In today’s age, it’s easier than ever to start a podcast and it seems like everyone you know has one. However, creating a podcast that you can monetize – with content that grabs listeners’ attention and keeps them coming back – is difficult. Dear Media is the podcast network built to foster and develop female-focused podcasts and talent. Dear Media helps to build the brand of the various podcast channels that covers topics that range from career development to advocacy. Unlike other podcast networks, Dear Media has placed an emphasis on monetization opportunities across various mediums, and the company is partnered with brands like American Express, Bloomingdales, Microsoft, and LinkedIn. For example, the company is investing and incubating early-stage direct to consumer brands that can leverage the podcast network for user acquisition and conversion.
LA TechWatch sat down with CEO and Cofounder Michael Bosstick to learn how he built Dear Media, which now hosts 40+ podcasts hosted by top-tier talent and has a following of more than 25M across social.
Who were your investors and how much did you raise?
Magnet Companies, Series A.
Tell us about the product or service Dear Media offers.
Dear Media, the largest podcast network focused on strong female voices and audiences. While we primarily lead into audio-first content, we have the ability to work across multiple mediums including, blog, social, video, etc. to create compelling content and campaigns for our partners. With this investment, we also have the ability to invest in new IP, content, and consumer product brands that this network will help launch and incubate.
What inspired the start of Dear Media?
My wife Lauryn and I started a podcast out of our living room in March of 2016 as a new channel to have deeper conversations with an audience she had established primarily through her blog, The Skinny Confidential. After our first 20 or so episodes, we joined a prominent podcast network that we thought would help grow and monetize our show. That experience led us to realize that the networks as they existed were singularly focused on the audio channel and had little to no understanding of how to incorporate and monetize the rest of the digital channels and brand. We left the network, went back to self-producing, and established the Dear Media business model. This attracted other talent we had met in the space and the rest is history.
How is Dear Media different?
We are completely focused as a network on amplifying female voices and attracting female listeners to the space. This medium has been male-dominated for a long time. We are also much more than just a podcast network. We have the ability to work with our shows across all of their channels which enables us to do much more than most networks in the podcast space. We are also positioned to invest and incubate early-stage direct to consumer brands and push them through the Dear Media network. We are not solely interested in podcast ad revenue. We believe our shows can do much more. We also don’t outsource any of our production, sales, content, or marketing efforts. It’s all done in house.
What market are you targeting and how big is it?
Primarily millennial and Gen Z women who are interested in long-form audio content ranging from career development, parenting, health and wellness, comedy, sex and relationships, activism and advocacy, and more. So… it’s a big demo and growing.
Who do you consider to be your primary competitors?
There are other large-scale audio networks that I imagine your readers would classify as our competitors. My feeling is that while we lean heavily into audio our model is much different. We are not only focused on the individual channels but on what those channels can launch or create. New brands, products, services, IP, businesses, etc. Our focus is to be a serious value add from the start to get those new ventures off the ground. We are not solely focused on the traditional podcast monetization model for growth opportunities.
What’s your business model?
We partner with creators who are interested in leaning heavily into audio to create compelling content. We typically enter into a revenue split or joint venture. In addition to this, we are funding and helping to incubate brands and products led by these creators or investing in brands that align with this network. We have a massive reach that targets a very specific demo which makes Dear Media an ideal place for these creators and brands to get their new ventures off the ground.
What was the funding process like?
It was long and challenging as any funding process is. There were many meetings with multiple firms until we found the right one with Magnet. Then it was months of back and forth to lock down the right deal structure to make this make sense for everyone involved.
What are the biggest challenges that you faced while raising capital?
Most of the firms I spoke with couldn’t wrap their heads around what we were really building here. With this investment, we are not only investing in the media network but multiple direct to consumer brands that this network is going to launch. It was a challenge to find investors who understood that this type of machine could be much more than an audio network. The majority of the firms wanted to classify or match this business to another model in the podcast space. The best piece of advice I can give to entrepreneurs who are looking to raise capital is to never try and fit into an investor’s mental model. Stick to your model and wait until you find the investor that gets what your building and gets excited to help you build it.
What factors about your business led your investors to write the check?
I think I was able to paint a picture of something much bigger than a podcast network with more sustainability, protection, and growth opportunities compared to other opportunities they were vetting in this space. They recognized that this is going to be much more than a podcast network with much smarter monetization and growth strategies.
What are the milestones you plan to achieve in the next six months?
We are getting ready to make some really exciting announcements for new voices and content coming into the space. There are two consumer products brands that we will invest in and launch which we will announce soon, and you will start to see the network do much more to update the podcast space.
There are two consumer products brands that we will invest in and launch which we will announce soon, and you will start to see the network do much more to update the podcast space.
What advice can you offer companies in Los Angeles that do not have a fresh injection of capital in the bank?
In this environment, the name of the game is to survive. These are challenging times that are going to test every company. We ran Dear Media with no outside capital for close to 2 years, so I understand what it means to run lean and efficient. If you focus on creating a rock-solid business first and capital second, that’s a winning strategy in my opinion. So many operators get that backwards.
Where do you see the company going now over the near term?
This round of capital gives us a ton of firepower to really build out and scale this venture. Expect to see and hear Dear Media shows a lot more and get ready to see some of the brands this machine will launch. It’s an exciting time for podcasts and brands focused on leveraging these channels.
What is your favorite restaurant in LA?
Does Barney’s Beanery count? When I closed this round, I celebrated there with a cold beer and a glass of Jameson Whiskey. My cofounder Raina texted me and said, “Nothing screams I just raised 8 Million dollars like a mozzarella stick.” Cheers!
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