Combatting Political Divisiveness with Annafi Wahed of The Flip Side

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Summary of Episode

#55: Annafi Wahed joins Ethan to discuss her political newsletter and social media platform, The Flip Side, which uses “equal bias” in order to explore both liberal and conservative perspectives. The pair chat about the polarization of American politics today, cultivating an audience by utilizing incentives as well as self-created luck, and the dire need for balanced discussion in America’s divided political landscape today. 

About the Guest: 

Annafi Wahed is a founder and CEO of The Flip Side, a balanced political newsletter which provides the opinions from both the left and the right. Annafi has a background in finance, even holding the title of Chartered Financial Analyst (CFA). 

Podcast Episode Notes

Introducing Annafi Wahed and her company, The Flip Side [1:16]

Annafi reminisces on her path to creating The Flip Side [3:48]

Annafi explores how she built her readership – mostly by letting luck find her [6:45]

Incentives are a great way to build a customer base. Annafi shares how she finds incentives that the best fit for her diverse audience [11:42]

Annafi currently works full time on The Flip Side, she reveals what made her decide to move forward with the newsletter full time [18:41]

Who is subscribed to The Flip Side, and how did users interact with one another before the forum was created? [20:44]

Annafi explores the users of The Flip Side’s social media platform as well as the current user base. [25:24]

Equal Bias is integral to The Flip Side’s platform. Annafi details the significance of having individually biased editors while creating equal partisanship. [30:02]

Annafi touches on funding as well as her business model to generate revenue. [36:42]

The Flip Side’s plan for the future [41:33]

The #1 advice for startup founders [46:01]

How to find and support The Flip Side [47:23]

Annafi’s final thoughts [48:15]

Ethan: Hey, everybody, and welcome to the start up savant podcast. I’m your host, Ethan. This show is about the stories, challenges and triumphs of fast scaling startups and the founders who run them. 

Our guest on the show today is Annafi Wahed. She’s one of the co-founders of The Flip Side, an online newsletter and community, working to bring smart, concise summaries of political analysis from both conservative and liberal media. 

And she’s set her sights pretty darn high. Stated directly from their website, The Flip Side is on a mission to help bridge the gap between liberals and conservatives. And I mean, that’s like cats and dogs, fire and water, ice cream and mustard.And we’re gonna get into that and a whole lot more. But before we do, remember to hit the subscribe button on your podcast player so that we can get this podcast in front of more cool folks, just like you. So let’s get it started and welcome Annafi to the show. Annafi, how is it going today?

Annafi Wahed: Happy to be here. It’s a, you know, beautiful day here in Pittsburgh, and I hear you’re having a beautiful day in Michigan, So Yeah, really excited to talk to you and then enjoy the rest of my day.

Ethan: Absolutely, the sun’s out, and now I feel like we’ve got you here on the video chat. The sun is double out, so I am super excited about this show. So let’s start right at the beginning. Can you tell us what Flip Side is?

Annafi Wahed: Yes, The Flip Side right now is a newsletter that goes out five days a week. We focus on one topic a day, and we fact check and curate the best arguments from both liberal and conservative media. We’re reaching a quarter million people via the newsletter and we just launched a new platform. Still very much in you now, MVP stage. But the idea of the new platform is that it’s a salon to Twitter’s town square. So instead of the cacophony of, you know, click bait headlines and trolling, you see, we are actually designing the algorithm, user incentives, the business model, Everything to highlight by partisan, by partisanship and compromise.

Ethan: That’s a pretty big, pretty big job here in this country, and I’m sure the rest of the world as well.

Annafi Wahed: Yes, unfortunately, polarization is a problem not just in the U S, but in a lot of different countries. We’re seeing, you know, the effects of cable news and social media and what it does to societies overtime. So yes, we’re working on a very exciting problem, to say the least.

Ethan: Yeah, absolutely so this may be. This question may be a bit vague or or or shallow, but I think you can probably give me a good answer. What about this product is helping to solve the issue of divisiveness as a whole?

Annafi Wahed: Great question. I think the best way I can describe it is we’re trying to get America back on the same page, literally, right? So right now you have folks. half half the country is reading the New York Times, watching CNN. The other half is you know watching Fox News, reading National Review or the Wall Street Journal, and we are just literally not on the same page until we’re faced with, you know, the worst Twitter thread that’s gone viral. Or maybe we see our uncle at Thanksgiving once a year, when he you know is giving us talking points we haven’t heard outside of you know, late night TV, or something right. And so our goal is to create that shared new source that shares reality for liberals, conservative, moderates, the a-political. Literally, get America on the same page.

Ethan: It’s a strong, strong goal, strong mission. I think we definitely need it, and we’re going to get a lot deeper into that, and kind of the approaches and the different products that you’ve got here in a little while. But first, can you tell us, how did you get into this?

