“Bills are like houseplants,” said Jason Hishmeh, an entrepreneur and tech investor. “Ignore them too long, and they’ll cause a mess. Nurture them on schedule, and they’ll thrive without much fuss.” ...

Brian Seymour II, CEO and founder of Prosperitage Wealth, said he advises clients to start with the largest bills, like the mortgage, and build a strategy around it to ease the cash crunch. “Once we ...