From Rock Bottom to Tech Leadership with Ray Freeman | Ep056

Manuel 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 I could buy a motherboard and a case and a power supply and I got some books and just figured out how to build my own computer to put something together installing an OS on it I didn’t think that could be something that I would ever really want to do but I don’t know I got kind of good at it I guess and you know one day I was helping my girlfriend who’s my wife now, we’ve actually been together since back then I was hoping to buy a car, her first car – I’m at the dealership and they couldn’t complete the sale because they were having some issues with Windows 95 and I knew how to work Windows 95 because I had been messing around with it on my own stuff at home so I fixed it and got into the registry and whatever I got it working so the guy’s like, “Give me your ‘beeper’ number”, is how old this is, like – “Give me your beeper number I’m gonna I’ll reach out to you if we have any challenges or tech stuff.” This is before any Geek Squad or any of that kind of stuff existed. So gave him my number, right away I went home and I made some handwritten flyers and start handing them out at car dealerships and like, “I fix computers: 20 bucks.” Put my number on there and he called me a few times he actually owned a couple of car dealerships around Arlington, Texas and I got a few more calls and when it’s time to go back to to college I’d be back there but then I come home and I had clients I was out “fixing” computers during the day so that was kind of the first work that I had was just independent work but eventually I was hired by Page Mart this pager company this of course out of business years and years ago they hired me as a helpdesk guy just doing analyst work going and fixing stuff in the office that was my first real tech job in a real office and I was like, “You know, this seems interesting I might could make a make a go of this, I guess.” That’s how I kind of got started into even thinking that technology may be an option for me.

Manuel Martinez: So a couple questions there with regards to kind of thinking that you’re going to be the music producer and- What were some of the skills that kind of looking back now, you probably didn’t realize it at the time, but you know – having to sell your music, were you marketing this to other artists? Did they just kind of, as you’re building this through school, like- I’m just curious how people came to know that D. Ray was the person that produced music.

Ray Freeman: Well, I figured out pretty early on that… know if I found it if I found something in a book I could retain whatever I read and I learned about copyright so I learned how to copyright the songs that I was creating and I learned how to reach out to record companies to say you know, “Hey if you have an artist signed-” I’d send them a letter, “If you have an artist signed, then send them to me and I’ll help to make some music for ’em and send them back then y’all can produce it.” So I was sending out letters everywhere I’m sending out demo tapes with my music and other artists on it I was you know going to little battles and little concerts and stuff and I’d hand out tapes no discs or digital back then I’d hand out tapes of my music to people you know eventually I got heard by someone who was a pre-established artist and he brought me in to be a co-producer and a keyboard player with his his group and so that was pretty pretty cool so I was like I’m “signed” kind of you know I’m working with an established artist.

Manuel Martinez: In that process, were you always comfortable talking to people and putting yourself out there? Because that’s… I’ve talked about it a couple of times, like transferable skills. Like at the time, you don’t realize, again, going out and… Like if we think about it now, it’s like personal branding, letting people know what it is that you do. Back in the day, the only way to do that was, again, you had to kind of put boots on the ground and hand out tapes and be able to go through and send letters. So is that something that just kind of… you had a natural… I don’t want to say natural, but maybe you kind of developed the skill of being able to talk to people and not being afraid of rejection. Because it’s no different than like applying for a job. Because you’re… basically, it’s the same thing. It’s like, “Hey, I’m applying. I’m applying.” Now, you’re going to get a lot of no’s. Most people might say, “This isn’t for me.” But you stuck with it. So I’m curious what led to you continuing to go on.

Ray Freeman: That’s a great question and actually I was terrible at it in the beginning absolutely terrible and when I think back on some of the situations that I was in – of course as everybody says Monday morning quarterback I wish I knew then what I know today because I didn’t know how to brand myself I didn’t know how to market myself I’d be in the room with major artists from major labels and I was just one of the guys hanging out in the studio doing what people do in the studio which is not always the greatest thing so I really didn’t know what to do or how to make myself stand out back then so I’ve missed a lot of opportunities that I really probably could have made that career take off better but no I wasn’t great at it I was just I would do my little part I’d make my music and I kind of just kept my head down and stayed down worse advice I could give somebody is just keep your head down and stay quiet stay in the background, worst thing you can do.

Manuel Martinez: So then, obviously, at that point in time, you’re not as vocal or as memorable. So the reason I ask is I have a guest that I interviewed just before you. She talked about like she was a drummer, Rebecca. And that skill of having to go through and market yourself, right? It’s different. It’s not like, hey, I can post stuff on social media. But it is, it’s going out and developing the skill of how do you talk to people and not being afraid of speaking up. Because I don’t… We’re similar in age where like my dad, that was what was instilled in me is keep your head down and just do the work. That might be good advice in certain industries. Like so he was in construction. So, OK, well, maybe that makes sense, right? Like you’re not going to be like, hey, I’m the best bricklayer in the city of Las Vegas. So it makes sense. But in most other industries, you do have to learn to, again, not boast and talk about how I’m the greatest, but make people aware of what you do. So how did… How did you learn from that experience moving forward? Was it not till later on when you were in tech? Is it just those first couple interactions with labels, you know, with these record labels and then you start to develop it? Like did it take you six months, six years? I’m just curious on the time frame.

Ray Freeman: It really took years before I developed the the confidence, and actually, you know I really wasn’t great in school when I was in you know in high school or in college – I wasn’t great in classes at all. You know later on I decided I needed a few credentials so I started taking these MCSE classes Microsoft Certified Systems Engineer classes and I said, “Okay I’ll – this seems like something I could do, and I couldn’t afford to take the whole course there was like a full course to take all of – I could only afford to take up the first few classes to get the Microsoft certified professional and then they used to have this bookstore – 50 off bookstore, half- off bookstore, and they had all these books you could go and buy about you know, learn how to take the exams and how to learn about networking and all these things. So, I just bought a bunch of books really cheap and read them. So I went in and I took my first certification class. I got one cert and I said, “Okay, this is good.” And so I was like, “Well let me just see if I can study on my own and take the next-” I think it was a series of five or seven classes you had – or tests you had to pass . So I went and took the next test and I passed it. Back then they used to show you the score and it was up to like a thousand, and I made a thousand on it – still got the document, like I scored perfect on it, and there were guys there who were, you know, 40 years old, 50 years old and I’m, you know, in my 20s at the time and someone would tell me, “This is my third time taking it I still didn’t pass.”

Ray Freeman: And I’m like, “Really? That’s weird, it was kind of easy for me.” So I went and I studied for the next one, it’s like, “Server in the enterprise for NT server” or whatever it was back then. Went in, took the test, got another thousand. Like, “This is crazy.” So there’s the next test and it was another Windows NT test I’m like, “I wonder if I could just pay for the test and go in and take the next one like right here, today.” So I did

Manuel Martinez: Without studying?

Ray Freeman: So I did. Without even studying and I went in and took the test and passed it. I was like, “Holy crap, I’m smart.” I didn’t have the confidence or even think that I- I mean my mom used to say, “Oh, you’re smart, you’re mr. know-it-all,” but I’m like, “I’m not smart, I do terrible in school.” But this is the first time that I was actually excelling in something and it just – that gave me a lot of confidence to feel like, “I really know this stuff.”

