How Cliff Scott found a second chance in business and in life

The story starts with a man. He was homeless but not entirely hopeless, not yet, though he tried to be, on more than one occasion. But God had a plan. He always does. 

This man had nowhere to sleep, he was struggling with a loss of unimaginable comprehension and an addiction formed to mitigate the pain of that loss. 

He was a kind man. Not angry. Not feeling sorry for himself. He was simply lost. Devastated by life’s circumstances. 

But that wasn’t the end of his story. That was not the end of Clifton “Cliff” Scott’s tale. 

Scott would go on to build a business, thanks to the help of his current wife, Velma. He would open a handful of assisted-living facilities, two of which he gave away, to help people, he says. 

He would become incredibly involved in his church, he would sing and learn guitar, he would be the person who orders hundreds of turkeys so he can pass them out to families before Thanksgiving. 

He would laugh and make memories and not sweat the small stuff because, after what he experienced, he found that the home he lives in, in Riverview, the family he has around him and the work he does, are all the blessings he would ever need. 

There are sad moments but this is not a sad story. Cliff Scott is far from a sad man. He’s joyful and grateful and he spreads those feelings willingly. 

This is his story and it deserves to be told. It begins in a small mill town, on the border of Virginia and North Carolina, where his grandmother ran a juke joint. The year was 1960. 

The Mailman in Mill Town

A juke joint, for those who may not know, is an informal establishment featuring music, dancing, drinking and maybe a little gambling, too. 

These gathering spots, primarily operated by African Americans, were created as a place to socialize, relax and have a little fun, in an otherwise oppressive, and sometimes abusive, time. These establishments provided a much-needed distraction to the difficult world lived in by the Black community, at the time. 

“Everybody gathered at my grandmother’s house. My aunt was the bouncer and my mom was the runner. She was the one who ran down into the woods and got the bootleg to bring back to the house,” recalls Scott. 

As a child, Scott was nicknamed the “Mailman.” 

“On my fifth Christmas, [my family] bought me a set of cowboy cap guns and a little belt and I, subsequently, went out that following Monday and held up the mailman, for a nickel, with my cap gun. So, from that point on, they called me the mailman.” 

Scott says he comes from a traditional family. He had a younger brother and two younger sisters. His father, like most people in Danville, Virginia, worked at the mill. His father later worked for The Goodyear Tire and Rubber plant, the largest employer in the area, at the time. 

His mother was only 15 years old when she had Scott, her eldest son. She quit school to take care of her family. When her children were a bit older, she took a job as a janitor for the local school. 

“We watched her work very hard to give us things in life and, I think, it kind of set the tone for all of us as kids,” Scott says. “Me as a business owner. My sister, closest in age to me, is a director working for Blue Cross and Blue Shield, and my baby sister, who basically manages three hospitals in Danville. We all developed a really strong work ethic, at a young age, and we just knew that if you’re going to have anything in life, you’re going to work for it.” 

Scott’s brother passed away when he was 37 years old. 

After high school, Scott wanted to get away from his hometown. He admits that he and his father didn’t have a very healthy relationship, at the time, and that it had a tremendous impact on him. So, he was looking for a fresh start which he found in the United States Marine Corps., and that led him to the other side of the country, landing in California. 

In the Marines, Scott was working in the administrative department. He served in the Marines for eight years. 

Scott’s last tour included being based in Charlotte. There, Scott met a mentor, Steve Spradling, the human resource director for ESM, a manufacturing company.  

“Steve took me under his wing,” Scott says. “He started working with me and gave me a different perception of what business, and life, was about.

“I came from a background that was sorely depressed,” Scott says. “Having been in the Marine Corps for eight years, I was still sheltered. However, Steve kind of opened my horizons. He told me, ‘You can do anything you want to do; you just have to figure out what it is you want to do.’” 

Scott ended up finding his way into the field of recruiting. 

He worked for Microsoft, for a few years, and enjoyed the perks of that job such as a paid-for condominium, and car, and private shopping tours at Neiman Marcus – for Microsoft-only employees. 

“They would bus us into Neiman Marcus and slash the prices down to dirt. Nothing, and nobody, was allowed in the entire store unless they had a Microsoft badge. We walked through, we picked up whatever we wanted and we bought it at a major discount. It was just a great atmosphere to work in.” 

Recruiting was where he found his niche. He enjoyed the process of helping other people find their path to employment. 

