Tents on sidewalks. Families in cars. Billions spent—and somehow, it keeps getting worse.
In this episode of Stay in the Gray Podcast, Ryan unpacks the uncomfortable reality behind America’s homelessness crisis. From bloated government budgets to personal encounters with career panhandlers, it’s time to question the feel-good narratives and look at what’s actually happening.
🎙 Topics include:
– Why rent, wages, and broken systems collide
– Personal stories of generosity, scams, and hard truths
– Programs that work—and why they don’t get funded
– San Francisco vs. Denver: same budget, different results
This isn’t about left or right—it’s about what’s real.
🎯 Hit Follow if you think compassion doesn’t mean ignoring the facts.
Chapters:
00:00 - Introduction: The Growing Homelessness Crisis
00:49 - Personal Reflections and Observations
01:55 - The Impact on Families and Veterans
02:46 - A Personal Story: The Christmas Encounter
03:52 - The Complexity of Homelessness
05:25 - Economic Factors and Housing Instability
06:39 - The Role of Mental Health and Addiction
09:23 - Challenges in Addressing Homelessness
12:30 - Potential Solutions and Policy Approaches
15:27 - Conclusion: A Call to Action
00:00:00
Why are there stories that we don't want to hear about with
00:00:04
the homeless? Why are the streets filling up
00:00:07
with tents? On a single night in January
00:00:13
2024 / 770 people in this country were experiencing
00:00:18
homelessness. That's an 18% jump from 2023.
00:00:22
That's significant. That's a big jump in one year
00:00:25
that came out and this woman was taking off her headscarf,
00:00:30
putting her child into a car seat of the Cadillac Escalade.
00:00:34
She proceeded to get into the driver's seat and drive away.
00:00:37
Behind every tent is a story. Behind every person in those
00:00:42
tents is a story. Some of them aren't appealing
00:00:45
stories and some of them are just bad luck stories.
00:00:49
Everyone, hope you're all doing very well.
00:00:53
It is. I have to look.
00:00:55
April the 9th. My goodness, feel like it was
00:00:58
just New Year's. Spring is upon us and good old
00:01:01
Texas temperatures are about to be in the 80s.
00:01:04
Here we go, summertime. I'm dreading it.
00:01:06
If you cannot tell. I was thinking about what I
00:01:08
wanted to talk about as I scheduled ahead.
00:01:11
And one of the things that I think is being lost in all of
00:01:15
the chaos of this country right now is the homeless situation.
00:01:21
I think that there are more people living on sidewalks and
00:01:25
under highway overpasses that I've seen in a long time.
00:01:29
And that's just here what I hear.
00:01:31
It's obviously worse in in other places.
00:01:34
There's a lot of reasons for that.
00:01:35
And that's what I'll kind of get into a little bit.
00:01:37
But it's almost like I just want to bring awareness to it and
00:01:41
assess it in a way that maybe stops looking at people, you
00:01:45
know, it, it just kind of like, I don't want to deal with this.
00:01:49
Maybe there's something that we can do or just our leaders can
00:01:52
hear us talking about it and try and figure out something.
00:01:55
But the big thing that's getting me is families that numbers
00:01:59
increase. Veterans, That's always a touchy
00:02:01
subject with me. The fact that our veterans can't
00:02:04
be helped is beyond me. It's not a distant issue.
00:02:06
Like I mentioned, you're seeing it, LA, San Francisco, New York,
00:02:11
Chicago, I mean, all the big boy cities.
00:02:13
People are just all over the place.
00:02:16
I had a friend that went on business in San Francisco and
00:02:19
said that he had to walk over people just to get into the
00:02:21
hotel. Literally a line of people just
00:02:24
laying out syringes floating down the street, human feces
00:02:29
floating down the street. And that's, that's sad.
00:02:32
This is not what our country is supposed to be.
00:02:34
I don't want that for anybody in the world, much less the United
00:02:37
States. So here's the question.
00:02:38
How do we get there? How?
00:02:39
Why is it increasing? Well, there's no one able to fix
00:02:41
it. I know that a ton of money has
00:02:43
gone into this issue and it hasn't been fixed.
