To stay competitive in our digital world, small and medium-sized businesses need to be equipped with and proficient in the latest technologies. Yet, unlike large companies, most SMBs lack the resources to staff an IT department. Along with lack of oversight, outdated software or hardware, inadequate cybersecurity, or one bad tech investment could seal the demise of a small enterprise.

In his new book, “Tech Debt 2.0®: How to Future Proof Your Small Business and Improve Your Tech Bottom Line”, senior global business and technology executive Michael C. Fillios offers expert insights and practical strategies to help small business leaders managing evolving technology to their advantage and avoid racking up debt that could put their company in peril.     

Fillios recent sat down with Young Upstarts to share his insights about the role of technology-related debt to the future viability of small and medium-sized businesses.

Here is some of our conversation:

Most of us are familiar with the term technical debt. What exactly do you mean by “Tech Debt 2.0®”?

In the software industry, the term “technical debt,” also known as design debt or code debt, is widely used as a catchall to cover everything from bugs to legacy code to missing documentation. That definition is nearly 30 years old, and hadn’t evolved with the pace of technology changes, from mainframe computers to the Internet to the cloud, and much more.

In “Tech Debt 2.0®, we offer an expanded definition that is more inclusive and contemporary with current technology, and shows the impact technical debt can have on an organization if it is not actively managed. My team and I felt it was important to revisit this definition, and in particular, with an emphasis on small to medium-sized businesses. For SMBs, tech debt is a potential existential threat that could impact their future viability and very survival.

Tech Debt 2.0 is any liability incurred in the development, acquisition, use, and retirement of technology — i.e. hardware and software systems, or the skills set needed to support them. And it’s something every business leader needs to be aware of.

How do small and medium-sized companies routinely accumulate tech debt, and often without realizing it? What are some common warning signs?

There are three types of tech debt: unplanned, creeping, and intentional. The first two can accrue undetected. Unplanned tech debt occurs because of an unplanned event, often caused by bad development practices, poor technique or poor communication of requirements. Creeping tech debt is caused by obsolescence of systems or equipment. Systems age because of improvements in upgrades or new products. Equipment ages over time or is obsoleted by new models with improved speed or functionality.

Right now, chances are tech debt is accruing in your business—and it is not showing up in your monthly variance reports or other accounting controls that your organization depends on for recognizing financial its well-being or warning signs of trouble. It is also likely that someone in your organization, without explicit or implicit authority or oversight, has taken action or made decisions that have added to the technical debt of your enterprise.

As it relates to symptoms, firstly, I would say a likely sign is that your underlying business could be underperforming, whether financially, servicing customers, or not being able to grow or expand. More specifically, tech debt can be detected internally before it escalates if leadership is paying attention to some of the early warning signs, such as:

  • The majority of IT investments are focused on keeping the lights on vs. helping to achieve business objectives.
  • Project are consistently delivered late and over budget.
  • Data is hard to access, its quality is poor, and it doesn’t drive decision-making.
  • Inability to attract and retain IT talent.

Rather than leave it up to leadership to connect these dots, my team and I wanted to develop a more intelligent way to uncover these underlying root causes. Therefore, we created the Tech Debt 2.0 Diagnostic to help organizations understand and measure their TD score.

We’re all familiar with high-profile cyberattacks on major business and government organizations. Why should small business leaders take cyber risks seriously? What are some simple ways to reduce them?

The reason cyber advisory is critical for every SMB is 60% of all targeted attacks are towards small to medium-sized organizations. And of those data breaches that are successful, 90% impact small to medium-sized companies. What explains the higher success rate? Research shows 82% of small to medium-sized businesses are not adequately protected from cyberattacks. And the data shows that most small business owners don’t have a plan for response if they’re hit. That’s a problem, because cyberattacks can range from the mildly annoying to the deeply destructive.

Here are a few ways SMBs can reduce cyber vulnerabilities:

– Outsource security monitoring and management to a dedicated resource or cloud provider with necessary resources.

– Establish, communicate, and enforce security policies governing passwords, policies, procedures, especially around physical access, network access, email policies, data security.

– Keep all systems and equipment patched and up to date on security upgrades, and discard equipment or systems that are no longer supported.

You mentioned intentional tech debt. When can tech debt be beneficial to a growing business?

Tech debt can be beneficial when it is deliberatively incurred with a specific goal in mind, such as speed to market for competitive advantage or release of prototypes to clarify customer requirements. It is essential that intentional tech debt incorporate a plan for remediation at some time in the future and that the organization has rationalized the consequences of performing that remediation.

In addition, tech debt can play a critical role if a business is in the process of being bought or sold. This can be a double-edged sword depending on whether you are buying or selling a company.  For an investor or PE firm looking to purchase a company, it is very typical to review the amount of financial debt that you will be purchasing as part of the transaction. Tech debt is similar to financial debt, but you aren’t necessarily paying back someone other than yourself.

