2009
Built by the Playbook
Coaching from the Sidelines
At just 17, Joshua joined his father’s coaching staff after graduating high school. Raised by a collegiate football coach and shaped by frequent moves across four states, he learned to adapt quickly and lead without familiarity. As the oldest sibling, he naturally set the tone for his younger brother. Coaching taught him how to motivate, plan, and manage under pressure—skills that would later shape his approach to leadership, systems, and mission execution.
2010
60 Soldiers. One Leader.
Forged in Formation – Army Beginnings
Joshua entered basic training with no military background—but quickly earned the role of platoon guide, leading 60 fellow soldiers through the first phase of training. He became the PT Champion, earning the top male physical fitness score in his class. His leadership continued through AIT, where he was named senior squad leader. That graduation—marked by an address from First Lady Michelle Obama—wasn’t just a milestone. It was the beginning of a mission-first mindset that would guide everything he built afterward.
2011
Overseas, Under Pressure, and Growing Fast
First Deployment – A Leader in the Making
At 21, Joshua deployed overseas for the first time in support of Operation Enduring Freedom. Guided by a master sergeant who shaped his work ethic and mindset, Joshua used the quiet of deployment to grow into a more disciplined, thoughtful leader. Without media or distraction, he focused on reflection, training, and learning how to lead from within. It was the year he stopped being just a soldier—and started becoming a builder of people, systems, and resilience.
2014
$8K, One App, and the Start of a Builder’s Journey
The First Raise – Finding Phones & Finding Focus
Joshua secured his first-ever seed investment—$8,000 to back a self-built mobile app developed overseas. The app solved a practical problem for solo dwellers: how to find a lost phone using a whistle, clap, or voice command. The project gained 500+ downloads and marked Joshua’s entry into product-building with purpose.
2015
One Week. One Flight. Everything Changed.
A Leap of Faith – The Call to Hawaii
Six months into his first federal contractor role in Maryland, Joshua was building a prototype that would eventually earn him a Technology Innovation Award. But before any of that, a deputy director in Hawaii saw the early work and asked, “Can you build this here?” One week later, Joshua was on a plane—stepping foot on the island for the first time to start a new job that would completely reshape his life and career.
2015–2018
Systems Thinking in a Global Arena
Scaling with DISA
At DISA, Joshua modernized defense systems, built dashboards for United States Pacific Command, and developed award-winning geospatial tools that were integrated into reporting and tracking systems used by both PACOM and Department of Defense components across the Pacific region. His work earned top federal honors and laid the foundation for system-level leadership.
2016
70% of Supplies. Under $70. For the People.
The School Supply Project – Innovation with Heart
Inspired by his son and the inefficiencies of school shopping, Joshua created a solution: affordable, custom-packed supply kits delivered to 95+ families in Hawaii, with every tenth box donated to families in need.
2017
Code, Community, and the Startup Spark
Leveling Up – DevLeague Bootcamp
Joshua completed a 16-week full-stack JavaScript bootcamp, sharpening his skills in backend development, front-end UI, and building full-stack web and mobile apps while diving into Hawaii’s startup ecosystem. Surrounded by driven peers and mentored directly by DevLeague’s founders it was the beginning of his evolution from engineer to technical founder.
2018
Turning Regional Signals into Global Systems
Innovation Recognized – AFCEA Tech Award
Joshua’s work with DISA Pacific earned him the prestigious AFCEA International Technology Innovation Award. By developing a real-time Authorized Service Interruptions (ASI) system and the region’s first oceanic trunk map, he transformed how the Department of Defense reported and responded to service interruptions—shifting from manual updates to global operational awareness.
2018
From Island Ops to Ground-Up Execution
Returning to Build – Lee Brothers LLC
After returning from Hawaii, Joshua launched Lee Brothers LLC, a logistics and transportation company that proved his entrepreneurial instincts were real. He bootstrapped $25,000 into a full-fledged operation and grossed over $50,000 in just the first quarter. More than a side hustle, this was the moment he realized he could build, launch, and scale businesses from scratch.
2020
From Operator to Architect
The Blueprint Begins – The Driving Bureau Seeded
In the stillness of the pandemic, Joshua reevaluated everything—especially how Lee Brothers LLC hired drivers. He realized the real opportunity wasn’t just in placing drivers, but in transforming how the industry vetted and connected them. What emerged was the foundation for The Driving Bureau: a platform focused on safety, speed, and equity in hiring. It wasn’t public yet, but the blueprint was in motion.
2021
From Idea to Early Traction
Building in Public – Startup School & Beyond
Joshua completed Y Combinator’s Startup School, learning from program lead Sam Altman and sharing weekly updates with early investors. That summer, he pitched to Techstars and was selected as one of the top 50 finalists for their accelerator program. He also received early interest from Y Combinator. With Amazon DSP pilots and growing user feedback, The Driving Bureau began gaining real traction.
2022–2024
From Consultant to Intrapreneur
Technology That Supports Life-Saving Work
Joshua joined a behavioral health organization to lead IT strategy and systems transformation. Over two years, he modernized infrastructure across 33 facilities, executed a company wide tech refresh, strengthened the organization's IT security posture, and led the migration of it's 988 crisis line. These changes improved how technology supported frontline care. For Joshua, it was more than modernization it was mission fulfillment through systems that save lives.
Present
Every Chapter Had a Purpose. This One Has a Platform.
Launching The Driving Bureau
After running his own logistics company, Joshua saw how outdated hiring practices failed commercial drivers and the companies that relied on them. He founded The Driving Bureau to shift the focus from time behind the wheel to real performance—leveraging data and workforce innovation to improve hiring, reduce risk, and ultimately save lives. For Joshua, it’s not just about building a platform—it’s about building a safer, smarter workforce for the future of transportation.
JOSHUA S. LEE'S JOURNEY
From tech enthusiast to strategic builder and entrepreneur.
My path in technology has been driven by a passion for building secure, scalable solutions that empower organizations and individuals alike. This timeline captures the key moments that have shaped my career and vision.
🏆 CAREER HIGHLIGHTS
Military Leadership
Developed core leadership skills and mission-focus discipline through military service that carries into every professional role.
Award-Winning Federal Systems
Built critical defense and geospatial systems at DISA that earned top honors and recognition across federal agencies.
Entrepreneurial Success
Founded and successfully operated Lee Brothers LLC, securing contracts with major corporations and building a profitable logistics business from the ground up.
Community Impact
Created the School Supply Project that delivered affordable supply kits to Hawaii families while incorporating a built-in giving model that supported families in need.
💡 MY TECH PHILOSOPHY
"Technology should empower people, protect data, and drive positive change. I build systems that scale with purpose, solutions that last, and teams that grow."
Throughout my career, I've approached every challenge with this mindset. Whether I'm architecting a secure cloud migration or mentoring the next generation of IT professionals, my focus remains on creating technology that serves people — not the other way around.
My work spans military, government, healthcare, and entrepreneurial ventures because I believe in building technology that addresses real human needs and solves complex problems.