Bob Hall, President of Green Gables Partners, evaluated whether to angel invest into an up-and-coming ski brand. As the son-in-law of the founder of Vera Bradley and having retired from a lengthy career on Wall Street, Hall was well-versed in both direct investing and the consumer goods industry alike. He also loved learning about new entrepreneurs pushing the boundaries of their industry-and taking a hands-on approach to his investments. With his lifelong love for skiing, he found himself drawn to emerging ski-preneur, Curt Nichols, and his ski goggle brand Glade Optics. Bob weighed Nichols' proposal for a direct investment deal and the terms. How should he evaluate the proposal, his increasing concentrated risk in ski apparel, and whether he could invest for both financial returns and the future of an industry he loved?