Matthew Entringer didn't grow up around homelessness. Then one bitter December in 2021, three or four people were bundled up in the lobby of his downtown Kansas City apartment just trying to stay out of the cold, and he couldn't unsee it. He started carrying care kits in his backpack, fell in with a Saturday outreach at Scraps KC, and by 2023 he'd filed the 501c3 paperwork for Street Support KC. The conversation starts there and ends up on dopamine, shame, and how a small business can use AI without losing the human part.
What You'll Hear
- Why homelessness in Kansas City is up roughly 193 percent in a few years and why housing alone won't fix it
- The December 2021 night in a downtown library district lobby that pushed Matthew to start carrying care kits
- How a Saturday outreach at Scraps KC handed off a decade of work and became Street Support KC in 2023
- Why an estimated 80 to 90 percent of Kansas City's homeless population is male and what that means for shelters
- The dopamine trap, why methamphetamine is so hard to kick, and how shame reinforces any addiction
- Why Matthew sees AI as a reset that lets a small business owner hire the equivalent of two or three staff for twenty dollars a month
- Sam's story of using ChatGPT as a neuroscience consultant to redesign a business card
- Why consolidation in tech, airlines, and telecom worries Matthew more than Skynet
- How a random sports editor role at Creighton pulled him out of pre-pharmacy and into a marketing career at KCP and L, Sprint, and UMB
Street Support KC and why homelessness is a nuanced Kansas City problem
Matthew started Street Support KC in 2023 and hit the two year 501c3 mark in May. The model is simple on purpose. Volunteers meet outside the downtown library on the first Saturday of every month from 9 to 10:30 and hand out blankets, sleeping bags, food, clothing, and hygiene supplies. This year the organization is on pace for about 40,000 dollars in donations.
Sam asks the blunt question. Can homelessness actually be solved, or is it an evil we just carry. Matthew pushes back on the on or off framing. He compares it to a sink faucet running at full pressure. The goal isn't to shut it off. The goal is to get it down to a trickle. By his numbers Kansas City has roughly 2,000 people experiencing homelessness and the count is up around 193 percent in the last few years.
He's clear that affordable housing alone won't close the gap. Even if every person on the street got a unit today, the underlying conditions, addiction, substance abuse, mental health, would put many of them back outside within months. He's met people working 40 hour weeks who sleep in a park or a car between shifts. The problem sits at the intersection of housing policy, mental health care, addiction treatment, and entry level job creation, and it needs cross collaboration between nonprofits, businesses, and government to move.
The lobby in December 2021 that started it all
Matthew didn't come to this work from lived experience. He grew up in South Dakota, where he didn't see much visible homelessness, and only really started noticing it after he moved to Kansas City. Living in a high rise in the library district, he started seeing more people sleeping rough on his walks to work.
One stretch in December 2021 hit him. A bitter cold night. Three or four people bundled in his lobby just trying to stay warm. He told Sam it simply felt bad to know he could help, even in a small way, and not do anything. So he started small. He put together care kits, stuffed them in his backpack, and handed them out when he crossed paths with someone who needed one.
A few weeks in he stumbled across a Saturday outreach run by Scraps KC, the creative reuse nonprofit. Their Saturday event had been going for about a decade. He asked if he could help, started bringing his own socks and drawstring bags to supplement their supplies, and a year and a half later told them he wanted to spin up something of his own. Their answer was pure serendipity. Scraps was growing fast and no longer had bandwidth for the Saturday work. They offered to help him stand up the new organization. What keeps him going now isn't the logistics. It's that Street Support runs monthly, so volunteers see the same faces over and over. He knows guests by name. His parents ask about them.
The dopamine trap, addiction, and the role of shame
The middle of the conversation moves from housing to the wiring underneath a lot of homelessness. Matthew frames addiction as a design problem more than a character problem. Methamphetamine hits hard and fast and is engineered to hijack brain chemistry in ways the brain isn't built to resist. The point lands whether you measure it in dopamine or anything else.
Matthew points out that the drug does not have to be illegal. Plenty of people who now battle meth started on a legitimate oxycodone prescription after back surgery, then lost access when the doctor stopped writing. PTA presidents. Postal workers. The audience for this is not other people. Shame keeps it invisible. People don't want to tell a friend that they're using, or that they're two paychecks from sleeping in a car, so they don't ask for help until the problem is much bigger.
The same pattern shows up with sugar, with alcohol, with gambling, with social media. Matthew points out that Instagram and Facebook are engineered to deliver the same dopamine drip, just at legal scale. The exit, in his view, has less to do with willpower than with having people close enough that you can tell them the truth. Being honest with yourself first is the step that makes being honest with anyone else possible.