“I loved to recruit. It was just what I loved to do, which was to find people jobs and help them take care of their families,” Scott says. He loves making the call to tell someone, “Hey, you got the job!” 

As he solidified his professional aspirations, his personal life took a devastating turn and he almost didn’t recover from it. 

A Loss Like No Other

When Scott was 36 years old, and successful in his recruiting career, he lost his eldest son. Kahari Scott was kidnapped and murdered by two men. One of the kidnappers was a childhood friend who had lived with the Scott family, for five years, and had been taken care of by Scott as a child. 

“I lost my mind. He killed my oldest boy. He was my heart. I just lost everything in me,” Scott says. “I didn’t want to do anything other than die, to be honest with you. That’s just the truth.”

Scott got involved in drugs, and drinking, he says. 

“I remember, a couple of times, being in places I shouldn’t have been. One time a guy pulled a gun on me and I said, pull the trigger. Pull the trigger, you’re not going to hurt me, pull the trigger,” Scott says. “I wanted to die.”

This period of deep darkness came to a head and Scott made the decision to get help. 

“One night it was pouring down rain. Here in Florida, they tolerate homeless people. In Charlotte, they don’t. So, if you’re sleeping on a bench, they’re waking you up and telling you to move. I was trying to sleep,” Scott recalls. “I was really tired. I was worn out and it was pouring down rain. A cop showed up and told me I had to move. I didn’t have anywhere to go. I didn’t know what to do.” 

Scott remembered that the local police didn’t have jurisdiction over federal property, so he made his way over to the Charles R. Jonas Federal Courthouse. 

“There were these columns, so I snuck in between two columns and that’s where I slept that night,” Scott says. “That night, I had a conversation with God. And I said, ‘Okay, God, I’m tired, I’ve been running and you’re obviously not going to let me die, so I might as well get up and start doing something.’”  

He promised God that if he helped him get back on his feet, he would serve Him for the rest of his life. And he has.

“That’s where I am now. Because he helped me get back on my feet, helped me get to a place…I don’t attribute any of this to me. I’m just like everybody else. I work hard, I try to make a living but for all these things that come to me, the way they’ve come, there must be more than me. That’s what I believe and that’s why I’m so happy, and jovial, all of the time. Because I have something to look forward to.” 

That was the night Scott started his life over again. 

From there, he found a mission that provided him with food and then he found a military drug and alcohol rehabilitation center. Scott stayed in that rehab program for 12 months. 

It was during this time that he met his future wife, Velma. 

“The real story here is not me, it’s my wife,” Scott says. 

Velma, a Jamaican immigrant, lived in Tampa, while Scott was still living in the rehab facility in Charlotte. They met on “It was like the old days. Remember, you’ve got mail?” Scott adds with a chuckle. 

“This is why I say she’s the biggest part of the story, even more than me, because I told her what I had done in my past and what I wanted to do in my future. I wanted to start my own company. I explained to her that when I got out [of rehab] I would need to get a computer. Then, one day, I go down to the mail room and there’s a computer there for me.” 

Velma had sent him a computer; they had never met. The computer was what Scott used to start his business, Career Match Solutions. 

For 14 months, Scott and Velma grew closer and decided to pursue a romance. 

“She was still [in Tampa]. I was still in Charlotte…we didn’t know if we were going to be in Charlotte or if I was going to move here. She won,” Scott says, laughing. 

Scott left rehab a healed man, a man with a business, or at least the beginnings of one, and a man in love. He relocated to Tampa and has never looked back. 

The man who took Scott’s son’s life has since been released from prison and Scott says he has forgiven him. 

“I have the joy of Christ in me. I’m a Christian and I love God. And God says I must forgive, whether I want to or not,” Scott says. “There was nothing I could do to change it. Nothing I could do to fix it. The only thing I could do was fix my heart and that was how I fixed my heart.” 

Building the Business

After Scott relocated from Charlotte to Tampa, it was time to get his business up and running. In 2008, he started Career Match Solutions, based in Riverview, out of one of his bedrooms while sitting at a discarded school desk with a little dog as his only “employee.”

“We did this for two or three years. Me and the dog sitting there. I had only one person working in the field for two and a half years. I don’t know how in the world we were making it,” Scott says. 

The Scotts lost their dog just days before the interview with TBBW. Scott was saddened, and a little shocked, by how much he missed the little guy. 

