Why I Sold My Podcast Company… To A Literary Agency.

Casey Helmick
6 min readApr 23, 2021

Before we dive into why I sold my podcast company to a literary agency, let me paint a picture.

It’s early 2020 and no one truly understands how big the global pandemic of COVID-19 is going to become. I have developed a podcast network — primarily focused in the religious genre of content — that is reaching roughly 75,000 unique listeners a month. Because of the strength of that network, my small production company is now being booked to produce larger independent shows. In 2019 our podcasts received just shy of 4,000,000 total downloads. In 2020 our independent podcast production requests were sky-rocketing, in part because of the virus-triggered lockdowns and in part because of executing good work the year prior. We were on trajectory to double our project workload in 2020 and I began to realize just what I had on my hands:

A Big Problem.

For those of you who read about entrepreneurship (or listen to a few podcasts about it), you are fully aware of the moment in the entrepreneurial journey I was facing as founder: Scaling Ourselves Directly To A Painful Death. This was me in June 2020 — growing so fast that the systems allowing our small production group to run Converge Podcast Network and a handful of independent shows successfully were the very things causing us to fail at real and sustainable growth. There was major opportunity ahead of us but the keys to unlocking the growth didn’t seem to be in my portfolio.

One of the hardest things for founders to do is to recognize their own deficiencies. While I struggle with this, I knew enough to know that I had gaps in my entrepreneurial vision and I began having discussions with a few key people.

The first of these discussions was with Liz Horowitz. One of my blindspots is that I had no “industry experience.” I had spent most of my career working inside of nonprofits helping market the amazing work happening around the world, assisting them in telling their stories, raising money, developing digital platforms, etc. I found Liz via a cold search on LinkedIn… here is the first message I sent to her:

Liz has worked at places like ABC Radio, AOL, WNYC, Wondery, etc. Her expertise in sales and partnerships with extremely reputable brands caught my eye. And she agreed to jump on a call with me and hear my story. After a few weeks we came to an agreement — Liz would meet with me weekly and advise me in the building of my podcast company. I set 90-day growth goals and we began to chase hard at not only legitimizing my company but also me as an entrepreneur in the podcast world. Liz helped me understand that the entire “industry” was only 20 years old — an infant compared to radio and television. My lack of “insider industry knowledge/experience” was starting to feel less like a mountain to climb and more like a puddle to jump over.

Liz gave me the confidence to believe in myself.

The second relationship that began to blossom during this season was with Whitney Gossett. The stepping stones of Whitney and I’s relationship are quite comical… I met Whitney on a call where we were both doing someone a favor (a common scenario we commiserate often). Our friendship simmered after that brief phone call but it was immediately clear that we were kindred spirits on a similar journey. Needless to say, when Whitney called me to tell me she moved into a new leadership role as President of Content Capital I was beyond excited. Her new path made it crystal clear how we could collaborate. Content Capital is a successful strategic content development firm with a focus on book publishing. They knew leaders who not only needed a book but also a podcast. Whitney and I spent about half of 2020 referring business and dreaming of collaborative efforts that could help both of our companies grow.

Whitney gave me the confidence to believe in myself and the content business.

Enter Clint Greenleaf. Clint is the founder of Content Capital. His background in publishing is strong enough that you can just do a quick google search to see all his pedigrees. I remember standing in California in late 2020 being on the phone with Clint spilling the beans that my company’s biggest need was resources to scale. At the time I was still working heavily in the nonprofit industry, consulting with contacts who needed marketing help, and building this podcast business that still felt like a “side hustle.” The idea that I could solely focus on building the podcast business was almost unreachable in my mind. After my first call with Clint, he challenged me: start acting like I was an industry leader. By the end of 2020 it became clear to us both that we needed to join together and carve out space for me to truly grow into a leading voice inside of the audio business.

Clint gave me the confidence to believe in myself, the content business, and a future as industry leader.

So… why did I sell my podcast company to a literary agency?

Because the future is not book publishing or podcast publishing. The future is building a holistic model of content strategy with strong foundational pillars in a variety of media types, media lengths, and media categories.

This is your formal introduction to Terra Firma. We build podcasts built to last.

We have ambitions to solve 3 major problems inside of podcasting and audio through Terra Firma:

Problem #1: Sustainability

As of the writing of this article (April 2021) there are over 2 million podcasts and over 45 million individual episodes. The first problem we are solving is sustainability. Out of the 2 million podcasts+, it is estimated that only 36% have produced more than 10 episodes. And roughly 520,000 of the 2,000,000 have produced 10 episodes and at least one produced episode in the past year (26%).

My new friend Steve Goldstein truly breaks down this problem on his blog. Check out this graphic he shared:

Anyone can launch a podcast. Only a few can keep it going.

Only a tiny percentage — Steve Goldstein suggests that it is possible single-digit percentage — can sustainably podcast.

By applying our strategic planning, production skills, and monetization strategies, Terra Firma helps build podcasts built to last.

Problem #2: Progressive Monetization

The second problem we are solving is creating progressive monetization models. Very few podcasters are “full-time” podcasters. In fact, that number is so small that I can’t think of a true and pure example as I write this. When our team thinks about what makes a podcaster successful we can’t help thinking about the progressive monetization that utilizes advertising, productization, and subscription models to build the strongest custom formula for each podcaster we work with.

While podcast advertising is set to scale over $1 billion this year according to a variety of sources, it is not going to be the main financial driver for most podcasters. It is critical, in our opinion, to build a diversity of revenue streams for our clients. Podcasters should be making money through advertising just like we do with our Converge Podcast Network shows. Podcasters should be making money creating digital experiences/events like we have done with our client Kait Warman. Podcasters should be integrating their book into their podcasts like our client Lorena Junco Margain does each week.

Terra Firma helps develop marketing and monetization strategies that create a firm foundation for sustainable growth.

Problem #3: Bigger Than Audio

The third problem we are solving is dismantling the walls that separate the book publishing world and the podcast publishing world. Because we are now a part of the Content Capital family, we have access to a set of resources and people that are the best in the business at book development. This year we will be opening up pathways to bring authors into podcasting and podcasters into authorship.

I love this medium article that Frank Racioppi recently wrote, “What Happens When Podcasters Publish Books.” Frank points out, “Authors and podcasters have a long-running symbiotic relationship.”

We’d love to hear what problems you are facing in the podcast industry right now. Shoot me an email to casey@contentcapital.com and let me know. For more insights like this follow me on Twitter.



Casey Helmick

President, Terra Firma™ | creating podcasts and audiobooks with a speciality in working with the world’s smartest people.