Hustle Her

Deshay Caines
  • 4.4 (16)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

Hustle.Her is about inspiring women through real-life experiences that have helped to mold and develop Deshay and her guest into the entrepreneurs and leaders they are today. Follow Deshay as she talks with female entrepreneurs, leaders, and ultimate hustlers. Hustle.Her will give you a little kick in the butt, leave you inspired, motivated, and give you some actionable takeaways to be the best you. 

  1. Hustle Her - Dr. Jana

    10/12/2025

    Hustle Her - Dr. Jana

    What if the bravest thing you can say is, “I became a psychologist to save myself”? That line from Dr. Jana Otterbridge sets the tone for a conversation that moves with heart and precision, from adoption and identity to trauma, triggers, and the radical act of finding a therapist who truly fits. We don’t stay on the surface. We talk about the unnamed questions adoptees carry, the long tail of psychological injury, and how healing starts when we stop calling our wounds a personality and start building new responses with care. We also zoom out to the systems shaping us. Jana shares how UK training sharpened her voice when leadership curricula erased Black examples, and why representation isn’t a buzzword, it’s a map. We get honest about the multigenerational workplace: Boomers, Gen X, Millennials, and Gen Z colliding over “work ethic” and mental health. Instead of the tired “work-life balance” script, Jana offers a practical capacity framework, adjustable daily “bubbles” that match energy to commitments without guilt. It’s a mindset shift leaders can operationalize and individuals can practice right now. Threaded through it all is purpose. Jana describes peace as the sign she’s on path, able to teach in a boardroom at noon and mentor on a street corner by dusk. She speaks to her younger self with tenderness, “you’re safe, you’re free”, and imagines a next chapter that includes anonymous giving and wider impact. If you care about mental health, organizational culture, representation, or simply living with more truth and less noise, this one will stay with you. If this conversation moved you, share it with a friend, subscribe for more honest stories, and leave a review to help others find the show. What capacity are you honoring today?

    44 min
  2. Hustle Her - Michelle

    09/21/2025

    Hustle Her - Michelle

    What happens when you step away from a successful career to rediscover your authentic self? Michelle Seymour-Smith's story offers a masterclass in intentional career transformation. Growing up in Spanish Point, Bermuda as a shy middle child, Michelle found her professional calling early – at just 13, she was helping with general ledger entries at an insurance company. This early exposure to accounting set her on a path that would lead to a 16-year career culminating as CFO. But when burnout hit, Michelle made the brave decision to walk away. "I literally just turned to my husband and said 'I'm done,'" Michelle recalls. His simple acceptance opened the door to what she calls her "year of yes" – exploring everything from Reiki certification to daily yoga practice. Most significantly, she challenged herself to have 200 meaningful conversations, a practice that organically led to board opportunities and a whole new career chapter. Michelle's perspective on leadership resonates deeply: "Leadership is respect for people." Drawing from mentors who valued her contributions from a young age, she emphasizes the importance of helping employees understand their role in the company's mission while giving them agency in how they accomplish their work. For women specifically, she advocates authenticity about the challenges of balancing career and family responsibilities. What makes Michelle's journey particularly compelling is her recognition that "those things that make you different are your superpower." Whether feeling like an outsider culturally (with a Bermudian father and Portuguese mother), being the only woman in executive meetings, or transitioning careers when others might have stayed the course, Michelle found strength in her unique perspective. At the heart of Michelle's story are two principles she hopes to be remembered for: knowing your own value and recognizing your agency to make choices. "When you hit that stage of empowerment, when you really truly realize what you're capable of, nothing can stop you," she shares. "It's this feeling of being unleashed." Ready to discover your own value and unleash your potential? Michelle's journey might be exactly the inspiration you need.