Annafi Wahed: Oh, my gosh, where do I begin? So I spent four years in finance after college. Well, mostly because I didn’t know what else to do with my life. I had student loans, I was a high achiever and I didn’t go to medical school or law school. I went straight into the workforce and so I entered finance. I was a CFA charter holder and it was the summer of 2016 when I had just gotten that charter and I was up for manager at Ernst & Young, and I realized I was climbing the wrong lot. And so somewhat on a whim, you know, I guess you could call it a quarter life crisis. I gave my two weeks notice and went to New Hampshire to knock on doors for Hilary Clinton the last four months of the 2016 cycle. 

I mostly just wanted to play my small part in helping elect the first female president. Things did not work out that way, and I think I started Flip Side honestly as a coping mechanism. Right after the election I was reading so much conservative news and talking to every Republican conservative. You know, you know Bernie supporters, anyone I could think of to help me make sense of how it led to such a surprise election result in 2016. Along the way, I found my co-founder who’s a staunch conservative. We grew our readership. I was published in the Wall Street Journal. 

Next thing I know, I’m on Fox and Friends, I’m on the Young Turks, and it was just snowballing and I still had gotten a different day job after Ernst & Young. And yeah, it was really, when we started to get emails from our readers, we only had, you know, five thousand, ten thousand. At that point. Who said “Hey, I’ve been sharing the flip side with all my friends. Are you raising? Hey, what? What is your five year plan?” And I said, “I don’t even have a five day plan.”

So it was really recognizing that we were fulfilling this really important need and I was looking around and no one else was doing what we were doing. And so that’s how the newsletter took off, and over time we were hearing from our readers. Again, we were reacting to the feedback addressing the need we were hearing from our readers, “Hey, I love getting the flip side in my inbox each morning. I really feel like I’m getting a nuanced viewpoint. You know, I don’t feel like tearing my hair out. But then I go back to my Facebook groups, I go back to Twitter, and I am back in the same echo chamber, the same fighting matches.” 

Even when Facebook and Twitter show you the opposite sides, it’s the worst of the opposite sides, right, not the best. And so we said. “Okay, well, how do we fix that problem?” And they kept asking us, you know, Is there an online community where I can share my thoughts and not be yelled at or have a nuanced conversation? And there really wasn’t anything that we could find you know. Reddit has a few subreddits that might be helpful that address certain topics well, but we really felt like there wasn’t anyone working on this problem And so and thus our new forum was born.

Ethan: So you said during that time this was early days. you still had a day job and you already had five to ten thousand readers And I don’t know what your readership is now. and well, I’ll ask you that in just a second, but that already sounds like you know quite a few people to have on a list for you know something that is essentially you know, a side project or a passion project. How did you go from zero to you know ten, and then, assuming that those were maybe friends and family, and that sort of thing, how did you break out of that? The friends and family group to go from ten to ten thousand?

Annafi Wahed: Great question. So yes, the first news that I went out to sixteen of my friends and family. I called them one by one and I said “Hey, you keep bugging me about what went wrong in the election. I only have so many answers. I’m working with someone who, you know, is from the other side.” Truly, you know, he has a Maga and everything right and the two of us are working to make sense of it all. Can I add you to my new newsletter? Right? And so it was you know, my best friend, my cousin, you know, my four Co workers, who might have just pitied me. Who knows, but it was those sixteen people who then started to share it with their fans and their families and their co-workers. We grew to about five hundred six hundred just via word of mouth, and in the meantime, I just wanted to go out and listen to people, right? Whether it was Republicans who were trying to explain, you know how, Trump won. Or liberals who were still devastated and still coping, or folks in the media, right, I have never done this before. I don’t have a background in media. 

So I’m going to tons of different new working events and I had. Actually, the week before this event, I had just gone to see CPAC, which is the conservative political action conference and a week later I am at a media event and happened to be standing next to James Toronto, who is on the editorial board of the Wall Street Journal. He thought it was amazing that I had worked for Clinton and then went to attend CPAC, and he said, “Are you writing about it?” And I said, Of course I am, and he gave me his card. That night I penned an op-ed and sent it to him in the wee hours at four AM. Three hours later he wrote back, “We’ll take it,” and I was very confused. Take it where? And next thing I know, I’m published in the Wall Street Journal. 

And so we went overnight from having five hundred subscribers to five thousand. Because you know the Flip Side hyperlink was at the bottom of my profile. So that really gave us, you know. that sort of launch point. And obviously, to a certain extent, the fact that I happened to be standing next to him and he happened to be in a good mood, et cetera, was one of the driving factors, but it’s also important to note how many events I had gone to how many people I had to spoken to. That I had gone to CPAC for three days and spent all that time talking to so many folks. So when I’m you know, talking to early start a founder, as I say, you have to create your own luck. You have to let luck find you.

Ethan: Yes, absolutely hundred percent. I’ve used the term manufactured serendipity for this.

Annafi Wahed: Yes, exactly. That’s a good way to put it

Ethan: Yeah, so going to these events you’re increasing your luck surface area. 

Annafi Wahed: Exactly.

