Ali Weiss chats with Rollacoaster...

New York on-air personality and content creator, Ali Weiss (@aliweissworld), is known for her anonymous confessions podcast, Tales of Taboo. Over 4 seasons, Ali has bridged the gap between host and audience by creating episodes around her listeners’ unique encounters within subcultures and roads less traveled. Now, entering Season 5, Ali’s going entirely solo to reveal her own juicy, unadulterated stories about failure and triumph, and the various ways she’s navigated the darker corners of the human experienced.

Armed with wisdom from her wildly adventurous and tumultuous 20s, and emerging from a particularly difficult 2023, Ali hopes to continue to fight the stigma and shame that exists for people – especially women – who choose to live life differently.

Read the interview below…

Hey Ali! For Season 5 of "Tales of Taboo," you're stepping out from behind the curtain of anonymity and sharing your own confessions. What prompted this change, and what can your audience expect from this deeply personal season?

Twenty-twenty three was simultaneously one of the best and worst years of my life. Going into it, I had my dream hosting job, a partner I thought I’d be with forever, and a body of podcast work I was really proud of. I finally felt set up for ‘adulthood’ (whatever that means). By June, I lost everything: I was unemployed and single at 30, and on top of that, a tech mishap led to 90% of my podcast archive getting deleted. I fell into a ‘2006 Lindsay Lohan getting hospitalized for exhaustion’-level burnout and decided to live off my savings for the summer to take time to reflect on the past 10 years. So much of my life has been a search for the next best thing: the next audition, paycheck, great story, crazy party, boyfriend, high. When it all came to a screeching halt, I didn’t know who I was. 

I needed to sort through some shit, and I figured by doing it out loud into a microphone, I might be able to make another lost, self-doubting person out there feel less alone. I’m in my ‘soft girl’ era right now, and it’s helped me build a lot of strength. I’m excited for my listeners to hear the duality, which is new for me.

Your podcast has been a safe haven for anonymous confessions, providing catharsis for many. Do you worry that sharing your own stories in this solo season might alter the unique connection you've built with your listeners?

Oh yeah! I was so paranoid about making them feel abandoned, or like I was selfish - there’s a tremendous amount of responsibility that comes with earning strangers’ trust and being told their secrets. I put off talking about myself for way longer than I wanted to, which is probably part of the reason I had this burnout-breakdown. But I’ve always chosen to leverage my parasocial relationships into a substantive mutual respect rather than just trying to sell them stuff. My hope is that after three years of being a safe haven for my listeners, they’ll be willing to step up and be the safe haven for me. Hopefully, at the end, they’ll end up feeling closer to me rather than resentful. 

Recording a solo season must have been a profoundly introspective experience. Can you share some insights into how this journey has impacted you on a personal level?

I thought sitting alone in a windowless room in front of a microphone and cameras and hot beauty lights with a full face of makeup on would feel artificial and emotionally stifling, but that setup forced me to really listen to myself as I talked. There were no distractions, no other places to go- man, it was intense. I wept in the studio every single session. 

I’m far away now from many of the experiences I talk about in these episodes, but it was shocking to feel how raw the emotions still are. Admitting to binging drugs and exercise in my lower periods wasn’t embarrassing - many of us do those things, right? - but saying out loud that I feel like a failure at 30? That I’m not sure I’ll ever be able to manage my ADHD and live up to my potential? It was so sad, and so cathartic. It’s the most authentic I’ve ever been, on or off-air.

You initially aspired to be an actress but found yourself taking a different path. Could you elaborate on how your journey led you from acting dreams to hosting gigs?

Performing is the only thing I’ve ever been good at - not just on stage with a script, but in life. Humor started as a coping mechanism to deal with middle school bullying and the extreme discomfort of going through puberty young; my public speaking skills came from talking my way out of poor grades and the principal’s office. To be honest, my involvement in theater began as a way to not fail high school and get myself into a decent college. Over the course of the next four years, it turned into my obsession, but I also grew resentful. As actors, our job was to hold up a mirror to humanity, but how were we supposed to know anything about humanity if we were trapped in the black box theater day and night, and discouraged from hanging with kids outside the department? Especially when we were all living and studying in a white, Republican California suburb?

