When New Yorker, comedian, investigative journalist, and Tales of Taboo podcast host Ali Weiss first dipped into the podcast scene, she realized that there was a hunger for brutal honesty in the digital community, and with her first podcast, Health is Hell, she embarked on a journey to cultivate that sense of transparency. While she thought she might end up in theater after spending her undergraduate years at Chapman University in Southern California, she took a turn into content creation to chase that sentiment.

In the spirit of talking about things that truly matter, she’s joining me on today’s podcast to discuss growing up in the great big city of New York, how she landed in the mental health podcast scene, and the way in which people use shock value and/or brutal honesty on the internet to stay relevant.

“We have become obsessed with feeling as though we matter.” – Ali (24:49) As comedians, public speakers, mental health advocates, and podcast hosts, Ali and I talk through what it looks like to tell your story and how sharing your triumphs and struggles with the world can make for an intense experience. Despite the difficulties she faced in creating Health is Hell, it informed how she built her current podcast, Tales of Taboo.

“Even if you are an extremely honest person online, you’re still only showing one small part of yourself.” – Ali (29:11) Finally, Ali dives into her experience growing up in New York, how privilege and money is often regarded in the mental health community, and ultimately, her abortion experience. She boldly analyzes how money and privilege influenced this recent procedure for her and why she felt she had to share her story.