Manuel Martinez: And do you think you did so well… And again, I believe that you’re smart and everybody’s smart. I think a lot of times, and just people I’ve talked to, do you think school just wasn’t interesting to you? Whereas this technology, that’s something that you have an interest in. So again, you’re going to put more attention to it. So if I think of my son, he doesn’t care much for… like… math. Now, he’s good at math. He just doesn’t put in the effort because it doesn’t interest him. Now, when it comes to history, I mean, he can rattle off facts, tell me about… ancient times and people. And I’m like… Sometimes I think to myself, “I’m going to fact check him.” And I’ll pull something up. I’m like, “Oh my God.” This is right. But again, it’s of interest to him. So again, it’s not that he’s not smart. It’s just he doesn’t have an interest in math. He has an interest in history and English and reading. So do you think that that had something to do with it?

Ray Freeman: A hundred percent, and you know in the 80s, 90s, back when I was little and going through school, education was a lot different then, you know. You were taught to not work in groups, not work together. You sit down and you fill out the bubbles on the Scantron or whatever and you do it on your own, and I was more social. I was at my mom’s house a few months back, she still lives in Texas, and she has some of my old report cards and my teachers used to always say, you know, “Donald is a social butterfly, he’s always talking, he won’t stay in his seat,” and I’m looking at this going like, “Mom, did you see this? Did you do anything about this?” But yeah I was always wanting to be social and out and doing something different, and not necessarily just sitting there by myself studying. So you know, this gave me the interest in something that was challenging in a different way, and I didn’t really know how – like I knew how to read I wasn’t saying I didn’t know how to read, but someone taught me that, you know, reading is different for most people. Some people start from the beginning of a book and they read it to the end of the book, you know. Others, they may start in the middle and maybe some in the back, some in the beginning and just kind of flip through and retain it. So I had to learn – how do I learn how do I read and and retain information. And I’m more of a flipper; I flip through and I go through. I may start at chapter seven and go back to chapter two and then go back to the beginning and the end, and… but for some reason I could retain that information and understand it and that had never happened to me before in the past or nobody ever taught me that it’s okay to do it your way and not the way that they say you’re supposed to do it.

Manuel Martinez: That’s interesting because I would say I’m the opposite. I’m one of those people that I have to go cover to cover. Like I have to read it from start to end. And then once I almost read things twice because I’ll go through it and just almost skim it. Like I’m reading it fast just because I need to know all the context. Then I will start to flip back and forth. Like, okay, I remember this part. Let me go dig into it. Like chapter three, oh, chapter nine, chapter four, chapter 10, like, and then bounce around. So that’s interesting. I didn’t realize that there’s people like you that will start doing the flipping from the get-go.

Ray Freeman: Yeah, if I start in the middle then I’ll be like, “I wonder how we got to this,” and that’ll intrigue me to go backwards a few chapters. Like, “Oh I wonder how this got started.” So I’ll intrigue me to go – you know it just – it’s something about flipping around that just makes me more interested of, “How did we get here?” How did this book- How did the author get to this point?” And that’s that’s where it came from.

Manuel Martinez: Interesting. So then now as you’re picking up some of these certs, you’re doing a lot of this learning on your own. You’re realizing that you’re able to retain this information and excel, right? Especially being able to take an exam and just – that same day and just pass it. Because again, it’s not like you went something completely different. You’re not doing Microsoft and like, well, let me go take a Cisco cert. Might’ve been a little bit different, but after you get a couple of these certs, I’m assuming you started to build some confidence that like, “I can succeed.” Not that you weren’t already kind of building that, but now you’ve got some credentials. So what do you decide to do moving forward? Because at this point, are you still at that help desk job? Or had you kind of moved forward a little bit?

Ray Freeman: They got rid of me a long time ago, but I started applying for other jobs. Back then when you wanted a job you had to get the newspaper and get the classified ads and in the classifieds – first I wanted to be a music teacher that was really what I was going to school for and when I would look in the classifieds there would be nothing about music or teaching. But it would be page after page of tech jobs just multiple pages and I can almost have my pick because a lot of the people who were around my age and just you know – computers and the Internet was all kind of new then, everybody didn’t have a computer at home and surely didn’t have the Internet at home. So, I did, I had a computer and I had an AOL account so I could get online and I had hands on experience of actually working on stuff and I had some people who were references for me, they could say, “Yes, he did this he fixed this he did a great job for us. So I found that I could get a job pretty easy and so I would apply and I’d get a job and then recruiters would be calling me and sometimes the recruiters would be kind of unscrupulous like they would be whispering “Hey, can you talk?” You know, “Are you at work right now because I want to talk to you about coming to work for us.” So I’m like, “Oh, OK,” you know, so I jumped jobs a lot during that time frame because I was just being poached by so many different companies and you know so having the confidence to excel and try things in technology to get those certifications – and I started getting more certifications I went into to Novell the CNE, CNA certifications. And just from learning more of that getting these jobs, working, getting on the job training – that just gave me more and more confidence that I can really do this. But there was a wrinkle at the same time – the music part was taking off pretty decent at the time. So the guy I was signed to his name – His name was Erotic, nothing weird like that but he had a production studio and I used to work during the day and I’d go to the studio every single night and there would be big artists coming through – Snoop Dogg, OutKast, they would be coming through and they were there to work with him as their producer but I was co-producer, keyboard player. So I had a chance to be featured on a lot of songs that are popular and that went you know – pretty big. You know so I was torn between, “Do I go this tech route or do I keep working on this music thing and see if it if it takes off??” Eventually I got a probably one of the better jobs I had at the time, it was for Citibank. They hired me to come in and work on a CRM system and it was paying pretty good money, it was more than most of the people in my family had ever made and it’s like, “I’m kind of balling right now, this is good.” You know so I had a great job, I’m doing this tech stuff, I was not in school for technology or music anymore, I had work, and I had this music thing going. So that that was the route and it was just a crossroads of “Which one is going to take off?”

Manuel Martinez: I have a question there regarding kind of some of the decision-making. So you mentioned earlier on, like where you had kind of gotten that big check as a young producer and kind of blew through it fast and at this point, again, I’m not that familiar with the music industry, but in tech, working for Citibank, like I said, you’re making good money but it’s a regular paycheck. On the music side, I’m sure that it’s not as steady, right? So if you get featured on a song and you co-produce and it does well, financially you do well but when it doesn’t, it’s not steady. It probably ebbs and flows a lot more, right? There’s probably really good months and then not so good months. Did that factor in a little bit into kind of the decision of where I wanna go or did you also think, like, “Man, I’m hanging around artists, I have the ability to maybe continue here and be a Timbaland, be a somebody that can go through and produce for these big artists?

