Sunny Ray interviews Josh, a 25-year enterprise technology operator now building Auroclara, an AI platform designed to help board members understand and act on complex information in the boardroom. The conversation traces Josh's path from a curious kid on Long Island who coded on an Atari computer, through a self-designed healthcare entrepreneurship major and a public health master's at Emory, into seven formative years at Deloitte Consulting. From there he moved through WebMD during the early internet shift in healthcare, took a risk joining mobile startup Xcify, experienced its 2013 acquisition by IBM, and spent nearly a decade inside IBM Watson watching the first wave of enterprise AI unfold. A return to consulting at Alvarez and Marsal exposed him repeatedly to boardrooms where directors, despite deep expertise, often feared asking basic questions. That pattern became the seed for Auroclara, which aims to give diverse board members the tools to comprehend information, ask better questions, and fulfill their governance duties with confidence.
A 25-year tech veteran explains why boardrooms are AI's next frontier, and how his own winding career led him there.
Can you tell us what Auroclara does?
Auroclara is AI for the boardroom. Board members face huge complexity and information they need to consume, contextualize, and challenge. We help each director, whether it's their first board or their tenth, understand what they're being presented with, ask the right questions, and improve the quality and preparedness behind their governance duties and responsibilities.
What kind of kid were you growing up on Long Island?
I was basically the same person I am today, inquisitive and always into technology. My uncle worked for Atari and gave me an Atari 400, then I graduated to an 800 and wrote my first program in third grade. Otherwise it was lacrosse, swimming, lifeguarding, and a normal suburban upbringing on the North Shore.
Why did you pick healthcare entrepreneurship as your undergrad major?
I was always entrepreneurial like my dad, but also genuinely interested in healthcare and medicine, and I was pre-med. So I built my own major combining business and pre-med. I intended to go to medical school, didn't get in the first time, and ended up at a school of public health instead, which redirected my whole career.
What did big firm consulting at Deloitte teach you?
Coming out of public health into Deloitte's healthcare practice was extremely formative. I learned how to conduct myself in business, analyze problems, build presentations, and work with people. The culture was about making others successful, pairing young analysts with seasoned executives, and I got real exposure to C-level leaders and board preparation.
What did you see inside WebMD that most outsiders missed?
It was 2005 and the world of advertising and information consumption was totally changing. I wanted to understand how consumers found information and how you could message and advertise to them using web analytics. Because it also owned Medscape, I saw how physicians were shifting from textbooks and monthly journals to a steady stream of digital information.
Why did you jump from a big internet company to a tiny startup like Xcify?
I wanted to see if my instincts were as good as I thought, to build a real product and company from scratch. It was right as iPhones and Androids emerged and brands were figuring out mobile. Xcify did location based push notifications, like a coupon when you walked past a Starbucks, which raised real questions about privacy that are now completely normalized.
What was it actually like when Xcify got acquired by IBM in 2013?
It was chaos. We were a small venture backed company with a bigger reputation than our headcount, and IBM brought fifty people in person and fifty on the phone to diligence just four of us who really knew what was happening. We had to build business processes we'd never needed before, and I went in a little kicking and screaming because we loved our scrappy Soho loft environment.
What pattern did you see in boardrooms at Alvarez and Marsal that led you to build Auroclara?
Boards are intentionally diverse, with supply chain experts, finance people, clinicians, and connectors all in one room. But when I interviewed board members, ninety nine percent admitted they were afraid of asking a dumb question. Not everyone can digest a hundred page report, yet each director still has a duty of care, so I wanted to help level the playing field for all of them.
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