The beauty of rolling with the punches – Interview with Hilton Augustine Jr.

By: The Millennial Source
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Recently, Dinocrates Group announced its acquisition of Global Management Systems, Inc. (GMSI), a networking and communications company. 

At the time of the acquisition, GMSI handled communication network systems for various private enterprises, as well as some of the most secure public-sector organizations in the world, such as the US Department of Defense. 

Hilton Augustine, Jr. founded GMSI three decades ago. Freed up from the day-to-day responsibilities of running a company, he is now hanging out in Buenos Aires. Hilton is living the dream in a Remote Year Program, a working community for freelancers and other globetrotting professionals. “I met some Buenos Aires natives last night at a bar,” he chuckled. “…I feel as if I’ve really integrated into the society now.” 

At the time he made this remark, Hilton had been in Buenos Aires for a mere week. 

While Hilton’s joke was by no means the core of his interview with The Millennial Source, it does capture a core quality of his character. 

The Millennial Source Interview with Hilton Augustine, Jr.  

A Millennial Source reporter called Hilton late one evening, right after his yoga class. “Hello Hello,” he greeted the reporter with a smiling voice and a mild New Orleans twang.

Even during a phone interview, Hilton’s energy was contagious, unrestricted by the land and seas separating him from the reporter. It was easy to imagine him offering his long, thoughtful insights into his life and career with his feet up on a table, head swung back, holding a beer. 

Early years in New Orleans

While Hilton now spends most of his time traveling, fulfilling his aim of becoming a “global citizen”, the seeds of his identity were first planted in the 7th Ward of New Orleans, Louisiana. There, he lived with his four siblings and parents until he was 10 years old. “I wouldn’t say it was ghetto – but a step above that,” he said. 

Many of Augustine’s childhood memories center on his father. “My dad was always interested in trying to find ways to get out into the suburbs and a better life….” And by the time Hilton reached the age of 10, the family was able to do just that. 

“For the five siblings in my family, statistically we’ve done on average better than what you would expect from average African American families in the United States. That is because of the side hustles my dad did…. He was a high school teacher by trade and training but he always had a side hustle. He sold vacuum cleaners, he sold encyclopaedias … door to door kind of stuff … that allowed us to move out of that neighbourhood into a better neighbourhood and better schools, etcetera. It’s still very unique that a black family can break the system. It’s generational,” Hilton explained. 

Although he was friendly and relaxed, all of Hilton’s answers to questions were matter-of-fact, and most were delivered without hesitation. His responses were also impeccably thought out, simultaneously addressing the question posed, clearing up any potential discrepancies with previous answers and anticipating follow-up questions. 

A large portion of the interview revolved around Hilton’s career, which began at a tender age. “You could say I’ve actually been in business since I was twelve,” Hilton partially joked.  

“One of [my father’s] side jobs, he was actually working at a car dealership…. All the salesmen get a new car as a demo and that becomes their private car for a while. They have to keep it clean and stuff like that…. So he had me come to the dealership to wash his car … and of course another salesperson saw me there and I started washing theirs. So I literally opened a car wash business at twelve years old, and I would come in every Saturday and start washing the salesmen’s cars for two dollars each. 

As my younger brother became older, he wanted to come in and do a little bit of the work, so my father forced me to split the work with him. But because it was ‘my business’, I sorta said, ‘Look, I’m doing the outside and you do the inside…. So you’ll get 75¢ out of it and I’ll get $1.25.'”

The arrangement didn’t sit well with Hilton’s younger brother. “He actually started protesting, because he felt as if he should have been getting half the money even though he wasn’t doing half the work. So I literally had to deal with labor issues at twelve.”


Education and early career

Young Hilton was also a hobby engineer. Fascinated with technology and what he referred to throughout the interview as “cool stuff”, as a kid he would purchase supplies at Radio Shack and build gadgets. 

This love for creating pushed him into the world of professional engineering. He graduated from college with an electrical engineering degree and soon began working at IBM. 

However, despite his love for the field, Hilton only spent two and a half years doing engineering work. “They told me that I was an engineer that talks too much … so I went into management…. But I guess I talked to much for management, too … so I ended up in sales.” 

