In this episode of The Grit Mindset, Host Matt Rosen sits down with longtime friend and Cloud Communications Group partner, Chris Moffett, for a candid conversation on entrepreneurship, innovation, resilience, and navigating the ever-changing world of technology.

Chris shares his unconventional entry into the tech world — from carrying luggage at a Houston hotel to installing one of the building’s first voicemail systems, sparking a career in telecommunications and network infrastructure. With no formal engineering background, Chris built his expertise through curiosity, problem-solving, and a relentless willingness to learn on the fly — a defining theme of grit.

Together, Matt and Chris unpack Cloud Communications Group’s origin story, born out of a grad school business plan in 2009 and built through persistence, networking, and countless uncomfortable first conversations. Chris reflects on the early days of blank office walls, unanswered phones, and refining the company pitch after 30 minutes in a meeting before realizing the prospect thought he worked for AT&T.

Chris also opens up about the moments that tested his resolve the most — including losing an entire executive client team overnight and fearing the loss of his company’s largest account. Instead of collapsing, the challenge expanded his network, strengthened relationships, and ultimately grew the business.

As leaders in enterprise network strategy and cloud infrastructure for companies $500M+, the conversation naturally shifts to the future — including:

The rapid pace of AI advancement and why adaptation is non-negotiable

The risks of “shadow AI” and unmonitored corporate data exposure

Why data hygiene and governance are the real competitive advantages

The importance of solving problems without always knowing the answer upfront

How technical leaders must carry grit in the face of constant pressure and change

Chris also shares personal lessons in parenting with an entrepreneurial mindset, encouraging his kids to earn opportunities, embrace work ethic, and reject entitlement — even when it means manual labor to fund a weekend trip.

When asked what grit means to him, Chris puts it simply:

“We’re going to solve this — even if we don’t know how yet.”

Matt and Chris close the discussion with insight on leadership, decision-making, and the mindset required to thrive when the finish line isn’t visible.

Key Takeaways:

Don’t wait for perfect information — make the decision and adjust

Entrepreneurship means solving problems before knowing the solution

AI is a tool, not a threat — adaptation beats resistance

True grit is choosing motion over hesitation

This episode is a masterclass in patience, perseverance, and staying gritty through uncertainty.

Stay gritty.