Ray Freeman: You know I didn’t have the business savvy then so as I mentioned I wasn’t really speaking up for myself and making sure that I’m mentioned in the credits and that I had the publishing deals. I was just glad to be in the environment and just glad to be there and so I didn’t really you know I made some money I got a chance to travel and go to some different places and meet some different people but it wasn’t paying off the way I want it to. The music thing thing was fun, I was having a great time but the tech was actually paying it was paying the bills and I was was doing pretty good on the tech side. And you know from from the technology side I was actually – since I had these certifications and I was able to pass these tests pretty – relatively easily I started a tech school, South Fort Worth, a friend of mine, we rented this fellowship hall on the side of this old church on the south side of Fort Worth, Texas, and I opened a computer school, called it “Dominion Training” since it was a church. And I had people that would come in and they would take certification classes from me to learn how to go and pass the Microsoft tests. So I was getting a lot of people who were coming to my classes getting certified and I was helping them get jobs and you know how to get into the industry. And this was an inner city area. And it’s kind of a rough area in Fort Worth so some of the people that were coming to this school they definitely would have never been able to afford going to some major either university or even one of the expensive tech schools. So it was a great service to be able to offer. We ended up getting into a voucher program where the city was paying people where they’ll give them a voucher if they’re on unemployment or something where they could bring the voucher as payment to us for them to come and take the class. And the tech side was really starting to just grow and the more that grew the less time I spent in the studio. It just kind of started to fade out and eventually I was making enough money to where I was doing the kind of stuff I wanted to do. I was buying fancy cars. I had a couple of BMWs and I was doing okay at the time. And so the music thing it wasn’t paying as well as I want it to and it just kind of started to fizzle out.

Manuel Martinez: That feeling that you mentioned at the very beginning where – like when you’re in the music industry, you were just kind of happy to be there and in that environment. And on the tech side, you’re doing a lot more. You’re getting poached. Like the contrast that I see here is where in the music, you enjoyed it. Not that you were speaking up a lot on the tech side, but it seemed like there’s a difference. Like, oh, I’m good at this. I can help. I can do a lot more. Whereas over here, you’re like, I’m just happy to be here. And I know that a lot of times in really any career, there’s a lot of times where people will get to a role and it is that feeling of, well, I’m just happy to be here. And kind of, I don’t want to say it’s imposter syndrome for some people it might be, but it’s just that feeling of like, I’m just lucky to be here and this is good enough. But on the tech side, it sounds like you didn’t feel that same way. It was almost like, not that you were like, hey, I’m lucky to be here. It’s like, “I worked to get here. I deserve to be here and I’m going to continue to grow and build my skillset.” What made you kind of – like, what made that difference in the tech space versus like in the music industry?

Ray Freeman: Great, great question. You know on the music side I was a side guy. I was under someone else who was the premier producer. So he had the spotlight. He had the fancy cars and everything was around him and I was just kind of working under him. And I just stayed down there in my little space. On the tech side I was the man. It’s like you know I had my own building. We had desks and computers. I had this great job. I had an office at my job with a door and stuff. You know so I guess I was in a more respected position on the tech side and I was looked to as an expert. When people came to the class I was teaching the classes. So they saw me as the guru, the tech guru who was able to disseminate this information. I could simplify it to where just regular average people could understand it. I’ve never had just this huge tech vocabulary that I was just so high up but I could just take what is really complex and make it simple for everyday people to understand. And people like that. They would come to me for advice and I was giving career advice and I was seeing people excel from what they were learning from me. And that felt good. On the music side, I was contributing but then my name wouldn’t be on the marquee or my name wouldn’t be on the front of the album. It would be somebody else’s name and somebody else’s production and somewhere in the credits it may say “keys by Ray Freeman.” But it would be in a small print way at the bottom of the CD or you know CDs by then.

Manuel Martinez: Where somebody has to search for it as opposed to just front and center.

Ray Freeman: Oh yeah, you’d need a magnifying glass to see my name in the credits but it’s in there. But on the tech side it was me and I had partners that I worked with but I’ve just always been a serial entrepreneur of starting little businesses and entities and this one was really taking off.

Manuel Martinez: And we kind of touched on it a little bit at the beginning, but you seem to be okay with kind of the rejection and having that entrepreneurial mindset. What is it that kind of kept you pushing forward? Did you experience a little bit of success at the beginning and just enough? And again, it doesn’t have to be, “oh, I’m getting nine out of 10.” Sometimes just one out of 10 or one out of 50 might be enough to say, “Okay, I can keep doing this.” So what is it in you that kind of started that? And then now at this point, like you said, hey, I have a building, there’s also a little bit of creativeness and I’m guessing that that comes from the music, like the art side of it is, okay, hey, I can build a computer business. I can start teaching other people, like most people that go in to kind of tech, they pick a role, they continue on and they progress. You did that, but at the same time, you’re also doing, you know, working for Citibank, but you’re also, hey, I’m teaching people, like you have this creativeness or seeing things a little bit different, like, “I’m really good at taking exams and studying,” and you didn’t just say, “Well, I’m gonna keep going and just gobble up every certification. You’re like, “Hey, there’s something here. Maybe I can teach other people.” Like how did that kind of all come together?

Ray Freeman: You know, I think it was the successes that kind of drove it. I’ve always been an ambitious person. I wanted to have things that were better. I wanted to travel different places and see different things. My mom used to take me on trips. Matter of fact, when I was like 14 years old she brought me to Vegas. We lived in Texas, she brought me to Vegas and we stayed at like the Circus Circus or something way back then. And just seeing the city and seeing the lights, I was like, “Man, when I get older I’m coming to that city. I’m going to be there.” So just the things that she exposed me to, she took me to Canada. I went to Toronto. I’ve always wanted to have better things, to be able to do better things and to be an inspiration to other people. And that kind of drove me to not just want to exist, not just get a job and stay stagnant in one area. But how can I keep moving up? How can I move to the next level? And what’s the next thing and the next thing? And I guess I would just get bored easily doing the same thing over and over. And I wanted a challenge. I wanted something new. So I’d always take on a new challenge. So another big stepping stone for me from the Citibank City Group job was I was recruited to come to Houston and work for a deregulated energy company. And I was like, “Wow, this is my first time being relocated. This company is actually going to pay to move me to another city and help me to get established.” I was honored to even be in that kind of position as a young guy. So we packed up and moved to Houston and I started working in that industry. And things were climbing up and that’s when there was a downturn in the industry and things started to change quite a bit.

Manuel Martinez: Yep, and it’s perfect, cause that was around, I thought this was around the timeframe. And you mentioned wanting to kind of do more and being comfortable with, “Okay, I’ve achieved more, I’m gonna go through and kind of enjoy a little bit of the fruits of my labor, right?” Like I worked, you worked hard, you got here, you said a couple of cars, you got a nice house, you’re being relocated, you’re being poached. And a lot of times people only see the end result, right? So at some point, you’re climbing, you’re climbing, you’re climbing, and it sounds like around this time is where some of the challenges come in. And you’ve mentioned like it’s a downturn. So this is around the 2008, 2009 timeframe where it wasn’t just a downturn in the tech industry, but I mean, in most industries just across the board.