Ethan: Your opportunity to get lucky goes way up. Just putting yourself out there. That’s an awesome story. And I think that this is something that you know founders from, it doesn’t have to just be a publishing type situation, or a newsletter. It can be really any type of business where if you can get in front of the right person who holds the keys to you know your next step or your next group of…

Annafi Wahed: Exactly.

Ethan: of clients, or whatever, do everything you can to put yourself in any situation to get in front of those people.

Annafi Wahed: Yes, as someone who receives lots of cold DM’s, mails now I recognize. “Oh, this is a great project you’re working on. I’m happy to help you.” That I would never have found them if they had not reached out to me. So you have to put yourself out there and you have to send that cold request DM, email, right? And continue to increase that surface area where you can get lucky. Exactly.

Ethan: Absolutely. So how many readers are you up to now?

Annafi Wahed: We’re at a quarter million.

Ethan: Sweet. That’s awesome.

Annafi Wahed: Yes.

Ethan: And then, so going from going, you know, I’m assuming that from that point it just kind of becomes a fly wheel where you keep making good content and people keep sharing it and it just gets bigger and bigger and bigger.

Annafi Wahed: Yes. We have a referral program. So if you make five referrals, you get stickers. If you make twenty, you get a you know bear mug with our logo and things on it. It’s been such a huge hit. We have easily, you know, thirty thousand plus subscribers who came from the referral links alone and then earn media doing great podcasts like this. And also, we’ve you know, run some paid ads during the election cycle and the COVID pandemic, and Yes, exactly, there are so many different things now working to keep that snowball moving.

Ethan: Let’s jump down into that referral program a little bit. You know, this is something that we’ve seen. It’s pretty common in the newsletter space. You know. all sorts of the newsletters like the Skimm and Morning Brew and the hustle and all that good stuff, have these kind of ambassador programs that seem to be a great way to incentivize sharing, and kind of build in that network effect into. You know, this product, which is a fairly simple product. I mean it’s not easy but simple. You know. It’s an email that gets sent out. 

Annafi Wahed: yep.

Ethan: So what have you discovered for the things that really work well for, you know, for this referral program? And what are some of the things where you’ve tried them and you’re like I’m not going to do that any more?

Annafi Wahed: Yeah, so we thought long and hard about what the incentives should be. On the one hand, we have a lot of you know, sort of professionals right? Managers at big tech firms, or you know political leaders and things like that. So we thought well, they really care about stickers. Turns out they do. Everybody loves a sticker.

Ethan: Hm,

Annafi Wahed: That is a winner across the board, regardless of age, regardless of, you know, profession. Whatever. Everyone loves the stickers, I think we also had a wonderful marketing agency. By the way, another thing a boot strap founder should not be afraid to do is ask for free help. So even while we were still boot strapped, we had a wonderful marketing agency who designed our logo, who designed our bear mascot. And so, because we had those assets already, we had people asking us. Hey, you know, are you selling any swag? I would love to show off Flip Side readership in some way. 

So the mugs are also a big hit, because on zoom, you know, if you have a bear mug, someone will ask you. “What is it that you’re holding?” Right? Some things we tried that didn’t work, we thought, oh, what if we had you know, someone, come in and do a webinar about our process, and the sort of the behind the scenes peak, and some people, our premium subscribers. We also offer a premium subscription now. We’re really interested in that, but the other folks said “No, I like the five minute read you give me. I don’t want to look behind the scenes. This is all I want.” So it didn’t work out so well at least when we had I think at that point only fifty thousand subscribers, so we might try it again now. 

Some other things we thought about hosting in personal events, but again people said, I don’t know if I want to sit face to face with a Clinton supporter or Trump supporter for an hour, so there was hesitancy there. So we nixed that idea as well. I think we’re not afraid to ask our readers what they want and they’re very vocal and telling us you know what they want. So we misstep that in terms of we have wrong hypothesis, but we find out pretty quickly right. So yeah, we just keep coming up with new things and seeing where it goes.

Ethan: So you’ve got these incentives. You’ve got, you know, you’ve got the swag, you’ve got the stickers. you’ve got this other stuff. That’s all well and good, But it seems like you’ve created something that works on kind of a deeper level. It seems like you’ve created a sense of belonging. How would you say that you’ve accomplished that?

Annafi Wahed: I think what we hear from a lot of folks is when I open, you know, cable news, or when I open Twitter or Facebook, I feel like I am going crazy. Because again, it’s always the loudest, most extreme voices that are being heard on these platforms, on these TV channels. When you, whether it’s, you know, Rachel Maddow or Sean Hannity, right, you have these screaming heads, these talking heads that are giving you so sort of a very biased and skewed perspective. 

So we again are focused on bringing you the best versions of both sides, and so we hear a lot of people say, “Oh my gosh,” this is my favorite feedback of all time. Someone once wrote, “You are the only liberal rag I can stand to read.” And I just want… that should be our tag. Like we’re done here, like we’ve done our job, and similarly we hear the same from the other side, right? 

And so we are helping people understand again, people that they are close to whether it’s Neighbor. It’s their co-worker, it’s a family member. It’s their kid who comes back from college with all these, You know, new ideas that they’re not familiar with. whatever it is. I think that sense of, “Okay. I feel better connected to this person, or I feel better connected to the rest of America even.” Right? And that’s very deep. 

