Three questions arrive early in any acquisition conversation. Are the earnings real? Do customers stay? Can the business scale without the person running it? For most mid-market companies, the honest answer to at least one of them is uncertain, not because the information doesn’t exist but because it hasn’t been assembled into a usable form before the deal room.
That gap is what Michael Cupps built Enterprise Diagnostics to address. The Carrollton, Texas company, which he founded in late 2025, focuses on AI-powered diagnostics for mid-market and private equity-backed businesses. The operating assumption is straightforward: operators generally have the capacity to fix what they find. Getting an accurate read on the business before anyone else does is the harder step.
The company’s free CRED assessment is designed for that first step. Available through the Enterprise Diagnostics site, the tool takes 16 questions and roughly 10 minutes to complete. It scores the business across four categories: Customer Health, Revenue Quality, Earnings Certainty, and Market Demand. What comes back is an instant score and an AI-generated 90-day action plan, no file upload required. According to the company, the framing is intentional. The questions mirror what a buyer’s diligence team would examine, and the score gives the owner that view before anyone else forms one.
That design logic carries through to the paid work. Enterprise Diagnostics‘ core engagement model starts with Baseline, which benchmarks financial health and EBITDA quality against sector peers. Alpha Vector analyzes customer retention, revenue concentration, and cohort growth patterns. Alpha Frontier identifies manual processes dragging margins and maps the AI automation case against them. The company describes the initial engagement as a two-week diagnostic producing a prioritized roadmap, followed by a subscription that keeps the intelligence running continuously. The platform is built on Palantir Foundry, which Enterprise Diagnostics says provides the digital twin and data integration capability that makes cross-functional analysis possible. Pricing is fixed-fee, with scope defined before work begins. By the company’s own account, this reflects something Cupps watched from the client side for years: consulting timelines that grew after the contract was signed.
Before he built Enterprise Diagnostics, Cupps had already been thinking about why execution breaks down at the individual level. In September 2023 he published Time Bandit: A Simple Method to Prioritize Your Focus and Energy to Do More (Rethink Press), a 114-page productivity book built around Eisenhower matrix principles and habit tracking. The argument is compact: most people don’t struggle with ideas or motivation. They struggle with a reliable method for deciding which ideas to act on first. Cupps hosts The Habit Architect podcast and extended the book’s framework into a free Priority Matrix tool, which applies the same logic to executive and team decision-making. The tool is built for the condition the operator described as the catalyst: leaders and project teams who have more initiatives than the bandwidth to run them, and need a way to sort the list rather than grow it.
Together, the book and the enterprise product describe a consistent premise. At the individual level and at the company level, the problem is rarely a shortage of information. It is a shortage of structure for acting on what is already there.
Cupps spent three decades building that perspective inside the enterprise software industry. He accumulated experience across business process management, content management, cybersecurity, and collaboration platforms at companies including webMethods, Global 360, McAfee, Telligent, Software AG, Vignette, and OpenText. He later served as Vice President of the Americas at Zimbra, and then as Senior Vice President of Sales at OpenConnect, a Dallas firm specializing in robotic process automation and mainframe integration. When OpenConnect merged with ActiveOps in 2019, Cupps moved with it, adding workforce analytics to a professional record that by then already spanned most of the enterprise stack. He holds a Bachelor of Science in International Trade from Texas Tech University and spent time working in North Carolina and New York before returning to Texas, where he has been based for roughly 20 years.
In May 2026, Enterprise Diagnostics launched Wingman, a competitive intelligence platform aimed specifically at Gen X and Baby Boomer executives who Cupps believes most AI products have overlooked. The tool scans up to seven competitors across 10 topics and runs entirely by voice if the user prefers, on the basis that leaders with 30 years of business experience shouldn’t need to learn prompt engineering to get useful information. Wingman is distributed primarily through executive coaches.
The company has a second co-founder, also from an agricultural background, one from Oklahoma and one from Texas. The About page describes that combination with 30-plus years of technology experience as producing a practical orientation that runs through the company’s approach: diagnose accurately, then act on what you actually find.
The full solutions suite is available on the Enterprise Diagnostics site. The CRED exit readiness assessment is free and takes about 10 minutes.