00:02:46
I'm going to give you a quick story and one of the reasons I'm
00:02:49
having difficulties with it and one of the reasons I think that
00:02:52
I have pushed it aside maybe subconsciously is it was 1
00:02:56
Christmas Day and my brother was in the car with me and we were
00:02:59
driving from our father's to our mother's to exchange presents
00:03:03
and all the things you do on Christmas.
00:03:05
And there was a homeless man standing there and his sign said
00:03:08
Merry Christmas, I'm hungry. And that was it.
00:03:12
Well, we had a huge, huge bag of leftover food, great food.
00:03:17
This wasn't scraps. This was fantastic beast, if you
00:03:20
will. And I pulled over and my brother
00:03:23
said, Hey, this is a good let's good idea.
00:03:24
Let's do this. And I just looked out the window
00:03:27
said, Hey, Merry Christmas, man. This is here's our this is a
00:03:29
fantastic meal. We want you to have it.
00:03:31
And he looked at me with disgust and he said the following.
00:03:34
I don't need your food. I make $500 a day sitting here.
00:03:39
Needless to say, it was about the reaction I'm getting you're
00:03:42
getting from me now, which is silence.
00:03:44
I didn't know what to say. My brother and I just kind of
00:03:46
looked at each other the entire ride the rest of the way, and it
00:03:49
left a mark. It left an impression.
00:03:52
Now, is this every single homeless person?
00:03:53
Absolutely not. But how do you know?
00:03:55
And that's the problem. So someone like me, now, every
00:03:58
time I see somebody that on the side of the road with a sign or
00:04:01
camped out in a sleeping bag, there's a part of me that just
00:04:04
wants to keep going and wants to avoid the situation.
00:04:07
I'm sure I'm probably not alone in that.
00:04:09
So how do we deal with that? Why are there stories that we
00:04:13
don't want to hear about with the homeless?
00:04:15
Why are the streets filling up with tents and sleeping bags
00:04:23
like never before? I've seen videos of Los Angeles,
00:04:27
just to use one example, that are literal campgrounds just
00:04:31
tents of homeless people. How do we fix it?
00:04:36
I don't know. So I'm just going to, I'm just
00:04:39
going to throw out some ideas. So we'll talk about some
00:04:41
numbers. On a single night in January
00:04:43
2024 / 770, people in this country were experiencing
00:04:48
homelessness. That's an 18% jump from 2023.
00:04:52
That's significant. That's a big jump in one year.
00:04:55
There are a lot of reasons for it.
00:04:57
New York reported more than 158 homeless individuals,
00:05:01
Los Angeles over 187. Family homelessness, which I was
00:05:06
just mentioning, is up 39%, Nearly 150 children without
00:05:11
stable shelter. And that gets me.
00:05:13
Usually I have an extra soft spot for the kids, and
00:05:16
rightfully so. These aren't just data points.
00:05:20
This is a cyber people. This is something that if we
00:05:22
care about our citizens, we need to fix it.
00:05:23
So what's driving the spike? How about rent?
00:05:26
I didn't know this. I knew it was up, but the median
00:05:28
rent has climbed to 20% since 2021.
00:05:32
I know I'm not a math, I don't have a math degree, but that's
00:05:36
four years ago. That's not a long time.
00:05:38
You add in end of COVID protections like no more rent
00:05:42
freezes, no more eviction moratoriums, all of these things
00:05:48
that COVID was delaying. Even student loans were delayed.
00:05:51
Sadly, it took a a pandemic to give some breathing room to some
00:05:54
to some people that needed it. Once that ended, reality hit and
00:05:58
people lost homes. I don't know if it was lack of
00:06:00
planning or what, but it was a huge hit when that happened.
00:06:04
So pile on inflation, which we've talked about a lot in
00:06:07
politics these days, stagnant wages, which again, that's
00:06:11
another topic, but it matters in homelessness when rent, it gets
00:06:15
to beyond where you can afford it and your wages don't increase
00:06:18
at all. And I'm not just talking about
00:06:21
minimum wage. That's again another topic.