Ray Freeman: Oh yeah. Back then I didn’t really know much about saving or investing, spending wisely. I mean, I may have been making a hundred thousand a year, but I was spending 150 every year. And that just puts you deeper and deeper in the hole. I think I was trying to live a music producer’s life on a tech salary because we were coming to Vegas a lot then. And I could buy a trip for a couple hundred bucks and we’d fly here 10, 12 times. We were coming to Vegas. And I was like, “Man, I’m going to live there one day. It’s just an awesome city.” But I was going on cruises and just doing the craziest stuff, spending so much money. And when that downturn happened, my wife was laid off like to say December 8th. And I was laid off like December 13th, like in the same time. And we hardly had anything saved up. We didn’t have any emergency fund. We had no investments. We had a six bedroom house that we had built in Houston, huge two story building. And when we lost our jobs, I had to start selling stuff out of the house. So eventually we sold most of the furniture, sold most of the TVs and clothes. We just had just us in this big house. I remember the echo in this place. I was so proud to have the house when I first got it, but it just became this albatross. I can’t believe now I’m strapped with this huge mortgage. And I don’t have a job and there’s nobody hiring. And we’re both just sitting here. We’ve sold most of our stuff. We don’t even have a couch to sit on. We’re sitting on the floor. It’s like, “What do we do?”

Manuel Martinez: And you make a good point there is a lot of times something that’s not talked about much, right? Is not having, you know, it’s one thing you get a job, you start making more money. And usually the more common thing is you make more, you spend more like, oh, I can, you know, I got a $20,000 raise. That means I can spend an extra $20,000 or I made, you know, another $40,000. You know, you kind of continue to go up and up and not having like that financial education or the literacy and understanding, or even just a mentor, just somebody, because it sounds like the good and the bad is, you know, you’re entrepreneurial, you’re figuring this out on your own, which sounds like you didn’t at the same time have mentors or people that kind of go through and explain to you and say, hey, are you maxing out your 401k? Are you putting away a little bit of savings? Like not having that, I mean, that was, you know, like you said, looking back now, like, wow, like what a huge learning curve that early on.

Ray Freeman: Oh yeah. Oh yeah. Oh yeah. I blew so much money during that time. And I mean, I don’t regret it because I had so many awesome experiences and I’ve got the craziest stories on places I’ve been and things I’ve done. So I have no regrets on that end, but the older wiser me says, “Wow, you should have done these things differently because we would be in such a better position today if I had done things differently.” So, you know, it happened.

Manuel Martinez: So then now you get laid off, you have this downturn, you’re selling off what you can to kind of continue to live and make ends meet. So like what transpires? Like, well, you know, was this going on for a couple weeks and then like, okay, I’m good to go. Somebody hired me. Like what happens and you know, kind of what’s the next step for you to go through and say, hey, you know, I went from having everything to now almost nothing and how long did that last?

Ray Freeman: Oh man, that went on for months, almost a year. I can remember calling BMW and because they were looking for my car to repossess my cars. And I remember just finally just giving up one day, call BMW and say, “Look, just come get both of them. I’m just going to park them outside. I’ll leave the keys in them. Just come get them. I’m tired of running and hiding from you. I don’t have any money to pay you. You can have them.” We’re close to foreclosure. We’re just about to lose the house. And so they came and got the cars and I took about, I had about $700 I got from selling some stuff in the house and I went and bought a 1982 Saab. And that was a beater, man. It was a beater. And I remember being okay with it because my first thought was how embarrassing that I had a huge seven series BMW and a convertible BMW and we’re just ballin’. And all of a sudden I’m driving this old clunker beater at the door doesn’t even say closed and I’ve got tape to hold the door closed. And I was just taking random jobs. I was a DJ for a while. I was DJing weddings, bar mitzvahs and birthday parties and stuff. So just whatever I could do. I was working at Best Buy, putting DVDs on the shelf. Just anything I could do to keep, just to keep the lights on and to keep some food going for my wife and I. But the first break I got for another tech job, it wasn’t even in Houston or Texas at all. It was in Pittsburgh, Pennsylvania. And so I’m like, “How am I going to get to Pennsylvania to get to work?” That was the first job that hired me and it had been almost a year without anything, without any savings and just scrapping by trying to make ends meet.

Manuel Martinez: And you mentioned that not feeling embarrassed, right? Cause a lot of times, it’s happened to all of us. It’s happened to me where at one point I’ve had to take those step back, take a job that didn’t pay as much just to kind of either, sometimes you’re just to get the experience, sometimes it’s just to keep income coming, right? To stay employed. And I think I would have had that similar mindset as you as- I don’t feel the embarrassment. Like I’ll tell you right now, I think I’ve have much more pride and I don’t know if maybe it’s your worth ethic or maybe it’s just knowing that you’ve done it before and you can do it again is, heaven forbid, like I don’t wanna lose my job, but if it did, I think I would do similar to you. Like I would go and anything I can do, I have to continue to bring in some sort of income. So was that kind of the mindset is like, okay, I did it once, I can do it again.

Ray Freeman: Oh, for sure. My mom, she worked on the same job for 25 years. She worked for a Miller Brewing Company, the Canning Division. And so I watched her work hard, take care of my brother and sister and myself and do things for our family. And just for her to get that job, she did something similar that I did. She went and got some certifications and she landed a job and she took care of her family. I used to watch her work 12 hour days, sometimes 10, 15 days in a row, no days off. And it was nothing for her to work overtime, do whatever it took to keep us going. So we’d never have to do without anything. But she busted her tail to make that happen. So that work ethic was always in me that if somebody’s hiring, I’ll go work for them. I don’t care what it is. If I’m building a fence or cutting yards, whatever I need to do, I’m going to make ends meet. So that’s what just instilled in me from growing up.

Manuel Martinez: And it sounds like, and for anybody that is kind of looking like – I wanna get to a certain place or I wanna be around people, I think one of the big things that I’ve taken from what you’ve mentioned is exposure. Your mom exposed you to her work ethic. Your mom exposed you to traveling and seeing other things. So you’re like, oh, there’s more than just kind of where I’m from. I guess the kind of takeaway that I get from there is for other people as well is, if you want to get into a specific area or if you want to be this person surrounding yourself with those people, and I think now there’s no shortage of it. You can go and there’s networking events, but there’s even user groups and all kinds of like-minded people, and if you start to get exposure to that, I think it really helps change or set your mindset similar to you. Where did it come from for you? It wasn’t from people in their neighborhood because you didn’t know other people that were in the tech industry. But there are certain traits, like the work ethic, the being exposed to, hey, I can do other stuff. So it sounds like at this point, you got this job in Pittsburgh, and you weren’t scared about saying, I’ve got to go somewhere else, right? Because you’re like, I’ve traveled before, it’s not a big deal. But from our conversation before, it wasn’t as easy as like, well, I’m just gonna go to Pittsburgh and I’ve got this job, and we’re back in business, right? We’re back to where we were.