So we also have a lot of folks who just forward our newsletter each morning, and sometimes they accidentally email us and it’s great because we get to, you know, see how they actually are referring to us. You know, they say things like this is a breath of fresh air, or stop subscribing to fifty different newsletters. Just, you know, subscribe to Flip Side instead. So it’s that mix of okay, we’re making politics sane again and also saving you time. It’s one topic a day. It’s five minutes, very durable for the average person.

Ethan: Absolutely. And so do you think that this has replaced media like replaced news intake for most of your most of your subscribers? Or do you think that it kind of works alongside of? They’re going to read this. Then they’re going to turn on CNN or then they’re gonna turn on Fox News.

Annafi Wahed: So different people have different needs. We’re reaching a quarter million people. So some people, you know, they can’t stand any news and commentary. That is, you know, highly partisan and so they read just the headlines may be from Axcios, or maybe you know, whatever the breaking news alert sends them. And then they read The Flip Side and then they go about their day. But we also have the news junkie that is clicking on every article we’re linking to because they want to read all of it and they want more. They want three newsletters a day on three different topics, and in depth, analysis, et cetera, et cetera. So we are actually now in the process of figuring out “Okay, where do we go from here?” Because we have such a diverse readership, our readers are all across fifty states across the political spectrum, everything from high school students all the way up to retirees. So I mean, we get emails you know from folks who are saying, I’m trying to print out your newsletter and it’s coming out funny and we said, “Oh, we haven’t formatted it to be, you know, easily printable. We didn’t think anyone would be doing that.”

Ethan: Right.

Annafi Wahed: Amazing problems to have. So trying to figure out “Okay, you know, how can we meet all these different people’s needs.” At the same time we’re curators, so we’re not afraid to say, “Okay, if you want an in depth analysis, go here.” And that’s what we’re doing at the forum as well. We want to create, again, that shared space where people can come together. Whether it’s you know, just reading the newsletter or participating in our new forum. We want them to know there is still sanity out there.

Ethan: So let’s jump back out to the business for a second. When it was five to ten thousand. You still have a job. Now that it’s two hundred and fifty thousand, You have, you know, removed that job, and now you’re working on this full time. What was the point? Where was the separation when you were like? All right, I can’t do it any more. I have to just go work on the Flip Side and that’s it.

Annafi Wahed: I mean, frankly, my roommates had an intervention. I was not sleeping. I was not doing my chores. I was overall, just a huge crank, and they said, “Okay, you got to do something. Pick a lane.” So I did. I think, again, at that point we had I think twenty thousand subscribers, so it was starting to feel real, right?

Ethan: Yeah.

Annafi Wahed: We hadn’t spent a dime. It was just word of mouth, earned media. We had Angie, who’s that marketing agency I mentioned who was reaching out doing all this work for us. I already had a co-founder who was devoting so much time. There were so many people who wanted to get involved and I just thought I got to see this through. So it was just that demand and the fact that I only have twenty four hours in a day.

Ethan: Yeah, absolutely, we all only have just those twenty four hours, and if we can’t spend them right then that’s going to dictate what our lives look like. So was the newsletter making any revenue at that time?

Annafi Wahed: No, not a dime. And so I sent a letter to our subscribers. Twenty thousand or so, “Hey, I just quit my day job. It would be great if we could get some funding.” And low and behold, one of our subscribers ended up becoming our pre-seed investor and you know he invested a half a million dollars. That really allowed me and my co-founder to pursue this full time, help it get to the next level. We just brought on a third co-founder, CTO, to build a new platform that I’m talking about. So it was really the fact that he had been a Flip Side subscriber for months, we had mutual connections, and after three phone calls he said, I’m sold. You know, let’s do this.

Ethan: So building this community, building this group of people who are all interested in, you know a similar thing, really kind of led to, you know, an explosion of activity which leads to an explosion of growth. That’s super cool to see. And so now you’re building on top of this community. You’re building this forum. Was there any way that your users were able to interact with each other before the forum was there, like a Facebook group or any other sort of online, like Reddit, subreddit or whatever? 

Annafi Wahed: I think you know twenty three thousand followers on Instagram. We have a Facebook page. We have you know a Twitter handle, et cetera and you know we have people commenting on it all the time. But we didn’t want to engage right because we knew that it was just going to lead to a fighting match. We didn’t really like the moderation tools that Twitter and Facebook provided, and we kept thinking, “Okay, how can this be better?” So it was by meeting our own needs as online moderators ourselves to say, “Oh my gosh, what if we had an algorithm that did this? Or what if we had vote buttons that said, helpful, unhelpful, agree, disagreed, not just like our, you know, angry emoji?” I don’t know what Facebook algorithm is doing today, but the last time it was revealed that the angry emoji is given five times the weight of a like button,

Ethan: Oh, jeez. 

Annafi Wahed: So just that alone should tell you where Facebook priorities are. And we wanted something different.

