Homelessness: billions spent, little built

September 29, 2026 · 21 min read

Rick Caruso details how Los Angeles spent billions without adding housing, Bill Murray describes bureaucracy blocking shared purpose, and Brian Simpson ties homelessness to addiction and mental illness. It points to execution and accountability, not just funding, as the problem.

12 questions on this insight. Answer in your head, then open the card.
What is the main argument of these three conversations about homelessness? Show answer

That California's cities have spent heavily without results, so the core problem is execution and accountability more than the size of the budget.

What figures does Rick Caruso give for the Los Angeles housing bond measure? Show answer

It promised 10,000 units and had produced fewer than 1,000 about a decade later, at roughly $800,000 per unit.

How do other building costs compare, according to Caruso? Show answer

Nonprofits on Skid Row build for about $300,000 a unit, and a company he cites mass-produces small units for about $60,000 to $70,000.

What are the three parts of Caruso's plan? Show answer

Cheap, fast housing on vacant city-controlled land, enforcement against open drug dealing and use, and redirecting money to organizations with a record of results.

What does Caruso say the successful providers offer? Show answer

Structure, treatment, training and hope, meeting people where they are. He credits them with around a 90% success rate.

How does red tape affect even the good providers? Show answer

Caruso says it takes one women's center about six years to build new housing on Skid Row, which is why he wants permits granted quickly.

What incentive problem does Joe Rogan describe? Show answer

People in homelessness departments are paid well whether or not the problem improves, so they have no incentive to fix it. He wants funding tied to progress.

Why does Rogan say allowing street camping is not compassionate? Show answer

He calls it a lack of empathy. Real care, in his view, means providing mental health and addiction treatment instead of leaving people on the street.

What is Bill Murray's caution about cutting the bureaucracy? Show answer

The people who can solve the problem are often inside it, so cutting blindly risks removing them.

What does Brian Simpson claim about drugs and homelessness? Show answer

That most homeless people are not primarily drug users before losing housing, and begin using afterward to cope with hopelessness, cold and constant fear.

On what points do the speakers disagree? Show answer

On whether to cut the bureaucracy or back the right people in it, whether homelessness is a political choice, and whether mental illness, drugs or the street comes first.

What caution does the article give about the numbers? Show answer

They are the speakers' own figures from conversation, and none of the sources shows how they were measured. Caruso also speaks as a political critic of the city's leaders.

This is the short form. The full insight has every expert's reasoning, their own words and the sources.