Tait Covert on Building Sentry Computing and Practical IT Leadership

In this episode of The Jason Cavness Experience, Jason sits down with Tait Covert, President and CEO of Sentry Computing, to talk about building a service-first managed IT company and what it really takes to support small and mid-sized businesses. Tait shares his path into entrepreneurship, how his background in retail sales, graphic design, and project management shaped his approach to IT, and why clear communication and transparent guidance matter more than technical jargon. He explains how Sentry Computing delivers contract-free managed IT services, prioritizes cybersecurity and reliability, and focuses on long-term client relationships over quick wins. The conversation also covers leadership, customer trust, running a people-first services business, and how business owners should think about IT strategy without getting overwhelmed. This episode is especially valuable for founders, operators, and business owners who want practical insight into IT, cybersecurity, and building a service company that lasts. Topics Discussed • Tait's background and journey into entrepreneurship • Founding and growing Sentry Computing • What "service-first IT" really means • Communicating technical concepts without jargon • Cybersecurity basics business owners must understand • Building trust with small and mid-sized businesses • Leadership lessons from running an IT services company • Balancing technical expertise with customer experience • What business owners should prioritize in their IT strategy Connect with Tait Covert LinkedIn: https://www.linkedin.com/in/taitcovert/ Connect with Sentry Computing Website: https://sentrycomputing.com Instagram: https://www.instagram.com/sentrycomputing/ Connect with Jason Cavness LinkedIn: https://www.linkedin.com/in/jasoncavness Instagram: https://www.instagram.com/thejasoncavnessexperience/ TikTok: https://www.tiktok.com/@jasoncavness Podcast: https://www.thejasoncavnessexperience.com