I started Courageous Strategies because it’s not enough to simply solve problems. Real leadership requires us to ask how we solve them, for whom, and at what cost. Those questions matter just as much as the outcomes if we’re serious about building a future that works for everyone.

Through this advisory practice, I work alongside mission-driven leaders and organizations to bring clarity, discipline, and courage to their work. Together, we turn strong ideas into grounded strategies and build the systems that make lasting impact possible.

Every engagement is guided by my core values of integrity, boldness, and courage. These values shape how I show up for the organizations I serve and how I help them lead with purpose.

Why Work With Me?

I’ve led a national nonprofit as Executive Director, overseen multi-million-dollar budgets, advised philanthropic institutions, and spoken at colleges and universities, tech companies, and government agencies about social impact and public leadership. Across each chapter, I have helped bold ideas move from vision to execution.

Offerings

  • Civic Innovation Strategy – Guidance on designing and scaling programs at the intersection of democracy, leadership, and social impact.

  • Retainer-Based Executive Advising – Ongoing support as a trusted advisor for senior leaders and boards, providing strategic counsel and an external perspective on complex decisions.

  • Operational Audits – External assessments of your organization’s key functions (People & HR, Communications & Operations, Governance & Leadership), highlighting strengths, vulnerabilities, and a roadmap for improvement.

  • Vision Setting & Strategic Planning – Facilitating collaborative processes that clarify mission, set priorities, and build actionable plans for growth and impact.

Integrity + Boldness + Courage = Transformative Impact

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Rashawn’s nonprofit management expertise positively impacted our strategic planning, and his insights on new fiscal strategies were invaluable.
— Eloise Samuels Founder & CEO New Jersey Orators, Inc.