter million readers every day. It’s hard to absorb all that negativity and not take it personally. It’s hard not to see your startup’s successes and failures as an indictment of yourself. Someone who’s never started a business or worked at an early-stage startup likely can’t fathom just how much each setback impacts you.”

When did you know it was time to quit your day job to focus on your startup?

“There wasn’t a single ‘aha’ moment. At some point, it just became untenable to try to accomplish everything we wanted to do without devoting our full attention to it. And it didn’t feel fair to our readers, who believed in us and trusted us to take this work seriously to keep moonlighting. I kept thinking to myself, ‘If not now, when?’, ‘If not this, what?’ and one day took the plunge!”

What was your first job and what did it teach you?

“Believe it or not, I started my career as a bank regulator at the FDIC. I don’t remember much about bank regulations a decade later, but I do remember my managers and mentors during that time who taught me so much about leadership and team building. One of the most valuable lessons I learned was that even the most tedious tasks can be meaningful if you feel like you’re a valued member of the team and working toward a greater goal.”

What is your #1 piece of advice for startup founders?

“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/stubborn (depending on your view) beyond what is “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.”

What is your advice for entrepreneurs seeking funding for the first time?

“I trusted an angel investor at his word that he was committed and would invest $500,000 when we found a CTO. (Spoiler: he reneged on his commitment.) I should’ve insisted on a term sheet! ALWAYS insist on a term sheet and do your utmost best to get the funds wired ASAP.”

What is the biggest lesson you learned and what can aspiring entrepreneurs take from it?

“Many people will want to share in your success, but few will help you get there. Steer away from talkers and toward doers. The guy who’s talked your ear off in three separate meetings but hasn’t made a single intro? Drop him. The woman who’s made two intros already AND just offered to look over your mockups? She’s a keeper. Actions speak louder than words. Surround yourself with doers!”

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