Closing Remarks with Jason Caras: Leadership, Failure, & the Fight to Rebuild

On this episode of Closing Remarks, host Dara Shareef sits down with Jason Caras, co-founder of IT Authorities, for a deeply honest conversation about leadership, culture, failure, and rebuilding after nearly losing everything.

Jason helped scale IT Authorities to $34 million in revenue. Along the way, the business earned recognition for growth, culture, and leadership. But at the height of that success, Jason made a decision many founders consider: to stay away from the day-to-day leadership and hand the company to an outsider CEO.

What followed changed everything.

Building a Business Designed to Scale

Right from the start, Jason and his team took the approach to IT Authorities that would foster growth. Influenced by books such as The E-Myth, Jason and his team emphasized process and documentation well before IT Authorities had hit their stride.

This structure became the backbone of the IT Authorities’ growth story. IT Authorities grew from just under $1 million in revenues to $34 million while taking on even larger projects.

But for Jason, the ultimate goal was not revenue. It was culture.

Why Company Culture was the Glue

Jason speaks about culture not as brand language or corporate slogan, but as a phenomenon that manifests itself in the feelings of people when they enter the office building daily.

“Your culture is exactly how you feel when you go to grab the front door and come into the office today,” he said. “Every soul, when they log on, they start their day; it's how they feel inside.”

That mindset shaped how IT Authorities operated during its growth years. Jason often talks about employees as “souls,” focusing on the responsibility of management to support people’s personal and professional development.

And during this period of expansion of the organization, Jason observed the spread of culture among employees themselves who helped each other, mentored others, and strengthened the values on which the company was built. That, to him, was when the business truly became real.

The Leadership Decision That Nearly Cost Him Everything

At the height of the company’s momentum, IT Authorities secured major opportunities that began attracting acquisition interest. Jason and his business partner believed the company could become bigger. That belief led him to one of the most important decisions in his career: bringing in an outside CEO. Jason stepped into the role of Executive Chairman while leadership took over daily operations. But almost immediately, the company began drifting away from the systems, processes, and culture that had made it successful.

Employees began leaving. Clients followed. Operational discipline disappeared.

“If we didn't come back exactly in April, we would have been bust by July,” Jason said.

Eventually, Jason returned to stabilize the business, rebuild operations, and salvage what remained. Although the company ultimately sold, it sold for far less than it once could have.

The Hard Lessons Founders Need to Hear

One of the most striking aspects of this episode was that Jason was willing to talk openly about his own mistakes; it’s the mistakes that many other founders often refuse to acknowledge publicly.

The episode explores the emotional reality of entrepreneurship: the pressure, the setbacks, and the resilience required to keep moving forward after failure.

Losing Everything and Starting Again

For Jason, success today is no longer just about financial growth. It is about helping others avoid the mistakes he made and showing people that setbacks do not have to define the rest of their story.

Jason openly shares that he lost everything multiple times throughout his life. Instead of hiding from those experiences, he uses them to mentor founders and help others navigate difficult moments in business and in life. Today, through the Caras Institute, he works with entrepreneurs on scaling, leadership, operational structure, and preparing businesses for future exits. He also spends time speaking at juvenile detention centers, sharing lessons on discipline, mindset, resilience, and personal growth with young people facing circumstances.

Jason’s Closing Remarks

This episode of Closing Remarks is a candid look at what happens when success, ego, culture, and resilience collide. Jason discusses the potential pitfalls of distancing oneself too much from the company before determining whether the new management is in sync with the business.

He advises entrepreneurs to listen to their gut whenever something seems amiss. His journey will also strike a chord with entrepreneurs and anyone who knows what it feels like to experience failure but is determined to keep going. Closing Remarks is now streaming on Spotify,  Amazon Music,  Apple Podcasts, and YouTube.

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