00:06:23
I'm talking about overall wages where employees aren't getting
00:06:26
raises and bonuses and to match the rise in, in housing and
00:06:30
rent. And then job instability.
00:06:32
I mean, that's what I was, I was trying to, to really get to was
00:06:34
unemployment up and down this and that.
00:06:36
And and with COVID, a lots of job instability.
00:06:40
So the different side of the conversation is where it becomes
00:06:43
difficult in my mind. There are a lot of homeless
00:06:46
people that have fallen into what I call the nothingness,
00:06:49
which essentially is people who see panhandling and begging as a
00:06:54
daily grind, as almost a job. Like the gentleman on Christmas
00:06:58
Day. He makes enough money out here,
00:07:00
he picked up the right corner. So why do anything else?
00:07:03
Why go make minimum wage at McDonald's when you can sit here
00:07:08
and make three or four times that in a day?
00:07:11
Personally, it's hard to get into that mindset because I, I
00:07:14
want to contribute something to this world and I feel like
00:07:17
people like this are a problem. Whether or not it was the intent
00:07:21
from the beginning where they dealt a bad hand maybe.
00:07:24
But there are some who choose this lifestyle versus working
00:07:27
out of it. And those are the ones that
00:07:30
cause a lot of people to kind of turn the other way.
00:07:33
When you see somebody and you pull up to a corner at a light
00:07:37
and you see somebody with a sign, what do most people do?
00:07:39
They don't want to make eye contact.
00:07:41
I don't. And I'll admit that to you.
00:07:43
You look away. You tap your steering wheel like
00:07:45
you're singing a song. You do anything possible.
00:07:48
Some people even hold their phone up so that they act like
00:07:50
they're on call, even though most vehicles should be hands
00:07:53
free by now. How do you separate the two?
00:07:56
The people who truly need the help and are willing to do what
00:07:58
it takes and the people who have fallen into the nothingness.
00:08:01
Do those people deserve help also?
00:08:03
Well, sure. But what kind of help?
00:08:04
I'll give you another example. I debated doing this because I
00:08:07
don't want to come down on the homeless people.
00:08:10
But there was a time when I was filling up her gas and I look
00:08:12
over and there's a, a woman who had a, a scarf around her head
00:08:17
and she had her, what I assume was her daughter with her.
00:08:20
And of course that tugs at people's heartstrings.
00:08:22
That's the intent. Sometimes it's a dog that they
00:08:25
have, sometimes it's tend to sell flowers, which at least are
00:08:29
doing something, but they're trying to get the sympathy.
00:08:31
But when you carry your daughter and you use her, that's already
00:08:34
a red flag to me. And it's, and it's upsetting
00:08:37
because I want to help the child more than I do the the adult.
00:08:41
And whether that's right or wrong, we can debate that all
00:08:44
you want. But I turned around and I went
00:08:45
inside and I picked up a bottle of wine or something.
00:08:48
I was in my not expensive bottle.
00:08:50
It was a gas station wine, but it was good.
00:08:51
And I came out and this woman was taking off her headscarf,
00:08:56
putting her child into a car seat of the Cadillac Escalade.
00:09:01
She proceeded to get into the driver's seat and drive away.
00:09:03
Now, I don't know exactly why she was getting into the
00:09:06
Cadillac Escalade, but there are only so many choices and so many
00:09:10
reasons, and none of them add up to her needing to beg for money
00:09:14
on the street. There was not another person in
00:09:16
the car. I promise, Again, it makes me
00:09:19
go, who are these people and who can I trust and who can't I
00:09:22
trust? That's a problem.
00:09:23
So it's not just about housing. It's often labeled a housing
00:09:27
issue. I get that, and housing is part
00:09:29
of it, but there's a bigger picture.
00:09:31
Again, like I said, you've got mental illness, you have
00:09:33
addiction, you have domestic violence issues that put
00:09:36
somebody on the street. You have natural disasters.
00:09:39
How about Hawaii a couple years back?
00:09:41
People are homeless because of it.
00:09:43
How about the wildfires in California, the the hurricane in
00:09:50
North Carolina and Georgia? People are homeless.