Ray Freeman: No, man. It wasn’t that easy. We were behind on everything and using credit cards and maxing them out, of course. So I had a card. I charged a one-way trip to Pittsburgh and didn’t know much about how to do the rental car and stuff. So I used the same card, got a rental car, and I get to this hotel I was going to stay at. The car doesn’t work anymore. So I’m like, “Uh-oh.” I had probably 40 bucks or something in my pocket, but this card doesn’t work, that card doesn’t work. I’m tapped out. It’s in the middle of a snowstorm. It is just ice cold where I’m at. It’s late at night, so I’m thinking, “Okay.” When I start this job on Monday, I think I got there on a Saturday night or late Saturday night or something. I start this job on Monday, I’m calculating, thinking, “Okay, I’ll get my first check by Friday, and if I could just survive until Friday, I’ll be good.” My wife’s back home at the huge, almost empty house in Houston, and she’s got what she needs there. So I’m figuring, “I’ll find somewhere to park, and I’ll sleep in the car.” I remember that first night, I went to a Jack in the Box or something and had some food and got a drink. It had ice in it, and I put it in a cup holder, and I just bundled up, and I parked somewhere, and I’m sleeping in the car. Next morning, the drink was just solid ice, and that was like a low point for me I’m like, “I can’t believe I’m sitting here sleeping in this car, and it’s so cold that my drink has turned into a solid block of ice.” So I was like, “Well, I made it through that night, so let me get up and figure out how to get somewhere and get cleaned up. If I can make it and just get to work Monday, I know I’ll be somewhere warm, and I can be at the office all day, and I can just figure out how to bed down at night in this car. If I make it to Friday, I’ll get a decent check. It was an okay job, and I’ll get somewhere to stay.” That’s what I did. I’ll stay in the car for a week. It did warm up, at least to be above freezing, and it was okay. That gave me…it’s a learning experience, but it didn’t take me out. I’m like, “I did not die from this.” I didn’t have to call anybody and say, “I’m down on my luck. Can you send me? I’ll deal with it.” I just figured it out. I started figuring out how to survive when you don’t have a place to really live. I got a styrofoam cooler, and I would get some cheap groceries and stuff. There’s a Dollar General that I could buy groceries from and just keep in this cooler. I go to the Goodwill store, and I found a little George Foreman grill and a rice cooker for a couple of bucks each. I found somewhere to plug up, and I cooked some food. I just learned how to make it and to be okay with it. It wasn’t a super long time, so no disrespect to people who have had to do that for months or years. It was only for a week. I survived it. I got through it, and it built a sense of character and appreciation in me for everything that I have.

Manuel Martinez: Right, and it’s funny that you mentioned, after that one, “I survived,” right? “I can do this,” as opposed to, and again, there’s nothing wrong with asking for help either, but there was something in you that says, “I can do this. I don’t need to depend on somebody else.” Now, again, people will say, well, you could have, you should have, again, everybody’s situation’s different, there’s nobody that’s gonna tell you what’s right for you, but I like the fact that you were like, “Nope, I did it once, one night, I could continue.” And you just – it seems like at that point you’re taking it day by day. You weren’t like, okay, I’ve got this job, and you were thinking, from here to Friday, you weren’t like, oh, from here to next month, that’s it, like my problems are solved. You broke it down into manageable steps, right? It’s almost like goal setting, right? Is it a glamorous goal? No, but it’s a goal, and you said, by Friday, okay, I survived one night, okay, one, now I’ve only got six more or five more to go. So is it – is that something that you continue to do forward, is just setting those goals and saying, okay, I did it, I’ve just gotta do this one thing or these two things, and I can continue to grow.

Ray Freeman: Oh man, 100%. Breaking big goals down into small chunks. That ended up being something that took my career a long way, but it’s something I grasped early on. That really was my mindset. I can just make it to this week, and I have a plan. I have a plan, but once I do get this first check, what’s going to be my plan? I learned early on, break big goals down into small tasks, have a plan of what you’re going to do, and be able to execute that plan. I knew, “Okay, if I get this check, there’s an apartment complex, and it’s like first month’s free.” You had to show where you had proof of income. I had proof of income. I got the first month’s free. Same thing at a Rent- A-Center or a rent-to-own place. I’m like, “I need a mattress, and I need a microwave.” It was like, “Okay, you get the first two weeks free. Great.” I just started to build up a little piece at a time. Eventually, I had a furnished apartment. After a few months of being there, I’ve had enough to fly home back to Houston and see my wife, or I could bring her to Pittsburgh, and we could stay there for a while so we could get back together again. I was working enough to send money home, but still not really enough to cover paying for that house that we couldn’t afford in the first place, plus my living expenses here. We were still nearing foreclosure there and just barely skimming by. But at least we had food, we had clothes on our back, and we were both in a safe environment.

Manuel Martinez: And I think that’s something that a lot of times is missed. We see the end goal, or it’s good to have that kind of that five year plan, but sometimes making sure that that’s not all we’re focused on, right? It just can’t always be the end goal. Sure, it’s good to have dreams and to have an idea of how you wanna move forward, where you wanna get to. But I’ve seen a lot of people that just go, and they’re like, well, that’s it. That’s all they think about, and your career’s a lot longer than, hey, within the next year, I’m gonna be a senior architect, or I’m gonna be a senior cybersecurity person. It doesn’t happen that quickly. And just knowing, okay, that’s something to aspire to. Could you do it in a year? Maybe, but what are the steps you’re gonna get there? Just thinking about it and saying, I wanna get there, I’m gonna get there. That’s not enough.

Ray Freeman: Definitely.

Manuel Martinez: So then, you get this job in Pittsburgh, you’re starting to kind of put things back together, and how long did that take to eventually, you can start to kind of reunite with your wife. And you’re in Pittsburgh now, right? So you’re going from Texas over to Pittsburgh. Did she eventually move with you? Did you guys move somewhere else together? So I’m just curious kind of what happens next.

Ray Freeman: We lived back and forth in different hotels and extended stays. I would book a place that was anywhere from a week to a month at a time. So we never really had a consistent place that we just lived. That went on for almost a year that we were in Pittsburgh. But we made the best of it. When we were there together, we ended up going to Pirates Games and Three Rivers Stadium. Well, it used to be Three Rivers Stadium. Not a big Steelers fan but, was able to go to some Steelers games just to see the city and learn the people and everything. We just embedded in that city and that culture there for a while. Eventually, I wanted to get back to Texas. This was a contract job that I was on. It was coming up on the year when the contract is about to be over. It was an IT contract. I was doing some CRM database transfer, some weird thing I was working on. Eventually, we had brought one of our cars there. Drove from Texas to Pittsburgh. Barely made it, but we had a car there. Just before the contract ended, we took about a two and a half week road trip. We left Pittsburgh, went up to Canada, and just zigzagged across the US. We eventually got to Florida and came all the way back across to Houston. For about two weeks, we just drove around and saw the whole East Coast.

Manuel Martinez: And as you’re kind of doing that and knowing that your contract’s ending, I’m assuming during that time period, you’re also kind of putting in applications and you’re like, “Hey, I know at some point I’m gonna go there, so let me kind of make the best of it.” And I do that pretty often, like when I’m going from one role to another, like I bake in a little bit of extra time and say, “Hey, I’m gonna take time and go do something for myself because I know that once I get into this next role, it’s full bore.” And that’s that whole drinking from the fire hose and everybody’s kind of all this information as you acclimate to this new job.

