In this When We're Not Hustling After Party episode, hosts Jessie Sage, Emily Foster, and Emery Fields discuss Josie Oakley's episode, highlighting her dedication to organizing safe, inclusive sex-positive events and her activism with SWOP Pittsburgh. They explore how Josie’s work extends beyond event planning, advocating for reduced penalties for prostitution to make sex work safer and more accessible. The hosts examine the social dynamics and thoughtful guest curation that go into Josie's events, balancing newcomers with regulars, while discussing the importance of consent, self-awareness, and accountability. Reflecting on Josie’s honesty about her personal growth around past consent issues, they emphasize the need for open communication and self-reflection in fostering respectful relationships.

In This Episode:

00:05: Introduction to the Episode

00:24: Meet the Hosts and Guest

00:59: Hosting Sex Parties with Josie Oakley

01:35: Similarities to Bartending and Event Hosting

03:15: Social Dynamics of Sex Parties

05:18: Gender Dynamics and Initiating Interaction

08:53: Importance of Emotional Safety

11:14: Trust and Curating Guest Lists

15:28: Navigating Consent and Boundaries

26:26: Validating Feelings and Effective Communication

People:

Guest: Josie Oakley

Hosts: Jessie Sage, Emily Foster, Emery Fields

Producer: Emily Foster

Music: Benjamin J Benamati

You can support the show at pateron.com/sapiotextual

When We're Not Hustling is a 501(c)(3) non-profit project of the Social Good Fund.

You can support our show with your tax-deductive donation HERE.

In this episode of When We're Not Hustling, host Jessie Sage sits down with Josie Oakley, a Pittsburgh-based escort and advocate. Josie discusses her personal journey and her efforts to create safer, more inclusive spaces, including organizing "No Boys Allowed" sex parties. These events prioritize safety, consent, and community, providing a much-needed refuge from the presence of cis men.

Josie also highlights her advocacy with SWOP Pittsburgh, where she is working to change local laws to reduce sex work penalties to civil violations. Additionally, Josie talks about her involvement in creative projects like the "Only Bans" game. Tune in to learn more about Josie's advocacy work and the importance of supporting sex workers’ rights and representation.

In This Episode:

00:01: Introduction to When We're Not Hustling

00:43: Welcome from Host Jessie Sage

01:23: Overview of Podcast's Purpose

02:46: Introduction of Guest Josie Oakley

04:12: Josie Oakley Introduces Herself

05:24: The Concept of "No Boys Allowed" Parties

08:42: Establishing Party Norms and Safety

14:32: Josie's Experience with Hosting Parties

29:00: Josie Discusses Local Pittsburgh Organizing

49:35: Final Thoughts and How to Connect

Guest:

Josie Oakley is a professional canoodler based in Pittsburgh. She's an advocate, an artist, and a general mischief-maker.

You can find :

X: @theJosieOakley

Instagram: @theJosieOakley

Recommendations:

Constraints by Stefan Triplett

The Seven Husbands of Evelyn Hugo: A Novel by Taylor Jenkins Reid

Thriving In Sex Work by Lola Divina

The Rest:

Host: Jessie Sage

Producer: Emily Foster

Music: Benjamin J Benamati

Sponsor: Assembly Four

Powered by Black Venom Digital

When We're Not Hustling is a 501(c)(3) non-profit project of the Social Good Fund.

You can support our show with your tax-deductive donation HERE.

In this episode of When We're Not Hustling: The Afterparty, hosts Jesse Sage, Emily Foster, and guest host Emery Fields discuss the concept of "bedrotting," inspired by a recent episode featuring Lana Hart—a New York City-based stripper, writer, sex worker, and stand-up comic. In her article for the Tryst Blog titled "Hobby Whores," Lana describes "bedrotting" as the intentional act of lying in bed to relax and recharge. The hosts emphasize the importance of viewing downtime as an active and valuable part of self-care, especially in a hustle-driven economy where constant productivity is often the norm. They highlight how scheduling time for rest is essential for mental health, creativity, and maintaining balance.

The discussion also delves into the challenges of separating personal life from work as artists and freelancers, where even moments of relaxation can feel tied to productivity. Each host shares their experiences with balancing work and downtime, striving to embrace rest without constantly measuring it against their professional output. They conclude by celebrating the joy of transforming everyday experiences into art and meaningful discussions while acknowledging the necessity of rest to sustain their passion and effectiveness.

In This Episode:

00:12: Introducing guest host Emery Fields

01:02: Discussing live event and upcoming episodes

02:02: Explanation of bedrotting and its origins

03:20: Bedrotting as a restorative process

05:04: Bedrotting compared to couch relaxation

06:47: Watching TV as part of bedrotting

09:02: TV shows and off-grid living discussion

10:49: Balancing work and life with active bedrotting

17:37: Scheduling downtime for mental health benefits

People:

Guest: Lana Hart

Hosts: Jessie Sage, Emily Foster, Emery Fields

Producer: Emily Foster

Music: Benjamin J Benamati

You can support the show at pateron.com/sapiotextual

When We're Not Hustling is a 501(c)(3) non-profit project of the Social Good Fund.

