Courtney chats with Hillary Comstock, a creative director of 13 years within the fashion, beauty, and media spaces for a deep-dive into career, confidence, and cultivating a matriarchal balance in the workplace. Hillary shares how moving to New York to pursue career dreams in her 30s was the right call, and why being bold in her 20s set her up for real evolving success. They explore the importance of an equitable workplace, leading with empathy, and shaping work cultures based on the lessons she wished she'd learned earlier. Plus, Hillary honors the matriarchs who shaped her: her mom, a teacher who instilled a love for work, and her powerhouse stepmom, who thrived in a male-dominated field and led by example.

Courtney sits down with award-winning filmmaker and videographer for Vice President Kamala Harris, Azza Cohen and her wife, personal stylist, producer, and public interest lawyer, activist Kathleen Borschow. From supporting each other's wildest dreams—even when it means pivoting careers in their 30s (and even missing their own honeymoon to work on Kamala Harris' campaign!), Azza and Kathleen's love story is one of deep admiration, bold choices, and showing up for each other no matter what. The two of them open up about the fierce, resilient matriarchs who shaped their families - especially their bold grandmother who helped bring an entire community to the U.S. to another who taught the power of kindness. Azza shares behind-the-scenes stories from working on VP Kamala Harris' campaign, the inspiration behind her documentary work, and how listening with compassion makes for the best storytelling. We also find out what is next on the horizon for Kathleen and Azza's newly launched company, Cohen Borschow Media - and how they are continuing their shared commitment to changemaking through storytelling that matters.

Courtney chats with Erin LeBre, a two time Emmy and Guild Award nominated makeup artist and creative force, for a conversation about reinvention, resilience, and the power of maternal influence. Erin opens up about her early dreams of working in fashion, and the burnout that led her to an unexpected career pivot into working in the film and television industry. They dive into the art of saying no, the courage it takes as a freelancer to bet on yourself, and why success is something you're allowed to redefine at every stage of life. At the heart of Erin's journey is her mother—a single mom who raised two very different daughters with wisdom, grace, and an instinct for knowing exactly what kind of support they needed. Erin shares how her mother's unwavering belief in her shaped the way she approaches her career and life. It's a conversation about evolving, trusting the process, and staying a kid at heart.

Courtney chats with Cynthia Addai-Robinson, American Actress for a heartfelt conversation about boundaries, balance, and the legacy of matriarchs. Cynthia opens up about recalibrating her nervous system through presence, re-entering real life after projects like The Rings of Power, and how playing a queen has shaped her sense of self and authority. They bond over their love for musicals and dive deep into the incredible journey of Cynthia's mother, Victoria Addai and her own fearless risks, entrepreneurial dreams, and the creative spirit she passed down to her daughter. From moving to the U.S. at age 4 to a full-circle premiere moment in London, Cynthia reflects on how the matriarchs in her life have shaped generations of resilience and inspiration. It's all about taking risks, creating legacies, and embracing the funny (and humbling) realization that we all become a little more like our mothers every day.

Courtney chats with Caity Bransby, a Social Media Strategist, for a deep-dive into family, perseverance, and of course, the magic of matriarchs. Together, they reflect on the eldest-daughter experience, the joy of built-in best friends via having amazing siblings, and finding self-reliance through family love. Caity shares behind-the-scenes stories from her work spearheading the 2024 Paris Olympics social strategy (!!!), how she identifies defining moments in her life and career, and the fearless producer who empowered her to innovate. They unpack ocean therapy, inner-child healing, and the hunt for the perfect cinnamon roll. Plus, hear from the legend herself—Grandma Jean!

Courtney chats with Alexis Linkletter, an Investigative Journalist and True Crime Producer for a deep-dive into ambition, empathy, and the realities of being a woman trailblazing in male-dominated spaces. Together, they embrace climbing "cringe mountain", reflecting on the awkwardness of finding your voice and recovering from people-pleasing tendencies. They unpack the emotional labor of working in the True Crime and Film industries, the magic of finding unexpected matriarchs, and how to keep kindness front and center—even when the "villain era" calls. Alexis shares stories of her mom's love, eldest-daughter grit, and a career low that turned into a defining moment of growth.

Courtney chats with Olivia Marks, an Entertainment Journalist based in the UK who is obsessed with all things film and pop culture. Olivia shares highlights from her amazing career and journey thus far, including interviewing iconic artists like Olivia Coleman, Amy Poehler and her idol, Lady Gaga. Olivia also shares about learning to embrace asking for what you want and we wax on about the experience of being eldest daughters and how it shaped our respective careers. Olivia reflects on her laid-back mom's calming energy and how her two role models / matriarchs, though so different, both have guided her and paved the way for her successes to date.

Courtney chats with Canadian actor, writer and producer, Mariah about growing up in a strong matriarch-led home, how being involved in sports translated into starting her own production company at 21, and that working hard and being kind will always lead you closer to your dreams. We also spoke about her late grandma Hazel's perseverance during the Great Depression and her great-grandmother Mary's immigration from Romania to Canada set in motion a legacy of love and wisdom, inspiring Mariah's passion for life and storytelling through film.