After graduation (I’m actually 3 credits shy of a diploma, but who’s counting?) I spent my early twenties exploring other creative avenues that would allow me to meet people from diverse backgrounds. I was an art gallery manager, artist’s model, nightlife photographer, stand-in and extra for movies and TV. The first hosting job I ever had was talking about my grandmother’s sex life for A&E. Things snowballed and eventually, I became a full-time ‘professional conversationalist’. 

It’s been an incredible journey, and I wouldn’t change it for anything, but 8 years later, I really miss live theater. It’s still my passion and obsession. My 30s are dedicated to getting back there. 

Your work has exposed you to diverse corners of society, from political rallies to forest raves. Can you recall an unforgettable moment that solidified your passion for exploring the uncharted territories of human experience?

In October 2020, I flew alone from New York to LA after hearing that these massive Trump rallies were happening on Rodeo Drive in Beverly Hills. At the time, at least in New York City, everyone thought that Trump supporters were all hicks living in the middle of nowhere. Now, they were a block away from the Gucci store. I asked Mike Krim of Paperwork, who I had met only once on a wild night out in Paris, to come infiltrate a rally with me and film interviews. I threw on short shorts and an American flag printed mask, grabbed a microphone, and sent it. I wasn’t trolling the Trumpers, just asking questions — how they chose to respond was up to them. Q-Anon, Fags for Trump, Mexicans for Trump, Big Tech and Walmart conspiracy theories, theories about Hunter Biden giving out free crack to people who vote for Joe. This stuff has made its way to newspapers now, but I was absolutely flabbergasted at what I was hearing then. The video I made from that day went viral.

So many people asked me, “how were you not scared?!” I was drowning in adrenaline. I had been let into a sector of culture that nobody in my world - coastal ‘liberal elites’ - would ever see up close. It was like being in a parallel reality - like getting late-night access to a zoo or being in a museum alone. And when I emerged from it, despite not agreeing with much of what I’d heard and seen, I had a totally different, more compassionate understanding of the world. After that day, I was hooked on subculture adventures. 

Your ability to connect with an array of people in your interviews is remarkable. Can you divulge the secret behind creating authentic connections with such a wide range of guests?

Thank you - this means everything to me. Some of it comes from growing up in New York City near the insanity of Washington Square Park and West 4th Street, taking the subway at 10, raving and in nightclubs by 15. 2000s downtown Manhattan was electric- I was exposed to so many radically different people and creative environments outside of my private school bubble. Then, I moved across the country for college and was a Liberal in ‘Trump’s America’ before that was even a term. My whole life has been defined as a certain loneliness, an ‘otherness,’ but it’s ultimately what made me able to connect with whoever, wherever. 

Secondly, I judge racists, bigots, and bullies: other than that, I believe in taking people as they are, and I show up exactly as I am in return. There are very few people and places in this world that encourage us to be ourselves, and I try to be one of them. Our differences should make us interesting, not scary! I think that mentality helps my work, too. 

While we eagerly anticipate your solo season, can you provide any hints about potential celebrity guests who might make an appearance? Or is this season entirely dedicated to your own tales?

As of now, the season is shamelessly dedicated to moiand my trauma dumping. But some of my favorite episodes are the interviews I did with Katie Maloney, Whitney Port, and Megan Barton-Hanson in Season 3, and my hope is that airing out my own dirty laundry will encourage more rebels and rule-breakers living in the public eye to come do the same next season. Rappers, filmmakers, comedians, DJs- I have a long list of people I’m determined to get real with. Manifesting!

Humor plays a vital role in your work, even when discussing sensitive topics. Could you share a memorable instance where a well-timed joke unexpectedly lightened the mood during a profound conversation?

