How YouTuber Madilyn Bailey Found Fame Far from the Mainstream

Bailey's primary concern is, and always will be, her YouTube family.

I discovered YouTube artist Madison Bailey Wold, now known as Madilyn Bailey, in 2013, during my freshman year in high school. I was browsing for covers of songs, and one of her videos happened to pop up.

Young Bailey began singing and songwriting when she was just 7 years old. Soon after, she made it her mission to learn the piano, guitar and drums. Self-doubt was her biggest set-back, as it led her to believe she would never make it as an artist.

She uploaded her first video on YouTube in 2012. Much to her surprise, Bailey began blowing up on the site instantly and her views started to soar.

Now, 26-year-old Madilyn Bailey is becoming one of America’s top self-made artists. From acting to singing and songwriting, she continues to create a name for herself.

The Struggle

Bailey’s youth was spent bouncing around different sports. Coming from a small village in Wisconsin, when it came to starting her career as a professional singer, the odds were not in her favor.

She began recording covers in her bedroom with a camera, and decided to post them on YouTube. When she began to sing seriously for YouTube, she realized she had to choose between sports or building her YouTube career. Deciding music is where she wanted to take her career, she pushed herself and graduated from high school six months early.  

The Beginning of an Era

VidCon, hosted in 2013 at the Anaheim Convention Center, was a memorable moment for the singer-songwriter. VidCon is a major convention for YouTubers, vloggers and pros, and it gives people the opportunity to interact with famous people in the industry.

The exposé is a learning experience for all to gain insider knowledge on how to make it, and for those on the top to share their personal endeavors.

There, Bailey received the opportunity to go on her first tour in 2013 with the band Boyce Avenue. The young artist also successfully released her first album that year at age 20.

Her Dedication to YouTube

Dedication is an understatement when used to describe Bailey. She started out on YouTube, and doesn’t plan to ever completely leave or give herself to the mainstream media.

She appreciates fan interaction on YouTube. Without YouTube, she would not be as successful as she is today, boasting more than 6 million subscribers.

In an interview with New Media Rockstars, she said, “I think mainstream is nervous. I think they’re really nervous about the fact that anybody in the world can post a video and with the right video or right reaction from the crowd, they can be on the same relevance level as somebody who’s mainstream.”

Dear to the young artist’s heart, her brother influenced her focus on pop music. Creating her own unique style to other artists songs, she takes rap lyrics and remakes them into clean melodic pieces for her fans to enjoy.

The hard part occurs in LA where she produces her songs and music videos, which takes a lot of patience and long hours. At home in Wisconsin, she is able to experience life in her own little oasis and put that toward her lyrics.

As her career progressed, she was forced to make the move to LA permanently. She needed to be closer to her work to continue upgrading her YouTube channel, which gives her a sense of community.

Part of the reason Bailey had to make the move was because she was using outdated equipment to produce her videos. By making the move to LA, she was able to gain access to the right software and got a personal team. Despite the fact that she now has a team and state-of-the-art equipment, Bailey still occasionally makes videos for her channel on her own. 

Now living in L.A so close to all of the mainstream influence, she is constantly forced to make the right call for her future as an artist. These are tough decisions to make, as one wrong choice could ruin everything you have worked so hard for.

Bailey should be considered an icon. She truly has thrived by choosing to not go full mainstream. She is staying out of trouble and avoiding being the tabloid headlines.

Something as simple as not falling into the mainstream industry’s trap brings adds respect to her name. Bailey is someone who is making a life for herself while avoiding the drugs and alcohol that often follow fame.


Bailey is someone to look up to. She chased her dreams and is constantly experiencing success at every corner. She is interactive with her fans, which is admirable compared to others who pay little to no attention to the fanbase that gave them a name in the first place.

Being able to interact with famous individuals is very rare, because not many are presented with the opportunity to converse with someone they look up to. But Bailey goes out of her way to answer questions, give advice and never leaves her fans guessing.

Whether she is doing a cover or singing one of her personal songs, you will be sure to fall in love with her creations. She is an exceptional artist who started from the bottom and worked her way up the ladder, inspiring people every step of the way.

Looking back when Bailey first started her singing career, she was very timid and had to have someone beside her while she performed. The countless hours spent practicing, rehearsing and trying new things paid off. She tested her limits and hasn’t let anything hold her back since.

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