Libsyn Directory

Tait Covert on Building Sentry Computing and Practical IT Leadership

Release Date: 01/13/2026

Why Podcasting Creates Opportunities You Can’t Plan For with Jason Cavness

The Jason Cavness Experience

Jason Cavness didn’t leave the Army to become “Major Cavness” in a different uniform. He wanted a clean break. That decision pulled him into startups, podcasting, tech events, Vietnam business relationships, and a career built around one simple habit: say yes when the opportunity is aligned, then figure it out. Mark Shriner talks with Jason about the transition from military life to entrepreneurship, why podcasting is more than content, how in-person relationships beat cold outreach, and what it really takes to keep building when you’re introverted, scattered, nervous, and still moving...

Why Clarity Beats Better Tech with Crystal Clarity

The Jason Cavness Experience

A better product does not always win. The clearer story often does. Crystal Clarity, Chief Operating Officer at s2s Public Relations, joins The Jason Cavness Experience to talk about why founders struggle to explain what they actually do. Why deep tech companies need to stop leading with features and how AI is flooding the internet with content that feels productive but often makes real connection harder. We also discuss: • Why founders often solve before they understand the problem • How to make complex science and deep tech understandable • Why people care less about...

Why Bad Leadership Works — Daniella Young

The Jason Cavness Experience

Daniella Young has built a brand by saying the thing most people avoid: bad leaders, bad groups, cult dynamics, and toxic loyalty are not fringe problems. They show up in politics, companies, the military, families, social media, and anywhere people stop questioning the room they are in. Jason and Daniella talk about turning trauma into work, why “followers” should not become worshippers, how she built a creator-led book business, why she focuses on bad leadership instead of good leadership, and what most people misunderstand about cults, scams, fame, politics, parenting, and platform...

Why AI Sales Should Make Selling More Human with Swetha Puvvada

The Jason Cavness Experience

AI sales is often framed as replacement. Swetha Puvvada sees it differently: the real opportunity is using AI to remove the busy work so sellers can get back to listening, understanding pain, and having better conversations. Swetha is Head of Product & Growth at Teameight, an AI SaaS company building an augmentation platform for sales teams. We talk about product, GTM, customer feedback, career growth, mountaineering, and how she went from early-career intern to owning product and go-to-market inside a startup. We also discuss: • Why AI should augment sales instead of replacing...

The Roti Robot Problem with Komal Kashiramka

The Jason Cavness Experience

Fresh roti is simple to eat and hard to automate. Komal Kashiramka is building Poshan, a robotics company developing next-generation kitchen appliances, starting with an automatic roti maker designed to create soft roti that lasts for hours. Komal shares how she moved from Microsoft and Meta into entrepreneurship. Why hardware requires a different level of patience than software and what founders can learn from customer discovery, AI, parenting, and building something people will trust in their kitchens. We also discuss: • Why soft roti is the real product challenge •...

How Grief Becomes Art with Eden Marryshow

The Jason Cavness Experience

Most people run from grief. Eden Marryshow turned it into a film. In this conversation, Eden breaks down the emotional process behind filmmaking, storytelling, creativity, and why the best art usually comes from the most personal places. We talk about losing family, directing actors, independent filmmaking, community, and the long path creators take back to who they were before the world told them to stop creating. This episode is also a masterclass on storytelling itself from Star Wars and Scorsese to creative discipline, ego, collaboration, and why limitations often produce better art than...

Most Entrepreneurs Should Quit — Nathan Kaiser

The Jason Cavness Experience

Entrepreneurship isn’t freedom it’s volatility, pressure, and constant uncertainty. Nathan Kaiser built 2bar Spirits by embracing that reality, not ignoring it. He breaks down why most people shouldn’t start companies, what actually keeps a business alive, and how constraints, not capital, create better outcomes. This is a raw look at building something real in a crowded, unforgiving industry. We also discuss: • Why starting a company is usually the wrong financial move • How constraint beats capital in building a business • The myth of overnight success (and the...

Why Most Founders Mismanage Money — Morgan Rogers

The Jason Cavness Experience

Most founders don’t fail because of bad ideas. They fail because they run out of moneyand don’t know why. In this episode of The Jason Cavness Experience, I sit down with Morgan Rogers from NOW CFO to break down what actually happens inside companies when the financial side isn’t dialed in. Morgan works with founders, operators, and investors every day cleaning up messy books, preparing companies for fundraising, and helping them avoid decisions that quietly destroy businesses. She’s helped scale a Seattle office by over 500% and has seen the same pattern over and over again. But the...

How Founders Actually Build Momentum with Nick Hughes

The Jason Cavness Experience

From a failed startup to launching Founders Live across 155 cities and 58 countries, Nick explains what founders really need early on: community, storytelling, validation, and consistent action. He also breaks down why most people wait too long to start, how 99-second pitches force clarity, and what he’s learned traveling through startup ecosystems around the world. Nick also shares how Founders Live evolved from a simple Seattle pitch event into a global founder marketplace connecting startups with legal, development, hiring, and growth resources. We also discuss: • Why founders overthink...

Why Most Teams Are Broken — Mimi Nguyen

The Jason Cavness Experience

Most teams don’t fail because of strategy. They fail because people can’t align. In this episode of The Jason Cavness Experience, I sit down with Mimi Nguyen to break down why teams struggle to work together and what actually fixes it. Mimi has lived across Vietnam, the United States, and Malaysia, and brings a rare perspective on culture, communication, and decision-making. She’s led initiatives that drove a $7M+ uplift and achieved 90% product adoption. But the real story is how she got teams to stop working against each other. We get into the uncomfortable truth: misaligned...

More Episodes

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/