Growing up on the water first as a part-time liveaboard, then full-time, and later as a seasonal cruiser shaped Sam in ways that never really left him. Life afloat has a way of teaching lessons early and without apology. You fix what breaks or you drift. You keep moving or you fall behind. Resilience, constant activity, and an ability to absorb hardship became baseline traits rather than learned skills. As a dock rat or boat kid, he lived a very Gen X childhood. It was loose, unsupervised, and built on freedom rather than guardrails. Consequences were distant abstractions. That upbringing fed directly into what would become a nonlinear and often confusing career path.
Sam served in the Washington Army National Guard for about nine months and attended basic armor training between his junior and senior years of high school at Fort Knox, Kentucky. He later transferred to active duty in the US Marine Corps. He completed boot camp the following summer in San Diego, attended the Basic Electronics Course at 29 Palms, and went on to Small Missiles School in Albany, Georgia. He returned again to 29 Palms, California, where he was medically discharged as a Corporal after breaking his back and neck in an accident. He was a Marine, and he is quick to admit that he was not a very good one.
After recovering for just over a year aboard his family’s boat, Alar, Sam took the civil service and police exams. His first role was as a part-time reserve officer, working between 16 and 24 hours a week for the Suquamish Indian Tribe in Suquamish, Washington. From there, he was offered a position as a corrections officer in Kitsap County and later transferred to Pierce County, Washington.
He was offered an opportunity to work with a family business, but it was only part-time. To fill the gaps, he attended college in Fort Myers, Florida, while working various jobs. He often refers to this period as doing anything for money that was mostly legal. He worked as a stringer for magazines and newspapers, as a photojournalist, as an information technology technician, as a Navionics technician rigging boats, and as an operations manager for several companies. The pattern was simple. If work came up, he took it. Saying no was not part of the plan.
After earning his associate’s degree in Fort Myers, Sam attended Westmar University in Iowa. He became editor of the school newspaper and was later elected student body president. Westmar eventually closed due to financial problems, leading to another transition. He transferred to Huron University and completed the degree requirements at both schools to earn his bachelor’s degrees. He then moved to Colorado Springs, where he experienced a divorce and earned a master’s degree in computer science systems engineering. Later, he remarried, completed his PhD at Purdue with a focus on cybersecurity at CERIAS, and wrote one of the earliest dissertations addressing cyber warfare as a formal domain of conflict.
Professionally, Sam worked with a wide variety of companies and sectors. He served as a contractor for MCI WorldCom, several technology firms, NCR, and TASC. His work focused on high-risk and high-visibility programs, often as a technical lead responsible for operations and integration across corporate and military environments. The pace was relentless. Working across five continents and living on a nonstop schedule is unsustainable. At one point, the head of a national laboratory suggested he consider academia as a way to escape the constant churn. Sam applied to four universities, received four offers, and chose a Midwestern university for what he assumed would be a short stay, likely no more than two years.
As an academic, Sam insists he was not very good, yet he earned tenure in five years, launched new programs, chaired the faculty senate, and helped define an entirely new discipline. He held tenured positions at Purdue University Calumet and Purdue University West Lafayette. While at Purdue, he also taught a summer session in Suzhou, China, at Southeastern University. Between his Purdue appointments, he served as an Associate Professor at the National Defense University, teaching courses on cyber conflict and the strategic use of power. Over the years, he lectured at the Army War College, Naval War College, Air War College, National War College, Naval Academy, and the National Intelligence University. Internationally, he taught at the Swedish National Defense University and lectured multiple times at the Marshall Center in Germany and the NATO Center in Estonia.
After leaving academia, Sam became the first Chief Information Security Officer of the US Army Corps of Engineers, where he helped establish the security program from the ground up. During his tenure, he guided the organization through multiple all-of-government responses to active hostilities. Based on his performance, he was chosen to lead the DHS Intelligence and Analysis cyber program’s technical efforts and was later appointed interim leader for just over a year. He is among a very small group of individuals selected for and completing the Senior Intelligence Leader program.
After government service, Sam joined Ultimate Software, a SaaS company in Weston, Florida. He initially served as a senior director and later as vice president of security operations. He led and grew a global team and supported the Chief Security Officer through multiple acquisitions and mergers. These included the company’s sale to private equity and its subsequent merger with another private equity portfolio company, along with several major operational events linked to those transitions. When buyout options became available, he attempted to retire.
That retirement did not last. Sam took a short-term role as Deputy CISO at Harley Davidson, later becoming CISO. The company culture and strategic direction proved to be a poor fit, which became obvious quickly. The organization was under significant strain, much of it visible in the press, and Sam helped outline potential future paths before leaving. He then accepted what was supposed to be a 90-day engagement with Blue Cross Blue Shield of Massachusetts. Only days into the role, he found himself leading the organization through the Change Healthcare breach and its aftermath. The 90-day assignment stretched into a year-long engagement. When it ended, he stepped away once again, aiming for retirement.
Since leaving government service, Sam has lived aboard his sailboat with his wife, Sydney. Working remotely since 2018, they have sailed the East Coast of the United States and the Bahamas, carrying their home and office with them. Life afloat sets a different rhythm. Weather, distance, and self reliance shape each day, and plans adjust to conditions rather than wishful thinking.
During this period in industry, Sam continued to bring an iconoclastic perspective to his work. He approached companies the way a sailor approaches a passage, skeptical of easy assurances and alert to what can go wrong when assumptions go untested. Watching the world from anchorages and offshore passages sharpened that habit. It reinforced a habit of questioning narratives, pressure testing decisions, and helping organizations steer toward more durable success while keeping a clear eyed view of events beyond the horizon.
By far, that isn’t everything but it is the highlights. We will see how long retirement lasts this time.