You can support our show with your tax-deductive donation HERE.

In this special crossover episode with Tryst blog's "Hobby Whores" column, host Jessie Sage sits down with Lana Hart, a sex worker, comedian, and writer, to explore the concept of "bed rotting." Described as the act of lying in bed to recharge and care for oneself, bed rotting is framed as an essential form of self-care—especially for those in demanding professions like sex work.

Together, Lana and Jessie discuss the mental and emotional demands of sex work, from the pressure of constant social engagement to the need for meaningful downtime. They challenge societal expectations around productivity, emphasizing that rest is a valuable activity rather than a guilty indulgence. The conversation also covers the balance between personal relationships and the intensity of their work, underscoring the importance of dedicating time to oneself. By embracing restorative activities like watching favorite shows or pursuing hobbies, the episode highlights the therapeutic benefits of rest and self-care.

Lana Hart's Article:

Hobby Whores: Bedrotting with Lana Hart

In This Episode:

00:01: Introduction to When We're Not Hustling

01:24: Overview of Podcast and Mission

02:44: Crossover Episode with Tryst Blog

03:58: Raffle Announcement and Future Episodes

05:16: Introduction of Guest Lana Hart

06:27: Lana Hart Discusses Bed Rotting

09:18: The Importance of Rest in Sex Work

17:30: Challenges of Maintaining Social Energy

20:08: Regular Clients and Relationship Dynamics

21:32: Bed Rotting as Self-Care Practice

Guest:

Lana Hart is a comedian, sex worker, and writer; a woman who wears many hats and sometimes wears nothing at all.

Lana moved to New York City in 2014 after graduating from Emerson College to pursue a career in stand up comedy and comedy writing. While doing nightly comedy shows, occasional tours, and various freelance gigs, she picked up multiple side hustles to support herself. In 2018, she finally found one that stuck when she began stripping. Lana’s experience with sex work made its way into her comedy writing, as she found a passion for presenting audiences with the radical idea that sex workers are people who deserve respect. She dedicated her punchlines to lifting up sex workers and punching down on narrow-minded people who discriminate against them. She also wrote multiple articles for Betches Media advocating for sex workers’ rights and the decriminalization of sex work. Her written work has also been featured on Reductress, Someecards, Paste Magazine, and Tryst.

You can find Lana:

X: @lanadelslayee

Instagram: @lanadelslayee_

Recommendations:

SLUTS: Anthology by Michelle Tea

Charli xcx

The Rest:

Host: Jessie Sage

Producer: Emily Foster

Music: Benjamin J Benamati

Sponsor: Assembly Four

Powered by Black Venom Digital

When We're Not Hustling is a 501(c)(3) non-profit project of the Social Good Fund.

You can support our show with your tax-deductive donation HERE.

In this episode of "When We're Not Hustling: The After-Party," the hosts explore the themes of singlehood, societal expectations, and the importance of friendships through the lens of Gem DeMilo's story. Gem, who has chosen to remain intentionally single after past relationships, sheds light on the societal pressure to prioritize romantic relationships and how she values friendships instead. The discussion also delves into how societal norms often restrict men from forming intimate friendships and how this contributes to a loneliness epidemic. Moreover, the conversation highlights how being single can be an empowering choice rather than an indication of loneliness, as it allows individuals to focus on self-growth.

The hosts share personal anecdotes about navigating relationship dynamics and challenge the traditional view of relationships being solely romantic or monogamous. They emphasize that friendships and professional relationships, including those in sex work, can also provide fulfillment when the transactional nature is understood and respected. The episode concludes with an affirmation of the value of diverse relationships and the importance of expressing love and appreciation for friends.

In This Episode:

00:34: Hosts Introduce Themselves

00:51: Gem DeMilo's Choice to Be Intentionally Single

01:43: Societal Expectations of Relationships

03:06: Cultural Views on Monogamy and Intimacy

05:23: Masculine Socialization and Emotional Isolation

07:21: Financial Independence in Single Life

09:14: Redefining Relationship Dynamics

14:42: Singleness as Self-Actualization

33:33: Closing Thoughts on Relationships

People:

Guest: Gem DeMilo

Hosts: Jessie Sage, Emily Foster, Melissa Milk

Producer: Emily Foster

Music: Benjamin J Benamati

You can support the show at pateron.com/sapiotextual

When We're Not Hustling is a 501(c)(3) non-profit project of the Social Good Fund.

You can support our show with your tax-deductive donation HERE.

