We were lucky to catch up with Reginald Gilmore II recently and have shared our conversation below.
Reginald , appreciate you joining us today. So let’s jump to your mission – what’s the backstory behind how you developed the mission that drives your brand?
Having spent ten years in corporate America, I gained a firsthand view of what the mental health industry offers—and, more importantly, what it lacks. I observed the constraints of bureaucracy and red tape that often prevent organizations from truly meeting people where they are. Traditional therapeutic spaces, especially within large corporations and hospitals, can be intimidating and impersonal, creating barriers to care. Stepping outside these confines into my own practice has allowed me to bring therapy into the community in a way that is accessible, approachable, and impactful.
As an African American male, I understand deeply the weight our communities carry. For generations, many of us have been denied the space to acknowledge and process emotions like anger, frustration, sadness, confusion, guilt, grief, and isolation. These emotions have often been dismissed or invalidated, leaving us to bear them in silence. This mission is personal for me because I’ve lived it, and I’ve seen how these unaddressed feelings affect individuals, families, and entire communities.
Being based in Portland, Oregon, where the population of African Americans and people of color is significantly smaller compared to the South where I grew up, has made this mission even more meaningful. It’s heartwarming to serve people of color who, before saying a word, light up when they see a familiar face in a therapeutic setting. That recognition, that comfort, is the first step in breaking down barriers.
My mission is to remove the stigma around therapy by reshaping how and where it happens. Therapy doesn’t have to take place in a sterile, clinical office; it can happen in spaces that feel safe, supportive, and welcoming. By doing this, I aim to create an environment where people feel empowered to share their stories, process their emotions, and begin healing.
For me, this work is not just professional—it’s personal. It’s about validating emotions that have gone unrecognized for too long. It’s about providing representation in a field where it is sorely lacking. And it’s about helping individuals reclaim their sense of self and connection to their communities. I am grateful every day to do this work and to see the difference it makes, one person at a time.
We need more clinicians of color to serve our communities effectively and meet individuals where they are, both physically and culturally. Recognizing the significance of culturally relevant spaces, I currently host a free men’s group every month called “Chop It Up Thursdays.” This group meets at an influential barbershop in the community, which is a deliberate choice.
Barbershops have historically been more than just places for grooming; they are cultural hubs where authentic, meaningful conversations naturally unfold. Within communities of color, they offer safe spaces for men to share experiences, discuss personal and collective challenges, and connect on a deeper level. By hosting this group in such a familiar and trusted environment, we aim to foster open dialogue, provide support, and address mental health needs in a way that feels accessible and impactful. This approach bridges the gap between mental health services and the community, ensuring that support is both relatable and readily available.
Reginald , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
As a college athlete at Freed-Hardeman University, my journey into social work began in an unexpected way. My freshman year was filled with early morning classes due to evening practices. Originally, I pursued pre-engineering, but balancing sports and such a rigorous major proved overwhelming. A conversation with my college advisor changed my path forever. They noticed my knack for connecting with people and suggested I explore social work. Coincidentally, my mother had made the same observation years earlier, standing with me in line at a food stamp office when I was ten.
Taking their advice, I enrolled in an Introduction to Social Work class and was hooked. But the real turning point came in a 7:30 AM class called Death and Dying. On the first day, I walked in tired and skeptical, but everything changed when the instructor entered—a short, gray-haired man with a ukulele. Without saying a word, he began playing and singing an Elvis song, instantly waking me up and capturing my attention. His passion and authenticity were magnetic. I later learned he was a licensed clinical social worker with his own practice—something I hadn’t realized was possible with a social work degree. From that moment, he became my role model, and every time he taught a class, I made sure to sign up.
After graduating in 2014, I worked as a behavioral specialist at a Title I elementary school in Chattanooga, Tennessee. This role shaped my approach to working with underserved communities. I supported over 600 students from kindergarten through fifth grade, addressing social and emotional issues that impacted their academic success. Whether it was leading peer groups, counseling families, riding buses home to prevent neighborhood conflicts, or breaking up arguments between parents, I poured myself into helping a community often in survival mode. Those five years were challenging, but they gave me invaluable experience in working under pressure and making a difference in tough environments.