Conversely, if you are selling a company, and have managed your tech debt such that your liability or debt rating is low, this could create an advantage for you in negotiating a potential premium, as you have built tech equity rather than accrued debt.

How can small businesses stay up to speed on evolving technology and compete with large companies with IT staffs and state-of-the-art resources?

Staying on top of tech debt is especially difficult for SMBs that might not have the technology departments, CIOs, and CTOs of larger organizations. However, independent, experienced firms and individuals with no interest in promoting any one solution are poised to provide their expertise to help SMBs differentiate real technology advances from technology-of-the day solutions. They provide not only fractional services as traditional consultants but also often as virtual CIOs or CTOs, available on-demand to fill these roles for SMBs and help manage technology investment and technology strategies for the future.

Another path open to SMBs dealing with tech debt is collaboration. There can be substantial value in a collective approach to addressing shared issues. Collaboration opportunities come in a variety of forms and have different advantages. Vendor user groups, Chambers of Commerce, Roundtable Programs, and others, foster collaboration among similar organizations and peers sharing a particular technology, brand, or product, and in some cases, provide technology agnostic advice from peers.

For leaders of small and medium-sized businesses, it is crucial to both invest in consultants and seek out collaborators in successfully managing and leveraging tech debt 2.0.

[This article was originally published on]

Michael C. Fillios believes that every business leader, and particularly leaders of small and mid-sized businesses, needs to be well-informed and actively involved in managing their company’s investments in technology. As a consultant, he brings his extensive experience as a global business and technology leader and entrepreneur to advise his clients on leveraging state-of-the-art tools, taking cybersecurity seriously, and avoiding escalating debt. We recently sat down for a brief interview. Here is some of our conversation.

Tell us your name and a little about yourself.

My name is Michael Fillios. I am the founder of IT Ally, an IT Advisory and Cyber Advisory firm serving the C-Suite at small and mid-size businesses (SMBs), based in a Cincinnati, OH.  In 2020, I also founded the IT Ally Institute, a nonprofit organization that provides SMBs access to knowledge, research, and practical tools to improve their tech bottom line. My new book, Tech Debt 2.0®: How to Future Proof Your Small Business and Improve Your Tech Bottom Line, leverage my 25-plus years as a global business and technology leader in multiple industries, including manufacturing, pharmaceuticals and banking, as well as a startup entrepreneur and consultant. My passion is serving privately held and family-owned businesses by helping them to grow, be secure, and to maximize the value from their technology investments.

What exactly does your company do?

Our fundamental purpose and mission at IT Ally and the IT Ally Institute is to play a significant role in future-proofing SMBs. Until very recently, SMBs comprised 99.9 percent of businesses and 47.5 percent of private-sector employment in the US. Sadly, SMBs have taken a tremendous hit in 2020, with the COVID-19 outbreak presenting unexpected obstacles to their success and survival. How SMB owners and C-suite leaders have deployed technology is turning out to be a major factor in how, or if, their company will survive those challenges. Therefore, we leverage our amazing experienced team of advisors, deep subject matter expertise, and our proprietary diagnostic tools, research, and thought leadership to assess the effectiveness of an organizations’ IT and Cyber capabilities and provide leadership services to bridge the internal gaps that often reside in the C-Suite.

What were the biggest challenges you have faced and how did you overcome them?

My biggest challenge, and one that defined the trajectory of the rest of my personal and professional career, was navigating my childhood and teen years growing up in the Bronx, New York, during the late 70s and 80s.  Don’t get me wrong—I wouldn’t change this experience if I had to do it again, as it provided a master’s level education on being street smart and reading people and situations around me. However, in many cases, the path for my peer group was one that led to drugs, crime, or careers that did not require education beyond high school. As a result, I defined a unique path that was grounded by sports (hockey), a rigorous work ethic (from my dad), and a desire to achieve a better life than my parents and generations to come. This began with my decision to attend an all-boys Catholic high school rather than the local public school and working to help my parents pay tuition, while not being Catholic; I was born Greek Orthodox! Many years later, I still attribute this to the biggest course correction in my life, which I credit for being in the position that I am in today.

What piece of advice do you wish someone had given you at the start of your career?

Life experience matters. Education is important and necessary to get in the door in many professional careers, but it doesn’t define you. As time goes on, people generally value your experience, including how you managed your failures, and these accumulated events will provide unique perspectives that cannot be taught. Also, risk-taking is expected if you want to have an impact in life, personally and professionally. Embrace it, learn from it, and run towards it with eyes wide open should you be given the opportunity. And finally, consider your legacy objectives much earlier in your life and make decisions that keep you on a path to achieve them.

