Personal transitions
Leaving home, leaving sport, leaving the military, changing careers, or trying to understand what comes next.
Navigate defining transitionswith confidence.
Some transitions are personal. Some are professional. Some are organizational. All require the clarity to understand what is changing, what matters most, and who you need to become for what comes next.
Mike Wisecup
Navy SEAL | College Athletics Director | Startup Strategist | Nonprofit Leader
What Fifth Law Does
We guide people and organizations through new roles, life changes, and uncertainty with clarity, discipline, and purpose.
Professional transitions
Becoming a founder, stepping into a larger leadership role, moving from individual performance to leading others, or carrying responsibility in a more complex environment.
Organizational transitions
Clarifying mission, redesigning teams, strengthening governance, or responding to a hard problem when the path forward is unclear.
01 / Personal Coaching
For individuals facing new roles or life changes.
Personal coaching is for people who are entering a new chapter and need help clarifying who they are, where they are going, and what the next version of themselves requires.
This work is direct, practical, and grounded in real experience. It is not therapy, admissions consulting, or generic life coaching. It is a structured coaching relationship for people facing questions of direction, identity, responsibility, and growth.
We work with high school and college students, young adults, athletes, veterans, founders, executives, and high performers.
- College launch and young adult direction
- Athlete transition beyond sport
- Military-to-civilian transition
- Founder-to-leader transition
- New executives or leaders
- Personal reinvention after a major life or career chapter
Who do you need to become for the next chapter of your life, work, or leadership?
02 / Advising
For leaders and organizations that need direct, experienced guidance.
Advising is for founders, executives, boards, and mission-driven organizations working through questions of leadership, structure, team performance, governance, and mission execution.
This is different from coaching. In advisory work, we bring a more directive role: assessing the situation, identifying gaps, naming hard truths, helping frame decisions, and providing practical recommendations based on experience leading teams in high-pressure, high-consequence environments.
- Mission, vision, and values development
- Organizational design and team structure
- Board and governance effectiveness
- Leadership roles and responsibilities
- Decision-making systems
- Culture building
Rapid response advisory support
Fifth Law also provides rapid response advisory support for leaders or teams facing urgent, complex, or high-pressure situations. This work is designed for moments when leaders need a calm outside perspective, direct counsel, and help moving from confusion to action.
03 / Speaking
For audiences that need a powerful message on leadership, responsibility, resilience, and growth.
Fifth Law speaking engagements draw from Mike Wisecup’s experience as a Navy SEAL officer, combat leader, senior college executive, athletics director, nonprofit board chair, technology startup strategist, advisor, and coach.
The talks are practical, personal, and built around the same core idea that shapes all Fifth Law work: people are capable of more than they realize, but they often need structure, guiding principles, and purpose to grow into what comes next.
- Earning your title every day
- Leading through discomfort and uncertainty
- Building high performing teams
- Decision-making in uncertainty
- Culture transformation
- Crisis management
- Creating resiliency in yourself, your people, your organization
- Lessons from military, athletics, higher education, and nonprofit leadership
Speaking engagements can be designed for schools, colleges, camps, companies, nonprofits, founders, boards, and leadership groups.
Proof of Work
Leadership tested. Results proven.
Fifth Law is built from a career spent inside pressure, not studying it from a distance. Mike Wisecup has led special operations teams in combat, advised at the highest levels of national security decision-making, transformed a college athletics department, worked inside a defense technology startup, mentored founders, and rebuilt nonprofit governance.
Military Leadership
Mike spent more than two decades leading special operations teams in some of the world’s most demanding environments. His experience spans combat deployments, multinational operations, and leadership roles from platoon-level teams to senior command positions across Navy, joint, and interagency organizations. He earned the Bronze Star with Valor and Purple Heart for actions during the Battle of Fallujah, where leadership, resilience, and sound judgment carried real consequences.
Innovation Leader
Throughout his career, he has challenged conventional thinking, built high-performing teams, and developed new approaches to solving complex operational and organizational problems. He created new operational models for global special reconnaissance missions, pioneered use of publicly available information to support counter-terrorism operations, and created new innovation pathways designed to move ideas from every rank to senior leadership faster. During his command of Special Reconnaissance Team ONE, the unit was recognized twice as the top intelligence unit in the Navy.
Senior National Security Advisor
Mike served in Washington, D.C. as aide-de-camp to General Martin Dempsey, Chairman of the Joint Chiefs of Staff. In that role, he supported senior-level engagements with the President, National Security Council, Congress, foreign chiefs of defense, and heads of state. He also worked across the interagency on coordination of complex special operations to achieve national security objectives and development of the first government-wide counter-ISIS strategy.
Higher Education Transformation
At Colby College, Mike served as Vice President for Strategic Initiatives and Director of Athletics. He advised the president, senior staff, and board of trustees on strategy and execution, then led a 32-team athletics department through cultural, competitive, organizational, and fundraising transformation, including the creation of a Peak Performance program and a new recreation department, resulting in a top-10% program national ranking.
Defense Technology & Startup Advisor
Mike worked as a mission strategist at an AI/ML-enabled defense technology company, helping translate ambiguous national security challenges into viable product and mission opportunities. He now advises founders, startups, and dual-use companies on strategy, mission alignment, government market entry, and use-case development through his work with the National Security Innovation Hub at the Northeastern University Roux Institute.
Nonprofit Governance & Civic Service
Mike has led significant governance and board operations reform as Board Chair of Camp Sunshine and serves in advisor, trustee, veteran, scouting, and service-oriented roles across Maine and national organizations. His nonprofit work focuses on mission clarity, board effectiveness, governance structure, execution discipline, and building organizations capable of sustaining impact. In 2019, he was recognized as the State of Maine Volunteer of the Year.
About Mike
A leader shaped by adversity, pressure and purpose.
Mike Wisecup has spent his life stepping into unfamiliar environments, learning quickly, and leading teams with clarity and discipline.
A graduate of the U.S. Naval Academy with an MBA earned in Mumbai, India, Mike served for 20 years as a combat-proven Navy SEAL officer before transitioning into senior leadership roles at Colby College, the defense technology startup world, and national nonprofits.
Through Fifth Law, Mike now brings that lived experience to personal coaching, advising, and speaking — helping people and organizations navigate defining transitions and prepare for what comes next.
20+
Companies advised
100s
Leaders, coaches, athletes, founders, and students coached
25+
Years leading people and organizations
Start Here
Navigating a transition, leading through pressure, or facing a hard problem?
Let’s talk about what you are facing, what needs to get clearer, and where Fifth Law may be able to help.
Contact Mike for a free discovery session.
Maine-based / Available for coaching, advisory work, rapid response support, and speaking