“How to Become the Center of Influence Through Digital Nomad Podcasting” with Kari DePhillips of The Workationing Podcast


part of my series of interviews about “How to Become the Center of Influence Through Podcasting”, I had the pleasure of interviewing Kari DePhillips, the CEO of The Content Factory, a digital PR agency that specializes in SEO, and co-host of The Workationing Podcast. Kari and Kelly Chase, her co-host/best friend/colleague, created the Workationing podcast as a way to document their decision to become full-time digital nomads. The podcast follows along as they travel the world, knock items off of their bucket lists and have adventures in living as intentionally as possible.


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Can you tell us the “backstory” about why or how you got started as a podcaster?

It all started with a conversation that Kelly Chase, my podcast co-host, and I had via Skype one day. In this conversation, I asked her if she’d like to become a full-time digital nomad and travel the world with me (we’re best friends and both work in digital marketing, and our jobs are location independent — I own The Content Factory).

It was a huge decision and it felt like a “big” conversation, so we hit record and that became our first episode of the Workationing podcast. We recorded a few more episodes as we packed up our stuff and shut down our old lives so we could travel full-time, and officially launched the podcast when we hit our first destination: Puerto Rico.

As our digital nomad experience developed so did the podcast. In addition to not-so-standard travel adventures, we also talk about life as single women in our thirties (or as we like to say, in our mid-to-late 27s).

Can you share a story about the most interesting thing that has happened to you since you started podcasting?

Because we focus on living as intentionally as possible, we aggressively started kicking our bucket lists. That has taken us everywhere including swimming in Puerto Rico’s La Parguera bio bay, cage diving with sharks in South Africa, flying a plane over Amsterdam, floating in sensory deprivation tanks, and a lot more that we wouldn’t have otherwise been able to experience if we weren’t digital nomad-ing.

Shortly after we started the Workationing podcast, we got some media coverage — Fast Company did a story on us, followed by Women’s Health, Bustle, and others. A Glamour article referred to us as “digital nomad role models,” NBC News called me a “CEO who takes job perks to the max,” and Thrive named me a “limit-breaking female founder.” The media coverage just kept snowballing.

As a result, our listenership exploded and we started getting a lot of fan mail — this seemed crazy to me, but we started a Workationing Facebook group and it now has several thousand listeners in it (and growing daily!). Turns out, people are very interested in this type of lifestyle and the Workationing community has become a huge part of my life. Fans of the podcast have even recreated our adventures around the world, including seeking out the people we met along the way.

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

Being open and vulnerable without oversharing is a fine line to walk, and we’ve crossed it a couple of times. In one of our early episodes we talked about The Yarlap, which is a pelvic floor muscle exercise device that a friend gifted us before we left to travel (to be clear, we each have our own).

Friends told us that it might not be the best idea for us to lead with our vaginas, so we took the episode down and edited that section out. We released it as a separate episode later on, after listeners had a chance to get to know us a bit better before we launched into discussing our hoo-has.

How long have you been podcasting and how many shows have you aired?

We have 60 episodes live right now, and have been at it for two years. We prefer quality over quantity, and are about to return from hiatus for Season 3.

What are the main takeaways or lessons you want your listeners to walk away with?

That you can live life on your own terms, you just have to set a goal and work toward it every day. Nothing is impossible, and you don’t have to life your life based on the expectations society (or your family) has set. There are no rules — you get one shot at life, and you should live out your experience in the way that best suits you.

Check out the full interview in Tracy Hazzard’s Authority Magazine article about Kari DePhillips!

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Podcaster Influencer, Kari DePhillips of The Workationing Podcast shares the best ways to:

1) Book Great Guests. You must have an interesting concept. For us, it was leaning into our mid-life crises and doing something that most women in their mid-to-late 27s don’t do. We prefer to keep the conversation and topics more fluid — as a result, we only have a few interview episodes and only feature guests who have inspired us and have something interesting to say.

Chemistry and vulnerability are also key. When Kelly and I podcast, we have real conversations and it sounds like you’re listening in to your sassy friends talking. In addition to the not-so-typical travel fare, we have an entire 4-part series on “relationshit” about the challenges of dating in your 30s (and beyond), and we also talk about our struggles with weight loss. Kelly has lost over 100 pounds since she started Workationing!

2) Increase Listeners. Media coverage was HUGE for increasing our listenership. I don’t think we’d have the Workationing community we do if it weren’t for all of the press coverage we were able to generate for the podcast. It helps that I own a digital PR agency — but anyone can do this. Find reporters who may be interested in covering your story, and reach out! If you don’t have their email address, LinkedIn (or even Twitter) are great outreach tools.

Facebook groups are also a great way to increase your listenership. Find groups that are centered on the same subjects you cover in your podcast, and start interacting. Kelly and I participate in digital nomad Facebook groups almost every day, which has increased the membership of our Workationing Facebook group but also our podcast listenership as well.

3) Produce in a Professional Way. Editing is absolutely critical. This is time consuming, and we outsource it to a professional. This makes our podcast much, much more listenable. We also have a fun intro (dramatic music, with a custom “in a time and place, when you can work from anywhere…” intro that tells the listener what the ep is about, as well as an “ear snack” outro that includes a funny outtake from the episode).

4) Encourage Engagement. If you create a space for people to come and interact with you, they will. For us, it was a Facebook group that we plug in every episode. The Workationing Facebook group gets a lot more interaction than our website does — although over 15k people per month visit our website, we don’t get too many comments there. If you actually want to engage with your listeners, Facebook groups are the best way to do so.

5) Monetize. If you’re just starting out, advertisers are not going to come beating down your door to give you money. In fact, you need to hit around 20k downloads per month in order to be attractive to most advertisers — and a lot of podcasts never get there, even after years.

What makes your podcast binge-listenable? What do you think makes your podcast unique from the others in your category? What do you think is special about you as a host, your guests, or the content itself?

Check out the full interview in Tracy Hazzard’s Authority Magazine article about Kari DePhillips!