From Rock Bottom to Tech Leadership with Ray Freeman | Ep056

Episode Information Show NotesThe Week That Changed EverythingRay Freeman’s tech career includes a chapter most people would rather forget. After the 2008 financial crisis, Ray lost his job, his wife lost hers, and their six-bedroom Houston house became a financial prison. Eventually, Ray spent a week sleeping in his car while working contract IT jobs.Today, Ray is President and Chief Strategy Officer of RTS Premier Solutions, serving government agencies with AI and cybersecurity solutions. His story isn’t about avoiding failure, it’s about what happens when you refuse to stay down.What Makes This Episode DifferentRay doesn’t tell the sanitized version of his career. He shares the real story: blowing through money faster than he made it, losing everything in five days, and the humbling experience of living out of his car with a George Foreman grill and a rice cooker from Goodwill.But he also shares how those experiences built the resilience, communication skills, and leadership mindset that drive his success today. You’ll hear about getting fired from AT&T for challenging leadership and then being called back by the CTO who vindicated him completely.Key TakeawaysOn Building Confidence:Ray discovered he was smart by accident. After struggling in traditional school, he took Microsoft certification exams on a whim and scored perfect. That moment changed everything. He learned that finding the right way to learn matters more than fitting into someone else’s system.On Resilience:When Ray lost everything, he didn’t call for help. He bought a styrofoam cooler, found a Dollar General, and figured out how to survive. One week later, he had his first paycheck and could rent an apartment. The experience taught him that survival builds character.On Leadership:Ray got fired from AT&T for going over his manager’s head to warn about a critical infrastructure problem. Weeks later, the CTO called him back, saw the problem immediately, and gave Ray’s company a contract. That experience taught Ray to speak truth to power, no matter the personal cost.On Communication:Ray studied DISC and Emergenetics, psychometric assessments that taught him to recognize how people think and communicate. He learned to modify his tone, pace, posture, and words based on his audience. This skill became the foundation for his ability to simplify complex technical problems for executives.On Goal Setting:When Ray was sleeping in his car, he broke survival into daily goals. Make it to Monday. Get through the week. Get the first paycheck. Find an apartment. This approach of breaking massive goals into manageable chunks became a career skill that serves him to this day.On Business Ownership:Ray used to think owning a business meant doing all the work himself. Learning that business ownership means assembling people, processes, and tools not doing everything personally, transformed how he thinks about scaling and creating opportunities for others.About Ray FreemanRay Freeman is President and CSO of RTS Premier Solutions and co-owner of Win-Win Operations. With over 20 years in technology and a background that includes music production with major artists, Ray brings a unique perspective to tech leadership.His journey from sleeping in his car to leading government technology contracts proves that setbacks don’t define your career, your response to them does.Connect with Ray on LinkedIn or learn more about RTS Premier Solutions.Listen & SubscribeCareer Downloads releases new episodes every week. Subscribe on your favorite podcast platform and never miss a conversation.Visit careerdownloads.com for more episodes and resources. TranscriptionManuel Martinez: Welcome everyone, my name is Manuel Martinez and this is another episode of Career Downloads. For each episode I basically hit the refresh button, bring on a different guest to learn more about their background and their experiences to help you uncover any actionable advice that you c...