Guidepost Philanthropy

Finding the Way Forward

What We Do

Guidepost Philanthropy provides customized advisory services and strategic consulting to individuals, families, and institutions. We also work closely with estate planning attorneys, family office staff, accountants, financial advisors, and other planning professionals committed to guiding clients through every step of their philanthropic journey. Whether you are just starting out or looking to enhance existing efforts, we can help you navigate the landscape, set meaningful goals, and maximize your impact.

Our Approach

Donating money is easy, but making smart charitable investments is more complex. Guidepost Philanthropy offers tailored services for donors at any experience level. We assist individuals, families, and foundations in understanding charitable ecosystems, setting achievable goals, and reaching their desired outcomes. We focus on specific projects and long-term partnerships, helping clients create or refine their giving plans, evaluate recipient organizations, and assess impact.

Advisory Services

We tailor our approach to each client. Every donor is unique, and we want to ensure that your personal views and experiences are valued. Some clients have been giving for years, while others are just starting out. Whether you are new to philanthropy or looking to advance your efforts, Guidepost Philanthropy offers a personalized process to uncover your history, goals, and values. From this, we provide specialized services and tools to help you make the most impact and achieve your goals.

Customized Services

Creating new foundations and purpose-driven Donor Advised Funds.
Providing administrative support for grantmaking, coordinating significant gifts, and troubleshooting discrete projects.
Helping donors express philanthropic goals that reflect personal values, priorities, and desired impact.
Conducting landscape analyses of specific charitable interest areas.
Helping to articulate and create a charitable legacy that resonates across generations.
Providing research on donor interest areas and best practices.
Designing effective grantmaking strategies, guidelines, and processes.
Conducting due diligence on recipients and potential partners.
• Monitoring impact and compliance for continuous learning.

Strategic Consulting

For over twenty years, we have helped institutional partners conduct research, design program strategies, assess impact, articulate priorities, and report outcomes. Our past clients include the Santander Bank Foundation, the U.S. Energy Foundation, KeyBank, the Charles Schwab Diverse Markets Group, the Barr Foundation, the Industrial Performance Center (MIT), the Surdna Foundation, the Hitachi Foundation, the Boston Foundation, the Annie E. Casey Foundation, and the Lincoln Land Institute.

Consulting Services

Write case studies and narrative reports
Conduct research, environmental scans, and stakeholder analyses
Identify, develop, and refine new program areas
Design and write strategic plans
Perform program process and outcomes evalutions
Design effective grantmaking strategies
Develop clear and efficient grantmaking guideines and procedures.
Conduct due diligence on grantees and potential partners.
Monitor impact and compliance for continuous learning.

Case Studies

Real examples from our individual and family engagements.

Engaging the Next Generation

A couple had a long-standing Donor Advised Fund (DAF) and wanted to include their “next generation” adult children in giving decisions but didn’t know how best to do it.

Services Provided
Engaging new family members in giving decisions provides an excellent opportunity to revisit the established vision and goals that guided previous giving. In our first meeting, we discussed their established philanthropic mission and vision for what full family participation could look like.

Managing a Growing DAF

The client had contributed to a modest Donor Advised Fund (DAF) for twenty years. Thanks to good returns and few disbursements, the DAF grew to a level that made the client feel guilty and anxious about how she would “ever manage to give away all of that money.”

Service Provided
The client made it clear that she doesn’t have the time or discipline to manage the DAF disbursements and fears being hounded by professional fundraisers. In our work together, the client decided to give away funds quickly through a set of large gifts based on her broad interests rather than through strategic change-oriented grantmaking. We also conducted a landscape survey and organizational assessments for potential large grantees.

Learning and Investigation

The client was a successful retired attorney who wanted to investigate the feasibility of creating a non-profit Fund that could support the development and expansion of minority-owned businesses in her home city.

Service Provided
As the client’s investigation partner, we took her on a learning journey. In addition to providing a landscape analysis of the existing small business support ecosystem, we arranged site visits and meetings with experts, practitioners, and small business owners. We also designed an organizational structure for funding and administering the fund.

Revising Donor Priorities

The client had been directing most of their funding to four organizations for many years but now questioned whether the grantees were still relevant and impactful.

Services Provided
We revisited the client’s interests, priorities, and vision and how they have evolved over the years. We then conducted due diligence on the grantees to determine their capacity, sustainability, and alignment with the donor’s current priorities. Based on this assessment, we developed a protocol for sunsetting existing grants and identifying new opportunities for the future.

Conceptualizing a New Foundation

Due to tragic circumstances, the client became the sole trustee of a substantial new family foundation. The client had no foundation running and little formal grantmaking experience.

Services Provided
We explored the client’s passions and the legacy he wanted to create with the foundation’s giving. Together, we mapped new foundation parameters that reflected his vision, mission, priority areas, and geographic focus. This map enabled the client to work on parallel tracks of identifying immediate grantmaking opportunities while building a more practical family foundation.

Due Dilligence

During the pandemic, the client wanted to provide no-questions-asked direct cash assistance to low-income families facing eviction. She did not want a large portion of her gift to go toward supporting the overhead of the organization that disbursed the funds.

Services Provided
We helped the client narrow the geographical focus of her gift to an area where it would have a meaningful impact. Through research and investigation, we were able to identify a community-based organization with the capacity and desire to quickly disburse the funds in accordance with the donor’s wishes.

Orson Watson, Ph.D.

Principal

Orson Watson is a 21/64 Certified Philanthropic Advisor with over 25 years of experience in outcomes-oriented social change investing. He works closely with foundations, donors, non-profits, and financial institutions to create meaningful impacts in communities. His expertise includes developing strategies to generate jobs and wealth for individuals in distressed areas, focusing on direct investments to maximize philanthropic impact by reducing middlemen. Known for his exceptional listening skills, Orson customizes his approach to help donors articulate their vision for social change, inspiring them to actively engage in their causes.

A New York City native, Orson holds an A.B. from Vassar College and an M.A. and Ph.D. in International Political Economy from the University of Virginia, gaining insights into global economic and social dynamics. Residing in Boston, he and his partner have dedicated years to restoring their Victorian home. They spend a portion of each year working working with health and children’s art initiatives in coastal Kenya.