Ray Freeman: After all of that was over, we finally got back to Houston. I found a realtor who was willing to help me get out of this house to get it sold. He was just such a really nice guy. He put in some of his own money to help me to get it sold. My wife, she’s in real estate. She was a realtor at the time, but we just needed somebody to help us get out from under this because we were so underwater. We finally got the house sold, but the next job that I got wasn’t in Houston. It was in Austin. We were like, “Okay, we’re moving to Austin.” We moved to Austin. We did something similar. We got a first month’s free apartment. We got some stuff that we moved into the place. That was another surreal moment, going from this huge house to this dinky apartment that wasn’t in a great location. There were some people fighting outside the day we moved in. It was like, “Oh my God, what have we done?” We moved in there. I started working with this company that was actually doing some public sector work. That was kind of cool. That was one of my first avenues into the public sector back then, working on a North Texas Tollway project. That was interesting. I learned how to build an office, physically build an office that was going to house all the public records and put in all the IT and telephony and the staff. I really learned a lot about just building a business and staffing a business and running a business. They taught me a lot there. That was a good time. We had a career restart. She got into relocation and doing more realtor work. We started moving back up again. We started buying nice cars and going on trips again. We went back up to the top.

Manuel Martinez: And this time when you’re doing it though, did you learn from the last time and say,

Ray Freeman: Of course not.

Manuel Martinez: let me, no, no, we’re not gonna save a little bit? We’re gonna go right back.

Ray Freeman: Of course not. It took me a while to really learn it. I was hard-headed. After being at the bottom for so long, I felt like I’m finally back, so-

Manuel Martinez: You’re like, man, third time’s a charm, right? (laughing)

Ray Freeman: Of course I didn’t learn it. It took me a few of those restarts to really get it. I was like, “Wait a minute. You need to do things totally different.” I didn’t get it right then. I made some of the same mistakes, but made some of the same mistakes again. At least this time, we were able to build a home and buy a home there in Austin. We just started living a nice life there. Eventually I was poached to another job that was back in Fort Worth, Texas. We got rid of that place, moved back to Fort Worth. Every time I’d get a better job, I’d move somewhere else and make more money. I could just keep spending because eventually I’ll find out a way to make more. It was working there for a while.

Manuel Martinez: So as you’re going through it, so again, now you’re kind of back into that working for other people and doing that. But now at the beginning, you mentioned that you have a business here and then also one in Atlanta. Correct? So how did that come about? Which one came first? It sounds like you’re in the kind of Midwest, probably a little bit East Coast like with Pittsburgh, but so you’re in this area. Did Atlanta come first and then eventually Vegas knowing that, hey, I want to be here. So how did it go from you working for other people and kind of getting poached to saying, okay, I’m going to build a business now?

Ray Freeman: You know… along this journey, I had some really good jobs before I even get into these businesses. I worked for American Airlines. I helped to build integration with US Airways. I went to work for Southwest Airlines. I was just good at bringing in methodologies from different companies and different teams who were merging together. I learned about agile methodology and became an agile coach and trainer. That led me to just so many other different positions. There was this whole thing where we moved to Jamaica for about six months, which is a whole other thing. I really wanted to work for myself. I wanted to have my own business, my own entity. I had a good friend of mine named Anthony. Anthony was my coach and also my business partner. We started this company called Agile Consultant Guide. We had landed a contract with AT&T. At the time, AT&T was like a Fortune 5 or Fortune 10 company, huge. We were working with this big entity. There were some things that they were doing that were going to fail. This is not going to work out right. He just gave me some encouragement of some things that I should go out and just say and do and be bold. I remember I had one of those elevator conversations with the CTO of AT&T. I told him, “You know what? Your whole agile release train that the team has put together, everybody’s going to be blocked. First sprint is going to be blocked. Promise you.” He was so pissed. He was shaking his fist and he was like, “What are you talking about? My teams are great…” The company I was contracting through, they got mad at me. They fired me. I went home. Two weeks later, he found me on LinkedIn and reached out to me and said, “Get in here. Everybody’s blocked. Show me what happened and why we’re blocked.” I went back in and we ended up getting that contract back and that was growing. They went to a freeze, moved to Jamaica. We had a contract with a bank on the island. We sold everything, moved to Jamaica. We did a bunch of transformation work there on the island. I moved to Beaverton, Oregon. I took a contract with Nike. I did an agile transformation with them for three months. Eventually, I got a management consulting position with a company called Adaptivate. That was back in Los Angeles. I moved to LA. We were in Marina del Rey, right on the water, right by the boats and everything. My living room window was facing the ocean. It’s a beautiful, beautiful place. This company, I was doing the management consulting work. I’m working for big oil and gas companies. I’m just traveling all over the place. They were starting a separate brand called Tribe. They wanted me to grow this business and just to build it and run the whole P&L. I did. It started growing. I hired staff and we had contractors working in different places. That taught me a different way of running a really sizable business. It wasn’t just me. I had people working in different countries that are reporting to me. This is amazing. I got people in Poland and people in Jamaica and people across the US. They’re all reporting to me. I run the P&L and I report to the CEO. It just gave me a different kind of confidence of not just running something that getting myself a job as an independent. Now, I’m starting to learn how do I get other people jobs? How do I help others to work? I can show value but bring in other people to actually deliver the value. That was another life-changing thing for me. I don’t have to do all the work. I don’t have to be the one who is always at the computer or at the whiteboard. I can bring in other people who are way smarter than me and scale this thing. I can do it globally. That gave me a whole different mindset, a whole different confidence in how to run a business. There was a lot in that thing there.

Manuel Martinez: No, there’s a lot, but I think the area that I wanna hone in on is, your friend Anthony told you to kind of be bold, right? And you went to the CTO and you had that moment of like, hey, it wasn’t just be bold, but is it pattern recognition? Was it, did you, you mentioned like, hey, in a week your team is gonna be blocked. Was it through experience? Was it things that you were seeing that kind of – and I’ve talked about this before, a lot of times like we make mistakes, right? And you’ve made plenty of them, but at some point you also start to see through experience, I think a lot of times it’s pattern recognition is you saw something that says they’re gonna be blocked. And here’s why. And like, maybe you saw the blocker, because you’re sometimes it’s just a different perspective. Like they’re so entrenched and here’s what they see and this is what they know. Somebody from the outside sees something different, but then also now you are bold. Again, it’s a different industry than kind of back in the music where you’re just like, hey, I’m gonna sit back, but now you have this confidence, you have this knowledge and you’re like, hey, you’re gonna have a problem. And kind of here’s why, did he even know why? Or was it just like, hey, you’re gonna be blocked and come talk to me.

Ray Freeman: You know, there was an infrastructure team who of course managed the infrastructure. The release trains that I was working on, we were building software that was going to sit on this infrastructure. But the way that they had built the organizational model, the infrastructure team wasn’t included in all of the big room planning and the growth. I, against their advice, went over and talked to the infrastructure folks. They were like, “I have no idea what you’re talking about. We’re going to put what on our what? We’re not ready for that. We don’t – no.” I was like, “Yeah, you can build all this stuff, but it’s got nowhere to sit.” I knew it’s going to be blocked and nobody else wanted to hear that. I had to have that confidence to just go and tell them, “This is all going to break. It’s going to break bad.” I was working under a contracting company. They have the contract. They’re the ones who put all this together. They didn’t like that I went to everybody’s boss and told him that the stuff that we’ve all built, this multi-million dollar

machine: All going to fail. My badge didn’t work anymore that day.

