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Tait Covert on Building Sentry Computing and Practical IT Leadership

Release Date: 01/13/2026

Tait Covert on Building Sentry Computing and Practical IT Leadership

The Jason Cavness Experience

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...

Shonta Riles on Building Poppin Notary, Community Trust, and Expanding a Local Service Business

The Jason Cavness Experience

In this episode of The Jason Cavness Experience, Jason sits down with Shonta Riles, CEO and founder of Poppin Notary, to talk about building a trusted local service business, expanding beyond traditional notary work, and staying deeply connected to the community. Shonta shares how he launched Poppin Notary in 2016, what it took to earn trust in an industry built on accuracy and reliability, and why customer service is the real differentiator for small businesses. He explains how his background hosting the Deprogram Talk Radio Show sharpened his communication skills and helped him connect with...

Taylor Black on AI, Startups, Microsoft, and Building a Life Through Foster Care and Adoption

The Jason Cavness Experience

In this episode of The Jason Cavness Experience, Jason sits down with Taylor Black for a wide-ranging conversation that spans AI, startups, big tech, and family life. Taylor shares his experience working at Microsoft, where he’s been close to how AI is being built, adopted, and misunderstood inside large organizations. He talks about how startups and founders should think about AI realistically not as hype, but as a tool that rewards clarity, discipline, and execution. Beyond tech, Taylor opens up about his family’s journey through fostering and adoption, what it’s taught him about...

Scott Strong on Sales Discipline, Customer Service and Building a Service-First Business

The Jason Cavness Experience

In this episode of The Jason Cavness Experience, Jason sits down with Scott Strong, founder of Strong Fiber Systems, to talk about building a service-first business in the telecom industry and why sales discipline and customer service still matter in a world obsessed with automation. Scott shares his journey into entrepreneurship, how he built Strong Fiber Systems by focusing on relationships and trust, and why doing the unscalable work, personal outreach, follow-ups, and real conversations creates a lasting competitive advantage. He explains the difference between motivation and discipline in...

Brandie Henry on Communication, Dance, Hip Hop, Leadership and Serving Youth and Families

The Jason Cavness Experience

In this episode of The Jason Cavness Experience, Jason sits down with Brandie Henry. A communication coach, consultant, educator and community advocate whose work bridges personal development, professional leadership, youth services and creative expression. Brandie runs S4S Management, where she coaches leaders on communication, clarity and emotional intelligence, while also serving the community through her work with Southwest Youth and Family Services (SWYFS). Brandie shares how her early foundation in dance shaped her understanding of expression, confidence and presence long...

Liz Galloway on Adventure, Branding, Storytelling and Building a Life Without Limits

The Jason Cavness Experience

In this episode of The Jason Cavness Experience, Jason sits down with Liz Galloway a global brand strategist, PR pro, experiential marketer, storyteller, TEDx curator, wellness advocate, and adventure-driven entrepreneur. Liz’s work spans luxury hospitality, wellness retreats, publishing, consulting, media production and high-impact brand development across Central America, Europe and the U.S. Liz shares how she built a life and career around curiosity, creativity and courage blending strategy with soul to help brands cut through noise and connect with people on a deeper level. She and Jason...

HR Laws Every Small Business Owner Must Follow: A Practical Breakdown for Companies with 49 or Fewer Employees

The Jason Cavness Experience

In this solo livestream episode, Jason Cavness walks small business owners through the HR laws you must follow when you have 49 or fewer employees. Jason draws from more than 30 years of HR experience, 25 years as a retired U.S. Army officer, and over a decade working with startups to explain complicated HR rules in a simple, practical way. Jason covers what federal government actually requires, why most HR mistakes come from confusion rather than bad intent, and how ignoring even one rule can lead to fines, audits, lawsuits, and massive headaches for small business owners. Using...

Marketing, Mindset, and Modern Strategy with Nicholas White

The Jason Cavness Experience

In this episode of The Jason Cavness Experience, Jason sits down with Nicholas White. A Seattle-based marketing strategist, startup advisor, entrepreneur, and operator with experience at Amazon, Microsoft, and multiple early-stage ventures. Nick has led digital marketing programs for major B2B/B2C brands, driven pipeline expansion, advised early-stage founders, and built systems that blend creativity, data, and practical execution. His approach to modern marketing is shaped by curiosity, experimentation, and a deep understanding of customer psychology. Jason and Nick dive into how marketing is...

Inside the Founder Grind: HR Laws, Wefunder, Startups, and Building in Public — Jason Cavness Live

The Jason Cavness Experience

In this solo episode of The Jason Cavness Experience, Jason goes live to break down everything he’s building across CavnessHR, the Wefunder campaign, HR law education, livestreaming strategy, and the behind-the-scenes founder grind people rarely talk about. Jason talks through his work on the HR Laws Livestream Deck, what small businesses keep getting wrong about HR compliance and why he’s pushing hard to create accessible education for founders who can’t afford expensive consultants. He also gives an update on the CavnessHR Wefunder campaign, the ebooks rollout, the Builders Club,...

The Legend Behind 300+ Games: Culturalization, Creativity & Courage with Kate Edwards

The Jason Cavness Experience

In this episode of The Jason Cavness Experience, Jason sits down with Kate Edwards. An award-winning 30+ year leader in the global game industry, culturalization pioneer, former Executive Director of the IGDA, former head of the Global Game Jam, CEO of Geogrify, and CXO/Co-Founder of SetJetters. Kate has worked on more than 306 games across genres including RTS, FPS, racing, horror, and AAA franchises like Age of Empires, Battlefield, Mad Max, Jade Empire, and Indiana Jones. She is widely known for establishing the discipline of game culturalization, helping studios navigate geography,...

More Episodes

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/