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Maxanne Caines joins me for a real, funny, and honest look at how she becomes who she is, from a childhood shaped by structure and love to a life built on pivots, service, and joy. We talk dyslexia, confidence, career turns, and what it actually means to sit on the City of Hamilton council and represent residents well. We get real about her experience with severe dyslexia and ADHD traits, what masking looked like in school, and why self-talk, tools, and grace still matter even when you’re confident. If you’ve ever felt embarrassed by how your brain works, this will land hard and hopefully bring you relief. We also talk about her academic comeback, from boarding school in Canada to thriving at an HBCU at Oakwood University, then making the tough call to leave the expected pre-law track for international relations. Maxanne shares what life is like living in Brussels, working with the Bermuda government office, and chasing a diplomatic future until COVID changed everything overnight. From there, we get into entrepreneurship and what it means to build The Pristine Group together with trust, boundaries, and room to learn. And yes, we break down what a City of Hamilton counselor actually does, what governance is versus operations, why legislation matters, and how accountability and transparency are supposed to work in local politics in Bermuda. If you’re into women’s leadership, learning differences, career pivots, entrepreneurship, or civic engagement, hit play, then subscribe, share this with a friend, and leave a review so more people can find Hustle Her Podcast.

You can’t solve a problem you refuse to name, and Bermuda has been trying to address homelessness without even having a legal definition for it. That’s why I invited Denise Carey, executive director of Home in Bermuda, to sit down with me after watching her take the room by storm at Disrupt HR. What she shares is clear, direct, and deeply human: homelessness isn’t a personality type, it’s an experience, and it can happen through far more pathways than most of us want to admit. We get into what “homelessness” actually includes using the European Typology of Homelessness and Housing Exclusion: roofless and rough sleeping, emergency shelter, housing insecurity, inadequate housing, hidden homelessness, seniors on fixed incomes, people aging out of systems, domestic violence displacement, people leaving institutions, and working people priced out of rent. Denise explains how Bermuda’s housing pipeline gets bottlenecked when “temporary” shelter turns into decades, and why derelict buildings and vacant properties have to be part of any serious housing strategy. We also talk about community safety and reentry housing for people leaving incarceration, including the uncomfortable truth that stability creates accountability. Housing, employment, and support reduce recidivism, lower public costs, and make all of us safer because we know where people are and how they’re being supported. Along the way, Denise shares the emotional toll of this work and the belief driving her forward: every person in our community has value, and none of us has the right to give up on them. Subscribe for more real conversations, share this with someone who needs a new perspective on homelessness in Bermuda, and leave a review if you want more guests like Denise. What part of this conversation challenged your view the most?

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?

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.

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.

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.

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.

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!

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.

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.

As we wade through the complexities of self-discovery and social justice, it's rare to find a beacon like Linda Bogle-Mienzer , who not only navigates these waters but also charts a course for others. On the latest episode of Hustle Her Podcast, I'm joined by Linda, whose 25-year tenure with the Bermuda Police Service has been a testament to the power of advocacy and the pursuit of equity. Her stories aren't just experiences to be shared; they're lessons to be absorbed, particularly when it comes to advocating for Black individuals and the LGBTQIA+ community. As Linda recounts her journey from an introverted child to a formidable force within her profession, we're granted a glimpse into the essence of true growth and transformation. The conversation transcends personal anecdotes, evolving into a nuanced dialogue on the role of work in our lives and the importance of maintaining boundaries between our professional and private worlds. Linda's insights extend into the significance of unions, underlining their role in fostering supportive environments where people do more than simply work—they thrive. The discussion is a contemplative exploration of labor struggles, the necessity of ensuring fair treatment in the workplace, and the personal equilibrium each of us strives to achieve in the elusive pursuit of work-life balance. Finally, we tackle the layered concept of empowerment, especially within the context of intersectionality, and the responsibility Black women carry in shaping a better future for the next generation. This episode is not solely a narrative thread of Linda's life—it's an imperative call to readers to stand for equality, to uphold each other through adversity, and to embrace the legacies we create. Join us on Hustle Her Podcast to witness firsthand Linda's inspiring journey and to absorb the wisdom she imparts on empowerment, empathy, and advocacy.

Embark on a voyage of heritage and tenacity with my nana Shurnett Yvonne Nathan-Caines, who finally graces the Hustle Her Podcast with her presence. Through laughter and candid reflection, she shares the essence of her Jamaican upbringing and the playful mischief that nurtured her benevolent spirit. As we explore her family ties, it’s more than nostalgia; it's a salute to the community service and values that continue to steer her compassionate course in life. We're not just reminiscing about days gone by; we're connecting the dots of a legacy that echoes through generations. Shurnett's tale weaves through the challenges of her athletic childhood in Jamaica, her life-altering relocation to Bermuda, and the courage that led her to embrace a career in nursing. Her story is a testament to adaptability, seizing new opportunities like joining the Young Ambassador Club, and the fortitude to leave an indelible mark on her community. In this conversation, we don't just uncover the journey of a woman who defied expectations; we uncover the resilience required to thrive in the face of life's pivotal moments. As we wrap up this episode, we delve into the impact of West Indian heritage in shaping Bermuda’s cultural landscape. Shurnett's pioneering spirit is evident as she recounts the struggles against discrimination and the prideful strides in preserving cultural identity. She doesn't just share her history; she gifts us a blueprint for advocating self-worth and racial equality. Join me as I offer gratitude to you, my listeners, and to my cherished Nana Caines, for an episode that celebrates the power of our roots and the unbreakable bond of family.

