The WBI founder has spent four decades turning a concern about investment losses into portfolios, books, and software. His biggest launch tells a quieter story about how an advisor builds something that lasts.

His first online advice business taught him how much people value a human conversation. At Dynamic Planner, Ben Goss has spent more than two decades building the technology that makes room for it.

A Budapest restaurant tip on a business card offers a clue to Michael Simon’s career. The LogMeIn co-founder keeps finding new uses for old partnerships, from online games to remote access and wealth management.