Ethan: Yeah, absolutely. I mean, so let’s talk about that for just a second and then we can get into the forum, But it seems like there are, you know, there are a couple of different groups of people. There are the folks who want to have a reasonable conversation and they want to learn about the other side. It’s freaking difficult to do it because it doesn’t seem like there is anything out there that isn’t obviously biased or that isn’t hiding some bias.

Annafi Wahed: Yes.

Ethan: And so and so you’ve got the people that really want, you know,this new format of news that they can trust that isn’t trying to just like, make their day worse. But then you’ve got the other people who are addicted to outrage. Who just go on the internet so that they can feel mad. Probably just so that they can feel something. But what is the flip side trying to solve for both of those groups of people? Or is it right now just trying to hit the folks that like want to learn, or maybe the other way?

Annafi Wahed: Great Point. So the business case we make to investors is we’re going after the low hanging fruit right. There is an exhausted majority over half the country. That would be your independents, your moderates, your, you know centrists, your slightly left, slightly right. Or what have you. There’s a huge population of Americans that are just fed up with the level of polarization that’s out there. They just want, again, some rational discussion.

They don’t want a revolution in either direction, right? So that’s the low hanging fruit we’re going after. In terms of the trolls and the outrage, I will say I was a psychology major in undergrad. Humans respond extremely well to incentives, right? So if Facebook is prioritizing the angry emoji five times as much as the like button, guess what you’re going to post. And so we thought long and hard about what our design and framework should be. So when you first sign to the Flip Side forum, we ask you, do you lean left or lean right, and that’s because we are actively prioritizing via the algorithm, via the numerical weights, we put right posts that are getting helpful votes from both sides. So a post that has only four helpful votes, but two from each side will be ranked higher than a post that has ten votes all from one side. We also, the vote combinations interact in interesting ways. So if you even vote on a post that it’s both helpful and you disagree with it, that’s a strong indication. It must be a thoughtful post.

Ethan: Yeah.

Annafi Wahed: So that gets four times the weight. That’s the exact opposite of the angry emoji weight that the Facebook algorithm gives. It’s also open to premium members only. We are thinking about offering a free trial option, but we’ll do so, you know, in a sort of staggered way we won’t let in our whole audience at once. And so we really think If we design this in structure, you know, incentives in such a way that people get a dopamine hit from being reasonable. They will start being reasonable. That’s our working hypothesis. 

Ethan: So that’s a… It’s a good hypothesis. So is it kind of based around? You know, news stories that drop and then? Does it kind of feel like a better moderated comment section? Or is it more like a.. Let’s call it like a traditional social media where one person makes a post that doesn’t necessarily need to reference an article, and then people can go on and comment and interact with that post.

Annafi Wahed: For now it looks like you know, Reddit. So each discussion thread is the topic of the day that we covered in the newsletter, so right now only The Flip Side team members can open a new discussion thread based on the topic of the day, so that we can give you that fact check, curate commentary before you can post or read people’s thoughts, right? Again, we have to get America on the same page before you can start or participate in a conversation you have to read, at least scroll through, our fact check commentary. That’s the dream, right. Start on the same page and go from there. Right now, you know, we don’t know how we feel about members being able to open a thread or start a discussion about an esoteric topic that the moderation team hasn’t done research on yet. So we really take the approach of less is more quality over quantity.

Ethan: Are you finding that your users are mostly well behaved? Or do you get some folks in there who are like turd in the punch bowl?

Annafi Wahed: We have folks who may or may you know, write in correct things, or you know things that might be stated differently if someone were, you know, to rewrite if they were speech writer or something. But now for the most part people have been very well behaved. So far we’re seeing daily engagement. We’re seeing folks asking for all kinds of features. We’re really crowdsourcing the whole build of this. 

You know, we have a huge triage list of things people want. Again, it’s the incentives right. There’s no need for trolling because that’s going to put you at the bottom of the feed, right? You don’t want to be at the bottom of the feed. You want your post to be seen, and so it behooves you to want to get helpful votes from both sides, even if the other side still disagrees with you. 

You know, and I think the other thing we’re excited about is we’re soon launching something called Ambassador of the Week badge. If you earn the most number of helpful votes from the other side, you will earn that badge that will automatically give your post a boost for the next two weeks, and people will be able to accumulate points over time. So that’s something else we’re really excited about and our members know that that’s down the line, so I think they’re gearing up to be the best advocates for their side.

Ethan: Gotcha. That makes sense. Always going back to those incentives. I love it.

Annafi Wahed: Exactly

Ethan: So what is the? And maybe this is different for everybody. But personally, when I read a news article I don’t feel my thumbs twitching like I need to make a comment about it. \What is it that drives the need for this discourse around events?

Annafi Wahed: Great question. We are actually helping with that by adding prompts of our own. So now if you open the newsletter you will see our fact check curative summary from both sides, and then you’ll see prompts for discussion. Right. So with the spy balloon incident we asked, “Do you think the U S government acted prudently? What could they have done differently? How do you think they’re handling the media situation?” So by asking those questions we’re prompting people to think and say, “Oh, I do have thoughts. I want to share.” The other thing is, you know, one of the biggest complaints we get is that our digest is too short. 

