213. Be Receptive Be Respectful Be Risky | LiboRisk Military Travel Tribe by Former Marine
- Sep 14, 2025
- 13 min read
Updated: Sep 25, 2025
Jess Quezada
In episode 213 of the Transition Drill Podcast, Jessica “Jess” Quezada returns with an honest and inspiring continuation of her journey from the Marine Corps to CEO of LiboRisk. In this episode, Jess reflects on her eight years of military service marked by isolation, her unexpected separation in 2020, and the difficult transition that followed. She shares how living out of a bus became the launchpad for LiboRisk, a veteran-centered travel and wellness company that now hosts transformative retreats built on adventure, cultural immersion, and mindfulness. Jess opens up about her personal struggles, including her battles with sobriety, the challenges of 2024, and her life-changing ibogaine treatment. She also recounts her participation in the 2025 Navy SEAL Swim in New York City, part of her year of Misogi challenges, and outlines her future goals for LiboRisk and her own growth. Above all, Jess offers practical wisdom and encouragement for veterans and first responders seeking resilience, connection, and purpose after service.
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Jessica “Jess” Quezada’s story begins with a deep love for the arts, particularly photography and storytelling. Drawn to the power of capturing human moments and documenting truth, she pursued photojournalism as a young adult. That passion soon led her to the United States Marine Corps in 2013, where she enlisted as a Combat Correspondent. For Jess, the military was not just a career choice. It was an opportunity to take her creative vision and apply it in an environment defined by discipline, challenge, and service.
Her first assignment placed her at Marine Corps Recruiting Command in Quantico, Virginia. Unlike many Marines who begin their journey in units filled with peers, Jess entered a space that was isolating. She was tasked with covering recruiting events across the United States, documenting stories that connected the Marine Corps to the broader public. While it provided valuable professional experience, the assignment also left her with little sense of belonging. She was often the only female in her environment and found herself navigating what she later described as a toxic space that lacked community.
From there, Jess transferred overseas to Marine Corps Air Station Iwakuni in Japan. She served as the current and future operations chief for the Public Affairs Office. The assignment broadened her exposure to international environments and honed her ability to manage communication at an operational level. Yet, despite the professional growth, she still struggled with isolation. The lack of peers and the structure of her assignments meant she had few opportunities to build close friendships or a support network.
Her final duty station brought her to the Recruiting Station in Orange County, California, where she served as the marketing and communications director. In that role she sharpened her skills in event coordination, branding, and outreach. These responsibilities would later become the seeds that grew into her entrepreneurial journey. She proved herself capable of leading projects, coordinating large-scale events, and shaping communication strategies. However, even in that role, Jess was reporting directly to the executive officer rather than working alongside peers. She carried the responsibilities of a sergeant without the grounding influence of a team around her.
Through eight years of service, Jess’s career was marked by a pattern of atypical assignments. While many Marines develop camaraderie within traditional units, she never experienced that same sense of family. She did not have her first true friend until she was twenty-six years old, near the end of her time in uniform. The absence of community left a lasting mark. The Marine Corps gave her structure, discipline, and skill, but it did not give her belonging.
Still, Jess held onto her natural creativity and her drive to build something meaningful. She had entered the service as an artist seeking to tell stories, and she left those formative years with skills in marketing, operations, and communication. What she lacked in traditional camaraderie, she carried forward as motivation to one day build the community she never had. The foundation of her future company was being laid, even if she did not yet realize it.
For all the discipline and structure that Jess Quezada gained in the Marine Corps, her time in service came to an abrupt and painful end. In 2020 she faced an Administrative Separation with a General Under Honorable discharge after a narcotic positive urinalysis. The moment was devastating. Years of service, dedication, and sacrifice concluded not with a celebrated farewell but with a forced exit that left her questioning what would come next.
What stands out about Jess is not denial or excuse-making. From the start she chose to own the reality of her discharge. Rather than framing herself as a victim of circumstances, she accepted the consequences and turned her energy toward what could be built afterward. Still, the emotional weight of being forced out was significant. Like many veterans, she confronted the sudden loss of identity, routine, and belonging that military life had once provided.