Embarking on a journey through the highs and lows of human experience, today's Hustle Heart Podcast is a tapestry of laughter, tears, and the indomitable will that defines us. As your host, Deshay Caines, I'm thrilled to bring to the table Tyka's transformative tales, Auntie's (Maxanne Anderson) legal aspirations born from a poignant childhood memory, and Chelseas' tenacity in the face of adversity. Our stories intertwine to paint a vivid picture of the grit it takes to chase dreams and the resilience needed to stand tall through life's tempests. Motherhood unfurls its complexity as Jasmine and Maxanne share their parenting philosophies, while Tyka imparts the wisdom she nurtures within her own daughter. Every misadventure, from hair removal cream fiascos to heartfelt moments of encouragement, shapes the profound insights we pass on to the next generation. These narratives are a celebration of the unbreakable bond between a parent and child, highlighting the power of love and understanding in raising daughters brimming with potential. As we mark the 50th episode of this series, we honor the journey of every individual who has graced this podcast with their truth. The echoes of laughter, the shared moments of vulnerability, and the collective strive for purpose—each story is a thread in the fabric of our community. Join us in this milestone celebration, where the spirit of giving back, the courage to lead, and the joy of service converge to inspire and uplift every heart listening in today.

As the curtains rose at the Earl Cameron Theater, the air was electric with the anticipation of reconnecting with my powerhouse panel of women entrepreneurs. It felt like only yesterday that Maxanne Anderson, Jasmine DeSilva, Tyka Edness , DeVika Bourne, and Chelsea Warren had taken their first steps into the spotlight on the Hustle Her stage. Since then, they've soared, taking their businesses to new heights and inspiring a wave of up-and-comers with their authentic tales and leadership savvy. We crack open the book of their journeys, leafing through chapters of vulnerability, triumph, and the undeniable impact that a personal narrative can have in steering others toward their own entrepreneurial stars. Ever wondered how love can not just survive but thrive in the entrepreneur's rollercoaster world? I peel back the curtains on a 16-year marriage odyssey, sharing nuggets of wisdom on cultivating a partnership that stands resilient amidst the whirlwind of business-building. Our conversation weaves through the intimate dance of balancing personal relationships with professional goals, revealing how mutual understanding and a little dedicated time can strengthen bonds. The heart of this chapter lies in the joy and complexity of intertwining lives and ambitions, underscoring the art of sustaining passion and commitment both at home and in the marketplace. Bringing it home, we toast to the power of enduring friendships and the kindred spirits that accompany us along our paths. I share tales from my own circle, a bond that has outlasted the test of time, distance, and the ebb and flow of adulthood. With my co-host chiming in on the essence of loyalty and the family we choose, we reflect on the influential figures who've shaped our trajectories and the importance of lifting as we climb. The episode wraps with a collective call to action: to embolden one another, celebrate the milestones, and cultivate a legacy of empowerment that echoes through generations of hustlers to come. Join us as we honor the relationships that fuel our fires and the shared victories that light up our world.

Embark on a remarkable journey with the effervescent Olamide Olowe, CEO of Topicals, as she recounts the ascent of her skincare empire and the discipline that fuels her groundbreaking achievements. From marking her territory on Forbes 30 Under 30 for 2023 to launching the fastest-growing brand in Sephora's lineup, Olamide's story is a testament to the power of bridging analytical acumen with creative business tactics. She opens up about her life as a 'left brain creative', offering listeners an intimate glance into the personal philosophies and skincare routines that mirror the innovative spirit of her brand. The narrative takes a vibrant turn, exploring the pulsating beats of the UK rap scene and the inspiring rise of young African women in the genre. As I groove to the rhythms of London's rap culture, we also pay tribute to how Olamide's athletic background and strategic academic decisions laid the foundation for her entrepreneurial prowess. It's a tale of sportsmanship, education, and sheer resilience that has seen her brand Topicals flourish on Sephora's shelves, defying the initial doubts of naysayers and empowering those with chronic skin conditions. Our chat winds down with heartfelt anecdotes about striking a balance between lofty business goals and personal life, including budding relationships and navigating self-awareness. Olamide's commitment to lifting women in business shines through, as does her love for Bermuda and how it plays into her vision for Topicals. Engage with us in this episode to hear how a visionary CEO continues to redefine the hustle while making strides in empowering others and imprinting her legacy in the beauty industry.