There’s a lot of things to say about the complexity of US- China relations that is not going to be covered in a five minute newsletter. And so we have a lot of people itching to add more to the conversation. More to what we have already said. They said, “Oh, here’s another great article you might have missed. Or, oh, let’s refer back to you know, the incident from 2001, et cetera.” So a lot of folks are looking to share information or looking to share their thoughts, are looking to say, “Oh, hey, you know, here’s how I found out about the spy balloon and this was my reaction.” So unfortunately, actually, there’s a lot of news going on and then people have a lot of thoughts and feelings they want to share. Sometimes we wish the new cycle would be slower, but

Ethan: Yeah, well, we’ve got twenty four hours worth of news to you know, to fill every day and sell some commercials, so there’s going to be news all the time.

Annafi Wahed: Exactly,

Ethan: So you’ve got editors on your team who are searching through all of these different articles and curating the best parts of each, the parts that make the most sense. The parts that are obviously factually accurate. What I’m assuming is that you started this like you were the one who was doing all this. And how many of these editors do you have now?

Annafi Wahed: So it’s still just me and my co-founder full time on the editorial team, And then we have a staff of contributors who are working one or two days a week. They’re about five right now.

Ethan: How are you ensuring… Because you can see inside your own head, and obviously you have massive trust with your co-founder. But how are you vetting these people? How are you ensuring that what they’re bringing isn’t in any way biased?

Annafi Wahed: Great question. And so we’re actually trying to change the conversation around bias. Not all bias is bad. We are who we are. We are humans, we are colored by our life experience, our you know profession, our environment, et cetera, et cetera, we are not non-partisan. We’re not even bi-partisan. We are equally partisan, So I bring my liberal bias to the team. Conservative co-founder brings his bias to the team. And so we vet people who are both comfortable in knowing where they stand and very open minded to hearing different perspectives. 

And so our slack channel is always on fire, because just even something as simple as topic selection is hard and is bias in and of itself right. So for the first two years of the Trump presidency, for example, the conservative side always wanted to cover the booming economy, you know, and the liberal side always wanted to cover the Mueller investigation. What choices we make about topic selection gets the you know, gets the conversation going in a certain direction. And so it’s very important that we have people from all across the political spectrum on the team. And so that’s the first thing we check, and the other thing is really, you know. Can they cite authors from the other side that they really like and enjoy, right? Are they open to having their viewpoints not questioned in a sort of you know defend your position way, but just open to that dialogue. So I think that’s something we really care about deeply. Because If you, if that’s not what you’re about, you’re not going to like being on our slack channel.

Ethan: Gotcha. So you’re still very intimately involved with all of the content that goes forward, correct?

Annafi Wahed: Yes,

Ethan: Gotcha. So you, you kind of currently act as the filter to make sure that you know you know. Here’s editor, Jerry. He does a great job ninety five percent of the time, but every once in a while you got to watch Jerry.

Annafi Wahed: Exactly, so we make it such that there was at least one left leaning and one right leaning eye, at least one from each side going into the final draft before we hit publish.

Ethan: That makes sense to me that that seems like a… Because that was my next line of questioning was how does this work at scale? Once you, you know, once you cannot… you can no longer involve yourself in the know, as the filter that goes that you know everything moves through. How do you continue to ensure that all of your editors are unbiased? Or not unbiased, equally biased? Yes, thank you.

Annafi Wahed: Exactly, there you go. Yeah, that’s how we do it right. So it’s that first step. Okay, you know, you have to have that tension there because that’s how we produce the best work. They actually did a study of Wikipedia articles, and they found that politically diverse editors ended up creating better content more, you know, in depth content because they were pushing each other to be better. And that’s our whole philosophy.

Ethan: So going back on that, going back to incentives. How are you going to ensure that the incentives that you are putting forward are always greater than the possible incentives that these editors may be receiving from third party actors? And let me give you an example. So like some of these large publishing companies, who understand that they kind of hold the keys to a platform. 

And if they are approached by a company or an individual who says this is the message I want to get across. And you know I’ll scratch your back if you scratch mine, type of thing. How do you think about ensuring that your editorial staff stays on the up and up?

Annafi Wahed: A very interesting question right again, my co-founder and I are still very hands on right? So there’s rarely, very rarely does the newsletter go out that he or I have not seen. Whether it’s the beginning draft or the ending draft right? Our hands are still very much in it. The other thing I will say is again, our open rates are in the high thirties. We have a very engaged audience, and so we get emails every morning right as soon as the news letter goes out at six AM with feedback. And so one way we measure how we’re doing is that feedback. 

