What Being Raised By An Entrepreneurial Single Mom Taught Hernan Silva About Running One Of Chicago’s Premiere MSP Firms

Growing up in Buenos Aires, raised by a single mother, Hernan Silva knew all too well the certainties of uncertainty. His mother did whatever jobs she could to keep Hernan and his two siblings together and fed.

The family lived paycheck-to-paycheck, and his mother worked “many, many jobs” to support the family. And Hernan helped as well. When he was 10, he began working alongside her at a tire shop near their home on the weekends and after school. “I was changing tires on cars, and my mom handled the administrative part of the business,” he recounts. Hernan appreciated everything his mom sacrificed for the family, and it didn’t take long for him to realize she was an entrepreneurial superwoman of sorts.

Hernan Silva- CIO Landing, Inc

“My mom was working for a package delivery service, doing canvassing to turn into sales,” Hernan says. Soon she got to know all the companies in the area and saw an opportunity to sell them products for their offices. So, in 1992, his mother started her own business, which Hernan named White Paper.  

Back then, the company was selling mostly paper, but as computers and technology became more and more necessary in businesses, they started getting requests for floppy disks, and eventually computer parts, and then service.

It was the opening of their own business that brought security to Hernan and his family, as well as a road to financial independence – and it introduced him to the world of IT.  

“We had a very old computer at home at the time. I was fascinated by it, and I always liked to fix stuff – anything that broke in the house, I was working on it,” he says. “So, one day my mom found me opening this computer to find out what was inside, and she says, ‘Okay, you’re going to be the technician for the company!’ There was no YouTube, so I had to learn how to fix everything myself.”

While he was still in middle school, Hernan found himself managing three other employees – kids his own age from high school – and the opportunity to spend time with his mother and siblings. “We all had lunch together, we had a lot of fun. It was a family atmosphere, but we all worked very hard,” he says.

The family’s small shop that originated in the garage soon took over the living room, and then the rest of the house, until they moved to a store location and changed the name to White Paper Computación. Hernan coordinated and trained other computer technicians, managed customer service, maintained and repaired hardware and software, and built and tested computer equipment.

Nine years after helping his mother build and sustain a successful from-scratch business, Hernan, at 21, was ready to strike out on his own. The technology field was evolving, and he wanted to find out where it was headed. Since the bulk of his IT equipment was shipping to Latin America from Miami, Hernan thought Miami was the “Silicon Valley of the East Coast.” 

So, in 2001, he left Buenos Aires for Miami – a move that was full of promise but not without anxieties.  

Hernan didn’t speak English, and he desperately wanted to. Though he found a shop in a computer store where he did repair work, everyone spoke Spanish. It was soon obvious that it was going to be impossible for him to learn English there, so he moved to Chicago – “with no English, no money and no coat!” he recalls.

Without knowing the language yet, Hernan felt lost and isolated. “It was very prohibitive. There were so many things I wanted to do, but I couldn’t,” explains Hernan. “I remember trying to get a job. I had several interviews with this one company, and they really wanted to hire me, but I didn’t have good enough English for them.” Hernan took that rejection as his motivation, and he devoted hours a day to learning the language. He went on to earn his bachelor’s degree in business administration and management from Northeastern Illinois University.

How He Found His Entrepreneurial Soulmate

In 2008, Hernan started his own IT business. Much of what he had learned about being an entrepreneur came from his mother. From managing people to taking care of clients to understanding the importance of company culture, he can trace it all back to her and the lessons she taught him while running their family business.

“Working for myself, it’s in my DNA,” says Hernan. “Even when I had to work for necessity for others here and there, I was always trying to open my own side hustle and do my own thing.”

In 2013, after five years, Hernan’s IT company was growing, but it wasn’t yet where he wanted it to be. That’s when he met Juan Carlos Bosacoma.

“He had his own IT business, and I found his website one day, and I thought, what a great website, maybe I’ll copy his!” Hernan says. “Two weeks later, I was attending a business breakfast, I sat down at a table, and who was next to me? Juan Carlos.” The synergies between the two were powerful. They decided to merge companies. 

The collaboration paid off; today, CIO Landing is a very successful and fast-growing managed IT services, cyber security and compliance firm serving legal and financial SMBs throughout Chicago. They are one of the most trusted cyber security specialists in the area.  

In 2022, on his 30th anniversary in the field, Hernan took the company to a whole new level, starting a franchise model and opening their first franchisee in Miami. Now they have their sights set on the rest of the country.  

With Hernan’s expertise in successfully delivering security-focused cloud solutions for clients in fields that live and die by regulations, their customers have embraced technology not just as a tool for growth and increased productivity, but as a necessity to manage risks and vulnerabilities in today’s digital business environment.   

Sometimes It Takes A Maniac To Keep You Safe

Hernan is a self-described “Cyber Security Maniac.” An alumnus of Evolve Security Academy, he is an expert in cyber security and computer forensics. He holds more than 40 industry licenses and certifications, and he co-authored a book on cyber security – with his partner Juan Carlos and other IT experts – called Sitting Duck.

“There are two types of businesses today: one that has experienced a cyber-attack and one that most likely will,” Hernan says. “We work primarily with financial institutions, law firms and other businesses in highly regulated industries, so protecting their systems, their data and their business from online threats isn’t something to put off until tomorrow. And firewalls and antivirus software isn’t enough,” Hernan adds. 

Cyber security becomes especially challenging when an organization operates across multiple locations. CIO Landing provides a centralized IT solution to help clients eliminate the security and regulatory risks when everyone isn’t in the same building – or state. 

“We have a client that operates in over 20 states, with multiple branches in each one. Their technology assets include hundreds of desktops for their in-house employees and a large number of laptops for their remote workers,” explains Hernan. “They come to us because they were challenged with this huge maze of technology they had to manage. We helped them put the security in place and manage the execution and monitoring of all their systems and networks, so they don’t have to. This makes a difference to their productivity, their bottom line and their peace of mind.”

Hernan’s Real Secret Sauce: Treat Them Like Family

Hernan strives to create a family-like company culture at CIO Landing, much like the one he grew up in. “I want my team to be happy, and I want them to have a fun environment to come to work to every day like I did,” he says. “They aren’t just a person who works here, but a person. I’ll do what I can to help them in all areas of their lives, not just at work.”

A Purpose That Extends To His Communities

Hernan’s passion for helping others happens outside the office as well. He started his own foundation, Argentina Chicago Foundation, in 2003, a nonprofit organization whose mission is to improve facilities and provide a safe environment for the education of underprivileged elementary school children in rural areas of Argentina, where poverty levels generally surpass 50%.

He also contributes his time and skills to multiple charities and organizations involved in economic empowerment and poverty alleviation, including the Hispanic Innovation Center Foundation, a nonprofit that seeks to create socially conscious alliances within Hispanic communities in Chicago. Through these alliances, the organization hopes to develop the next generation of technology leaders and promote the use of digital technology by Hispanic businesses.

Hernan came from the edge of poverty in Buenos Aires, and were it not for his entrepreneurial-minded single mom who just wanted to put food on the table for her children, his life’s trajectory could have been much different. “I really want other people to have access to resources and education and opportunities that could change their lives, like I had,” he says. 

For more information on CIO Landing, Inc., please visit www.ciolanding.com.



MSP Success Magazine

MSP Success Magazine is a print and digital publication dedicated to helping the CEOs and owners of managed IT services businesses build strong, profitable, growth-oriented businesses. Written and published by Robin Robins, founder of Technology Marketing Toolkit, this magazine is uniquely focused on the topics of marketing, client-acquisition, sales, profitability, leadership and personal development.


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