Her separation magnified the absence of community that had characterized her career. She had spent eight years in roles that were often solitary, disconnected from the shared camaraderie that most service members describe as the glue of military life. When she left the Marines, she did not have a broad network of peers or a ready-made group of friends to lean on. Instead, she faced transition alone, with limited support and no clear path forward.
The period immediately after her discharge was marked by uncertainty and hardship. Jess had to navigate life without the steady income, housing allowances, and structure that the Marine Corps had supplied. More than that, she wrestled with feelings of shame and doubt. In her own words, she had gone from wearing the uniform to waking up each day without a mission, without a role, and without a community. That emptiness is something many veterans and first responders understand deeply. It is not only about leaving a job. It is about leaving an entire identity behind.
Rather than retreating, Jess embraced the challenge. She pared her lifestyle down to the bare minimum. To save money and stretch her resources, she moved into a converted bus. The bus was not just a practical choice but also a symbol of survival and grit. It gave her shelter, mobility, and the chance to live frugally while figuring out her next steps. She describes those early days after separation as the most frugal period of her life. Yet they were also a time of discovery. Living with little allowed her to focus energy and resources on new goals rather than clinging to the past.
During this time, she began experimenting with the concept of a military travel community. She knew firsthand the loneliness that came from a lack of connection. She also knew the healing power that travel and adventure had provided in her own life. From those ideas the vision for LiboRisk started to form. What began as a fragile concept became a source of hope. Jess saw a way to transform her personal struggles into an opportunity to serve others.
Her military career had ended under difficult circumstances, but her next chapter was already beginning to take shape. Out of hardship, Jess began to sketch the outlines of something that would give her a mission once again.
When Jess Quezada left the Marine Corps, she did not immediately step into success. The road ahead was messy, uncertain, and filled with lessons that could only be learned through trial and error. Her vision for LiboRisk was born during those early years of instability. She was living in a bus, scraping together what money she could, and learning to embrace a minimalist lifestyle. That season of scarcity became a crucible that forged her determination.
The bus was more than just a place to sleep. It was her headquarters, her workshop, and her first investment into herself as an entrepreneur. By stripping life down to the essentials, Jess gave herself the one thing she needed most: time. With no excess expenses to drain her resources, she was able to dedicate herself fully to her idea of building a community around travel. At first it was vague. She described it as an enigma, a cool idea that got people excited but one they could not fully understand. Even Jess struggled to articulate exactly what it was. But in her heart, she knew she was on to something important.
She began by hosting small gatherings. These early events were far from perfect, yet they were the first steps in building what would eventually become LiboRisk. Jess leaned on the skills she had developed as a marketing director in Orange County. Event coordination, messaging, and community outreach were second nature to her. Now she applied them not on behalf of the Marine Corps, but for a vision of her own making. She poured everything she had into learning from mistakes. As she often says, she believed in failing early, failing often, and failing forward.
From 2020 through 2023, Jess experimented relentlessly. She tried different formats for gatherings, tested ideas for trips, and pushed herself to figure out what did not work so she could move closer to what would. During this time, she also attended an Outward Bound course in the Northern Cascades of Washington. The program immersed her in the wild, stripped her of distractions, and introduced her to the discipline of outdoor education. That experience became a turning point. It gave her the clarity and structure to transform LiboRisk from a loose idea into a business model.
Initially, she launched LiboRisk as a travel agency. It was a way to establish a legal framework, but the deeper vision quickly outgrew that model. Jess began focusing on retreats and experiences that combined three pillars: adventure, wellness, and cultural immersion. Adventure tapped into the military spirit of pushing boundaries and embracing challenge. Wellness introduced the tools and practices needed to heal the nervous system and absorb the full benefits of travel. Cultural immersion expanded perspectives, reminding participants that the world is bigger than their corner of America.
By 2022, LiboRisk had moved beyond being a side project. It was an operating business, though still lean and grassroots. Jess had carried it from an idea born in a bus to a functioning company. More importantly, she had built something that reflected the community she had longed for during her military years. What once began as survival was now becoming purpose.