Happiness is a temporary state, fulfillment is the long game
That line about shame leads into a short but sharp detour on the phrase "pursuit of happiness." Sam has heard it criticized and he's starting to agree with the critics. If happiness is just pleasure, the pursuit of happiness is the dopamine trap with nicer branding. Matthew reframes it in a way he's clearly sat with. Happiness is a temporary emotion. It spikes and falls. Fulfillment and contentment are the long term states worth building toward.
He goes further. The amazing moments in his life only register as amazing because they're juxtaposed against low ones. A life of constant happiness isn't actually the goal, and he's not sure it would be good for anyone. The practical takeaway ties directly back to the addiction conversation. You can't chase a permanent high. You can build a life where you feel fulfilled, and the way you build that life is by clearing the shame and isolation that block honest relationships. Remove the roadblocks, then pursue the happiness if you want. But the foundation is people you can tell the truth to.
From pre-pharmacy to marketing VP, the accidental career path
Sam rewinds the clock and asks the usual origin question. Matthew laughs his way into the answer. He started Creighton as a pre-pharmacy student. His mom was a nurse, he'd shadowed a pharmacist in high school, and it seemed like a reasonable paying medical adjacent job. Then as a freshman he signed up for the school newspaper as an extracurricular. No other guys had come out that year, so they made him sports editor on day one. That single random decision moved him from pharmacy to a journalism major with PR and graphic design concentrations, and launched a run of marketing sports columns that won him a few writing awards.
After graduation he took a corporate communications role at KCP and L covering energy efficiency, the electric vehicle program, and yes, the DemandGen thermostat program. He confirmed for Sam on the record that enrolling your Nest in the utility's program does give them the ability to adjust it during peak demand. From KCP and L he went to Sprint retail marketing, got burned out, moved back to South Dakota for an ad agency role, realized within a year or two that Kansas City was home, and came back. He's been in Kansas City for over six years and is currently a VP of digital media at UMB.
The through line he names is media buying and strategy. How you allocate a million dollar media budget across traditional and digital, how billboards and print and search and social fit together, and how that same thinking applies to running a nonprofit on a much smaller budget. He runs Street Support's advertising the same way he'd run a bank campaign, just with far fewer zeros.
AI as a reset for small businesses, and the consolidation problem that scares him more than Skynet
The last stretch is the part Sam clearly enjoyed most. Matthew's view on AI is pragmatic. For a small business owner or a nonprofit director, a twenty dollar a month ChatGPT subscription is the equivalent of two or three employees if you learn to prompt it. He uses it for social posts, to critique emails before he sends them, and to model run rates from screenshots of Street Support's finances. His public financials are in the 990 anyway, so he leans in on data. He's not uploading passwords or bank credentials, but he's past the fear that giving it context is giving it too much.
Sam shares his own story. After watching a neuroscience marketing expert talk about the weight and feel of a business card, he asked ChatGPT to play the role of that expert and walk him through a redesign. The bullets got reordered, an underline here, a shield emoji there to anchor trust on a cybersecurity bullet, a heart to anchor emotion on the money back guarantee line. When his wife, not the over the top type, looked at the finished card and said she liked it, he knew the exercise had worked. He essentially hired a brand expert and a designer without leaving his office chair.
Matthew's caution isn't about AI taking over. It's about consolidation. We've gone from many airlines to effectively four, from many wireless carriers to three, and tech is the worst offender. Salesforce and Microsoft explicitly sell the idea that you should buy their entire stack. When one of those providers has a bad day, the CrowdStrike outage being the obvious example, everything downstream breaks at the same time. His hope is that the existence of ChatGPT, Anthropic, Perplexity, DeepSeek, and others keeps AI from collapsing into a single chokepoint the way other categories have.
Sam closes the loop back to small business. The companies that go all in on AI call centers and cut the humans usually end up with a story eight weeks later about bringing everyone back. AI is table stakes now, but the differentiator is still a real person who answers the phone, knows your name, and can solve your problem. As Matthew puts it, if you want to go fast, go alone. If you want to go far, go together.
About Matthew Entringer
Matthew Entringer is the founder and Executive Director of Street Support KC, an all volunteer 501c3 that runs monthly outreach events for people experiencing homelessness in Kansas City. He started the organization in 2023 after spinning off a decade old Saturday outreach from Scraps KC. In his day job he is a VP of digital media at UMB, with prior marketing and PR roles at KCP and L and Sprint. Street Support KC