1. Bits and Bobs and Judy Garland with Debbie Wileman Jeff Dwoskin 43:46

Following in the footsteps of Judy, Barbra, and Gaga, Debbie Wileman seems to be creating her very own A Star is Born story.

Over the pandemic, Wileman began singing “A Song A Day” and posting videos of timeless songs on Facebook. With over one million views later, she became an internet sensation with global fans. Following two sold-out performances in November 2021 in London starring in Little Massive Voice, Wileman won the audience award for “Best Vocalist” with the Broadway World Cabaret Awards.

My guest, Debbie Wileman and I discuss:

  • Debbie’s background and early aspirations of being a singer
  • How the pandemic re-ignited her passion for singing to help entertain her friends lonely at home alone during lock-in
  • How Debbie decided to sign a song a day on Facebook
  • Going viral singing as Judy Garland with the help of a Judy Garland Facebook group
  • Being signed by an agent in LA (America)
  • Recording the album “I’m Still Here” – a collection of songs song as Judy Garland
  • Landing her first USA date at Carnegie Hall singing as Judy Garland for the 100th celebration of Judy Garland
  • Touring as Judy Garland

You’re going to love my conversation with Debbie Wileman

Our Guest, Debbie Wileman

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Jeff Dwoskin Podcast Host

I'm a tech entrepreneur, podcaster, and professional stand-up comedian. I started my journey in the tech industry back in 1997 when I founded my own website development company, which was one of the pioneering companies in the country at the time. While working in technology, my comedic talents couldn't be contained, and I eventually took to the stage as a stand-up comedian.

My passion for comedy led me to create Hashtag Roundup (@hashtagroundup on Twitter), a platform that has contributed to over 8000 top 10 USA trends on Twitter. With the growth of social media, particularly Instagram, I founded Stampede Social, a company aimed at helping creators drive traffic to their content without relying solely on a link in their bio.