Anthony Loiacono needed to learn something his colleague already knew. So he moved his desk. Beside hers, he could listen to the conversations, watch the decisions, and discover how the work happened between the formal explanations. For someone whose career would involve founding companies and persuading customers to change their routines, it was a refreshingly unceremonious education. The useful change was a shorter distance to a person with experience.
He told that story in a 2023 conversation about mentorship. The detail is easy to overlook amid the companies on his résumé. It is also unusually revealing. A founder can hire expertise, ask for advice, or arrange a meeting. Loiacono made himself available to the ordinary, repetitive business of learning. The lesson could arrive whenever the next conversation began.
Publicly, he goes by A. J. His full name is Anthony Joseph Loiacono. Truveris is one chapter of his career; Judi Health, the business he co-founded as Capital Rx, is the current one. Across those chapters, his job has included selling, recruiting, developing software businesses, and making room for people who understand a problem differently.
The next desk was the classroom
In discussing mentors, Loiacono described several varieties, including people whose teaching happens without a formal arrangement. His colleague belonged to a world he was entering. Sitting close enough to hear her work gave him access to knowledge that a scheduled question-and-answer session might miss.
There is a modesty to the act. Someone who relocates his desk to learn has acknowledged that the next useful answer may belong to another person. It is a good precaution against the occupational hazard of becoming the person everyone else asks.
The move also gives the rest of his career a useful scale. A company biography measures experience in years. A funding announcement measures it in dollars. Neither tells you much about the moments when an executive stops talking and pays attention. Here, the unit of measurement was a desk. You could push it across the floor.
A résumé with more than one beginning
Loiacono studied finance at Manhattanville College, where he also played varsity soccer and rugby. The combination supplies a concrete glimpse of his student life without requiring an elaborate theory about how a rugby match produces a chief executive. Sometimes a game is allowed to remain a game.
His first venture was Victrix, a supply-chain consultancy sold to Chrysalis Solutions in 2007. He also co-founded SMS Partners, a joint venture with Realogy, and exited that partnership through a buyout in 2010. By the time Truveris occupied his working life, company building already meant more than a single launch.
At Truveris, he held several jobs across an eight-year tenure, including CEO, chief innovation officer, and board member. Those titles describe different kinds of responsibility. An executive selling the company’s work meets objections from buyers. An innovation leader has to decide what can be built. A board member must consider what the organization can sustain.
In 2017, he co-founded Capital Rx with Ryan Kelly and Joseph Alexander. Kelly became the technology co-founder and chief technology officer. Another company meant another beginning, even for someone with earlier ventures behind him. Experience travels with a founder. Customers, colleagues, and operating routines still have to be assembled.
Finding the people who can make it work
In 2014, while he was co-founder and executive vice president at Truveris, Loiacono discussed a practical hiring problem: finding people capable of doing complex analytics. The company had recruited through universities and word of mouth. It also agreed to hire graduates of a new data-science fellowship program.
What interested him was the mix of analytical knowledge and applied programming. The distinction matters to a software business. An elegant explanation is pleasant company; a working implementation has to survive the customer’s Tuesday afternoon.
He was cautious about relying on the company to bring every new recruit up to speed. Training took work, and the program’s attention to pragmatic skills appealed to him. His comments put a less glamorous question beside the product ambition: who will actually do this?
That is a founder’s question as much as a recruiter’s. The product may be described in a few sentences. Making it useful requires people who can pass information between disciplines, understand the task, and produce something others can use. Loiacono’s attention to those skills places the team inside the story of the product, where it belongs.
The customer before the references
Starting Capital Rx brought an old sales difficulty into a new company. In his 2026 account of the early period, Loiacono described selling with very little customer history to offer. Prospective buyers wanted references. The fledgling business needed customers before it could accumulate them.
The dilemma has an almost comic neatness. You can prepare the explanation, demonstrate the system, and answer the questions. Then someone asks who else has trusted you. All those preparations suddenly have to carry the weight of a missing list.
Loiacono said the company spent nothing on marketing during its first two years, relying on customers to help spread its reputation. The point carries more weight as a description of that early period than as a rule for every business. A recommendation is valuable because someone has put their own judgment behind it.
The first sale therefore creates an obligation that reaches beyond the first customer. Delivery supplies evidence for the next conversation. A satisfied buyer can explain what the company is like when the presentation is over and the service is being used. For a founder seeking a reference, ordinary competence becomes part of the sales process.
Thirty-six states, no next desk
Later, the work environment itself changed. By January 2024, Loiacono described a company whose workforce had spread across 36 states. Earlier, roughly 90 percent of the team had been in New York City. Employees came into the office five days a week. That was the working model he had learned.
The geography changed alongside the size of the team. He recalled about 70 employees before the shift and more than 600 by the interview. Leadership and the board were more dispersed too. The old assumption that people would learn simply by being in the same building needed another look.
It posed a pointed question for someone who had once moved a desk to learn. How do people watch experienced colleagues when the colleagues are elsewhere? Training, mentorship, and identifying future leaders all became questions of organizational design.
There were gains too. Loiacono recalled commuting about an hour and twenty minutes each way. Flexibility returned time to employees and their families. The next task was to preserve the opportunity to learn while keeping those advantages.
A launch is a date. A company is a commitment.
In an October 2024 interview, Loiacono returned to the need for continued development. His concern was the organization that becomes too comfortable with the thing it already sells. Customers change their requirements. Software has to accommodate new work. A business can keep its name while its job changes considerably.
“Companies that stay static are displaced over the long term.”
A. J. Loiacono, October 2024
The sentence is plain, and so is its demand. A company must fund the next version while supporting the present one. It has to recruit people who understand today’s work and remain willing to learn tomorrow’s. A launch photograph can mark progress; it cannot settle those questions.
Loiacono’s interest in infrastructure makes this a long conversation. Software used inside an organization becomes entangled with the organization’s routines. Replacing it asks people to change how they work, and keeping it useful asks the software company to listen after the sale.
That brings the founder back toward the next desk, at least in spirit. Listening is useful when you are new to a field. It remains useful when your company has become familiar to customers. Familiarity can make questions easier to ask. It can also tempt an executive to believe he already knows the answer.
The big numbers, and the smaller habits
There are public milestones to set beside these working habits. Loiacono was named an EY Entrepreneur Of The Year New York award winner in 2023. Capital Rx appeared on the Inc. 5000 for four consecutive years through 2025, when it ranked No. 955.
In September 2025, the company announced a $400 million financing package and adopted the Judi Health corporate brand. The package included a $252 million Series F and investment involving existing shares. The company valuation was $3.25 billion. Those figures mark a substantial financing chapter; the distinctions between them matter when describing what was raised.
By July 2026, further changes included the Judi Rx and Judi Cloud brands. Loiacono remained CEO. The company’s name and structure continued to evolve around a product-development career that had already stretched through several ventures.
There is room for a less solemn detail, too. Loiacono has a lucky Costa trucker hat. It is a small, agreeable accessory to a career full of software systems and financing rounds. A founder can insist on better infrastructure and still allow a hat a little credit.
The desk story offers a more practical closing image. Before the newer company names and the larger numbers, a colleague knew something Loiacono needed to understand. He arranged his working day so he could learn it. As his organizations grew, the challenge became giving other people that same opportunity, wherever their desks happened to be.