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It’s back! ComSpark 2018 is nearly here and bigger than ever. As a result, IT Ally™ is playing a larger role this year with two panels and a booth at the vendor expo. IT Ally, a company dedicated to providing IT Advisory services, is excited to be a part of ComSpark 2018.

Here’s a brief rundown of IT Ally’s events at comSpark 2018 and FAQs about the event.

IT Ally at comSpark 2018

IT Ally is hosting two panels at comSpark 2018, plus a booth at the vendor expo full of freebies. Learn more about our events below.

IT Ally at the Vendor Expo
September 18 & 19
10 a.m. – 4 p.m. | The Manor House
Say hello to IT Ally at the Vendor Expo at Booth #18. Snag some swag and take our quick Diagnostic. While you’re there, putt on our putting green and enter to win a putter of your own.

Technology Management: Future Proofing Your Business
Wednesday, September 19
9:30 a.m. – 10:30 a.m.| The Manor House, Manor III
Learn the C-Suite essentials on how to grow, secure and modernize your business.

Moderator: David Duffy, Manager of Partner Experience at Info-Tech Research Group


  • Kip Fanta, Principal at Kip Fanta Group
  • Neal O’Farrell, Executive Director at The Identity Theft Council
  • Michael Fillios, Founder and CEO at IT Ally
  • George S. Paras, Managing Director at EAdirections
  • Tim Westbrock, Managing Director at EAdirections

Mastering the Customer Experience
Wednesday, September 19
2 p.m. – 3 p.m. | The Manor House, Board Room
Learn how leaders in the C-Suite are using technology to build customer experience and what they’re looking to do in the future for their organizations.

Moderator: Michael Fillios, Founder and CEO at IT Ally


  • J.R. Howard, CEO at Upic Solutions
  • Peter Katz, Business Development Manager at Trellispoint LLC
  • James McIntyre, CIO at YMCA of Greater Cincinnati

comSpark 2018 FAQs

  1. What is comSpark?
    ComSpark is a two-day tech summit that takes place in Cincinnati, Ohio. It celebrates people and innovations in the tech community and draws IT leaders across the region.
  2. When is it?
    ComSpark 2018 is September 18 – 19 at The Manor House in Mason, Ohio.
  3. Who attends comSpark?
    The majority of comSpark 2018 attendees work in all facets of tech. Consequently, that includes CEOs, executives, managers, developers, entrepreneurs, students and more. On top of that, ComSpark 2018 also draws a wide range of companies including corporations, tech companies, tech vendors, startups, non-profits, young professionals and anyone else interested in tech.
  4. What events are on the schedule?
    There are a number of sessions at comSpark 2018, but here is a brief look at the main schedule of events. You can find the full schedule on the comSpark 2018 website.

    Tuesday, September 18
    8:15 a.m. – 9:15 a.m. – Keynote & Kickoff
    9:30 a.m. – 10 a.m. – Executive Host Committee Photo
    10 a.m. 4 p.m. – Vendor Expo
    10 a.m. – 4 p.m. – Startup Expo
    10:30 a.m. – 12 p.m. – Rising Star Awards
    10:45 a.m. – 12:15 p.m. – C-Suite Summit
    1:30 p.m. – 3 p.m. – Spark Ideas
    1:30 p.m. – 3:30 p.m. – Women in Tech
    3:30 p.m. – 6 p.m. – Craft Brew Party, Wednesday, September 19
    7:30 a.m. – 9 a.m. – The Circuit Breakfast Bytes
    8:30 a.m. – 10 a.m. – Cyber Security Summit
    10 a.m. 4 p.m. – Vendor Expo
    10 a.m. – 4 p.m. – Startup Expo
    10:15 a.m. – 11:45 a.m. – Spark Ideas
    11:30 a.m. – 1:15 p.m. – Corporate Tech & Innovation Awards
    2:30 p.m. – 3:30 p.m. – College Tech Awards
    3:30 p.m. – 4:30 p.m. – Job Fair
    3:30 p.m. – 6:30 p.m. – Power Player Cocktail Hour
  5. Where can I register?
    General admission tickets for comSpark 2018 are still available and free. Register for the event here.

About IT Ally
IT Ally offers IT Advisory services to business and IT leaders and boards at small and mid-size businesses. We pull in our network of proven, experienced IT advisors to help your business grow, secure and modernize for the future. Our IT Ally team is available to assist you during our business hours from 9 AM to 5 PM EST.

With over 30 years of experience and perspective, our cyber advisors at IT Ally can provide the best knowledge and insight for your organization. For more information about our participation in ComSpark 2018, feel free contact us. Or, take our Business Agility Test and one of our advisors will happily sit down with you to explain your results.

Visit our ‘Services‘ page to learn more about what IT Ally can offer.