We caught up with the brilliant and insightful Deryck Jones a few weeks ago and have shared our conversation below.
Deryck, appreciate you joining us today. Often the greatest growth and the biggest wins come right after a defeat. Other times the failure serves as a lesson that’s helpful later in your journey. We’d appreciate if you could open up about a time you’ve failed.
In 2007, I launched a managed IT services company that I grew to $4.5M in three years. In 2011, I was offered 11.2M for the business by a former partner that was launching a billion dollar startup in the smart city space. He had secured capital from a group of investors out of the EU. His plan was to purchase a series of companies with key assets in the areas needed to allow for a rapid launch. However, later in 2011, the Greek Finance Minister declared he was going to default on his loans to the EU and when that happened, the investors withdrew. The buyer then convinced us to give him some time that he would find another investor(s). Sure enough, not more than a month later, he announced he’d found a new investor and he flew everyone to Florida to meet him, his wife, and to begin preliminary planning for our launch. Unfortunately, in hindsight, I believe that he was under so much pressure to perform that he failed to vet the new investor well enough. After our meetings and each of us returning to our home states to prepare our teams, he flew to Vegas to sign papers with the investor and when he landed, he was, instead, greeted by the FBI as he got off the plane. As it turned out, the “investor” was part of a group that had been skimming off the gambling boats down in the Mississippi Delta region for years to the tune of around 1/2 billion. It turned out that they were looking to use this deal as a means to launder all this money. By the time the fed was done, I lost my company and around $1,5M personally. The following year, my wife and I sold our home in Boston and we moved to Northern Virginia. My wife took a senior advisory post with the Department of Energy and I launched a new company that was a Salesforce development and integration partner.
In essence, at the age of 59, instead of having my planned retirement, I had to start all over again. I’d like to say it was smooth sailing from there — but it wasn’t. I had some false starts, misperceptions about some things and by the time it all really began to settle COVID hit. I had a marketing agency called Leatherneck Tech and a small safari company in Tanzania by that time. Needless to say, the safari company didn’t survive and, well, the marketing agency was a bit crippled. In truth, it wasn’t until November of last year when I finally got my act back together. My mindset had taken a significant hit…and thanks to the best sales trainer I know – Eric Lofholm, I finally got my mindset back together. I went through ten years from hell — loss of the business, both my parents died, my niece committed suicide, and one of my four boys, who has some serious issues, ended up in prison. Not to mention losing even more money due to a couple of bad investments, and the like. That all changed last year. Today, I am back on trajectory to grow my current business to at least 1/2M in year one and quite possibly, I might just hit a million. My goal today is to grow this business so I can sell it in 5-7 years and finally retire.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
My journey into technology began with a screwdriver and an unhealthy disregard for danger. I was just seven years old when, left alone one evening while my parents went out, I decided to take apart our family television—just to see how it worked. When they walked in early to find parts strewn across the living room floor, I braced for punishment. Instead, my father simply tapped me on the shoulder and said, “Johnny Carson comes on at 11:30,” before heading upstairs. I still don’t know how I pulled it off, but I got the TV reassembled in time for the show. That moment taught me two things: curiosity drives creation—and if you’re going to break something, make sure you can fix it.
That mindset has guided me ever since.
After serving in the U.S. Marine Corps and completing advanced avionics training at the Memphis Naval Air Station, I transitioned into civilian life with a vision for how software could reshape entire industries. In the late 1970s, I founded my first company, Sentech, to build software that optimized heavy equipment operations—a precursor to modern AI logistics. That work introduced me to Jim Farnsworth, a brilliant engineer whose civil engineering software for firms like Bechtel and Fluor Daniel was trapped on mainframes. Together, we brought it to the personal computer era, launching Civil Image Systems. Our tech powered everything from dam builds to airport expansions, helping reshape the American landscape.