Motivation from sibling rivalry

Eight years after Hilton started at IBM, the same younger brother who had demanded higher pay during their car washing days had become a business owner. His sizing up of Hilton’s prospects prompted another dramatic change of direction. 

“He pointed out that after eight years [at IBM], I would quickly get to all the things that would trap me in – more money, more stock…. So that posed as a challenge for me…. We all knew that entrepreneurship was the ultimate independence…. And it really was, am I gonna let my brother beat me?!”

By this time, Hilton was married with a one-year-old son. 

Never one to back down from a challenge, Hilton took a leave of absence from IBM and started a home automation business called Global Home Management Systems (GHMS). “It’s what people refer to now as Internet of Things,” Hilton explained. 

GHMS was also Hilton’s “first failure.”

“It was just too early for what I was trying to accomplish. There was no internet, there was no bluetooth, there was no wifi, so every job was custom work. You literally had to wire devices together, open up [customers’] appliances to figure out how to turn it on and off with extra switches….” 

A year and a half later, Hilton arrived at a crossroads. “It wasn’t stressful until the end … when reality overtook, which was ‘You’re not … delivering your half of the income to the family, you gotta do something.’ 

That’s when I pivoted and said, ‘OK I gotta get out to customers that pay … like the federal government,’” he laughed. 

Soon after that, the “H” in GHMS was dropped, and Global Management Systems, Inc. was born. 


Reflecting on 30 years of success

From a monetary standpoint, Hilton calls himself a “success.” However, he often refers to the business he built, ran and then sold after 30 years as “a business based off opportunity.” It was never his “dream business”; it was “safe.” 

He explained that over the years, “…whatever the customer base was looking for, that’s the skills I recruited and I went after that kind of business … the low hanging fruits…. We’ve done everything from the early days, web development, web design, network designs, network administration. We’d run call centers and network centers. Literally for different agencies in the government, we’d be the Help Desk you’d call to fix the [government] computers…. This business just became, ‘I need income for my family.’” 

After a few years, Hilton started making acquisitions. “I literally started trying to start a company by buying other companies. Some worked, some didn’t.” 

One of the companies that “worked” was a network maintenance company. This acquisition, later turned into a GMSI subsidiary, was sold in 2011. 

With the funds from that sale, Hilton started reducing his hours at GMSI and started angel investing. “My company was never [the] exciting engineering startup that most engineers dream of. This was my way of getting involved in high tech companies … but not being operationally responsible for any of it…. I’m done with the operational stuff.” He chuckled. 

Around this time, Hilton had an epiphany. In spite of all his success, he had actually been subconsciously waiting for three decades for an opportunity to become an engineer again. Still, as life continued and his malleable goals and definitions of success adapted with it, Hilton just kept rolling with the punches and taking things as they came.

“That’s also what IBM taught me… If you know you gotta make a hundred calls to get one customer, you gotta get ninety-nine no’s out of the way as quickly as possible. That’s the way I approach dating,” he laughed. 

“You gotta look at all of them, and if you’re not willing to face rejection then it’s not going to be a fun game for you. But if you know you’re working towards that one and I gotta get through that ninety-nine, then it becomes fun.”

What’s the secret behind Augustine’s achievements?

Starting from the age of 12, Hilton has parlayed an upbringing in a disadvantaged but ambitious family into a level of success that most people from privileged backgrounds would envy. Asked how he has done it, he focused on the math of it all.

HILTON: I’m not one of these people who calls themselves a self-made millionaire, pull yourself up by your own bootstraps and all that kind of stuff. I truly believe we are all products of our environment…. I think I just happened to be an outlier in my family, who had already taken it a step further [than the generation before them]. I just happened to be the one. I don’t think my skill set or work ethic or anything was any different from my siblings. I just happened to be the one at that end of the curve, period. 

The Millennial Source: So, luck?

HILTON: Well, no … I wouldn’t call it luck. It’s really, you know, just statistics! 

The Millennial Source: So there was an outlier, and it just happened to be you?

HILTON: Exactly.

The Millennial Source: Is the engineer in you reluctant to call it luck?

“Probably,” Hilton laughs. “Some people call it luck, religious people say I’m blessed, and I just say I’m an outlier on a statistical chart.”