The bigger the check, the grander the expectations. That’s the pressure put on any venture-backed startup—and especially so for Remind, which has raised $59.5 million from investors including Kleiner Perkins and Social Capital, two of Silicon Valley’s toniest firms. Since its launch in 2011, the company’s communication app has amassed more than 20 million users—none of whom had to pay a dime. It’s relied on that explosive growth to sidestep questions about its business model. But that’s no longer the case.