For the Staten Island entrepreneur, taking a risk has never meant ignoring the numbers. His path from consulting to company ownership, and a childhood interest in racing, shows how he approaches the unexpected.
By SM Media
Staten Island, New York, October 29, 2026 – By the time Rich Ramm made the decision to leave McKinsey, he had already accomplished something he once might not have expected: building a career at the global consulting firm after dropping out of high school.
Walking away meant exchanging a well-established professional path for a venture without a track record. He returned to Staten Island without even having an apartment secured. The business was still an idea that would have to survive contact with reality.
The question he kept coming back to was deceptively short: “What if it works?”
An Unconventional Starting Point
Ramm did not follow the usual academic route into consulting. Without a conventional educational background to lean on, he had to demonstrate his value through preparation, persistence and the quality of his work. Reaching McKinsey became a defining career milestone, but it did not settle the question of what he wanted to do next.
Consulting offered him a familiar kind of challenge: understand a problem, analyze the available information and make decisions with the consequences in mind. Entrepreneurship presented a different one. The decisions would be his, as would the responsibility for carrying them out.
“I have a high tolerance for calculated risk, but calculated is the important part,” Ramm said. “I want to understand the downside, understand the numbers and understand what it will actually take to make something work. At some point, though, you also have to ask: what if it works?”
Choosing an Unfinished Plan
Before returning to New York, Ramm had spent time in Miami. His experiences there changed the way he thought about the everyday details that make an organization effective: listening to people, explaining expectations and following through on commitments.
He saw room to apply those ideas back home. Making that move was less straightforward than describing it. Leaving a salary behind required him to confront the immediate practical questions of housing, financing and getting a new operation off the ground.
The early period demanded a different kind of discipline than the one he had practiced as a consultant. Instead of examining what another organization should do, he had to decide where his own resources should go, what could wait and which responsibilities could not be delegated.
As the operation grew, the choices became more complicated. Hiring, systems, budgets and leadership all called for attention. Ramm remained closely involved in the details, with an emphasis on addressing problems early rather than allowing them to become part of the routine.
An Interest That Never Left Him
Cars have been a constant in Ramm’s life, long before his move into entrepreneurship. What began as a personal interest also became a way to meet people whose paths might otherwise never have crossed his.
Conversations around cars introduced him to entrepreneurs, owners and other people familiar with the uncertainties of building something. The connections were not easily reduced to a number on a spreadsheet, and the time and expense involved occasionally drew questions. He kept showing up because the interest was genuine.
That enthusiasm eventually led to a moment he could once only have imagined: a business he founded sponsored NY Racing Team, with its logo appearing on a NASCAR race car. For Ramm, watching the car on the track connected a childhood fascination with a later chapter of his working life.
The sponsorship was not the reason he entered business, and it was not a substitute for doing the work. It was a reminder that the rewards of an unconventional career are not always the ones a person can predict at the beginning.
What Comes After the Leap
Ramm’s experience has not made him dismissive of risk. If anything, it has given him a more practical view of it. Decisions made with incomplete information still require follow-through, and a promising start is only useful if the work behind it can hold up over time.
He continues to put weight on preparation, financial discipline and remaining close enough to day-to-day operations to recognize what needs attention. The habits are less dramatic than a career change, but they are what allow the initial decision to become something lasting.
The most striking part of Ramm’s journey may not be that a high school dropout reached McKinsey, or even that he left it. It is the willingness to make a second unconventional choice after the first one had already worked.
“What if it works?” gave him a reason to begin. The years since have been about answering the question through action.
