Sample Giving Roadmap

ROBERT H CALDWELL S A M P L E F O R I L L U S T R AT I V E P U R P O S E S O N LY

TA B L E of C O N T E N T S

Philanthropic Vision & Identity

01

Giving Priorities

03

Giving Structure & Distribution

05

Protecting Your Legacy

08

Execution & Acknowledgment

09

ROBERT H. CALDWELL

This Legacy documents the philanthropic vision of Robert and serves asand theserves governing instruction set for all ThisRoadmap Legacy Roadmap documents the philanthropic visionH. ofCaldwell Robert H. Caldwell as the governing charitable giving carried out in their name. Anonymous Philanthropy designed this Roadmap. Catalyst Philanthropy Fund — a 501(c) instruction set for all charitable giving carried out in their name. Anonymous Philanthropy designed this (3) public charity — receives and deploys assets according to the Roadmap, with oversight from its independent Advisory Board. The Catalyst Philanthropy Fund —governing a 501(c)(3)documents public charity — receives deploys assets to RoadmapRoadmap. is made enforceable when reflected in the of each relevant and giving vehicle.

Lastaccording updated: 2026-07-17.

the Roadmap, with oversight from its independent Advisory Board. The Roadmap is made enforceable when reflected in the governing documents of each relevant giving vehicle. Last updated: 2026-07-17.

Legacy Roadmap | Anonymous Philanthropy

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PHILANTHROPIC VISION and I D E N T I T Y

CORE VALUES

Service • Loyalty • Integrity • Courage • Discipline • Responsibility • Resilience PHILANTHROPIC GOALS

1.

End veteran homelessness Direct resources to organizations and programs with credible plans to eliminate veteran homelessness to the greatest degree possible in the next 10 years.

2. Reduce veteran suicide Fund mental health programs with proven clinical efficacy, particularly for combat veterans and those living with traumatic brain injury. Track outcomes rigorously.

3. Transform the veteran transition experience From separation to deployment into civilian leadership. Veterans are assets to society, not charity cases. This giving should reflect that belief.

SPECIAL INSTRUCTIONS & RESTRICTIONS

No funding for organizations engaged in partisan political activity. Priority goes to organizations with measurable outcomes and transparent financials. Catalyst should apply a veteran-first lens to all grant decisions — if an organization’s work does not directly benefit veterans or military families, it should not receive funding under this Roadmap.

GEOGRAPHIC FOCUS

ANONYMITY PREFERENCE

National focus

Always named

This Legacy Roadmap documents the philanthropic vision of Robert H. Caldwell and serves as the governing instruction set for all charitable giving carried out in their name. Anonymous Philanthropy designed this Roadmap. Catalyst Philanthropy Fund — a 501(c)(3) public charity — receives and deploys assets according to the Roadmap, with oversight from its independent Advisory Board. The Roadmap is made enforceable when reflected in the governing documents of each relevant giving vehicle. Last updated: 2026-07-17.

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M I S S I O N S TAT E M E N T

ROBERT H. CALDWELL

To honor the sacrifice of those who served by ensuring that no veteran is left without the support needed to live with dignity, purpose, and peace.

We believe that service does not end at discharge — it evolves. Our giving reflects that belief: Sustaining those who gave everything, advancing the systems that failed them, and inspiring the next generation to serve in new ways.

This Legacy Roadmap documents the philanthropic vision of Robert H. Caldwell and serves as the governing instruction set for all charitable giving carried out in their name. Anonymous Philanthropy designed this Roadmap. Catalyst Philanthropy Fund — a 501(c)(3) public charity — receives and deploys assets according to the Roadmap, with oversight from its independent Advisory Board. The Roadmap is made enforceable when reflected in the governing documents of each relevant giving vehicle. Last updated: 2026-07-17.

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GIVING PRIORITIES

.01 - MILITARY

.02 - MENTAL HEALTH

Military Transition Veteran Suicide Prevention Veteran Employment

PTSD Drug & Alcohol Addiction Mental Health Access

“Thirty-two years of service gave me everything — and I watched the system fail the people who gave it that same service.

Veterans transition out with no roadmap. We owe them one.”

“My son James came home from Afghanistan a different person. He got help eventually — but most don’t. Veteran suicide is preventable, and it demands urgent, fully funded attention.”

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.04 - HUMAN SERVICES

.03 - HOUSING & HOMELESSNESS Veteran Housing Permanent Supportive Housing Homeless Services

“No one who wore this country’s uniform should sleep on a street. Zero veteran homelessness is an achievable goal within a decade. This foundation will pursue it.”

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.05 - EDUCATION

.06 - CRIMINAL JUSTICE REFORM

Veteran Education Scholarship Creation Job Training & Placement

Employment & Career Counseling Disability Services

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Veterans Treatment Courts Reentry Systems

“The GI Bill is a “Veterans end up in the “The civilian world promise. We need to criminal justice system doesn’t speak military. make sure every at alarming rates — The transition gap — veteran can access it, largely due to untreated from deployment to complete a credential, PTSD and TBI. Veterans employment — destroys and enter civilian life Treatment Courts work.

Roadmap documents the philanthropic vision Robert H. Caldwell and serves asThey the governing careersThis andLegacy families. with skills thatoftransfer need national scale instruction set for all charitable giving carried out in their name.

Anonymous Philanthropy designed this We can close it with the and earn respect.” and sustained funding.”

