Homeless Guy Makes His First App

What was the offer on the street?

Leo Grand, a homeless man in New York City, made news in 2013 when a software developer named Patrick McConlogue approached him on the street and offered him a choice: $100 in cash, or daily coding lessons. Grand chose the coding lessons. Within several months, he had developed a functional app — Trees for Cars, which connected commuters to carpooling opportunities and calculated the environmental benefit of sharing rides.

Why did the story go viral?

The story landed in a particular cultural moment, when Silicon Valley mythology was at its height — the narrative of meritocratic opportunity, of technical skill as the universal solvent of circumstance, of the App Store as a democratic platform where anyone with the right idea and the ability to execute it could find success.

Was the story as simple as the headlines?

Grand's story was both genuine and more complicated than the headline version. He did develop the app. He did demonstrate real aptitude for coding. The story of his perseverance, and the specific skill of a single developer teaching a motivated student, was real.

The complications were also real. The app, once built, did not immediately transform his circumstances. The path from functional app to financial stability is not linear, and homelessness is typically the result of systemic failures — insufficient affordable housing, mental health and addiction services, the fraying of social safety nets — that a coding skill does not directly address, however valuable it may be.

The story attracted enormous media attention, much of which focused on the inspirational dimension while giving less attention to what happened afterward — which is to say, the difficult, non-linear, ongoing work of actually building a different life.

Grand's story was genuinely inspiring. It was also not quite the simple parable about technology and opportunity that the media appetite shaped it into being.