Willow Avalon Explains How One Billboard She “Swindled” Ended Up Changing Her Life

Willow Avalon
Dean Bradshaw

Let this be a lesson that one billboard can change your entire life.

Willow Avalon joined the Whiskey Riff Raff podcast recently to talk about growing up in Georgia and moving to California (and eventually New York City), pursuing music at the young age of 15 , honing her skills as a songwriter and some of her musical inspirations, her debut album Southern Belle Raisin’ Hell, playing with Zach Bryan at Stagecoach, her plans for future music and much more.

When it comes to Willow’s story, there are certainly a lot of “right place, right time” elements. If you were wondering how she became a name in the country music world, there’s really two moments in her life that rocketed her into the fame she has now… and one literally happened overnight.

Willow Avalon had already signed a record deal with Atlantic when she was 18, and as she described it, things kind of went south. The label didn’t like the “country thing” she was trying to do, and wanted her to be more “indie” and a “Lana Del Ray” type.

Around that time, the COVID lockdown happened, and everything of Willow’s got shelved by Atlantic. They even cut her contract, and released all of her music back to her as a parting gift. So then Avalon once again had a song of hers that she really felt good about… the same In order to promote it, she went old school and decided to slap it on a nearby billboard.

“I release it, and I’m not good at public relations, and I wasn’t really using the internet at this time. So I was like, ‘What’s the best way to get it out there that I did this without me having to, you know, feel like I’m pulling out teeth (and telling people) to stream my song?’ So I swindled a 48-foot billboard in front of my ex-fiancé’s band’s billboard in Los Angeles, and I got it for a crazy deal.”

Her ex-fiancé is one of the members of Grouplove, just in case you were wondering.

As for the specifics of the billboard, Willow Avalon said she kept things very simple and incredibly low budget. But that’s apparently all it took for someone in town to see it:

“The photo was me in front of my friend’s red garage holding my possum on my shoulder and my girlfriend was fanning me with a Tupperware lid. That photo was on a 48-foot billboard for like three months.

I paid for a week or two weeks and they kept it up for three months. That billboard was the whole reason that I made it to New York, because I ended up finding management from that – who saw the billboard.”

@whiskeyriff @Willow Avalon on how a billboard changed her life. // The new Whiskey Riff Raff podcast is LIVE now on Spotify, Apple, and YouTube. #whiskeyriff #whiskeyriffraff #willowavalon #countrymusic #billboard ♬ original sound – Whiskey Riff

Pretty wild, right? Here’s the photo:

But that’s not all…

Avalon told us that she had agreed to do a “How much do you pay for rent?” video online when she lived in New York (she now lives in Nashville). So she ended up recording that around the same time that she posted a video of herself (with her late possum Bowie) onto her own personal TikTok. Then she went to bed… and this happened:

“I woke up the next morning and my phone was so hot you could fry an egg on it. My whole life 180-fully-flipped. Everything changed. The video of me and Bowie had gone to 30 or 40 million (views) overnight, and it had been tied into the algorithm with Caleb who posted the same night without telling me…

That put the one single I had on Spotify, which I self released through DistroKid – it’s a GarageBand, unmixed and unmastered demo – called ‘Drivin’ that I made when I was 17 into a Spotify algorithm. Because people kept going and clicking on the link in my profile and going to Spotify.”

When the song got hundreds of thousands of clicks overnight, all of the labels started calling, and the rest is history. As I said earlier, there were a lot of stars that had to align for Willow Avalon to be where she is today… and boy did the stars just keep aligning.

If you want to hear more from Willow Avalon, make sure to download the podcast on Apple Podcasts by searching “Whiskey Riff Raff” or click here.

We’re also available on Spotify and wherever else you can listen to podcasts.

Cheers, y’all.

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