Manuel Martinez: Had you let the people that you worked for, did you let them know first?

Ray Freeman: Yes. Tried to let them know, like nah, nobody wanted to hear that. “That’s irrelevant. It’s going to be in a test environment. It’ll be fine.” No, this is not going to work. It won’t sit and test. It has to sit on this environment. They’re not ready for it. It’s not going to work.

Manuel Martinez: And I think communication and being comfortable having those uncomfortable conversations, right? That’s uncomfortable to then, okay, it’s one thing, it’s probably not so uncomfortable to kind of tell you about. Hey, there’s a problem, again, we’re gonna have this issue. But once they tell you no, you could have just sat back and said no and then run into that issue, right? But again, you could have kept your head down and just be like, oh, it failed. And then, why did we not know and try and fix it after the fact. But you went through and having that confidence, And I think a lot of times, I think that’s good for people to hear, to say, okay, go through the regular chain, right? Like you’re supposed to, like it doesn’t sound like you skirted around it and like, ooh, I wanna be the guy. Nobody’s listening. Find the person that will or the person that can make that decision. And I talk about it a little bit on LinkedIn as the things that I’m posting is learning how to ask better questions. And once you get that information, like you said, well, wait a minute, pattern recognition, like the infrastructure team’s not here. Hey, are you aware and being okay knowing that I’m making the right decision, I’m telling the right person, I get it, you don’t want me to and I’m gonna go around and you paid the consequence, right? Like my badge doesn’t work, but in the long term, it was better for you.

Ray Freeman: It was so much better for me. It gave me the confidence to speak up no matter who or what level I’m talking to. Because of that experience, if I’m talking to a CTO, CEO, or whoever, and something’s bad, I’m going to tell them. I think they appreciate that about me. I’m not going to hold back or even try to protect myself. I put my whole job on the line in order to say, “This is a problem. Nobody’s paying attention to it. This is a big problem.” I take that with me today. I’ll still do that. I’ll still stand up in the biggest board meetings with the person at the top of the chain. If I have to tell them, “Look, your stuff is garbage, man. It’s going to break.” They’ll be pissed off. They won’t like it. But that changed my life to be able to have that confidence to stand up to any role, any level, and say what needs to be said.

Manuel Martinez: And have the information to back it up, right?

Ray Freeman: Yeah.

Manuel Martinez: It’s not like you were just saying like, “Hey, this isn’t gonna work for no reason, but it’s–

Ray Freeman: I made PowerPoints. I drew it on whiteboards. I tried to have meetings on it. Nobody wanted to hear it. I’m like, “Okay.”

Manuel Martinez: I’ll find the person that will.

Ray Freeman: When he called me back into his office, so I showed up a couple of weeks later, I showed back up at AT&T and they were looking like, “Here’s Ray. He was just fired. Why is he here?” I’m like, “Nope. I’m going up to the top floor. I have a personal invite.” His secretary came down, his admin, she came down, she badged me in. Took me way up to his office. He was like, “Okay, show me what you were talking about.” I brought my PowerPoints. I drew it on the board. I showed him that. “Here’s your infrastructure team sitting over here. Here’s the whole release train.” The reason they didn’t do it, it violates Dunbar’s law. It’s over 145 people in a group. So they just excluded them because the numbers were too big. That’s the wrong thing to do. He saw it right away. He was like, “You’re in.” So we ended up getting bypassed through all procurement, everything that a company would normally have to go through to get a contract with a company that big. With his endorsement, we bypassed all of that. Boom, we’re in.

Manuel Martinez: And the reason that you were able to articulate all that, probably not just the technical problems, right? Because the CTO, he understands the technology, but it’s also why is this a problem for the business? Looking back now, is it all that experience of you being able to teach other people, right? Like taking these complex ideas and be able to simplify them, because that’s another thing that a lot of times people don’t understand is to really be successful. And it sounds like by this point, it’s not just the confidence, but it’s the communication skills. Like, hey, being able to whiteboard and break things down simply and understand, hey, this is a problem, here’s why. in, you know, PowerPoints, sometimes it’s spoken. So it sounds like you did all three. You had to speak it. You probably had to write it out. You had to present it in a PowerPoint. You had to be able to draw it on a board. Like all these different experiences now kind of come together and would you say that that’s probably one of the biggest skills that’s helped you throughout your careers being able to communicate?

Ray Freeman: Definitely. Where I learned that from is just more certifications. A couple of the certifications I got back in the day were one for DISC, the D-I-S-C personality testing. Another one is a similar psychometric testing, but it’s called Emergenetics. It’s like the psychology of workplace dynamics. It’s how to recognize how people think and behave in the workplace, and then how to modify your posture, your speed of speaking, your tone of voice, whether or not you articulate with your hands or if you keep them to the side. All of those things taught me how to communicate with different people in different ways. I knew how to reach him and to not come across as offensive or just being brash. But having that skill to be able to communicate and then those skills I learned from way back in the day of being able to take these complex technical things and just simplify the language and how it’s presented, all of that meld together. That’s what I used to be able to demonstrate that.

Manuel Martinez: That’s amazing. I never thought about using kind of those discs and understand like I’ve taken that disc assessment and it helped me understand how I work, right? One of the companies I work for as part of the hiring process, they did one so that they knew how to work with me. And it gave me an understanding, kind of when they broke it down, it made sense to me. Because all of a sudden, yes, money wasn’t, I mean, it’s important, right? Like you wanna be able to pay your bills, have a little bit extra, you know, you have a little bit of fun money. But one of the things that came out of that is what really motivates me and its challenges and learning. As soon as I become stagnant, like if I get bored, I jumped around a lot and that was a big thing. And I never understood why I did it before. I had that test or that assessment and I was like, oh my gosh, that’s it. It nailed it to a T, but now understanding how to use that to communicate with other people, that’s impressive.

Ray Freeman: That taught me a lot. One of the best analogies that I learned from it is how people react when… Just say you book a conference room and you have your team with you and you get to that conference room, but there’s already a team in there working. So there’s some mindsets that would say, “Oh, room’s full. Let’s just go get another one.” There’s another mindset that’ll just say, “Oh, I’m going to barge in. Hey, get your stuff. Get out here. It’s our room. We booked it.” There’s another that would just kind of hover around the outside. “We’re just going to stand here. Maybe they’ll see us and maybe they’ll think we’ll leave.” Whichever one you are, when you’re a leader, your team is going to perceive you one way or another. They may respect you for going in there and taking charge and getting the room, or they may respect you for letting someone else have it and going in and getting another one. So understanding things like that helped me to really recognize mindset, recognize patterns, recognize how other people want to be communicated with. It’s that platinum rule, that Tony Alisera – platinum rule over the Golden Rule. Golden Rule says, “Treat others the way you want to be treated.” Platinum Rule says, “Treat other people the way they want to be treated.” I learned to use the Platinum Rule whenever I’m communicating with people or leading people. That has helped me so much in just knowing how to quickly bond with someone and to either get my point across or to help them to get their point out of them so we can communicate better and get what they want us to – What do you want me to know? How can I get you to tell me what you want me to get from this conversation?

