About Us


Join in the conversation after the episode. Share what you have been through that was similar and suggest topics for us to discuss.


Where we share our favorite excerpts from each episode and the photos relevant to what we have been chatting about.


Do you prefer video over podcasts? We video as we record so although the sound is not as strong, these are the unedited versions.

Our Why

We’re Sierra and Darren, two friends who are similar in some ways: we moved to Austin from NY in the same month in 2011, we got married (not to each other) a week apart in 2012 and we both love a good system. And that’s pretty much where it stops. In almost all other ways, we are polar opposites. We have however delighted in getting to the bottom of each other’s issues for years. Mostly because we each offer such a unique perspective on what the other is going through.

Over a year ago, we started musing about how our conversations would make a great podcast. Sierra because she is so obsessed with podcasts that she has abandoned TV and music for them. And Darren because his role models are Howard Stern and Frasier Crane, and the siren call of the microphone was calling to him. So here we are. Pouring our hearts out each week as we dive deep into the subjects that we all love to talk about but no one is doing out loud.


Meet the faces behind the voices.

Sierra Bailey

Co-Host, Writing & Marketing

Sierra’s life mission is to help people feel confident, supported and like they can do anything, which she does through coaching and speaking. In her free time, Sierra is obsessive about jigsaw puzzles, reading and exploring Austin with her husband Adam and dog Faye.

Darren Rootstein

Co-Host, Editing & Audio

Darren thrives when immersed in a life of nurturing, be it in raising his two sons with his wife Michele or tending to his plethora of plants. During his downtime, he can be found exploring new technology and listening to or making music (or watching Frasier).