Michael Ciullo and the Trouble With Doing Everything

Michael Ciullo had a company, customers and a problem that would be familiar to anyone who has ever watched a promising business relationship quietly go cold. Clients were leaving. Referrals were scarce. Partners seemed to forget his company at precisely the moment a recommendation might have helped. The advice he received was brisk: “Build better relationships!” Splendid. He was already doing the accounting, sales, software work and customer service. Presumably he could fit friendship somewhere between Thursday and exhaustion.

His response was unusually concrete. After reading John Ruhlin’s Giftology, Ciullo tried sending clients thoughtful, personalized gifts at unexpected times. In his own account, customer losses fell from an average of 15 percent to virtually none over two years, while referrals increased 300 percent. Those are his reported results. The revealing detail is the question he was trying to answer: how does a busy founder make people feel remembered?

Today, the Miami-based founder and chief executive of Nsight Health writes about a related difficulty: how to build a company without making yourself the person through whom every decision must pass. His career keeps circling the same human complication. A business needs attention. Its founder has a finite supply.

A salesman’s education

Ciullo began in business-to-business software sales. Before the collection of companies and the chief executive titles, there was the practical work of finding customers and persuading them to buy. His early roles included director of sales at Mobile Solutions, later Brightfin, and vice president of sales and marketing at MP Cloud Technologies. Sales was the route through which he learned technology and business development.

There is a useful modesty to that starting point. Selling software requires an idea to survive contact with somebody else’s priorities. A prospective customer may admire the presentation and still decline to sign. A founder who begins there learns early that enthusiasm does not automatically travel across a desk.

His public career account places roughly four years in sales before his first independent venture. He went on to found Nsure and later Nsight. The pattern was to carry experience into the next business, including the less flattering lessons about keeping customers after winning them. A signed contract, it turns out, has no sentimental attachment to the person who secured it.

The business after the sale

Client Viral, another of Ciullo’s ventures, dealt with client relationships through a concierge software offering. Its place in his career makes sense beside the gift-giving experiment: he was interested in the work that comes after a customer says yes. Acquiring an account and sustaining someone’s enthusiasm are distinct jobs, even when the same overextended person is assigned both.

In May 2021, he appeared on Dude. I Want That Job! to discuss his beginnings in Clayton, California, work at his cousin’s software company in Denver, losing that job and starting out on his own. The conversation also covered Client Viral and The White Label Method. Its premise was a traveling business owner explaining the route that had taken him there.

That early appearance gives the career a different texture from an executive biography. There is a hometown, a relative’s company, an interruption and another attempt. The itinerary is less tidy than a row of job titles. It also places his interest in teaching and explaining business well before his more recent leadership essays.

When a founder becomes the queue

By February 2026, Ciullo was addressing the transition from founder to chief executive in his own writing. He argued for careful early hiring, genuine authority for division leaders and a change in how the person at the top measures progress. Revenue growth, margins and retention deserve attention; the sheer number of tasks personally completed is a less useful trophy.

The distinction has a certain comic cruelty. The founder is initially rewarded for doing everything. Later, the company requires that same person to stop doing quite so much. Competence can become a very comfortable hiding place. It feels responsible to check one more detail, approve one more decision and remain the answer to every question.

Ciullo’s argument gives that impulse a practical consequence: decisions accumulate behind a single person. His proposed response is to establish the outcome, responsibility and purpose, then allow the team to determine execution. Read beside his early experience juggling functions, the argument sounds like the next question in a continuing conversation about where a founder’s time belongs.

“If every decision requires your approval and oversight, it only creates bottlenecks that impede growth.”

Michael Ciullo

The glamour of a written process

The same concern runs through his discussion of businesses that can operate without their owner’s constant involvement. The ingredients are workaday: documented procedures, clear roles, people who have been trained and regular reviews. Independence is something to prepare for gradually, observing what happens when the owner steps away for increasing periods.

A written process has few of the theatrical attractions of a founder story. Nobody queues for a film about a well-maintained handover document. Yet this is where Ciullo’s business commentary becomes most useful. It concerns the unglamorous transfer of knowledge from one person’s head into a form another person can actually use.

For a serial founder, that question travels from company to company. How much depends on the original builder being available? What happens when someone needs an answer during a meeting elsewhere? A business that can explain itself to its own employees has gained something more durable than a particularly energetic owner.

And then say the awkward thing

Ciullo’s January 2026 writing on management takes up another drain on a company’s attention: the conversation everyone knows is needed and nobody wants to start. He describes managers avoiding a difficult subject because they fear the reaction, want to remain liked or hope the problem will resolve itself. The calendar, unfortunately, is an unreliable conflict-resolution department.

His examples concern familiar workplace situations, including a productive employee whose manner damages the team and a promotion that can no longer be offered. They are management illustrations, not disclosures about particular Nsight employees. The proposed response combines directness with empathy, supported by practice in how to phrase and time a difficult discussion.

There is a connection here with his earlier preoccupation with clients. Relationships require actions that the other person can recognize. Appreciation must be expressed. Changed circumstances must be explained. Delegated authority must actually be handed over. The common subject is the gap between a leader’s good intentions and another person’s daily experience.

A second microphone

Ciullo’s public life also includes a partnership that has nothing to do with an organizational chart. With his wife, Angelika, he co-hosts Finding Faith. She had previously developed Bring Back Femininity, and he had joined her in episodes before they began their shared faith-focused project.

The couple have described making church, prayer and Scripture part of their lives. Their podcast grew from conversations with others who asked about that change. Their stated aim was to make room for personal experiences of faith, including guests describing their own journeys. The scale is intimate: two people talking through something that matters to them.

For a person whose professional identity includes several companies, sharing a microphone is a useful change of proportions. The conversation belongs to a couple. Angelika brings her own experience as a host. Michael’s place in it is as a husband and participant as well as a business owner.

What the work is for

Giving has become another part of the couple’s public account of their lives. In 2024, they described the Ciullo Foundation as a self-funded project intended to support community work, with Angelika handling its daily activity. Their ambitions included helping churches, housing projects and animal shelters, and encouraging other entrepreneurs to contribute through organizations of their choosing.

“If you’ve been blessed, you have a responsibility to be a blessing,” Ciullo said. That statement is more revealing than a general declaration of charitable intent. It attaches an obligation to success. Earning money, in this view, creates a further decision about who else should benefit from it.

His personal interests include guitar, cooking and travel with Angelika. He also describes serving on his church board and belonging to Legacy Leaders, a Christian business network. These are ordinary details beside a company ranking, which is part of their appeal. A guitar offers very little respect for a chief executive’s title. The chord still has to be played.

The scorecard keeps changing

The business milestones remain substantial parts of his story. Nsure appeared at No. 1,546 on the 2022 Inc. 5000. Nsight, founded in 2021, reached No. 78 in the 2026 ranking, alongside a No. 12 position in the Southeast regional list. Nsight also received Best Workplaces recognition in 2026. Each distinction measures a particular part of company life; together they show successive businesses reaching national attention.

Ciullo’s current interests extend through Ciullo, Inc., an operating company whose portfolio includes software and real estate businesses. Its stated approach pairs dedicated company leadership with shared operating resources. That structure brings his writing about delegated responsibility into view again. A collection of businesses demands people who can make consequential decisions without waiting for the founder’s next available minute.

The interesting progression is from the young salesman trying to win attention, to the owner trying to remember his customers, to the executive arguing that other people need room to lead. Each stage asks him to reconsider what useful work looks like. The next entry on a ranking may be welcome. So, by his own reasoning, should a day when the company needs fewer answers from him.