Female Founders: Annafi Wahed of The Flip Side On The Five Things You Need To Thrive and Succeed as a Woman Founder

An Interview With Candice Georgiadis

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

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Annafi Wahed.

Annafi Wahed, CFA, has a broad array of experience spanning the federal government, non-profit, political, and private sectors. In 2016, she left her role as a Senior Consultant at Ernst & Young to join the Democratic campaign. Walking door to door, she saw firsthand how next-door neighbors could be completely isolated from one another by the media they consume. Annafi launched The Flip Side in 2017 and has spearheaded each new stage of the venture, including an innovative social platform for exchanging ideas with an algorithm that rewards thoughtfulness and bipartisanship.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Sure! 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.

Can you share the most interesting story that happened to you since you began leading your company?

There have been so many moments. Most recently, we received an email from a Congressman wishing us luck on our next phase — it turns out he’s been an avid reader for years! I asked for a phone call, and he graciously accepted. We chatted about life in Congress, The Flip Side’s evolution over the years, etc. It was really cool.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I thought things like where the ‘Sign up’ button is or the specific font or shade of purple we use don’t matter — THEY MOST DEF DO! Looking back, it’s comical how naive I was about the importance of good design.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’m eternally grateful for my best friend Katherine. I’ve lost count of how many times I’ve called her in tears or in a panic in our 20 years of friendship. She’s my rock!

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

I think plenty of women are founding, or at least trying to found, companies actually; I just don’t think they’re being encouraged or funded at the rates that they should be. VCs and angels still lean heavily male. I have a running joke that in a given week, I’ll have spoken to more Andrews than women, or more Jakes than women. The prevalence of male decision-makers is why, even though women account for 50 percent of the global population, products and services catering to women are bizarrely seen as a niche market. Until we have more female investors, I don’t think we’re going to solve the problem of too few female founders.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

Here are some ideas for VCs:

1. Normalize detailed pitch decks. If we founders could have 40 sentences instead of only 20, you would save yourselves a lot of calls. It would be much more time efficient, and there’s be less room for biased error if the data is in writing.
2. Get rid of the need for warm intros. Make clear your investment thesis on your website and create a form for founders to fill out that asks specific questions that help you evaluate whether their company meets your criteria. If criteria are met, schedule a call.
3. So much of the decision-making process rides on the vibes a junior analyst is feeling (or not feeling) on that first call. There needs to be systematic audits of the decision-making process (another reason to have detailed pitch decks). Why did THIS founder warrant a second call but not THAT one?
4. Not always of course, but on average, women and men communicate differently. Me saying “I’m reasonably confident we can do x” is the equivalent of male founders’ “hell yes, we can do that by next week no problem.” I try to correct myself now, but it’s also on VCs to listen better.
5. Always ask, “is there anything you want to add that we didn’t cover?” at the end of the meeting. Sometimes an investor will get sidetracked on a side quest and it’s hard for me to revert the conversation back without seeming rude. That five minutes at the end would be super helpful.
6. If you are not the target market and haven’t spent a considerable amount of time researching the target market, don’t use your wife/girlfriend/son/dude at the gym as your single data point when evaluating a product or service.
7. Outreach! The Seven Sister colleges would be one low-hanging fruit (I’m a Bryn Mawr alum myself). There are tons of other easy ways.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

There’s nothing like the adventure of building something from the ground up. When you’re a bootstrapped founder, you must do literally everything; you’re the IT person, customer service rep, janitor, social media manager, editor, and chief strategist. Even now with an incredible team behind me, my hands are in everything. There’s no such thing as “I can’t/don’t know how to do that”; there’s only “Ok, let’s figure out how to make this happen.” It’s incredibly empowering.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

That founder tweeting about waking up at 4 am, downing a protein shake, hitting the gym, and getting into a flow state by 5 am? Yeah, chances are they’re a hot mess the other six days of the week. We’re all faking it til we make it!

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

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.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. Everything takes twice as long as you think it will; sometimes it takes weeks just to get on someone’s calendar. Plan accordingly.
2. 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!
3. Design matters! We more than tripled our conversion rate when we hired an agency to rebuild our website.
4. Few people understand just how stressful starting a company is; be patient with family and friends who may not always know how best to be supportive/helpful.
5. Remember to take care of yourself and invest in things that will make your life easier, whether that’s meal delivery service or weekly therapy sessions, or a snazzy desk setup.

How have you used your success to make the world a better place?

My startup is very much mission driven. We’re working to bridge the gap between liberals and conservatives in this polarized era. We hear from readers weekly that our humble newsletter makes a tangible difference in their lives — helping them understand and connect with family, friends, or coworkers with whom they disagree. We also just launched a new online forum that we hope will become the intellectual salon to Twitter’s chaotic town square!

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Our future is bleak if we continue living in the world Mark Zuckerberg and Jack Dorsey created. 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. The Flip Side is leading the way, and I hope everyone reading this will join us!

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would love to meet Elon Musk and talk about the future of Twitter and ways to design online spaces where thoughtful, nuanced conversations can flourish. The trillion-dollar question remains: is there a way to marginalize the bad actors and trolls without squashing free speech? We have some ideas and would love to partner with Twitter to test them at scale.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.