Thirty-two. That’s how many years John Deasy has spent in education as a teacher, high school principal, and superintendent in four different districts across three states.

Of all these roles, his stint at the Los Angeles Unified School District may be the most memorable—and controversial. As superintendent, he led one of the largest and most highly-critiqued 1:1 device deployments in the country—one that that led to a frenzy of media reporting, and a number of columnists from L.A.-based and national publications alike asking, “Where did it all go so wrong?”

After leaving LAUSD in October 2014, Deasy joined the Broad Center as a Superintendent-in-Residence, where he’s been working to develop school district leaders from across the country. But now, he’s gearing up for the next chapter: creating an organization to address juvenile incarceration and, eventually, reduce juvenile recidivism by 50 percent.

EdSurge caught up with Deasy to chat about the up’s and down’s of superintendencies, where he made mistakes, and whether technology is adding to issues of inequity.