That success led to a pivotal chapter in my career. I was recruited by Spectra Physics Laserplane—at the time, the leader in construction instruments—eventually rising to Vice President of R&D at Spectra’s now parent company and division of Thermo Electron, a $3.2B MIT spinout. There, I led an international team that built and launched the world’s first fully autonomous robotic machine control system for heavy construction. We combined GPS, lasers, real-time computing, and early machine learning into one groundbreaking platform—years ahead of its time.
In 2002, I was honored as one of Computerworld’s Premier 100 IT Leaders for my work in global knowledge management, following my role as Global CTO of a multinational PR firm overseeing infrastructure across eight brands in 55 countries.
Over the past 50+ years, I’ve launched seven companies—two scaling to seven figures and one to eight—each fusing technical innovation with strategic business execution. One of those ventures, a managed services provider, hit $4.5M in revenue within three years and earned an $11.2M acquisition offer.
Today, I lead iGloo Digital Marketing, a boutique firm at the intersection of marketing, AI, and fractional CTO services. We serve clients ranging from scrappy startups to enterprise giants, helping them navigate the fast-evolving tech landscape with clarity and confidence.
At iGloo, I oversee:
LinkedGeniusAI – our proprietary LinkedIn automation and lead-gen platform
Helping Hand – a blend of tech stack optimization, coaching, and automation strategy
The AI Ambassador Program – a flagship executive training curriculum that equips organizations to integrate AI as a strategic advantage
Through it all, my mission remains the same: to help organizations innovate boldly, operate intelligently, and build trust through technology. Because while tools and platforms will always evolve, the heart of transformation is still the same—it starts with curiosity, courage, and connection.
Do you have any insights you can share related to maintaining high team morale?
For whatever reason , this has always been second nature to me. I guess in one part, it’s due to having two great very strong parents — my father a former Naval Commander during WWII and my mother, a nurse and right-hand person to a local doctor’s office as we were growing up. I’ve always found that if you genuinely respect and treat with respect those that work with you and that you make it your mission to do all you can to help them grow in their career’s despite where it might take them (even if it’s away from you), you get so much more from your team. I also make it a point to get to know them and their families as it’s a demonstration of genuine interest in them as a person. Help them be confident in making decisions and when they make the wrong decision, rather than burying them in guilt, educate them so they do better next time. I also believe it’s critically important to give them a “Why?” For example, I had to move my entire development team from Dayton, OH, to Decatur, GA, Most of my team at the time were all born and raised in the Dayton area. All but one followed me to Atlanta. Why? Because I asked them one simple question, “When you are driving around on your Sunday’s with your family and you pass a large construction site and you see those pieces of construction gear that are yellow, isn’t it incredible knowing that you can turn to your kids and say, “This is what Daddy/Mommy does – and it’s changing the construction industry around the world..” “How does that make you feel knowing you can say that to them?” Give them a reason to believe. Let them know you will fight for them. Let them know you believe in them. And give them the opportunity to make their own mistakes without fear of job loss or retribution and you will have loyal staff for life. I simply treat people the way I want to be treated myself.
Can you tell us about what’s worked well for you in terms of growing your clientele?
The most effective strategy I have ever had or used is through the development of strategic partnerships and/or joint ventures. For example, for the past several months, due to the partnerships I have developed, not only have I been closing a new client every week, sometimes two. I’ve also closed one million dollar development deal and I have two more in the pipeline. When I prospect, I don’t just prospect for potential clients, I am always prospecting for potential JV partners or prospective collaboration opportunities. The strongest method in my opinion is to find partners that deliver to your very same markets but different solutions. Then, arm them with a way to make even more money by introducing your solution set. You will find clients you might never have found in the first place plus, you strengthen their position with their clients allowing them to solve problems they couldn’t previously solve.
Contact Info:
- Website: https://igloodigitalmarketing.com
- Instagram: https://www.instagram.com/igloodigital/
- Facebook: https://www.facebook.com/igloodigitalmarketing
- Linkedin: https://linkedin.com/in/deryckj
- Youtube: https://www.youtube.com/@igloodigitalmarketing
- Other: https://www.alignable.com/ashburn-va/igloo-digital-marketing-llc?user=476647
