John R.
Siver II
Service. Leadership. Experience Earned Under Pressure.
Built in places where accountability is non-negotiable
From military service and national security work overseas to high-level athletics, entrepreneurship, and community leadership, my career has been built in places where accountability, preparation, and execution are non-negotiable.
I've operated on the lacrosse field, in combat zones, in the boardroom, and in complex professional environments that demand clarity under pressure. Those experiences shaped how I lead, how I assess risk, and how I move forward with purpose.
Today, I focus on building businesses, supporting veterans, mentoring others, and being a present, engaged father. My work and my life are guided by discipline, responsibility, and service.
Veteran, entrepreneur, public voice
- Non-commissioned officer, U.S. Navy
- Senior contractor for the Department of Defense and Department of State — Iraq, Afghanistan, Jordan, and other high-risk areas
- Founder of Second Ascent Group; registered federal lobbyist with the U.S. Senate
- Appeared on The 700 Club, Conversations with a Vet, Financial Blueprint Seminar, and Capitol Hill panels on military readiness
- Featured in the NYT bestseller Lone Survivor by Marcus Luttrell, Big Boy Rules by Steve Fainaru, and Internal Volume by Lee Deckelman
- Contributor to discussions with the Virginia Attorney General's office on Department of Corrections improvements
Leadership through service
Service has always come first.
Military service and work in the government and national security space instilled discipline, decisiveness, and the ability to operate effectively under stress. Those experiences continue to inform how I lead teams, build organizations, and make decisions when stakes are high.
Leadership isn't theoretical. It's earned through responsibility, consistency, and follow-through.
Forged in service to country
My military career began in the U.S. Navy as a non-commissioned officer. After sustaining injuries during Naval Special Warfare training (BUD/S Class 225/226), I transitioned into roles that allowed me to contribute meaningfully during active conflicts.
I later passed on a traditional career path to support U.S. government operations overseas, serving as a senior contractor for the Department of Defense and Department of State across Iraq, Afghanistan, Jordan, and other high-risk regions.
That work required discretion, adaptability, and sound judgment in unstable environments — experience that forged perspective and professional maturity.
Building with purpose
Hospitality & Legacy
Entrepreneurship began early, working alongside my father, John Sr., who ran The Sugar Bowl tavern. Together, we restored a 145-year-old building that became Toliver House, followed by the opening of Fellini's. These ventures weren't just about business — they were about stewardship, legacy, and building something that lasts.
Siver International
I later co-founded Siver International during the height of the Middle Eastern conflict, providing training, technical, and security solutions to the Department of Defense and Department of State. Operating in complex and hostile environments, we built solutions where none existed — aligning mission needs with operational execution on a global scale.
Publications & Press
Featured in Charlottesville's well-known Cville Weekly and The Hook newspapers, as well as the California Business Journal.
Preparation, discipline, and the will to compete
From competitive skiing to collegiate lacrosse, sport taught me preparation, accountability, and how to perform consistently over time. Success in athletics isn't accidental — it's built through repetition, discipline, and the ability to respond when conditions aren't ideal.
Skiing, in particular, has been a lifelong pursuit spanning continents and generations. Today, I share that passion with my sons, Jack and Bennett, passing on the values that sport instilled in me: perseverance, respect for the process, and embracing challenge.
My relationship with the mountains began almost as soon as I could walk. I grew up skiing constantly — after-school nights on my home hill, weekends all over Canada, Lake Placid, Vermont, and eventually the American West. Alpine racing ignited a lifelong love of speed and precision, and I went on to become a PSIA-certified instructor. The mountains paused briefly during early Navy service, but they never left me.
While based overseas supporting the Department of Defense, skiing evolved into full-scale big-mountain exploration across Europe — Courmayeur, Chamonix, Parnassos in Greece, and two winters living in Switzerland, skiing nearly every major range in the Alps. I competed in bucket-list events like the Inferno Rennen in Mürren and the British Alps Ski Challenge, before eventually pushing beyond Europe to Haines, Alaska, where skiing reached its most raw and consequential form.
A legacy rooted in service
The Siver family legacy is deeply rooted in service, resilience, and a profound sense of duty passed down through generations. Guided by the values instilled by grandfather, Harry J. Siver — strong work ethic, unwavering moral fiber, and answering the call of service — his 15 children and their descendants have continued this proud tradition.
The men of the Siver family have primarily served in sea-faring branches like the U.S. Navy, yet their commitment extends across all branches of the U.S. Armed Forces, participating in every major conflict since World War II.
Their family home, a historic landmark listed on the National Register of Historic Places, served as a waypoint for Union officers during the War of 1812 — a testament to a legacy that honors both family and country.