• S2 E20 AP: I Throw Sex Parties, and There's No Boys Allowed
    Nov 20 2024

    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.

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    34 mins
  • S2 E20:I Throw Sex Parties, and There's No Boys Allowed with Josie Oakley
    Nov 18 2024

    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 for sex workers, 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.

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    50 mins
  • S2 E19: The Holy Hour Book Launch Special Live Episode
    Nov 11 2024

    In a special live episode of *When We’re Not Hustling*, host Jessie Sage collaborates with Stay Gold Books, Working Girls Press, and SWOP Pittsburgh to celebrate the launch of *The Holy Hour: An Anthology of Sex, Work, Magic, and the Divine*. The event features impactful readings from the anthology, alongside discussions on the intersections of sex work, spirituality, and identity. Emily Foster leads panel discussions that dive into themes of integrity, emotional labor, and boundaries, bringing depth and nuance to the conversation around sex work.

    Speakers underscore the importance of community support, highlighting how solidarity helps sex workers navigate societal stigma and limited resources. Listeners are introduced to *I Hate My Job: Thoughts on Labor, Sex Work, and Capitalism*, written by Adrie Rose and set for publication by Working Girls Press, with a call for Kickstarter support to uplift sex worker voices. The episode concludes with reflections on radical boundaries, self-empowerment, and the strength rooted in collective resilience.

    In This Episode:

    01:25: Host Jesse Sage introduces the podcast

    04:02: Opening remarks and event sponsors

    06:49: Musical interlude by Emily Foster

    08:05: Molly Simmons discusses Working Girls Press

    12:21: Introduction of panelists and discussion format

    14:47: Jesse Sage reads her essay on religion and sex work

    25:24: Panel discussion: Religion, motherhood, and sex work

    44:08: Brita Love's essay on power dynamics in sex work

    1:05:28: Intermission and musical performance by Emily Foster

    1:13:13: Elena Egusquiza's essay on sex work as resistance

    1:35:43: Ashley Ramos reads Amber Délice's essay on integrity in sex work

    2:06:59: Announcing new book project by Adrie Rose

    2:07:27: Audience Q&A session

    2:42:32: Closing remarks and group yell: Radical Boundaries

    Collaborators:

    Working Girls Press

    Stay Gold Books

    SWOP Pittsburgh

    Sponsors:

    Inclusive Aesthetics

    Buzz Me In

    Music:

    Emily Foster

    Sound:

    PJ Patella-Rey

    Panelists:

    Molly Simmons

    Adrie Rose

    Readers:

    Nicci

    Melissa Milk

    Ashley Luz Ramos

    Writers:

    Amber Délice

    Britta Love

    Elena Egusquiza

    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.

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    2 hrs and 43 mins
  • S2 E18 AP: I'm a Proud Bed-Rotter, and I Think Everyone Should Try It
    Nov 6 2024

    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.

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    36 mins
  • S2 E18: I'm a Proud Bed-Rotter, and I Think Everyone Should Try It with Lana Hart
    Nov 4 2024

    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.

    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.

    Lana’s stand-up comedy, published articles, and social media content aim to rid people of their whorephobia and inspire them to cherish whores as much as she does. She wants you to laugh but she also wants you to shut up and listen.

    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.

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    41 mins
  • S2 E17 AP: I'm Happier, Wealthier, and More Satisfied Single
    Oct 30 2024

    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.

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    34 mins
  • S2 E17: I'm Happier, Wealthier, and More Satisfied Single with Gem DeMilo
    Oct 28 2024

    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.

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    58 mins
  • S2 E16 AP: It's Not Funny to Get Punched in the Face, but I Do It Anyway
    Oct 16 2024

    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.

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    34 mins