    41 min
  3. Hustle Her - Nicole

    05/18/2025

    Hustle Her - Nicole

    Nicole Fox knows the depths of loss and the heights of resilience, and she shares her inspiring journey with us in this moving episode. A devoted mother and tireless advocate from Bermuda, Nicole opens up about the heart-wrenching loss of her son Rico to gun violence and how it transformed her life. Her story is not just about tragedy but about finding purpose through pain, as she co-founded Mothers on a Mission to support families affected by violence. Nicole’s candid reflections invite us to understand the profound impact of violence on families and communities, and her unwavering commitment to advocacy and healing. Nicole's journey is one of profound personal transformation, as she navigated her path to sobriety amidst relentless grief. Through spirituality and a 12-step program, she found strength and guidance, even in the darkest times. She talks openly about her battle with addiction, the role of divine intervention in her recovery, and the immense challenge of maintaining faith after her son's tragic death. Her narrative is a testament to the incredible power of forgiveness, inner resilience, and the light that can guide us through the darkest moments of life. As our conversation continues, Nicole emphasizes the importance of community and shared experiences in healing. She speaks passionately about her mission to provide hope and solidarity to those grieving, highlighting the significance of parental forgiveness and community advocacy. By founding a support group for mothers who have lost children to violence, Nicole not only honors the memory of those lost but fosters a supportive environment for others facing similar struggles. Her story is one of legacy and overcoming adversity, rooted in faith and the unwavering strength of family, offering inspiration and guidance to anyone navigating the painful journey of loss.

    52 min
  4. Hustle Her - Polina

    12/01/2024

    Hustle Her - Polina

    Discover the inspiring journey of Polina Branco, CEO of Two Point O Collective, as she shares her unique life story from growing up under communism in Southeastern Europe to leading a thriving creative agency in Bermuda. With compelling anecdotes from her childhood in diverse countries like Iraq and Cuba, Polina’s narrative is a testament to the power of education and resilience. This episode promises a rich tapestry of insights into how her early experiences have shaped her worldview, leadership style, and personal philosophy, offering valuable lessons on love, happiness, and contentment. Explore the responsibilities of leadership through the lens of Polina’s  personal experiences, especially during challenging times like the economic impacts of COVID-19. She candidly discusses the transformative rebranding of Two Point O Collective and how her move to Bermuda led to meeting her husband and forming a life-changing partnership. Polina’s reflections on leadership, resilience, and personal growth provide a nuanced understanding of the profound connections that shape both personal and professional journeys. The conversation also highlights the struggles and triumphs of women in leadership roles, particularly in board positions. Polina shares her journey to becoming a board director and the hurdles women face, especially in Bermuda, due to historical gender biases. We discuss the importance of building a personal brand, advocating for diversity and inclusion, and supporting local businesses. Polina’s insights are aimed at empowering women to break barriers, foster meaningful change, and embrace the balance between career and personal growth. Join us for an episode filled with empowering stories and strategies for genuinely impactful leadership.

    54 min
  5. Huste Her - Laurie

    11/10/2024

    Huste Her - Laurie

    Laurie Shiell from the Center Against Abuse joins me on the Hustle Her Podcast to share her heartfelt journey and insights into combating domestic violence. From her passion for Somerset cricket and morning rituals to her adventures in Korean skincare, Lori offers a personal glimpse into her life. We uncover the vital services the Center Against Abuse provides, such as counseling and legal advocacy, while discussing the pressing challenges of finding safe housing in Bermuda and the critical role of community awareness and support in addressing domestic abuse. Understand the complexities behind why victims remain in abusive relationships by exploring psychological and societal factors. Our discussion dives into the addictive nature of brain chemistry and how societal norms pressure both women and men to remain in toxic environments. We also touch on the unique difficulties faced by men, highlighting financial dependency and emotional manipulation as significant barriers to leaving. This conversation aims to foster a deeper understanding that can translate into more effective support for those trapped in the cycle of violence. Recognizing early signs of abuse is crucial, and Laurie and I walk through subtle indicators that can easily be overlooked. By examining behaviors like excessive control disguised as care, we stress the importance of trusting one's intuition and seeking help. We talk about the profound effects of abuse on children and the vital role of child services and school counselors. Friends and family play an essential role in supporting victims, and our discussion offers actionable guidance on how unwavering support can break the cycle of violence and create a path toward healing.

