This project highlights relational philanthropic advising, where I served as the lead advisor alongside Kaia Sand on the Street Roots capital campaign to simplify and deepen the giving experience for Charlie and Darcie, two deeply committed, seasoned philanthropists.

Managing a massive portfolio of 60 significant community gifts, serving on multiple boards, and balancing a successful career and family made their philanthropy into a demanding, full-time job. Our goal was to take the overwhelming burden off their shoulders and bring some joy to their giving.

The process was entirely different from the sterile, high-pressure pitches most philanthropists are used to. We stripped away the corporate stiffness, meeting for a relaxed dinner at their home, sharing laughs, including Charlie teasing me about watching Love Island, and even petting their beloved goats.

But beneath the relaxed atmosphere was a strategy of deep trust. My role was to uplift Kaia, an expert ingrained in the community who writes weekly on homelessness and possesses local data to prove her impact.

She demonstrated the tangible success of the Street Roots newspaper program, where unhoused individuals buy papers for a quarter and sell them for a dollar, earning a reliable income. By bridging the gap between Darcie and Charlie and a leader already delivering consistent, visible results, we eliminated the need for them to micromanage the weeds. They could confidently trust the expertise, step back from the heavy lifting, and focus entirely on a transformative, relationship-driven investment.

If you are a seasoned philanthropist or managing a family foundation with a heavy portfolio of gifts, this project illustrates exactly what I can do for you. You shouldn't have to treat your generosity like a stressful second career. I handle the heavy lifting, vetting the organizations, cutting through the noise, and connecting you directly with trusted, best-in-class leaders who have the data and track records to prove their impact.