Over the years, I’ve learned a lot about business—what works, what fails, and what has real staying power. But if there’s one thing I’ve come to believe even more deeply than any business lesson, it’s this: if you’re going to give, make it count.

That might sound obvious. But in the world of philanthropy, especially when it comes to helping the homeless, it’s easier said than done. Good intentions are everywhere. Real results? That’s a little harder to find. And lately, the lack of accountability in how we approach homelessness has become impossible to ignore.

We All Want to Help. But Are We Helping?

Like many people, I’ve had a long-standing desire to help the homeless. It’s one of the most visible, heartbreaking problems we face in cities across the United States—and especially in California, where I’ve spent much of my life.

Through our church and soon a small nonprofit effort called Joshua’s Collective, my family and I have supported local programs focused on feeding, clothing, and caring for people living on the streets. We’ve done it quietly for years because we believe in serving without a spotlight.

But even with that hands-on involvement, I’ve had growing concerns. Not because the need isn’t real—it is. But because we often throw money, energy, and resources into systems that don’t show us where that effort is going. And if we can’t see results, we can’t know what’s working.

$24 Billion and Still Growing

You’ve probably seen the headlines by now. California has spent over $24 billion on homelessness over the last five years. That’s not a typo. Twenty-four billion dollars. And yet homelessness hasn’t gone down; it’s actually increased nearly 20%. In many places, it’s gotten worse than that. 

A recent state audit showed that there’s no centralized tracking system to measure whether the programs funded by that money have actually helped people move off the streets. That should concern everyone—whether you’re a taxpayer, a donor, or simply a citizen who wants to see people treated with dignity.

Now, I’m not here to criticize every person working in this space. There are good people trying to make a difference. But $24 billion with no measurable results? That’s not just a missed opportunity—it’s a wake-up call.

In Business, You Track What Matters

Coming from a business background, I can’t help but compare it to how we operate in the private sector. If you invest $24 billion in a product and it doesn’t deliver, you don’t just shrug and keep going. You look at the data. You pivot. You find out what went wrong and how to fix it.

The same mindset should apply in philanthropy. Compassion without accountability leads to waste. And waste in this context isn’t just inefficient—it means people are still living outside, still suffering, still stuck. We owe it to them to do better.

When I founded ClearTV, I had to build relationships with more than 200 content providers—from NBC and CBS to the Tennis Channel—while also making sure the content we displayed actually served the viewer. We didn’t just install screens and hope for the best. We measured engagement, we reviewed what worked, and we adjusted along the way. That’s how sustainable systems are built.

Real Help Starts With Real Questions

If we want to help the homeless in a way that actually works, we need to start asking tougher questions:

• Where is the money going?
  
• How many people are getting off the street permanently?
  
• Which programs have long-term success, not just short-term visibility?
  
• How can we support solutions that are working and stop pouring money into the ones that aren’t?
  

These questions aren’t negative. They’re necessary. They allow us to identify what’s effective and amplify it. They help us protect the dignity of people we claim to care about.

Local, Faith-Driven Solutions

Some of the most impactful work I’ve seen happens at the local level, often through church-based programs. These efforts may not have big budgets or press releases, but they often make the most direct, personal impact. Volunteers know the people by name. They offer more than just a meal—they offer community.

With Joshua’s Collective, we’re working on expanding that kind of personal, hands-on support. But even in that setting, we’re starting to ask harder questions about what kind of help leads to actual transformation. Feeding someone for a night is good. Helping them find stability, a job, or permanent housing? That’s better. And we want to do more of what works.

A Call to Business Leaders

To my fellow entrepreneurs and executives: we know how to build, measure, and improve. We do it every day in our companies. What if we brought that same mindset to our giving? What if we treated donations like investments—not in profit, but in people?

That doesn’t mean becoming cold or transactional. It means being thoughtful, strategic, and committed to results. It means moving from guilt-driven giving to outcome-driven action.

Moving Forward With Purpose

Helping the homeless isn’t about being a hero. It’s about being responsible. We don’t need more programs. We need more impact. We don’t need more spending. We need more accountability.

If we really care about those sleeping in tents or under bridges, we have to stop settling for good intentions alone. We have to measure, learn, and act with purpose.

We owe it to the people we’re trying to help—and to every person who’s ever donated, volunteered, or simply hoped for a solution that truly works.