    47 min
  6. Hustle Her - Christie

    09/29/2024

    Hustle Her - Christie

    Have you ever wondered how embracing courage could transform your life? Join us for a candid conversation with Christie Hunter-Arscott, advisor, speaker, and author of "Begin Boldly," as she shares her wisdom on authentic interactions, the importance of deeper conversations, and the power of choosing courage over confidence. Christie reveals the happiest moments of her life, often spent with family by the sea, and highlights her extraordinary ability to connect with people from all walks of life. From her favorite color to her allegiance to Somerset in Cup Match, we paint a vivid picture of Christie's vibrant and multi-faceted personality. Together, we navigate the journey from childhood dreams to reality, discussing the impact of childhood asthma on sports participation and the creative vs. athletic dichotomy. Christie and I explore the societal pressures children face about future careers, advocating for broader aspirations and identities over rigid professional paths. Reflecting on our teenage years and unpredictable career trajectories, we emphasize the importance of using one’s voice and gifts for meaningful impact, rather than being confined by a single professional label. Christie also opens up about the complexities of balancing marriage, motherhood, and career, sharing personal anecdotes about her life with her husband Ramon, a distinguished MD. We delve into the challenges of interracial parenting, the importance of a supportive partnership, and the joys of rediscovering personal identities as mothers. This episode is packed with invaluable insights and practical advice for women striving for personal and professional growth, making it a must-listen for anyone seeking inspiration and empowerment. Tune in and be inspired to live boldly and authentically!

    1h 2m
  7. Hustle Her - Tina

    09/08/2024

    Hustle Her - Tina

    When Tina Laws, renowned intimacy coach and relationship expert, sat down with me, Deshay Caines, we didn't just rehash the common relationship rhetoric. Our conversation unearthed the raw and often silent battles within abusive relationships, the importance of maintaining one's identity after saying "I do," and the powerful legacy we can build when we properly balance our work and personal lives. Tina's revelations about the significance of seeking professional help and her insightful advice for couples and women in leadership roles offer a blueprint for those navigating the complexities of love, ambition, and self-discovery. Ever wondered how to keep your sense of self when your world revolves around others? This episode is a treasure trove of wisdom on embracing individuality in marriage and the transformative power of stepping back from a high-stress job for the sake of your health and relationships. From the simplicity of Tina's skincare routine to the intricate dynamics of family silence amidst abuse, we journey through personal anecdotes and expert insights that remind us of the strength in vulnerability and the growth that comes from hardship. As Tina Laws shares her admiration for 50 Cent and opens up about her own personal journey, you'll find yourself moved by the honesty and encouraged by the advice imparted. We tackle the heavy topics with heart and clarity, unafraid to confront the silent struggles and celebrate the triumphs of women everywhere. Join us for an episode that's as much about finding your pathway to joy and success as it is about the honest conversations we need to have along the way.

    1 hr
  8. Hustle Her - Dad (Dwayne)

    06/14/2024

    Hustle Her - Dad (Dwayne)

    What does it take to transition from a protective parent to a supportive mentor? Join us on this special Father's Day edition of Hustle Her, where I sit down with my father, Dwayne Caines, the CEO of The City of Hamilton, for an intimate and enlightening conversation. We share family traditions like celebrating Cup Match in Somerset and recount our unforgettable trip to Colombia. My dad, a night owl and lover of Jamaican cuisine, opens up about his daily routines and the inspiring figures that have shaped his life, while describing each of his daughters with just one word each: tenacious, compassionate, and passionate. Together, we explore the complexities of parenting, particularly the intricacies of co-parenting and blended families. My father reflects on his upbringing and the influence of having ambitious friends and strict yet loving parents. We dive into the emotional challenges and rewards of raising children in different circumstances and stages of life, emphasizing the importance of honesty, unconditional love, and putting the child's well-being first. His heartfelt anecdotes about navigating co-parenting decisions highlight the significance of mutual respect and the positive outcomes that can arise from non-traditional family structures. As we continue, the conversation shifts to the evolving dynamics between a father and his growing children. From discussing the transition of roles as children reach adulthood to the lasting impact of childhood experiences, we underscore the importance of effective communication and understanding. My dad also shares his thoughts on the unique challenges men face in fatherhood and the critical need for a supportive village. This episode is a heartfelt celebration of fatherhood, filled with reflections, lessons, and the enduring bond between a father and his daughters.

    54 min
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4.4
out of 5
16 Ratings

About

Hustle.Her is about inspiring women through real-life experiences that have helped to mold and develop Deshay and her guest into the entrepreneurs and leaders they are today. Follow Deshay as she talks with female entrepreneurs, leaders, and ultimate hustlers. Hustle.Her will give you a little kick in the butt, leave you inspired, motivated, and give you some actionable takeaways to be the best you. 

Information

  • Creator
    Deshay Caines
  • Years Active
    2020 - 2025
  • Episodes
    60
  • Rating
    Explicit
  • Copyright
    © 2026 Hustle Her
  • Show Website
    Hustle Her