How Darryl Cresswell Emerged From Horrible Foster Care Upbringing To Become A Leading SMB Cybersecurity Expert In the Greater Toronto Area & Simcoe County

Growing up, Darryl Cresswell never felt safe and secure.

With parents he says he “wouldn’t wish upon anyone,” he ended up in foster care becoming a Crown Ward of the Children’s Aid Society in Canada before his 10th birthday.

He was forced to constantly move, sometimes as frequently as every two weeks. Continually having to change schools, he lost friends with each move and had no one he could depend on. Plus, because the foster homes were often at full capacity, he frequently spent time in group homes. “It was awful,” Darryl recounted. “Group homes are not family settings. There are kids that had trouble with the law. Some have an addiction. Some have been sexually assaulted… a mix of everything. There are no parents, just social workers, and strangers. There was no stability and no feeling safe.”   

It was his introduction to technology that brought him relief and a path to independence. For a truly short while when he was nine years old, he had access to an electronic typewriter and a book that taught him how to type. “I thought it was cool how people can type any letter on the keyboard without looking at it,” Darryl said. “I practiced and memorized the keys so I could do that too.”

He soon discovered his affinity towards technology when other kids at school asked him to teach them how to use a keyboard. “I was going to all these different schools with computer labs,” Darryl recalled. “The other kids struggled to learn how to type on the keyboard. They looked at me in amazement and wanted to know how I did it. It was the first time I was good at something that people recognized. After that, I noticed no matter what I touched in technology, I was always ahead of everyone. It just came naturally to me. It’s still that way, others will struggle to learn something in technology whereas I don’t.” 

By the time he was thirteen and a freshman in high school, he was being paid for his computer skills. “I was lucky to go to a high school where they had just built a brand-new computer department,” Darryl said. “They had new teachers that were excited about their jobs, new computers, new programs, new everything, and it was all state-of-the-art technology.” Darryl took every single computer course offered, including advanced computer technology and computer science, excelling at all of them. Proficient at coding, he was paid to help students with their homework and to restore crashed computers. “It was a side hustle for me,” Darryl said. “I always felt rewarded when I saw how much people appreciated my time and willingness to help them fix their computers. Sometimes I would get paid to do the other kids’ homework so they would pass. I know it wasn’t right, but I needed the money for basic things because no one was going to buy those for me.” The money he earned went towards things such as school supplies, clothes, and the occasional splurge item, so he didn’t feel left out. “I saved forever to buy that Hewlett Packard calculator for school,” Darryl said. “Sometimes we’d have pizza days at school. I was always the only kid without pizza, so if my friends were doing something fun like that, I’d use my money to be a part of it, although I mostly tried not to waste my money.”

He joined every computer club, devoting hours to learning everything he could about computers. “The computer clubs allowed me to stay at school longer,” Darryl said. “It was a better environment. I could stay and learn instead of going back to the toxic environment of the group homes I was living in. My teachers would let me work until six or seven o’clock at night when they had to kick me out of the lab. Computers offered me the ability to support myself without help. I was determined to succeed, so I took every opportunity to learn.” Towards the end of high school, Darryl began writing software for Windows, which he sold on shareware websites (you can still find his software there today). “My most successful program was a security software used for password protection, I called it DSecure,” Darryl said. “I made enough money selling that software to put myself through college.”

Having aged out of foster care, and completely on his own, Darryl supported himself and put himself through college by fixing computers and tutoring fellow college students in computer science. In 2000, while still in college, he officially launched MYDWARE IT Solutions to serve Small and Medium-Sized Businesses (SMBs) in Simcoe County and the Greater Toronto Area (GTA).  

Fills Void To Protect SMBs

After graduating with a degree as a computer programmer analyst with the highest marks in his class, Darryl added services such as web hosting and Voice over IP (VoIP). He changed his business model from break-fix to managed services to better protect his clients. He hired highly qualified technicians so he could offer true 24/7 coverage that maximizes clients’ uptime and mitigates issues before they become a service impacting problem. Four years ago, seeing a rise in cybercrime and predicting it would hit SMBs particularly hard, he increased his focus on cybersecurity and grew MYDWARE into a mature Managed Security Service Provider (MSSP), a prediction that has paid off and filled a void.   

Today he brings Enterprise Grade IT products, services, and support to forward-thinking SMBs with 10 to 100 employees who otherwise would not have the resources to learn, procure and implement the IT support and Cybersecurity necessary to keep their business protected and operational. “I despise when good people are taken advantage of and exploited,” Darryl said. “In the early days, this came in the form of super-expensive phone systems and IT services that were out of reach for nearly every SMB I helped. More recently, its cybercriminals stealing from hard-working entrepreneurs. I am passionate about cybersecurity and made it my personal mission to protect as many local small businesses as possible.”

Keeps Clients Ahead Of Curve

As the programs he offered matured, MYDWARE exploded, growing 887% in the last four years alone. Darryl also emerged as one of the leading cybersecurity experts and co-authored a #1 best-selling book in three categories on the subject titled “On Thin Ice” with a second solo-author book due out in early 2021.

A leader among his peer groups and constantly evolving, he stays a step ahead of others in implementing the latest protection and technology to keep clients safe and secure. “I participate in meetings with cybersecurity experts all over the world and constantly look ahead,” Darryl said.

Clients Rank Dependability And Authenticity High

SMB clients who understand and appreciate the value of technology, remain clients long-term. Many have been with him for a decade or longer. His clients say Darryl is “dependable,” “authentic,” and “trusted”; that they feel “safe and secure” and that MYDWARE “actually cares and treats you like a person.”

“Growing up, I always had to be the one looking out for my own back,” Darryl said. “I partner with SMBs so they’ve got someone protecting them from cybercriminals that could wipe them out and do my utmost to go above and beyond to help them.”

His commitment to authenticity is linked to the lack of it in his upbringing. “It would be easier to tell you the things that were authentic when I was growing up because it was that rare,” Darryl said. “There was only one team, Sheila and Nancy, that stood out towards the end of my life in child services care. They always helped, always kept their word, and were the one stable thing I could always depend on. They were there when my parents weren’t. I’m still friends with Sheila to this day. In my whole upbringing, she and Nancy were the only people I can remember that did that out of all the adults surrounding me. I’ll never forget that and it’s why it’s so important for me to show up in that same way for my clients today.”

Darryl is committed to his community too. He provides winter hats, gloves, mittens, and food to local schools and the Helping Hand Food Bank and financially sponsors the Bradford Bulldogs Minor Hockey Association and Brunch with Santa to support families in need.

The Positive Effects Of Foster Care Make MYDWARE A Champion Partner

“I’ve drawn on the skills I developed as a result of growing up in group homes and foster care,” Darryl said. “I was always in a situation where my back was against the wall. I had to be a critical thinker and a logical thinker just to survive. It forced me to get good at adapting quickly in bad situations and solving problems, which is helpful because technology changes so fast.”

“As bad as it was experiencing the horrible things I did growing up, it taught me how NOT to do things,” Darryl continued. “I experienced broken promise after broken promise. I grew to resent that, so I make every effort to ensure I NEVER do that to people. It influenced me to be ultra-dependable and drove me to build MYDWARE into a stable, long-term viable company built on honesty and integrity, where my word is my bond. It motivated me to give the little guys—the SMBs who don’t have the resources—a partner who would have their back, so they always feel safe, secure, and protected.”



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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