Roadmap. Catalyst Philanthropy Fund — a 501(c)(3) public charity — receives and deploys assets according to right organizations.” the Roadmap, with oversight from its independent Advisory Board. The Roadmap is made enforceable when reflected in the governing documents of each relevant giving vehicle. Last updated: 2026-07-17.

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GIVING STRUCTURE and D I S T R I B U T I O N GIVING VEHICLES

Vehicle

Approx. Value

Details

DAF

$4,500,000

Fidelity Charitable

Foundation

$100,000,000

Robert H. Caldwell Family Foundation

Estate

~$3,000,000

5% of estate

LIFESPAN

DISTRIBUTION RATE

Spend-down — exhaust all funds over time

10% of remaining fund balance per year, distributed annually. In year 10, the full remaining balance is distributed regardless of amount.

TIME HORIZON

PREFERRED ORGANIZATION TYPES

Both lifetime and estate

Direct service organizations Policy and advocacy organizations Research and data organizations

GRANT DISTRIBUTION SCHEDULE

Vehicle

Recipient / Cause

%

Amount

Frequency

Duration

Notes

Foundation

Catalyst Philanthropy Fund

70%

$7,000,000

Annually

10 years

Deploy to veteranfocused causes per this Roadmap

Foundation

Wounded Warrior Project

10%

$1,000,000

Annually

10 years

Comprehensive veteran support

Foundation

Travis Manion Foundation

8%

$800,000

Annually

10 years

Veteran leadership development

Foundation

Fisher House Foundation

7%

$700,000

Annually

10 years

Military family housing

Foundation

Iraq and Afghanistan Veterans of America

5%

$500,000

Annually

10 years

Policy advocacy

Distributions should be front-loaded in years 1–3 to organizations with the highest immediate impact. Catalyst Philanthropy Fund has discretion to accelerate distributions during a declared veterans’ crisis.

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ADAPTIVE GIVING GUIDANCE

1.

If a Named Cause is Effectively Solved If veteran homelessness is effectively eliminated during the life of this Roadmap, redirect those funds to veteran mental

2. If a Named Cause Becomes a Crisis or Epidemic Yes — Catalyst has discretion to surge funding toward any named cause in response to a declared national emergency affecting veterans. Reallocations must remain within the cause areas named in this Roadmap and be documented in the annual impact report.

3. If a Named Organization can No Longer Fulfull its Role Catalyst has full authority to pause, reduce, or redirect funding. If an organization closes or drifts from its mission, Catalyst selects a replacement in the same cause area, prioritizing similar size, approach, geographic scope, and demonstrated outcomes. If underperformance is sustained for two consecutive grant cycles, funds are redirected without delay. No named organization is irreplaceable — the cause is.

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A N O T E F O R F U T U R E G E N E R AT I O N S

“To my children, and to James in particular: I built this because I watched what happens when good intent meets no plan. Thirty-two years in uniform taught me that preparation is the deepest form of respect — for the mission, for the people you serve, and for the future you’re trying to protect.

The men and women who served alongside me — and especially those who came home changed by what they saw and did — they deserve better than what the system has given them. This is my way of continuing to serve after I no longer can.

I trust you to honor it. And I hope, someday, you’ll find a way to continue it of your own choosing.”

This Legacy Roadmap documents the philanthropic vision of Robert H. Caldwell and serves as the governing instruction set for all charitable giving carried out in their name. Anonymous Philanthropy designed this Roadmap. Catalyst Philanthropy Fund — a 501(c)(3) public charity — receives and deploys assets according to the Roadmap, with oversight from its independent Advisory Board. The Roadmap is made enforceable when reflected in the governing documents of each relevant giving vehicle. Last updated: 2026-07-17.

P R O T E C T I N G YO U R L E G A C Y

Successor Advisor Designation

SUCCESSOR ADVISOR DESIGNATION

Catalyst Philanthropy Fund

In order to secure donor intent: (1) Legacy Roadmap will be placed on file with the relevant Donor Advised Fund sponsor, who agrees to honor it as grant-making guidance. (2) Catalyst will be named as a Successor Advisor and is formally granted the legal authority to execute this Roadmap when the donor is no longer able to direct it.

LEGACY GOVERNANCE

Special Instructions & Restrictions

No funding for organizations engaged in partisan political activity. Priority goes to organizations with measurable outcomes and transparent financials. Catalyst should apply a veteran-first lens to all grant decisions — if an organization’s work does not directly benefit veterans or military families, it should not receive funding under this Roadmap.

ANNUAL IMPACT REPORT RECIPIENTS

Name

Relationship

Email / Contact

Patricia Caldwell

Spouse / Partner

pat.caldwell@caldwellfamilyfoundation.org

James R. Caldwell

Adult Child

james.caldwell@veterans-first.org

Margaret Howarth

Attorney

mhowarth@wc.com

REVIEW FREQUENCY (LIFETIME) Annually LEGAL COUNSEL Margaret Howarth, Williams & Connolly LLP, Washington DC — (202) 434-5000 - To be confirmed

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EXECUTION and A C K N O W L E D G M E N T

By signing below, the donor acknowledges that this Legacy Roadmap reflects their philanthropic vision and intent. This document should be filed with your Trust and Estate Attorneys. Your will, trust, and other legacy instruments must be aligned with this document for it to be enforceable.

Robert H. Caldwell

Date

bobcaldwell@sample.com 123 Sample Street, Madison Wisconsin, 53703 (555) 123-1234

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