AJ Loiacono and the things you learn before the deal closes

AJ Loiacono had helped get a promising business meeting almost to the finish line. Then somebody asked to use the bathroom. His first company occupied an office on the Brooklyn waterfront, with facilities that apparently required a stronger constitution than the sales presentation. The visitor insisted she could manage. The next day, an email arrived with a subject line expressing considerable alarm about the bathroom. They won the account anyway. When Loiacono later told the story, he added that he now personally inspects the bathrooms when considering an office.

It is a useful introduction to a founder whose working life has involved software installations, several companies, and the unglamorous business of making something function. A contract can survive a dreadful first impression. A handsome office can conceal a dreadful product. The job is to discover which details matter, preferably before a prospective customer discovers them for you.

Today, Loiacono is co-founder and CEO of Judi Health, the company he helped start as Capital Rx in 2017. His earlier ventures include Victrix, SMS Partners, and Truveris. Read the names in sequence and the career looks orderly. Listen to him describe the work and it becomes a succession of practical educations, some more comfortable than others.

A working education, acquired by accident

Asked how he entered his field, Loiacono gave a wonderfully economical answer: “By accident.” He began on the manufacturing side, helping convert older supply-chain systems into enterprise software, including Oracle and SAP platforms. He spent almost eight years doing that work. The apparent detour became experience he continued to draw on long afterward.

There is a particular education in installing software where people already have jobs to do. A new system must accommodate routines, information, deadlines, and the habits nobody thought to include in the specification. The implementation has to work after the demonstration ends. That is a less theatrical beginning than a sudden revelation on a whiteboard, though it offers considerably more opportunities to learn what can go wrong.

Loiacono's account of those years gives his later interest in infrastructure a concrete beginning. He had worked on replacing the underlying machinery. He knew that a business could want a different result while still depending on the systems that produced the old one. The question of how to change those systems would follow him into his own companies.

The desk beside the expert

When Loiacono encountered work he did not yet understand, his solution included moving furniture. He placed his desk beside a colleague who knew the field. From there, he could hear conversations and observe how she approached decisions. The arrangement made an ordinary working day into an extended lesson.

He later described several varieties of mentor, including unwilling, invisible, formal, and passive ones. The categories are amusing because they allow for the possibility that a person can be teaching you without having agreed to an impressive title. Advice can arrive through a scheduled conversation. It can also arrive while somebody else is handling the next problem.

The desk story supplies a modest corrective to the founder biography in which competence arrives fully assembled. Loiacono recognized a gap and put himself where he could fill it. That requires a willingness to be the less informed person in the conversation. It also requires enough patience to listen when the lesson takes the shape of everyday work rather than an inspirational speech.

For a future chief executive, the arrangement had another advantage: the teacher remained close to the task. The explanation and its application occupied the same room.

Who actually does the work?

By 2014, Loiacono was confronting the other side of the learning problem. As co-founder and executive vice president of Truveris, he needed people who could perform complex analytics. Recruiting through universities and word of mouth had helped. The company also agreed to hire graduates from a new data-science fellowship program.

What interested him was the combination of analytical ability, applied programming, and pragmatic skills. He was cautious about assuming a company could simply bring anyone up to speed internally. There is a cost to teaching, even when the people involved are bright and willing. A growing business has to make room for that cost or find people with the preparation it needs.

The concern is revealing because it puts staffing inside the product story. Software does not emerge from a statement of ambition. Someone has to understand the data, write the code, test the result, and explain it to somebody whose working day depends on it.

His attention to practical preparation connects the installer to the executive. Earlier, he needed to learn the work. Now he needed to assemble people capable of doing it together.

Starting again, with experience

Victrix was sold to Chrysalis Solutions in 2007. SMS Partners, a joint venture with Realogy, ended for Loiacono with a buyout in 2010. At Truveris, he spent eight years in roles that included CEO, CIO, and board member. Each venture added experience, though a résumé compresses the difficult stretches into very economical lines.

In 2017, he founded Capital Rx with Ryan Kelly and Joseph Alexander. Kelly became the technology co-founder and chief technology officer. The partnership matters in a story often told around the CEO: the company required people with different responsibilities to turn a shared intention into a working organization.

Starting another business also means encountering a peculiar inequality. The founder brings years of accumulated experience. The company arrives with no equivalent history. Buyers still need reasons to trust it. Employees still need reasons to join. A previous venture can establish that someone has built before, while the new venture must establish that this particular thing works.

That gap between personal experience and institutional proof is where a great deal of early company building happens. It is also where a familiar name offers only so much assistance.

The customer who lends you a reputation

Looking back on the early selling period, Loiacono described the difficulty of approaching buyers without an established customer list or references. He also said the company spent nothing on marketing for its first two years. Existing customers became advocates. Eventually, a Fortune 500 company contacted him after seeing a post.

Those details make the early progress sound more awkward, and more recognizable, than the usual smooth account of finding a market. A potential buyer wants evidence. The young company needs a buyer to generate it. Someone has to accept the inconvenience of going first.

The later incoming call mattered because a recognizable customer was asking to do business directly. The direction of the conversation had changed. Instead of introducing an unfamiliar company, the founder was responding to interest it had already earned.

There is some humor in a business spending zero on marketing and still finding that a post can open a door. The larger point is the work that gives the post credibility. A customer recommendation carries the experience of someone who has already taken the risk. It is a form of borrowed reputation, earned one relationship at a time.

“By accident.”

AJ Loiacono, on how his career began

The office becomes a map

Growth eventually changed the setting of the work. In January 2024, Loiacono described a company that had moved from a workforce roughly 90 percent concentrated in New York City to employees across 36 states. The team had grown from about 70 people to more than 600. Leadership and the board had dispersed too.

He remembered a commute of roughly an hour and twenty minutes each way. Recovering that time was welcome. Recreating the everyday opportunities to learn from colleagues required thought. Training, mentorship, and identifying future leaders became explicit management questions.

The earlier desk move makes this a particularly interesting problem for him. Proximity had once made learning easier. A distributed company has to arrange its own opportunities for people to observe, ask questions, and take on responsibility. Useful knowledge can no longer be expected to travel simply because two chairs happen to be nearby.

Loiacono talked about generations within a company: associates becoming managers, junior engineers becoming senior engineers. Growth, in that description, includes the careers developing inside the organization.

Twenty-three years to an award

In June 2023, Loiacono was named an EY Entrepreneur Of The Year New York award winner. An independent judging panel assessed candidates on entrepreneurial spirit, purpose, growth, impact, and other contributions. It was a regional award recognizing a business career already well underway.

When discussing the recognition later that year, he joked that it had taken twenty-three hard years. He credited family, mentors, colleagues, business associates, and co-founders. The award carried one person's name, while his explanation distributed the work among many people.

That is a useful way to read a founder profile. A title identifies responsibility. It cannot list every person whose judgment, patience, or technical ability helped the business keep going. The co-founder beside him in a photograph and the colleague beside his desk belong to the same account.

By September 2026, another connection appeared: Manhattanville University named Loiacono, a member of its class of 1994, among the founding members of its President's Executive Leadership Council. The council's purpose includes strengthening the relationship between education and the working world. For someone who has spent years thinking about practical skills, it is a fitting assignment.

The bathroom inspection remains a rather good closing detail. Experience changes what a founder notices. Sometimes it produces a new company. Sometimes it produces a better hiring question. Occasionally, it means checking the facilities before inviting anyone over.