00:09:53
Then you get into leadership and why this can't be solved, which
00:09:56
is part of it. The visible heartbreak for me in
00:09:59
that regard are the young people.
00:10:03
I don't mean children. I mean, 20 year olds, early 20s,
00:10:07
maybe late teens, college age, people who are in the streets
00:10:11
begging. And that happened to me a lot in
00:10:13
the state of Maine when I lived there.
00:10:15
There was an opioid issue. You have fentanyl issues in this
00:10:19
country and a lot of hard drugs that are more addictive than
00:10:23
anything in the world and they cause problems.
00:10:26
I was warned when I moved there by everybody that I knew.
00:10:29
Do not give any money to the people on the roads because they
00:10:33
are looking to buy drugs. I have been known to want to
00:10:39
help, have been known to want to give at least a little bit, toss
00:10:43
some of fiber, something, try to give food.
00:10:45
That didn't work out. And the idea that somebody
00:10:48
that's 20 years old could be in this situation where they're
00:10:51
spending their day begging for money for drugs is so sad.
00:10:55
When I think about that, it makes me happy to do a show to
00:10:59
raise awareness for the issue, to bring up all of these very,
00:11:02
very difficult stories and scenarios that 'cause people
00:11:06
like me and likely you to kind of put this aside, Hey, we can
00:11:10
bitch about Gaza conflict. We can complain about Ukraine.
00:11:14
We can talk about our president. Whether you like him or you hate
00:11:17
him, that's easy to talk about because in reality, it doesn't
00:11:20
affect us. Day by day.
00:11:21
We have ignored this issue, in my opinion.
00:11:24
Overall, there are people that work for this.
00:11:27
There are nonprofits, there are all sorts of organizations, but
00:11:29
in the big scheme, it's few and far between.
00:11:31
And then of course, migration. This is an issue where people
00:11:38
are going to finally probably turn on me.
00:11:40
Some of you won't and some of you will.
00:11:42
When you have illegal immigration and people seeking
00:11:45
asylum and legal immigration to a point, you have the shelters
00:11:50
filling up fast, the resources are up, then the food,
00:11:53
everything that's available is being distributed to these
00:11:56
people and not our own homeless citizens, our veterans, our
00:12:00
children. So when they're included in that
00:12:02
equation, then things get even more chaotic.
00:12:06
And Chicago is a great example of that.
00:12:08
I lived there for a couple of years and I have friends there
00:12:09
that continue to tell me that the steps in front of the
00:12:13
Capitol building are illegal immigrants and they're waiting
00:12:16
for shelter and they're waiting for this and they're waiting for
00:12:18
food. And again, those resources could
00:12:21
be going to our own homeless. Not telling us.
00:12:23
I'm not saying we should. Who cares about all the other
00:12:27
people. I'm just saying This is why
00:12:28
there's a problem. So here we go.
00:12:30
How about some numbers, some more numbers.
00:12:33
San Francisco dropped $846 into homeless
00:12:37
services. The result was actually a 7%
00:12:41
increase in homelessness. It didn't do a damn thing.
00:12:46
What is that money being used for?
00:12:49
That's a lot of money. Insert sending that amount to
00:12:52
Ukraine joke here. That's a lot of money.
00:12:55
What did they do with that money?
00:12:57
And maybe that needs to happen. Maybe there needs to be some
00:12:59
sort of investigation as to how these homeless services are
00:13:03
utilizing that. Meanwhile, Denver tested a basic
00:13:05
income pilot. They directly gave cash to
00:13:09
unhoused residents. A year later, 45% had secure
00:13:12
housing. So is there a little economic
00:13:14
boom there with homeless people that says at least it gets them
00:13:16
in the home and it maybe inspires them to go further?
00:13:19
New York launched a $650 million plan to support mentally ill
00:13:22
homeless residents. The plan got a lot of attention,
00:13:25
but it also got backlash because of privacy issues and
00:13:28
enforcement questions on how it was being handled.