The feedback is usually, “Oh, you forgot this article or you didn’t include this or that as the other thing.” If we start to get, you know, feedback that we’re leaning one way or the other, we take that very seriously. We’ve worked hard to make sure our readership is very politically diverse. And so if everyone is saying the same thing, that means we’re screwing something up. Rather than, you know, at least a handful of folks get angry with us every week because they think we’re leaning one way or the other, but that’s healthy engagement versus you know, fifty people all email us to say XY and Z. And so I think that real time feedback is very important. We also have you know not just the everyday consumer but New York Times reporters and Wall Street Journal reporters and folks who are, you know, leading advocacy organizations and folks who work in Congress and state offices, all reading the Flip Side. And so they are very engaged. And they will, trust me, let us know if we screwed up.

Ethan: It’s good to have good to have the watchful eye of your constituency beside you/

Annafi Wahed: Yeah.

Ethan: All right, let’s jump back into the business side a little bit. At this point I know you’ve got the premium model.

Annafi Wahed: Yeah.

Ethan: Is that the current business model? Is there any advertising or any other business models alongside that?

Annafi Wahed: We also have advertisements, yes. So the premium model is for people who want to participate in the forum who want to get extra in depth content on the weekend. We also have a cartoonist for the extra in depth content.

Ethan: Nice.

Annafi Wahed: He is amazing. Oh my god, so talented. Someday we’re going to make a you know coffee table book of just his cartoons. So that’s the premium membership and we also have advertisements for the free newsletter. Now it’s really funny. We get a lot of folks who want to put partisan ads in our newsletters that we have to say no to. So we are making you know so sort of a business, sacrifice for our social mission. For example, this hasn’t happened, so I’m giving you the extreme cases, but if say Nike or My Pillow were to want to run an ad with Flip Side, we would say no.

And obviously you know any kind of advocacy organization that has a partisan leaning. And so we stick to very, sort of you know, boring ads. A few times we have done things that we did not think were partisan than our readers again told us were. We try things and we take the feedback and we say you know what, “Okay, we, we hear you, and we’re not, you know, going to do this any more.” So that’s a learning process. Moving forward, we want to focus more and more on that premium membership and have the free newsletter. We act as sort of a funnel to get people more engaged and you know, convert eventually to premium membership.

Ethan: That makes sense. So you’ve got you’ve got the. You’ve got the revenue now from those two sources. 

Annafi Wahed: Yep,

Ethan: You had the five hundred thousand dollars of funding before. Are you planning on taking any more funding?

Annafi Wahed: We are raising a new round. Actually, we’ve raised four hundred thousand of new funding. So far, two hundred seventy five thousand came from our subscribers. We actually crowd funded through the WeFunder platform. And again, these are folks who are highly engaged and they want to see us succeed. And then the remaining hundred twenty five came from two new angel investors. That gives us, you know, twelve months runway, we’re really excited to be able to again. Just focus on continuing to build. 2023 is the year to build, and 2024 we will raise a proper series A. And really, you know, make our sort of big splash on the national stage in tandem with the presidential election cycle.

Ethan: Yeah, that sounds like it’s going to be something where people are going to need some news they can trust.

Annafi Wahed: Yeah, just a little bit.

Ethan: All right, so going back to scale. When do you think that you will be able to kind of pull yourself a little bit back from working in the business and start spending more of your time working on the business?

Annafi Wahed: Great question. I think we’re struggling with that right now just because we have such a great system set up that’s working really well, but I need to devote more time to meeting with investors and meeting with, you know, the marketing person that we are bringing on and meeting with going to conferences, what have you, right? So I think this this year, especially because the forum just launched and it’s at such an early stage. 

I still need to be very hands on to make sure that we’re guiding, you know, the build in a sort of prudent way again. We have so many people asking us for fifty different features we really need to prioritize and things like that. Hopefully when we raise a proper series a round in 2024 I’ll be able to take a step back and sort of focus more on strategy. 

We really think that, especially with Facebook pivoting in different directions and Twitter’s new leadership, people are starting to recognize that the era of horizontal media platforms is ending right. So look, I just talked about the evils of Mark Zuckerburg’s, you know, world, and I can go on and on about that, but the fact of the matter is it’s really hard to design an online platform that will meet the needs of civic dialogue groups and your DND and your engagement photos, and your birthday announcement. And you know your soccer team meetup right? So we are seeing now platforms being built exclusively for  clubs or your DND meeting or your neighborhood watch group, or people who just want to talk about stocks. The future is vertical, the future is niche. We want to be at the forefront of the civic dialogue conversations. That’s what we’re laser focused on, and we can build features that will optimize specifically for our needs. Whereas Facebook and Twitter could never do that because they have too many users and communities to serve.

Ethan: So how are you going to take this community that you’ve got from a niche community to a mainstream community to where to where The Flip Side is, just as known as Facebook or CNN, or Fox News or any of these things?

Annafi Wahed: Oh, my gosh, the billion dollar question. I don’t know yet. Is the long and short answer. We are so excited about this new funding. We know where our current subscribers are coming from. Right, these are again the centrists, the moderates, we are going to be, you know, engaging more with the civic dialogue and political advocacy organizations and schools and colleges and things like that. But in terms of going mainstream, that’s an unanswered question. We have a few sort of high ranking folks in the political space. But if we want to create something different, we can’t, you know, go back to the same old ways so we’re still figuring it out. What does it mean to go viral when our goal is not to go viral?

