This project highlights how I partner with philanthropists to move beyond standard giving and discover their true capacity for community impact. Working directly with Street Roots Executive Director Kaia Sand, I stepped in as the lead advisor to design a deeply personalized giving journey for Bob Scanlan, a prominent commercial real estate developer in Portland.

The breakthrough came when, with compassion and care, we examined the unwritten rule of elite real estate circles: Bob had a literal formula showing that if he gave "too much," his peers would consider him an idiot. For six months, we tried to loop in an even bigger developer who ultimately refused to give. But instead of backing down, that rejection sparked something in Bob. He looked at the peer pressure, said, "Damn it, I'm in!" and committed $50,000 on the spot, plus a stock transfer depending on how the market went.

By guiding him through the physical buildings to see the programs in action, and having a series of conversations to challenge his traditional thinking, I helped him find something deep within himself: the strength to step up for his community despite what his peers may think of him. (Which ultimately he got positive public recognition too.)

If you are a philanthropist or family foundation looking to maximize your giving, this is exactly what I do for you. I help you navigate the social friction of wealth, cut through peer skepticism, and conduct the deep due diligence needed to find best-in-class organizations.