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As LiboRisk began to take shape, Jess Quezada refined it into something more than a business. She often says that she does not just run a company, she runs a community. That distinction became the foundation of what makes LiboRisk different from other veteran-oriented organizations. For Jess, the central goal was not simply travel for travel’s sake. It was about cultivating a tribe, a circle of belonging, where veterans and service members could connect with one another and themselves in ways that many had never experienced.
The heart of LiboRisk is built on three ethos: be receptive, be respectful, and be risky. These guiding principles became non-negotiables. They were designed to mirror the values Jess wanted to see not only in her company but also in the people who participated. Every retreat, every excursion, every gathering was filtered through these core standards. If something did not align, it was not pursued. These ethos shaped the culture of LiboRisk into one where authenticity was expected, curiosity was encouraged, and respect was demanded.
To carry those ethos into practice, Jess developed three central practices: mindfulness, movement, and connection. Mindfulness ensured that participants learned how to be present, to experience each moment with clarity and intention. Movement gave the group physical challenges that reinforced resilience and camaraderie. Connection allowed for deep conversations and shared experiences that bound participants together. The combination of these practices created transformation. When layered with the three retreat categories of adventure, wellness, and cultural immersion, LiboRisk became more than a travel company. It became a formula for personal growth and collective healing.
A hallmark of LiboRisk’s success has been the way Jess prepares participants. Rather than dropping people into an experience cold, she insists on one-on-one orientations before each trip. She asks intentional questions: Where are you at in your life? What do you hope to walk away with? These conversations often surprise participants, who may have thought they were signing up for a fun group excursion. Jess challenges them to reflect before they even arrive, priming them to absorb the full value of the journey.
Group calls before departures add another layer. They allow participants to meet one another virtually, easing anxieties about traveling with strangers. More importantly, they plant the seeds of collective wisdom. People realize that they are not alone in their struggles or ambitions. The group begins to form bonds even before stepping into the field. By the time the retreat begins, the foundation of trust and familiarity has already been built.
Growth also came from Jess’s willingness to share leadership. Training new facilitators became an essential step forward. She invested time into mentoring others, handing off responsibility, and watching them thrive. For her, seeing someone else step up and succeed in leading a retreat was as fulfilling as hosting it herself. It meant that LiboRisk could expand while still keeping its soul intact.
Through this approach, LiboRisk transformed into a space where veterans could rediscover resilience, self-reliance, and purpose. It was not about escaping life. It was about learning how to engage with it more fully. The company’s growth mirrored Jess’s own evolution, proving that intentional community can change lives.
While LiboRisk was growing, Jess Quezada was also navigating her own personal evolution. Running a company rooted in service and healing did not mean she was free from struggle. In fact, she often describes the tension of being married to her project. Leaving the Marine Corps had been its own divorce, but her obsession with work quickly became another consuming relationship. Her devotion to building LiboRisk was total, and at times it came at the expense of her own well-being and personal aspirations.
One visible shift came when she decided to sell her bus. For years it had symbolized independence, grit, and the scrappy beginnings of her entrepreneurial journey. Watching it drive away was difficult. The bus had been her first true home, one she built with her own hands when uncertainty defined her future. Yet she realized that clinging to it also meant clinging to instability. Selling the bus represented a choice to seek grounding, both professionally and personally. She moved into a stable residence, created a healthier workspace, and allowed herself to consider what it might mean to one day have a family or a long-term partner.
Sobriety was another battle she faced head-on. Jess has shared openly about her decision to step away from alcohol. It was not because she never enjoyed it, but because she recognized how easily society normalizes destructive coping mechanisms. For her, sobriety became an act of resistance against patterns that left her mentally, physically, and spiritually unwell. It was also a statement of leadership for the community she was building. She wanted to model self-reliance and clarity rather than numbing or avoidance.
The year 2024 became one of the hardest in her life. Challenges mounted, and she felt the crushing weight of exhaustion. It was during this period that she turned to ibogaine treatment, a powerful psychedelic medicine known for its impact on trauma and addiction. Jess had not planned to pursue ibogaine. In her words, it felt as though God placed it directly in her path. A chance encounter with someone connected to the practice led her to explore it further. The timing could not have been more critical. She was at a breaking point and needed a path toward healing.