I was very open about the medical abortion I had in 2022. It was not an emotionally traumatic experience, but physically? WOW. All of the cramping and hormone fluctuations made me - sorry boys - insanely constipated, which led to the development of a truly gorgeous hemorrhoid. I had to place a Postmates order for both laxatives and Preparation H suppositories, and I’ll never forget the look on my delivery man’s face when the woman who opened the door was 28, not 82. He couldn’t even look me in the eye, just threw the bag at me and ran away. Telling that story on the podcast was the definition of finding humor in pain, which is imperative to making the pain bearable. 

The entertainment industry is evolving towards greater inclusivity. How do you plan to continue pushing boundaries and championing diverse voices and stories in your work?

My #1 goal over the past 3 years has been to make everybody feel welcome, seen, and heard while listening to Tales of Taboo. Of course, each audience member won’t relate to every story (most people aren’t drug dealers or in green card marriages, much to my chagrin), but there are larger philosophical questions embedded within each episode that I hope start honest conversations about fear, shame, judgment, and why we’re all so afraid to be different. Even this season, where I’m talking about myself, I’m airing out elements of my ‘darker’ sides to help people feel less alone in their own.

Looking ahead to your future projects, can you provide a glimpse of something that's been brewing in your creative mind, a project that has the potential to make a profound impact?

First and foremost, I’m working on making Tales of Taboo a live experience - creating a place where people can come lock away their phones and share secrets with open-minded strangers. I’m desperate for a more offline community, and the idea of creating a sense of anonymity in a world of constant surveillance makes me really excited. 

I’m also finishing up my one-woman show, which like - yes, groan, we’re seeing a lot of these days, but I’m excited to get back to my Theatre roots and share very secret, raw parts of myself in a more stylized, character-centric format. I’m hoping both of these projects allow me to be a full-time stage performer within the next few years.

As a trailblazer in taboo conversations, what legacy do you envision leaving in the ever-evolving media landscape, and what's your ultimate goal as you continue to break boundaries and challenge norms?

That’s very nice to say. I definitely hope my eyebrows go down in history- it would alleviate some of the childhood trauma. I hope to be seen as someone who helped redefine the idea of what it means to be ‘ladylike’ or a ‘good girl’: showing that women can be brilliant even with their tits out, family-oriented (or not!) yet uncompromising in their independent identities, loud and opinionated yet deserving of tenderness. I hate that “complicated” is used as a bad word when describing women. For some reason it’s seen as threatening when women aren’t easy to classify. I hope that not shying away from ANY of my many different sides - and embracing that none of them can exist without the other - it’ll encourage other women to be a little more okay with not fitting the mold.

What will listeners take away from season 5 of Tales of Taboo and why should they listen to it?

I’m excited for both longtime and new listeners to understand my motivation for wanting to explore subcultures and tell unconventional stories. Sometimes I get paranoid that it looks like I’m fetishizing people who come from less privileged backgrounds or live on the fringes of society. Nobody’s ever accused me of this, but again, with trust and vulnerability comes great responsibility. The idea that someone might think I’m taking advantage of them for content makes me sick.

By sharing the same parts of myself I have asked my audience to share with me, I hope the host-listener dynamic will become equalized and expose all the ways we’re not so different. In certain ways my life has been blessed beyond measure, and in others it’s been insane. Both sides have equally contributed to my desire to learn about what it means to be alive.

Ali's decision to share her own story is a testament to the evolving landscape of podcasting. Season 5 of "Tales of Taboo" promises an intimate journey through vulnerability, authenticity, and the blurred lines between host and storyteller. As Ali steps into the spotlight, this season of the podcast is an exploration of self that mirrors the rhythm of the human experience. This season redefines taboo conversations and invites the listener to join the journey of an enigmatic host embracing their own narrative in the unfurling chapters of “Tales of Taboo.”

Words by Tristen Jithan

Photography (35mm): Emma Louise Swanson

Creative Direction: Emma Louise Swanson

Lighting: Evadne Gonzalez

Makeup: Christina Siordia

Hair: Kristin Arrigo

Red Dress: Magda Butrym

Green Dress: Costarellos

Snake Necklace: Whiting & Davis

Bracelet: Cartier