In 2014, the business got a big break. He signed his first million-dollar contract with the state of North Carolina. 

“We’re a staffing agency, so you have to pay people before you get paid. I had no money to pay anybody,” Scott says.

Once again, Velma takes the starring role in another pivotal moment in Scott’s life. She took her entire 401k, which was $104,000, and handed it over to Scott and said, “Go. Make it happen,” Scott says. “She gave me all of her money, so I had no choice but to make it work.” 

From there, the company started to grow. 

In 2019, the company was a $2 million-to-$3-million-dollar company, but it was established as a virtual company and continued to operate that way. Enter 2020, the year that everyone else had to catch up to the virtual workplace. 

“Remember, I had worked for Microsoft and I knew what a virtual company looked like,” Scott says. “When COVID[-19] hit, everybody was scrambling to be virtual. We were already virtual. We were just working. We were like, okay, nothing will stop us here, keep moving forward.” 

Career Match Solutions already had its remote infrastructure in place. They were ready and took on a slew of new clients because of it. 

“We quickly went from a $2 million company to a $12 million company, in six months,” Scott says. In two years, it was a $15 million company. In 2023, Career Match Solutions is now a $20 million company and operates in 37 states. 

He’s considered selling the business, telling his sons, both who have had a hand in the business, that “Dad’s tired,” Scott says with a laugh. But his sons urge their dad to keep the business going. His youngest son, Xavier, is executive vice president and his middle son, Daunte Scott, is the financial auditor. 

Dad might be tired, but there’s still work to be done and jobs to be had. With his sons showing interest in Career Match, Scott and Velma are pursuing other passion projects. 

One of those ventures is a group of assisted-living centers called Angel’s Touch. 

“When Velma’s mom got sick, about seven years ago, we went looking for a place for her and we didn’t like what we saw,” Scott says. From there, Velma opened the first location of Angel’s Touch, with the support of Scott. It was his turn to propel her dream. 

Eventually, the Scotts owned multiple assisted-living facilities. They have since sold one, and rented out or leased a few others. They also gave away two to former employees. They currently operate in only one location. 

Another business Scott is launching is, an online application, and portal, which is designed to complement the work the Scott’s are doing in the assisted-living space. 

It will help match skilled, and reputable, home-assistance providers with patients in need of the service. For the people who want to stay at home, or can’t afford to be relocated to a facility, this service helps find professionals to help them. 

“People who are getting older deserve the very best that we can give them, the very best. They have raised us, they have fed us, bottled us, put clothes on our backs and given us a path to get where we’re going,” Scott says. “We owe them this, it’s not something that we take for granted. To toss people aside, it’s not right. Not on my watch, not by me.” 

Spreading Joy

With the business side of Scott’s life taken care of, he spends his time enjoying his family, traveling and giving back to his community. 

Every Thanksgiving, for the past eight years, the Scotts purchase and donate turkeys, and all the fixings, to local families in need, via their church. 

Scott has also formed his own nonprofit, the Awake Coalition, to help raise awareness about homelessness and other issues relating to poverty. 

“We will never alleviate those two things but if we can impact them, we can have an effect on people’s lives, especially young folks and children,” Scott says. The organization provides things like bus passes, clothing and other items to give people a leg up, if needed. 

“We’re very lowkey and we purposely stay that way because if it’s about me, I’m doing it for the wrong reasons. It’s not about me, it’s about other people,” Scott says. “If you just live your life to impact your own life, then you’re a waste. You should impact somebody else’s life.”  

After struggle, heartache and a renaissance of his own, Scott, with Velma by his side, keeps moving in a purposeful direction. 

“I go out of my way to try to make people feel good. I’ll smile for them. I laugh with them, I kid with them and, if they need something from me and I can provide it, I give it to them. I give it wholeheartedly, without any reservations, because none of this is mine,” Scott says with a twinkle in his eye.  ♦ – Photos by Pamella Lee


If you or someone you know is struggling with grief, homelessness, substance abuse or thoughts of self-harm, there are local organizations available and ready to help. 

The Central Florida Behavioral Network (813) 740-4811

The Crisis Center of Tampa Bay
(813) 964-1964 or 211

Personal Enrichment Through Mental Health Services (PEMHS)
24-hour suicide hotline:
(727) 791-3131

24-hour mental health assistance: (727) 541-4628

Tampa Bay Thrives
(813) 803-5630

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