Rob Chesney built his career as an operator before becoming an investor, running eBay Motors as VP/GM, serving as COO of Trunk Club, and sitting on boards like TaskRabbit, Cameo, MAX, and LandscapeHub—companies built around matching buyers and sellers or simplifying how people do business. Born and raised in Toronto before earning degrees at McGill and Kellogg, he brought that hands-on operating experience to Chicago, where he's known for helping build consumer companies like Cameo and for hiring people who make a team better, not just people who fit in.