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From Rock Bottom to Tech Leadership with Ray Freeman | Ep056
Episode Information
Show Notes
The Week That Changed Everything
Ray 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 Different
Ray 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 Takeaways
On 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 Freeman
Ray 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 & Subscribe
Career 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 can use as you’re managing your own career. For today’s episode I have with me Ray Freeman. He and I have met at a couple different networking events. We talked a little bit about his career. He’s got some very interesting stories and even inspiring, just understanding the different things that people go through. This one’s gonna be really fun for me and hopefully, you know – like I mentioned, inspirational for everybody else. Ray is very open and he’s gonna tell us about some of the struggles and everybody always likes to kind of talk about the successes but he’s very interested in talking about some of the challenges that happened along the way so that you can go ahead and hopefully relate to them or like I mentioned get a little bit of inspiration. So with that I’ll go ahead and introduce Ray.
Ray Freeman: Thanks for having me.
Manuel Martinez: I appreciate you coming on. It’s been interesting and fun talking to you, getting to know a little bit more about not only what you’re doing now but just what it took to get there.
Ray Freeman: Yes, yes.
Manuel Martinez: And if you don’t mind just so that people get in a sense of who Ray is now, tell me kind of what your current role is and some of the responsibilities of what it is that you do for this role.
Ray Freeman: Sure, sure. So my name is D. Ray Freeman. D is for Donald but I just go by my middle name by Ray Freeman. I’m originally from Texas but I’ve been here in Las Vegas for about five years and I’m a co-owner of RTS Premier Solutions. We do all kind of IT work and you know AI and cyber security around the public sector. I’m also co-owner of a company out of Atlanta Georgia called Win-Win Operations. My partner Shayna Benjamin is there in Atlanta and together. We have about 30 OEM partners that we we work with and about 15 teaming partnerships with other small and medium-sized businesses and we just bring together some of the best technology to the public sector. We serve federal government and state and local and education as well
Manuel Martinez: Awesome. I’m excited as part of the conversation to learn a little bit more of kind of what brought you to want to serve the public sector, right?
Ray Freeman: Yes, you know when when I first met my my business partner she actually reached out to me on LinkedIn. I was serving as a career advisor and business advisor and she found me on LinkedIn and was like hey I’ve won these government contracts and I’m not sure I know exactly what to do but I’ve won them and I’m starting to service them and I’m like well I’ve started this company and I have a 20-year background in technology and I’m actually going to some of these networking and meetups and I’m not sure exactly what I’m gonna do but I’m making a lot of connections in the public sector and we’re like well why don’t we try to work together? So we decided to partner up and become partners in each other’s business and figure out you how can we work together to serve not only the market that she had already but then the network that I was starting to build here in in Las Vegas and so we ended up closing more contracts and building more together and it’s just been a great partnership and you know so she really got me into a public sector environment that was already established. I just helped to grow it.
Manuel Martinez: Got it, okay. So now, as we kind of lead to what you’re doing now, tell me a little bit about where you grew up and then eventually kind of what got your career started because I know that you didn’t necessarily, I mean there’s some technology in there but you know we talked about kind of that fork in the road where you kind of had a couple decisions so you know just tell us a little bit about that.
Ray Freeman: Sure, sure so I grew up in Fort Worth Texas you know just outside of Dallas there and you know as a little kid I used to always say I’m gonna go to night school and I’m gonna learn technology and I’m gonna do some kind of job working during the day. I was probably six years old and I was saying that but you know as I grew up of course I got into music more and started playing piano and trumpet but eventually I started making just music just beats for people you know R&B hip-hop music that was just going out and people were getting my songs and starting to use them in their own productions and so I was like forget about this tech stuff I’m gonna be a music producer man that’s where I’m going and I thought that’s where I was gonna be and actually when I was in college I was on a music scholarship in Weatherford College in West Texas I was playing trumpet and a really good jazz band there and some guys I had made a track for, they got signed to a record label in Houston their manager came and he gave me a wad of cash and said “Hey, we want to buy this song from you,” and I was like, “Where’s the pen?” – No lawyer no nothing I signed over and you know gave him that and I immediately thought I’m rich you know I’ve got some money I dropped all my classes left school went and got an apartment in Arlington and blew through that cash in about a month really smart for a 19 year old but I started working during the day I was working on the back of a you know one of those recycling trucks where you buy aluminum cans and stuff like old stinky trucks buying basically garbage from other people I was doing that and I had a little bit of little bit of cash left and I enrolled in a computer class at night so it’s kind of like what my six-year-old self said I would be doing but it was just like a plus stuff just weren’t learning to work on hardware things like that but from from there I just kind of had a knack for computers and technology and I couldn’t really afford to just buy a computer
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By Career DownloadsEpisode Information
Show Notes
The Week That Changed Everything
Ray 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 Different
Ray 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 Takeaways
On 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 Freeman
Ray 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 & Subscribe
Career 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 can use as you’re managing your own career. For today’s episode I have with me Ray Freeman. He and I have met at a couple different networking events. We talked a little bit about his career. He’s got some very interesting stories and even inspiring, just understanding the different things that people go through. This one’s gonna be really fun for me and hopefully, you know – like I mentioned, inspirational for everybody else. Ray is very open and he’s gonna tell us about some of the struggles and everybody always likes to kind of talk about the successes but he’s very interested in talking about some of the challenges that happened along the way so that you can go ahead and hopefully relate to them or like I mentioned get a little bit of inspiration. So with that I’ll go ahead and introduce Ray.