In 2019, I moved to Portland, Oregon, to pursue my dream of opening my own practice, Gentle Giant Counseling. With Oregon having one of the highest suicide rates in the country, I saw an opportunity to sharpen my skills and make a meaningful impact. I began as a crisis specialist in the emergency department at Providence, and now, I work as a Behavioral Health Consultant at Kaiser Permanente, balancing that role with managing my private practice.
My approach is client-centered, focusing on narrative therapy to empower individuals to tell their stories. By listening closely and identifying recurring patterns, I help my clients uncover the barriers to healing and growth. I specialize in working with individuals facing suicidal ideation, substance-induced psychosis, depression, anxiety, life transitions, grief, divorce, and gender incongruence, among other challenges.
What sets me apart is my ability to connect with clients in a way that feels safe and transformative. Conversations, under the right circumstances, can be magic—and I consider myself a magician of sorts, helping people unlock their potential and reclaim their narratives.
I’m proud to serve communities that are often overlooked and underrepresented, providing representation and support where it’s needed most. Whether it’s in a corporate setting or my own practice, my mission is to create spaces where healing is possible, one conversation at a time.
What’s a lesson you had to unlearn and what’s the backstory?
One of the biggest lessons I had to unlearn was tied to what I was taught growing up—specifically, the idea that I must always remain humble, to the point of diminishing my confidence. My grandmother instilled in me values that helped me navigate the environment I grew up in, and those lessons were invaluable. However, as I’ve grown and stepped into uncharted territory, breaking generational curses, I’ve realized that some of those teachings, while helpful in the past, don’t always serve me in my current journey.
In my work, I interact daily with doctors, healthcare professionals, lawyers, and engineers—people I once thought I’d never have the confidence to hold a conversation with. Over time, I’ve learned that they’re just people, and that my skills, knowledge, and experiences are just as valuable as theirs. This realization was both empowering and unsettling because it forced me to question what I had long believed to be true.
Unlearning the idea that being confident in myself was somehow a lack of humility was a challenging process. It felt almost like betraying the values my grandmother taught me. But I’ve come to see that there’s a balance: I can honor where I come from while embracing the confidence that comes from dedicating time and effort to my craft.
The first time you realize that something you were taught doesn’t always apply to your current circumstances can shake you to your core. But operating in your own truth and adapting as you grow is essential. Confidence isn’t arrogance—it’s a recognition of your worth and abilities. As long as you remember where you come from, it’s impossible to lose your way.
This lesson has been a cornerstone in my personal and professional growth, allowing me to step into spaces I never thought I’d belong in and to thrive while staying true to who I am.
Can you open up about how you funded your business?
I’ve always believed in the importance of having multiple streams of income. This mindset allowed me to approach funding my business with stability and patience. While building my practice, I worked full-time as a Behavioral Health Consultant at Kaiser Permanente and as an on-call crisis specialist in the Emergency Department at Providence. These positions provided the steady income and financial security I needed to invest in my private practice without feeling pressured to rush the process.
As my practice began to grow, I made the decision to step away from my role in the Emergency Department to focus more on my private clients. I now balance working four days a week at Kaiser Permanente with dedicating three days a week to my practice, Gentle Giant Counseling. Having the benefits and stability of my corporate job has reduced the financial pressure that many entrepreneurs face, giving me the freedom to shape my practice the way I envision it.
This approach has allowed me to build my client base intentionally, ensuring I can provide the best care possible. Today, I’m proud to say that my private practice serves 30 clients, and I’m continuing to grow at a pace that aligns with my values and goals. By leveraging multiple streams of income, I’ve been able to create a solid foundation for my business while maintaining balance and sustainability.
Contact Info:
- Website: https://www.gentlegiantcounseling.com/
- Instagram: Mentalhealth.ggc
Image Credits
Photos by “Victor Andrew” {Vctry.visuals}