Jenny Kaplan is Bringing Women’s Stories Front, Center and to Your Ears Every Day

“I wanted to tell the story and I realized that the best thing I could do was do that on my own.”

By Callie Schweitzer

Jenny Kaplan, explain your company in a sentence.

Wonder Media Network is an audio first media company that is working to amplify underrepresented voices by creating our own podcasts and developing podcasts for other organizations.

You spent four years as a journalist on the global business team at Bloomberg. You quit when you were 26 to start Wonder Media Network, and you talked about how your mom deciding to run for Congress was a big part of the reason why. Can you talk more about that?

I have been obsessed with politics all my life, and it was something that was a family dinner table conversation. Through college, I was debating whether I wanted to go into journalism or politics, because both of those were things that I’d always wanted to do, and I decided on journalism because I felt like it was easier to be a journalist first and then go into politics, rather than vice versa. Then my mom decided to run for Congress in the 13th District in North Carolina where I grew up. I looked around and realized that the statistic that a record number of women were running was everywhere, but there really wasn’t any publication that was telling the human stories of who these women are and why they decided to run. The more I started to dig into that, the more I started to think about why there are so few women in office to begin with, and what our government would look like if it generally looked more like the people it represents. I wanted to tell the story and I realized that the best thing I could do was do that on my own.

“The power of podcasts is that it’s a personal medium. Someone’s talking in your ears. So the relationship that you develop between host and listener is quite close.”

What made you decide to bootstrap the business instead of raising capital from the get-go?

One benefit of podcasting is that it isn’t super expensive to do if you’re willing to do everything yourself. I was introduced to podcasts at Bloomberg. I pitched, developed, and co-hosted a narrative style show there called Material World, so I knew how it worked. We really wanted to get proof that we could create a really amazing podcast, a narrative style show, and we could get people to listen and to invest. Once we were putting together our second and third shows, we realized that people would pay us for this. It got to the point where we were bringing revenue in, so why raise money if we don’t need it? We’re now thinking about what a raise might look like, but generally,, we don’t want to give away the company if we don’t have to, and we’re cash flow positive.

And what does the business model look like?

The revenue model is twofold. Our original shows are sponsored by different companies that are mission aligned. For example, our show, The Brown Girl’s Guide to Politics, was exclusively sponsored by Act Blue for its first season. Instead of going with a CPM (cost per thousand impressions aka eyeballs) model, which is the norm of the industry, we’ve instead created a flat fee model for a season or for a certain number of episodes. For the white-labeled side, where we’re creating podcasts for other companies, we’re creating both internally facing and externally facing shows for different organizations, large and small, and they pay us. We have a couple of different payment structures. But they pay us to produce the project.

What kind of stuff would be internal versus external?

We produced for an internally facing show for a big tech company that was totally redoing their compensation structure. Their employees were confused and anxious, so they hired us to create six podcast episodes where we explained what was going on. We do everything from concept development through script writing through recording and producing the interviews, through editing and audio engineering to delivery and marketing. Another thing we’re talking about is town hall meetings. The goal is often to connect people at the top and people at the bottom and having someone on a stage doesn’t necessarily do that. The power of podcasts is that it’s a personal medium. Someone’s talking in your ears. So the relationship that you develop between host and listener is quite close. Anything that companies are currently using a newsletter for can be transitioned to a podcast.

Spotify recently bought Gimlet Media, which is a five year old podcasting company, for more than $200 million. If you were to raise capital, what would you tell investors is your major differentiator?

We’re filling a white space not only in podcasting, but in media generally. Our mission is to amplify underrepresented voices, and to introduce empathy into politics, business, and culture. We’re very mission driven. I think that that’s a differentiator — the stories that we’re telling are significantly different.

In a really crowded landscape where “anyone” can be a journalist, and anyone can start a podcast, what sources of distribution are you relying on for mostly brand discovery and audience growth?