Her ibogaine experience was transformative. The medicine forced her to confront deep layers of pain and trauma that she had carried for years. It was not easy. The process demanded surrender, honesty, and courage. Yet when she emerged from it, she described feeling a profound shift. The treatment gave her clarity about her purpose, her struggles, and her resilience. It reminded her that trauma does not need to be ranked or compared. Pain is valid because it is lived, and healing comes when we face it without judgment.
This chapter of Jess’s life was not defined by perfection or triumph alone. It was marked by mistakes, setbacks, and hard lessons. But it also showed her capacity to transform pain into wisdom. The same qualities she wanted to cultivate in LiboRisk—mindfulness, resilience, and intentional living—were the ones she was cultivating in herself.
By 2025, Jess Quezada was not only leading LiboRisk with greater clarity, she was also pushing herself into new frontiers of service and adventure. That year she joined the Navy SEAL Swim across New York Harbor, an annual event that honors fallen warriors and challenges participants to swim through rough waters toward the Statue of Liberty. Jess admitted she had not trained as she should have, and the experience tested her limits. Her legs cramped, the current was strong, and the chaos of the water unnerved even seasoned swimmers. Yet she pressed forward, reminding herself of the value of embracing difficulty. For her, the event was part of a larger practice she called Misogi: setting one extreme challenge each month that pushes body, mind, and spirit into uncomfortable places. The swim was not just a test of endurance, it was a reaffirmation that growth only comes when comfort is left behind.
As LiboRisk continued to expand, Jess’s vision grew with it. She was no longer content to simply organize retreats in familiar settings. Trips to Alaska, North Carolina, and South America opened new possibilities. Plans for Europe were on the horizon, and she had begun training additional facilitators to lead experiences without her direct presence. That expansion mattered because it meant LiboRisk could scale while still protecting its small and intentional culture. Jess believed in staying strategically small rather than churning out mass-produced retreats. By doing so, she ensured each trip retained authenticity and the ability to transform lives.
Her future objectives reached beyond business operations. Jess committed herself to ongoing education, pursuing a master’s degree in consciousness and transformative psychology. For her, the academic pursuit was not about credentials alone. It was about equipping herself with the tools to better guide others, to merge science with the experiential learning she had crafted through LiboRisk. She viewed her role not as a leader who dictated answers, but as a facilitator who helped people arrive at their own epiphanies. Education sharpened that skill.
Looking ahead, Jess envisioned LiboRisk as a community that would empower veterans and service members to carry their strength into civilian life with intention. She wanted to see participants leave with tools for mindfulness, strategies for resilience, and experiences that reminded them of their capability. She also believed that veterans are uniquely positioned to be stewards of the world. In her view, service does not end with taking off the uniform. It continues in the way veterans travel, respect cultures, and represent American values abroad.
Her advice to veterans and first responders is direct and rooted in her own journey. First, embrace resilience. Setbacks, whether in uniform or after, do not define you. Second, cultivate self-reliance. Dependence on substances, systems, or even other people can limit growth. True strength comes from being able to rely on yourself. Third, be intentional. Every action, every trip, every decision carries weight. Lead with intention, and the outcome will follow.
Jess Quezada’s story is not just one of surviving separation from the military. It is about transforming hardship into purpose. Through LiboRisk, through her personal healing, and through her commitment to service, she offers a roadmap for others who are navigating their own transitions. The message is clear: the mission continues, and the adventure is just beginning.
In Closing
Jess Quezada’s journey reminds us that transition is never a straight path. From the Marine Corps to building LiboRisk, she has faced separation, uncertainty, and personal battles, yet turned each obstacle into a foundation for growth. Her story is about more than travel or entrepreneurship. It is about resilience, intentional living, and the power of community. Through retreats, wellness practices, and cultural immersion, she continues to create spaces where veterans and first responders can rediscover their strength. Jess proves that service does not end with a uniform. It evolves into new missions that inspire, heal, and connect.
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