Host Jessie Sage sits down with Gem DeMilo for a heartfelt discussion about redefining fulfillment beyond romantic partnerships. Gem opens up about her solo journeys to Mexico City and Iceland, sharing how travel has deepened her life’s meaning and enriched her sense of self. Together, they explore the importance of close friendships, the unique joys of single life, and the ways society’s expectations can often obscure personal happiness. Gem emphasizes that her connections with friends and her beloved pet have brought her profound love and contentment.

Their conversation also delves into the challenges and misconceptions surrounding polyamory, as well as the critical role financial independence plays for women. Gem shares insights from her path of healing past relationship traumas, finding empowerment in being single, and reclaiming her self-worth beyond societal standards. The episode wraps up with Gem's excitement for her upcoming 40th birthday celebration in New Orleans, and her commitment to financial literacy as a tool of empowerment for herself and others.

In This Episode:

00:01: Introduction to When We're Not Hustling Podcast

02:44: Updates & Upcoming Events

05:20: Announcement of Collaboration with Tryst

07:52: Introduction of Guest Gem DeMilo

09:08: Gem DeMilo Discusses Being Single

17:20: Gem's Life Changes & Moving to North Carolina

21:31: Finding Love & Fulfillment Outside of Relationships

32:25: Discussion on Solo Poly & Single Life

42:34: Reflections on Self-Worth & Letting Go

54:44: Conclusion & Excitement for Future Plans

Guest:

Gem DeMilo is a North Carolina based escort, originally from Chicago. She got her start in sex work back in 2009 working for a commercial dungeon as she worked on her MFA in creative writing. She quickly transitioned to sugaring, and transitioned to escorting quickly from there. In her spare time, she enjoys reading, writing, traveling, barre and volunteering with animals. She often snuggles with her feline son and soulmate, Jean-Claude.

You can find Gem:

Website: professordemilo.com

X: @meetgemdemilo

Instagram: @shesageminnc

Recommendations:

The Financial Feminist by Tori Dunlap

Girls Just Wanna Have Funds by Camilla Falkenberg, Emma Due Bitz and Anna-Sophie Hartvigsen

Conan Obrien Needs A Friend

Crime Junkie

Important Note:

This episode was recorded prior to Hurricane Helene. Gem, who lives in Western North Carolina, would like to highlight several charities providing essential relief to Asheville and nearby communities.

Beloved Asheville

Manna Food Bank

Brother Wolf Asheville

The Rest:

Host: Jessie Sage

Producer: Emily Foster

Music: Benjamin J Benamati

Sponsor: Assembly Four

Powered by Black Venom Digital

When We're Not Hustling is a 501(c)(3) non-profit project of the Social Good Fund.

You can support our show with your tax-deductive donation HERE.

In this episode of "When We're Not Hustling: The After-Party," the hosts discuss Kaytlin Bailey, a multifaceted individual who has significantly influenced the podcasting, sex work, and activist communities. Jessie Sage, Emily Foster, and Milk Glass delve into Kaytlin's extensive contributions, including her critical feedback shaping the show's messaging that sex work is legitimate work. They also highlight her historical insights and her juxtaposition of personal experiences, such as her father's military service and her own sex work, to explore broader societal issues. The conversation underscores Kaytlin's impact on the hosts and the themes of their show, emphasizing the importance of recognizing sex work as valid and respectable.

Additionally, the hosts discuss Kaytlin's dynamic career, which includes being a comedian, sex worker, historian, and boxer. They admire her ability to weave together various aspects of her life into a cohesive narrative that challenges societal norms and addresses issues like misogyny, PTSD, and legislative impacts on sex work. The episode is a tribute to Kaytlin's intelligence, resilience, and the transformative power of her work, encouraging listeners to appreciate the depth and complexity of her endeavors. The hosts' admiration for her as a "main character" in their lives reflects the profound influence she has had on them and their audience.

In This Episode:

00:02: Introduction to the After-Party Podcast

00:23: Host and Co-Hosts Introductions

00:42: Kaytlin Bailey's Impact on the Podcast

01:44: Validating Sex Work as Legitimate

03:38: Comedians' Intelligence and Timing

04:21: Discussing Rap's Cognitive Demands

05:22: Kaytlin's Show and Social Commentary

07:54: Boxing and Kaytlin's World Tour

10:33: Gender, Kink, and Feminine Rage

14:00: Transformative Experiences and Emotions

People:

Guest: Kaytlin Bailey

Hosts: Jessie Sage, Emily Foster, Melissa Milk

Producer: Emily Foster

Music: Benjamin J Benamati

You can support the show at pateron.com/sapiotextual

When We're Not Hustling is a 501(c)(3) non-profit project of the Social Good Fund.

You can support our show with your tax-deductive donation HERE.