00:13:31
But those types of policies and all that kind of look good on
00:13:34
paper. People talk about them, which
00:13:36
ones reach people? San Francisco cleared
00:13:38
encampments, but a lot of people argue that it just pushed people
00:13:42
into darker alleyways with no real support.
00:13:45
Houston tried something a little different.
00:13:46
They coordinated housing with healthcare and case management,
00:13:50
actual follow up. They seem to work.
00:13:52
So maybe we should look at that and try to mirror it.
00:13:54
And again, so the lesson becomes simple, it's not just about how
00:13:58
much you're spending to this, it's how smart we're spending to
00:14:01
try and help experts. I don't know who those experts
00:14:04
are, but experts do believe there are solutions.
00:14:07
In my research, that's all I saw.
00:14:09
We can do this, we can do this, we can do this.
00:14:11
I didn't see enough how we can do this to match that, but they
00:14:15
believe it's there. Build more affordable housing.
00:14:18
Well, that's number one in my opinion.
00:14:19
Rental support number 2. Obviously somehow we approach
00:14:24
the drug issue in our young people and old people, mental
00:14:28
health. That's an issue with so many
00:14:30
things, with the senseless crime and the senseless deaths in this
00:14:35
country. There's so many of them that
00:14:37
could be prevented with mental health care.
00:14:39
And I'm not a professional at that.
00:14:41
I don't know how to do it but there are people that do and I
00:14:45
need to light a fire under that ass I suppose.
00:14:48
Invest in wrap around services. These are things like the mental
00:14:51
health and job training, long term case management with city
00:14:54
workers and people that do go and get educated for this that
00:14:58
want to help. That's all there.
00:14:59
We need to pump it up. Hopefully this isn't just a a
00:15:02
pipe dream of mine. I mean hopefully it's something
00:15:04
that we can get accomplished. Solutions mean nothing though if
00:15:09
we don't have the political will and the public support to do
00:15:15
this. And it's not just tossing 840
00:15:17
something, $1 at the issue and then backing away from
00:15:21
and going, well, we try. There's got to be a follow up
00:15:24
and there's got to be some sort of conclusion to it.
00:15:27
Like I said, it's very difficult, but until we stop
00:15:30
seeing it as a nuisance and start seeing them as neighbors
00:15:34
who need help, I don't think anything is going to change.
00:15:37
And again, I can only do so much.
00:15:38
This has opened my eyes a little bit to look into something,
00:15:41
anything that we can do, but if we get more and more than maybe
00:15:44
we can help to close this out. This is a quick segment.
00:15:46
I just want to bring awareness and say let's not forget about
00:15:49
this. Behind every tent is a story.
00:15:52
Behind every person in those tents is a story.
00:15:56
Some of them aren't appealing stories and some of them are
00:16:00
just bad luck stories and some of them are stories of bad
00:16:03
choices, bad decisions. But everybody deserves another
00:16:06
opportunity. And that's how we why we need to
00:16:09
help in behind though a lot of the stories, the system has
00:16:11
failed, the leadership has failed and that's what we need
00:16:13
to fix. And some of it never showed.
00:16:16
Some of it, like I said, you know, everybody wants to talk
00:16:18
about doing it, but they don't. Let's ask questions, let's
00:16:20
demand answers. All the things I always say
00:16:23
thanks for staying Gray with me on this.
00:16:26
This is a topic that I think is easy to stay in the middle and
00:16:29
say let's talk. I cannot imagine getting
00:16:31
backlash about this topic, which will be refreshing.
00:16:35
It'll be a nice breather and I don't have some people yelling
00:16:38
because they think they know more.
00:16:39
This is something we should all get behind and there shouldn't
00:16:42
be some sort of divide on this issue.
00:16:44
I hope it made you think a little bit and made you feel.
00:16:47
And if you did, or you know anybody going through these
00:16:51
issues, tag us like us, pass the word along and have people
00:16:56
listen. Like I said, it's a quick little
00:16:57
snippet here with some numbers to back it up on the problem.
00:17:01
It's something to think about. I'll be here for that, so let me
00:17:04
know. Keep asking hard questions, stay
00:17:07
in the grey and see you next time for the next topic.
00:17:11
Love you guys.