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

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

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