Manuel Martinez: Wow. This has been such a great conversation. It’s even better than I thought it was. Just based on our talks separately, I could talk to you for another probably two hours. And I know that you have a bunch of stories and just each time I ask you something, I see something else that I’m like, ooh, I wanna know more about this and I wanna know more about that. And I’m lucky enough that I’m gonna have those conversations with you outside of here, but then at some point, I haven’t had repeat guests, but I’m kinda slowly working that in to try and do that. And I would definitely love to bring you back because I know that there’s still so much that we haven’t covered, especially how you got your businesses started. We touched a little bit on the beginning, but kind of what led you to kinda doing that. So I’d like to definitely bring you back and kinda continue that.

Ray Freeman: Most definitely.

Manuel Martinez: But before we end this one, I just wanna kinda

give you the opportunity: Is there anything that we didn’t cover, at least in kind of the conversations we’ve had now that you’re like, hey, we kinda breezed by this or hey, I forgot to mention this one part that you think is important out of kind of what we’ve covered or anything that you wanna bring up?

Ray Freeman: You know… in launching and leading the businesses that I work on today, one of the biggest things that I’ve learned that I’d like to impart to people is you don’t have to do all the work yourself. I used to think that owning a business was the same thing as owning a job. And it’s not. I just think that I need to know everything. I need to have all the certifications. I need to do all the work. But that is not the case. And if you’re a business owner, you run the business. And it’s your job to run the business. So if that business needs people, processes, tools, technology, then it’s your job to assemble those things and govern them in a way that drives your business. And man, if I had known that a long time ago, I wouldn’t have been getting jobs for me. I would have been creating jobs and creating opportunities for others. So that’s where I am today. And that’s where my mindset is today. And whatever I’m talking to, especially small and medium sized business owners, don’t try to do all the jobs yourself. And that’s my premier advice I want to leave to people.

Manuel Martinez: It’s perfect timing, because recently I had been recommended by somebody else a book called “Who Not How.” And the concept is exactly what you’re talking about is finding those people. And it sounds like you and I have a similar mindset – You like to learn, you’re able to pick things up. So you’re like, oh, I can do it, so I need to do it. But it sounds like at some point you realize that, okay, just because I can, doesn’t mean I need to or that I even should. It’s finding those people that – and the concept of the who not how is – you don’t need to figure out how to do it. You need to find out who is the person that can do this and let them thrive in that role. And again, you’re creating opportunities for them, people, for people and for yourself, right? Because now you’re bringing them in, it’s helping you grow and scale. So now that you can build more opportunities and it just, that’s how you scale, right? It’s not you doing everything by yourself.

Ray Freeman: Yes, sir. That’s my best advice I can give to people, especially small and medium sized business owners or business leaders. Just learn how to scale.

Manuel Martinez: Well, and I wanna get your, I know we’re trying to wrap this up, but I wanna get your thoughts on this. As you mentioned, small and medium business, but would you say that also within an organization, like as a manager or as a leader, that same mindset sounds like it would apply there, right? Is knowing who to bring in to make your team, your organization run better is, okay, a lot of times I’ve seen it and I’ve heard where people get promoted because they’re really good at doing this thing and they get brought up and they continue to do that thing and not learn to kind of like, well, I’m the lead architect, now I’m the manager. It may seem like it’s a small, but it’s a big difference. It was now I have to coach people, I have to bring people and I have to bring that person. So, does that translate?

Ray Freeman: It’s a whole different job. And there’s so many organizations that promote people based on tenure. And now someone is, like you say, the manager or the lead of people when they used to just be someone that’s leading their own job in the domain. So there are there’s a lack of leadership skills that exists in a lot of companies because of that. So that does translate. It’s slightly different in an organization because there’s a – trust but verify. It’s like, yes, you bring in people, but then there’s a verification because you’re still ultimately the one who’s responsible for that work product that’s being delivered. So if you’re the leader, you can’t say, “Oh, well, Joe didn’t do it right.” No, man, it’s on you. So when I’ve been in those leadership type of positions in other companies, I don’t really know how to test code, but I need to at least look over your shoulder and say, well, can you run that test case and let me see it and we see it pass? I can’t just say, oh, yeah, he ran the test. It’s good. Let’s go to production. No, I need to actually be there and verify that I saw it. I saw it work. And if you tell me that it won’t compile, well, show me what you’re doing. I don’t know how to read code. I don’t know JavaScript. I don’t know Java. I don’t know any of it. But at least let me be there and let me see it. And because if you’re the leader, you are ultimately responsible for everybody in that department, or that reports to you. So that’s my advice to leaders is you’re still responsible and you can’t pawn it off that somebody else did it. You have to actually be there. Even if you don’t quite understand the work that they do, you’re still responsible for that work and you have to oversee it and verify that it’s done. It’s working. It’s ready to go to production or whatever that next step is.

Manuel Martinez: That’s great. I love that; trust, but verify. And the accountability, right? You’re accountable for that and you have to go through and make, not make, but really go through to each individual contributor and make them accountable. You’re saying that this is working, show me. Okay, it works great. Oh, it’s not working. Okay, I don’t know how to read it. I can’t help you troubleshoot, but tell me what’s the problem or what you think the problem is because you may have a resource or you may be able to ask a question that gets them to go, ah, I know what it is now. Like, you don’t know how many times I’ve walked through a problem with somebody and just talked it out and figured out my own issue just by verbalizing it.

Ray Freeman: Definitely. And I’ve been burned on that a couple of times. Like I’ve had teams that brought down AA.com for like nine hours because they weren’t really, we’re doing manual testing. They weren’t really completing test cases. If you were just like, oh, I’ll take a screenshot and just upload the same screenshot over and over to say that I did the manual tests. And it wasn’t tested and there was a defect and it did get into prod and everything went down and they didn’t go back to those developers and say, hey, you deal those testers. Oh, they went to me. Like you brought down the system, we’re losing millions of dollars. You know, so, um, yeah, if I had been looking over his shoulder and said, no, man, you can’t just copy that and you have to actually run this test. What are you doing? I could have averted that whole situation.

Manuel Martinez: Yeah, it’s not micromanaging. It’s just, again, verifying that what you’re reporting or what you’re telling me is really what’s going on.

Ray Freeman: For sure.

Manuel Martinez: Again, awesome conversation. I’m glad that, you know, we communicated and I definitely, at some point, you know, I’ll give it a couple months and, you know, we’ll be in touch because, you know, we’ve had such good conversations just in the couple of networking events. And definitely I want to have you back and tell more of your stories. This will be amazing.

Ray Freeman: Manuel, let’s do it, man. I’m excited.

Manuel Martinez: Thank you.

Ray Freeman: Thanks for having me.

Manuel Martinez: Of course. And for everyone that continues to support by watching and listening, thank you so much. And again, it means a great deal to me that you find value in the conversations that we’re having, the guests that I’m bringing on. And really, if there’s anything that you’re looking for specifically, definitely let me know so that I can continue to make sure that I’m making this better for all of you. So with that, continue to plug in and download the knowledge. And until next time, thank you.