Ethan: Right.

Annafi Wahed: We are also thinking about changing the referral program, actually. Bringing back some of the old ideas we have tried. That didn’t quite work because I think the best, especially in this age of you know saturated media. The best referral comes from a personal friend. So how do we make that fly wheel, you know, even stronger for the forum we’re thinking about creating. So you, Ethan, would be able to create a closed space for just your friends or a teacher would be able to create a space for just their students or a Congressman would be able to create a space just for their constituents on their mailing list with a unique link. 

So that could be another way where we say, “Hey, you can use our fact check, curate commentary, our moderation tools, our platform to have a conversation with your members, your students, your friends, et cetera in a way that you are not able to in Facebook groups.” So the premium membership could allow you to open a closed forum with up to say fifty people for free before you get into the next tier. All of these are things ideas that we have on the table right now

Ethan: Yeah, I love that idea. It’s like you want to make sure you know if I’m having my own private forum here. I want to make sure I’m bringing in the voices that are going to keep things. What would we say is equally biased? Keep things equally biased. But you know I only want to hear from this particular group of people. I think that’s really cool. It’s a really good direction to test out. I really like that.

Annafi Wahed: I’m glad. Yeah, we’ll see how it goes. It could also be the moderation tools are meant to be sort of elastic right so they can change, so if it’s you know all democrats, you can make it so that the helpful buttons are split between center left and far left, and you know sent right and far right, so you can tweak our moderation tools as needed, because there’s plenty of trolling within each party as well. So unfortunately, where we see a lot of opportunity to just again, the end goal is to lower friction. We can lower friction between the parties among the parties. There are so many ways that we can be helpful.

Ethan: So I know we’ve talked about several things that are going to be attempted, tried and all that good stuff. Is there anything big on the horizon for the Flip Side here in the next year or so?

Annafi Wahed: So many things I can’t talk about yet.

Ethan: Oh no.

Annafi Wahed: One thing is we have a John Hopkins researcher and we are co-applying for a grant with Stanford, where we will allow people to enter into the forum for a three month free period and there will be a control and experimental group. We’re going to test one of you know, our many hypotheses around how to decrease polarization and do semantic analysis and see how the interactions go to see if our form and our intervention is actually, you know, scientifically significant in terms of decreasing polarization. So getting that, you know, research, study and showing and proving that our methods work will be really valuable, and I think very attractive to investors as well.

Ethan: I’m excited and I’m looking forward to seeing what happens. So here’s the question that we ask all of our founders and that is, could you please give us your best advice, your number one piece of advice for early stage startup founders?

Annafi Wahed: You will learn faster by doing than, you know, reading a hundred books. Like Lean Startup, The Hard Thing About Hard Things. There are a whole bunch of books you’re supposed to read and you should, but also just jump in. Send that newsletter to sixteen people you know. Send that cold email. Cold DM, what have you. You just have to do things, try things, put yourself out there. It’s going to be really hard and don’t be afraid to ask for help, right? I’m not shy at all about asking people to, you know, pitch in for free or work for sweat equity. Our CTO got on the payroll literally two weeks ago. He’s been working on sweat equity for six months. He built the platform from the ground up. Just know you can have incredible amounts of effort put i.n If you continually put yourself and your vision and what you’re working towards out there right, you have to be. You have to allow the people who are looking for you to find you. If that makes sense.

Ethan: That is great advice. That is awesome advice. I love it. Thank you very much for bringing that on. We have just one more question for you and that is where can people find you online? And how can people support the flip side?

Annafi Wahed: Great for now, we would love to reach more people. So if you go to, you can subscribe to our newsletter, we work really hard to keep it short and sweet. We do not spam you. It’s just one email a day and I myself am active on Twitter, LinkedIn, Annafi Wahed, you can find me on all the socials. I’m the only Annafi Wahed on the internet practically so it won’t be hard to find me. Our website again is 

Ethan: Well, thank you Annafi for coming on to the show. This has been so much fun. Folks listening, you can find everything we talked about today, all the links, all the socials, all of everything on the show notes, and that will be over at And Annafi, is there anything else that you’d like to share with us before we jump out?

Annafi Wahed: No, I think one thing I didn’t say is I think so many people have already disconnected from politics, from hoping that things might get better that Congress might be functional again, and I think that’s the wrong way we have to lean in, as some might say, we have to create the future we want. Don’t give up on politics yet. There’s a lot of good that can be done when we come together, and the Flip Side is creating a community, a platform to make that happen.

Ethan: Awesome. Thank you. Alright that’s a wrap for this week’s episode of the Startup Savant Podcast! Thanks for joining us.

Remember, the best way to show us some love is by rating and reviewing the podcast. Apple Podcasts or Spotify are the best places to leave these reviews, so give them a look.

We’ll be back next week with another awesome founder! Until then, go build something beautiful.

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