The biggest challenge in the podcast industry is discoverability and the best way to deal with that is by creating relationships with the different platforms — Apple Podcasts, Spotify, Stitcher, etc. — to make sure that you can get featured on their top pages, which is where people are discovering podcasts most. The other techniques are really the same as other kinds of media — it’s digital advertising, social advertising, trying to create earned media. We’re doing all of the above.

In talking about how discovery is harder than ever, what’s your plan to take back the word content, which I think has become very bastardized in the last few years?

I don’t feel strongly about using the word content. I think that it has lost valuable meaning, and now is more about brands than it is really about journalism. Instead, I really focus on, what are the stories we want to tell? How do we use stories and think about that, whether it is original or branded content? No matter what it is, people want to hear stories. That’s how we connect as human beings. And from our clients’ perspectives, what are the real human stories that people will want to listen to and latch onto?

“Our mission is to amplify underrepresented voices, and to introduce empathy into politics, business, and culture.”

Tell us about Encyclopedia Womannica, which is your newest show.

Encyclopedia Womannica is a five minute show every week day about women from throughout history who you may or may not know but should. It incorporates people from around the world and also from different time periods, so there are women from antiquity to today.

Has storytelling particularly women’s stories always been a big part of your life? Would five year old or 15 year old Jenny Kaplan be surprised at where you are right now?

Storytelling certainly has always been a big part of my life. We used to joke that at night, my parents would ask me what I did that day, and I would start by saying I woke up, I got out of bed, I brushed my teeth, I went to the bathroom, I got dressed. It was every second of the day, I needed to chronicle everything that I had done. I have always been an obsessive reader, and at one point, as a child, I wanted to be an actor. I don’t think I would’ve necessarily expected that I would be focused on women in particular, but I am not surprised that I am focused on telling undertold stories. I feel like part of the reason why I love what I’m doing and why I feel really driven is because the mission of the company feels really aligned with my personal mission.

What would you say is the biggest misconception about what you do or about the industry that you work in?

I was on a couple of panels this weekend at my five year college reunion, and I think that there are a lot of misconceptions about media as a whole and journalism right now. Trust is really difficult to repair and that’s a huge challenge to anyone in the media industry.


“No matter what it is, people want to hear stories.”

If you were starting the business today, what would you do differently?

I don’t think I would do anything differently. We’re not even a year in, so I don’t have that much hindsight on my side.

What are three podcasts that you think every entrepreneur should listen to?

First, The Daily, because I think it’s just a good way of getting news on the go, which I think is challenging for entrepreneurs. Next, The Slowdown, which is a daily five minute podcast that is hosted by the Poet Laureate of the US, Tracy K. Smith, and every day, she reads a different poem. It’s a really excellent way to start the day from a grounded place. Lastly, My Dad Wrote a Porno, which is one of my absolute favorite podcasts of all time because it is so funny, and I think that people need a way to relax and laugh, because entrepreneurship is a very stressful endeavor.

What’s a bad habit you’ve had to break on the entrepreneurial journey?

I feel like in my mind, it’s just a matter of working more, always working more. I think that that is something I’ve had to reconsider, that working more is not always actually more productive. It’s important to listen to where I’m at and adjusting accordingly. There are times when I’m just not going to get work done, and instead of sitting in a room and pretending I’m going to get work done, it’s actually much better for me to leave and go work out or go do whatever.

What’s your process for working on yourself when you’re not working?

I’m big on my morning routine. I’m a big fan of morning pages, which I have done to varying degrees of consistency, but the idea is you wake up and you just write three pages of handwritten stream of consciousness, and then you start your day. I’ve also incorporated reading a meditation or something first thing in the morning or listening to The Slowdown. Working out is another thing that I’ve had to just retake on as something that’s necessary for me to feel sane.

What’s a productivity tool you would be lost without?

I’m a bullet journaler, but generally, I’ve always loved to do lists. That’s a really old school productivity tool, but I’m big on notebooks.

Last question. What is your favorite female founded product?

One brand that I’m pretty into at the moment is Cuyana.

Invest in a woman. Check out Wonder Media Network’s podcasts here.

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