‘If you’re not hearing no, you’re not asking for enough’: 10 questions with The Flip Side founders

The Flip Side is a bipartisan media startup that provides fact checking and curated commentary from both liberal and conservative sources. The Pittsburgh-headquartered company’s founding was partly inspired by United States’ political division following the 2016 election.

RustBuilt Pittsburgh recently caught up with cofounders Wahed and Jihan Varisco to talk about the startup’s growth, their “lightbulb moments” and trusting in the product. Read the full Q&A below.

1. How did you come to do this work at The Flip Side and why is it so important to you personally?

Annafi: 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 skirt financial 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 sneakers, and 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. A few months later, I launched The Flip Side as a passion project.

Jihan: As a conservative growing up in New York and going to school in Chicago, I’ve long been living a liberal bubble. I was vaguely aware of the growth of identity politics and increasing partisanship, but after the 2016 election everything kicked into overdrive. Otherwise normal, rational people suddenly decided that anyone who disagreed with them (half the country!) was evil and should be shunned/punished/etc.

I remember one friend who posted on social media just after the election that she was going to wait for all the Trump voters to apologize for their obviously terrible decision, which she was convinced would happen quite soon. I assume she’s still waiting. It became clear to me that huge numbers of people (on both sides!) just had no idea what half of the country believed, let alone why. The Flip Side is an effort to bridge that gap.

2. What was your lightbulb moment for The Flip Side?

Annafi: I recall it vividly. It was one week before the 2016 election. We were in the “get-out-the-vote” phase of the campaign, where we make sure that registered Democrats and others who are voting for our party candidates have a plan to get to the polls on election day.

I pulled up to a modest one-story home, grabbed my clipboard from the dashboard, and jogged to the front door. It was the last address on my list that day so I was eager to cross it off.

An elderly woman with a walker answered after a few knocks. I was wearing my Stronger Together T-shirt, so there was no need for introductions. “Don’t waste your time. I’m voting for Gary,” she said. I glanced down at my clipboard — yep, right address, registered Democrat. I launched into my usual spiel: This is one of the most important elections of our lifetimes, the stakes could not be higher, every vote matters, etc.

“I get $400 a month from social security. That’s barely enough to get by, and I can’t afford my property taxes. My house is about to be in foreclosure. If you can tell me right now what Hillary plans to do about that, you can have my vote.”

I was dumbfounded. I started mumbling something about Hillary having a plan for the middle class. She was not impressed, and shut the door in my face. I deserved it. As obvious as it sounds, it hadn’t sunk in until that moment that I have no idea what anyone is going through and have no right to judge what choices they make —  in the voting booth or otherwise. My journey to truly explore and try to understand other people’s perspectives began that day.

Jihan: While I was in graduate school studying public policy at the University of Chicago, a few friends and I hosted an event called “Ask A Conservative.” This was basically a Q&A session where fellow students asked us why conservatives supported various policies, and we explained the rationale behind them. After we had finished, one student approached me and explained that while she didn’t agree with everything I had said, it wasn’t entirely unreasonable. She went on to explain that it had never occurred to her that there were actual reasons for people to hold conservative views. This was a graduate student at one of the top policy schools in the country. If our future leaders have such little understanding of the other side, how can we hope for compromise or even just basic cooperation among elected officials?

3. What is the elevator pitch for The Flip Side?

Annafi & Jihan: The Flip Side is on a mission to bridge the gap between liberals and conservatives.

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 five-minute curated email.

While our newsletter is already making a tangible difference in people’s lives — helping them understand and connect with family, friends, or coworkers with whom they disagree — we always knew it was just the first step. 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.

We recently launched a new platform that uses human-centered design and a custom ranking algorithm to reward thoughtfulness and bipartisanship, rather than trolling or clickbait. Pioneering a new approach to news and user-generated content, we will not be “just” another platform, but rather curators of content and conversations.

A less divided future begins with all of us getting on the same page — literally.

4. Talk through your strategy in building a team around you.

Annafi: My formula for a happy and productive team: 1.) a mission worth getting excited about, 2.) a clear understanding of how their work is directly tied to the mission, and 3.) respect and appreciation. Even if it’s obvious to you, whenever you introduce a new project, you need to explain how the project fits in with the broader roadmap. How is X project furthering the goals you set for yourselves this month, quarter, or year? How will the world be different if you achieve the goals you set out to? You then need to ask and answer the following questions for yourself: How will you thank your team when they bring your vision to life? How will you keep them motivated when the going gets tough? For each person, make sure you know what drives them specifically and what kind of management and communication style they prefer/thrive under, and do your best to meet their needs.

Jihan: In addition to everything Annafi said, it’s crucial to have a diverse team. We’ve made it a priority to recruit a politically diverse group, which sets us apart from many similar efforts that skew to one side and/or are mostly centrists. As we like to note, we’re not unbiased, but equally biased. That’s crucial for us to maintain the trust of readers who span the political spectrum from Bernie-loving socialists to MAGA diehards.

5. What has surprised you most about starting your own business?

Annafi: I hadn’t realized just how much of your identity becomes wrapped up in your company. We delve headfirst into the most controversial topics of the day: abortion, gun control, immigration. No matter how hard we try, inevitably there’ll be a handful of pissed-off people among our nearly quarter million subscribers 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.

Jihan: All the little details. Filing taxes. Running payroll. Keeping the books up to date. I’ve gained a newfound respect for HR and operations professionals.

6. Talk through one of your daily rituals.

Annafi: I have to take a walk for at least 20 minutes every day or else I get cranky. I usually do it first thing in the morning — walk to a coffee shop a half mile away and then meander back — but if that’s not possible, I’ll find time in the afternoon or evening. Days when it’s 20 or 90 degrees outside are quite unpleasant, but I’ve learned the hard way that it’s better to be freezing or sweating for a few minutes than in a bad mood all day!

Jihan: I make sure to walk my dog every day for a least a mile, along with shorter breaks in the yard. When you work from home it’s important to get outside, even for just a few minutes at a time.

7. What is a recent challenge you’ve faced as an entrepreneur and how did you overcome it? What lesson(s) did you take away from it?

Annafi: Last year 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.

Jihan: After our first year of full operations, the payroll provider we were working with told us that they were going to triple our health insurance premiums. This would have been well out of our budget; we were forced to scramble to find a new provider with more reasonable rates. This taught me not to neglect things that might seem less fun, because it’s a real problem when something goes wrong.

8. What does the next year look like for The Flip Side?

Annafi & Jihan: Our goals are to double the number of newsletter subscribers to 500,000 and have at least 10,000 premium (paying) members on our new discussion platform.

9. What is a key piece of advice you’ve received that you’d want to share with other founders?

Annafi & Jihan: If you’re not hearing no, you’re not asking for enough! Send the email. Ask for the meeting. Set the price at the “high end” and see what happens. Remember to take care of yourself and invest in things that will make your life easier, whether that’s meal delivery service, weekly therapy sessions, or a snazzy desk setup.

Jihan: Trust in your product, and make sure it’s the best it can be. It’s important to have pretty graphics and a good pitch, but at the end of the day it’s your actual product that will determine success or failure.

10. How can our regional startup community help your efforts?

Annafi & Jihan: Subscribe to our newsletter! It’s hard to convince liberals to watch Fox or conservatives to watch MSNBC. But if everyone takes five minutes a day to read The Flip Side, we’ll have a starting point when talking to our friends and neighbors.