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Meet Riley Billingsley and Eleanor Drake of The Break Up

Today we’d like to introduce you to Riley Billingsley and Eleanor Drake.

So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
Riley: Our friendship really blossomed out of heartbreak. When Eleanor went through a significant breakup, I really wanted to be there for her because I knew how hard and lonely breakups can be. As a result, we became even closer friends than we had been before. We always bonded over conversations about heartbreak and dating, so it just made sense to create a more public conversation about stuff that every single person has to go through. It started as a text from Eleanor to me saying “we should do a podcast about breakups” and that’s how The Break Up was born!

Eleanor: Riley and I became friends when she moved to LA from Chicago and grew even closer after I went through a breakup. We both love podcasts, and we’re sharing our favorites with each other, and the idea came to me very organically. We both talked about relationships, dating, and breakups a lot and a podcast seemed like a natural progression of those conversations. We were really curious about how other people were affected by similar situations.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Riley: We’ve learned so much from our first episode to now. Riding the line between sadness and humor can be tough. We want listeners to feel inspired by our guests’ overcoming their heartbreak, but we also want them to connect to their story and not feel so alone in their breakup-which means sometimes we really have to get into the heartbreak, and it can be really heavy… We’re working on expanding our audience beyond the heartbroken. The Break Up is really for anyone who is fascinated by how people deal with trauma, dating, and growing up with a side of laughter.

Eleanor: We continue to learn as we do the podcast. The topic of conversation tends to make us closer to our guests, but some stories are particularly heartbreaking. We’re always trying to make the episodes lighthearted, but that can definitely be challenging.

Alright – so let’s talk business. Tell us about The Break Up – what should we know?
Riley: We have a podcast called The Break Up where we interview guests about their breakups and how they’ve overcome adversity. Heartbreak is a universal human experience, and we wanted to create a space to have open conversations about breakups, which are a bit taboo, in order to laugh about it and learn from it.

After my last breakup, I felt so sad and alone in my grief and actually googled “how to feel better when going through a breakup” in the hopes I could find someone with a common experience. The listeners that reach out often mention they find us by searching a similar topic.

We really like being that support for people because we both valued our support network in dealing with heartbreak. We’re both major proponents of therapy and have received several emails from listeners telling us that listening to the podcast has encouraged them to find a therapist to help them cope – we love that!

Is there a characteristic or quality that you feel is essential to success?
Riley: I think LA has been a great place to have our podcast because most of our guests are based here and we have been able to find a lot of creative and outgoing people who are interested in talking about their breakups. I think we’ve been able to create a little community here and it’s been amazing to experience. Dating in LA is awful though, so… would not recommend that.

Eleanor: LA is an amazing city with great opportunity for people who are interested in starting their own podcast or business. I grew up here, and though I’ve lived other places, I’m always drawn to LA. People here are all about forward momentum – what makes them better, healthier, more successful – and being surrounded by that energy has encouraged me to reach for my fullest potential.


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Image Credit:

Ali Suddith, Tracy Win, Chloe Mcgregor

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