What’s the Worst Thing That Ever Happened to You

Brett Maloley, founder of Ladder, usually wears a pin that marks the date of Oct. 31, 2014. Halloween. He remembers that day because that was the day he watched his employees’ children come into the office in their holiday costumes and weighed an incredibly difficult choice: Would he pay his employees or his landlord?

The rent was due and so was payroll, and Maloley wasn’t sure he could afford to pay both.