Before becoming a venture investor, Max Brickman ran his own real estate and contracting businesses, buying his first rental property at 14 and eventually growing a 450-unit property portfolio and a $5 million contracting company, and he also patented an academic software product he invented while at Indiana University. At Heartland, he built his investor base mainly from private, often multi-generational business owners rather than typical institutional investors, and turned that group into a network that gets startups real customers—for example, connecting Workstream’s founder with 12 Midwestern manufacturers, which led to 11 signed contracts.