Skylar is a transgender singer-songwriter, activist, educator, writer and artist currently living in Boston. Most often known on the internet as his pseudonym “Skylark” or “Skylarkeleven,” he began documenting his transition on YouTube in 2009 when he began hormone therapy, and as a result of his vlogs and written blogs has been invited to speak at numerous events across the United States. Skylar’s latest EP Tell Me A Story was released earlier in 2015, and there’s more music on the way. In this episode we talked about the importance of having a connection with your audience, songwriting, and how attitudes towards the LGBT community have changed over time. Enjoy!


  • We all have a Skylar (or Skyler) in our lives!
  • Skylar tells us about transitioning from female to male, and how music helped him through the process
  • Ross always goes with his heart
  • We talk about the importance of being vulnerable when writing and performing music
  • Skylar tells us how he’s always been influenced by artists...  

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