There’s this common saying you hear in academia: those who can’t do, teach. But that axiom certainly doesn’t apply to Jeremy Caplan. Not only did he have a decade of reporting experience before he started teaching entrepreneurial journalism at the City University of New York, but in 2020 he launched his own entrepreneurial media outlet: Wonder Tools.

Wonder Tools is a free weekly newsletter that highlights the most useful websites and apps to make your life and career easier. Since launching on Substack, it’s grown to over 23,000 subscribers and it’s generated a million visits in the last year.

In my interview with Jeremy, we talked about his journalism career, why he went into teaching, and what compelled him to launch his own media outlet.