Ray Freeman: Thanks for having me.
Manuel Martinez: I appreciate you coming on. It’s been interesting and fun talking to you, getting to know a little bit more about not only what you’re doing now but just what it took to get there.
Ray Freeman: Yes, yes.
Manuel Martinez: And if you don’t mind just so that people get in a sense of who Ray is now, tell me kind of what your current role is and some of the responsibilities of what it is that you do for this role.
Ray Freeman: Sure, sure. So my name is D. Ray Freeman. D is for Donald but I just go by my middle name by Ray Freeman. I’m originally from Texas but I’ve been here in Las Vegas for about five years and I’m a co-owner of RTS Premier Solutions. We do all kind of IT work and you know AI and cyber security around the public sector. I’m also co-owner of a company out of Atlanta Georgia called Win-Win Operations. My partner Shayna Benjamin is there in Atlanta and together. We have about 30 OEM partners that we we work with and about 15 teaming partnerships with other small and medium-sized businesses and we just bring together some of the best technology to the public sector. We serve federal government and state and local and education as well
Manuel Martinez: Awesome. I’m excited as part of the conversation to learn a little bit more of kind of what brought you to want to serve the public sector, right?
Ray Freeman: Yes, you know when when I first met my my business partner she actually reached out to me on LinkedIn. I was serving as a career advisor and business advisor and she found me on LinkedIn and was like hey I’ve won these government contracts and I’m not sure I know exactly what to do but I’ve won them and I’m starting to service them and I’m like well I’ve started this company and I have a 20-year background in technology and I’m actually going to some of these networking and meetups and I’m not sure exactly what I’m gonna do but I’m making a lot of connections in the public sector and we’re like well why don’t we try to work together? So we decided to partner up and become partners in each other’s business and figure out you how can we work together to serve not only the market that she had already but then the network that I was starting to build here in in Las Vegas and so we ended up closing more contracts and building more together and it’s just been a great partnership and you know so she really got me into a public sector environment that was already established. I just helped to grow it.
Manuel Martinez: Got it, okay. So now, as we kind of lead to what you’re doing now, tell me a little bit about where you grew up and then eventually kind of what got your career started because I know that you didn’t necessarily, I mean there’s some technology in there but you know we talked about kind of that fork in the road where you kind of had a couple decisions so you know just tell us a little bit about that.
Ray Freeman: Sure, sure so I grew up in Fort Worth Texas you know just outside of Dallas there and you know as a little kid I used to always say I’m gonna go to night school and I’m gonna learn technology and I’m gonna do some kind of job working during the day. I was probably six years old and I was saying that but you know as I grew up of course I got into music more and started playing piano and trumpet but eventually I started making just music just beats for people you know R&B hip-hop music that was just going out and people were getting my songs and starting to use them in their own productions and so I was like forget about this tech stuff I’m gonna be a music producer man that’s where I’m going and I thought that’s where I was gonna be and actually when I was in college I was on a music scholarship in Weatherford College in West Texas I was playing trumpet and a really good jazz band there and some guys I had made a track for, they got signed to a record label in Houston their manager came and he gave me a wad of cash and said “Hey, we want to buy this song from you,” and I was like, “Where’s the pen?” – No lawyer no nothing I signed over and you know gave him that and I immediately thought I’m rich you know I’ve got some money I dropped all my classes left school went and got an apartment in Arlington and blew through that cash in about a month really smart for a 19 year old but I started working during the day I was working on the back of a you know one of those recycling trucks where you buy aluminum cans and stuff like old stinky trucks buying basically garbage from other people I was doing that and I had a little bit of little bit of cash left and I enrolled in a computer class at night so it’s kind of like what my six-year-old self said I would be doing but it was just like a plus stuff just weren’t learning to work on hardware things like that but from from there I just kind of had a knack for computers and technology and I couldn’t really afford to just buy a computer