Cause Champion: Jason Roberts Transforms Essential Workforce
Jason Roberts admitted he was embarrassed when he realized that his kids’ constant movie days at school were attached to a much bigger problem in his industry. Teachers were leaving at unprecedented rates because they couldn’t afford to live in the communities where they teach.
As a housing development entrepreneur, Jason started talking to school and city officials and their staff about what could be done to retain essential employees. He knew he could not fix their income problem— often tied to taxes and politics— but as a developer, he could create an amazing community they can afford that offers a tangible benefit to their career.
“Why are we not building up the best real estate for the best real estate tenant?” Jason proposed to his team.
Without the infrastructure of these jobs in his community, he understood that his world would be completely different. Jason has started Upward Communities— a project that is a private, non-government venture that does not create income-based housing, but rather exclusive neighborhood communities contracted to be filled by city or school employees at attainable rates.
It is a project with great risk, thin margin for error, and a ton of relationship-building for Jason that he sees as his cause and a chance to leave a lasting change on essential workers. The first communities are located in central Texas, south Florida, and west Tennessee.
“All I know is in 20, 30 years from now, I’m still going to want a police officer to knock on my door, and a fireman to show up to put out a fire. I’m still going to want a nurse to take care of me, and I’m still going to want a teacher with a heart pulse to teach my kids,” Jason said.
Watch how Upward Communities becomes the first major developer in the country partnering with essential services to change a housing crisis in our cause champion featured video above.

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Jason Roberts: We know the real estate’s gone up, but we didn’t know it had gone up to that much. This wonderful teacher said, “I really just want to live in a single-family house. Like what I got when I took this job. I thought that was available to me.” So, from a faith perspective, this will be our legacy, what we leave to our kids and let’s really pay attention to this problem.
When you talk about Upward Communities, and what we try to do is we try to provide these essential houses for essential staff to incentivize people to seek these careers in these professions.
Keely Hennig: When you have police officers and nurses and teachers who are making what you think is a good living wage and they can’t afford housing, it’s a it’s kind of crazy. And, you know, costs and expenses have gone up so much over the last especially five years, and pay has not.
Jason Roberts: And when we realize the school district has 20% of their staff resigning every year, we realize it cost the school district $24,500 per person. The district has to pay to replace that person.
Adam Miller: The vast majority of our teachers don’t live in Lockhart. They commute. I believe it’s somewhere upward of 70% of our teachers drive in every single day. And so to have a place that you can call home that is within a close proximity of where you spend the vast majority of your week is absolutely important.
Jason Roberts: When I was interviewing the staff and interviewing the people, I went in with a completely blank slate. Like, what is going to change the way you view your life in your day? And I show them examples of physical communities of Rosemary Beach, Florida, seaside, Florida, Alyssa’s Beach. We looked at the real estate values of those communities, and the staff said, oh, that would be nice, but I could never afford to live there.
Brittany Phillips: As a single parent. That’s been a little tough. It hasn’t been easy to find affordable housing. Apartments, duplexes, it that’s… that’s been an option. But as far as getting me and my family, my kiddos into a house, that’s. Yeah, it’s been a struggle. The market is still high. It’s not for someone in my position. It’s still not affordable.
Bringing in something that is affordable for families like me. Single moms like me. That that would be great.
Jason Roberts: My essential employee has to say, wow, I get this amazing house at this amazing price and they need to have physical features that separate them and make their physical asset where they raise their kids and the family better than all the competition in order to feel like it’s a real benefit. Everybody’s got their own character or their own, different rails.
And then that rolls into the own the side of the house, which would be like in your picket fencing, which we’ll do more universal picket fencing in, in our communities. We take care of the landscaping. We take care of all the maintenance. So that way the entire street and the look of the entire place is always maintained very, very well.
Keely Hennig: But if your rent or mortgage payment goes down $500 and $800 a month, like, what does that mean to you? And for some of them, it’s like I can retire. I can take my kids on vacation.
Jason Roberts: When we did meet with them, we said, look, if you did have a nice, wonderful place to live, single family home and it was this price, would you stay being a teacher? They were like, absolutely. We love being a teacher. We’ve been second, third generation teacher. I love my job.
Mark Estrada: I would argue that there’s actually not a teacher crisis. We have a lot of teachers, just too many of them are choosing not to be teachers. They’re going into other fields and using their skill sets outside of the education system.
Jason Roberts: What we realized it was… it was all essential staff, anybody that works for the county, anybody who works for the city, anybody that works for the school district, and you have to go to town halls, like, and you have to tell people and you have to put your face on this and you have to you. The numbers are razor thin to make this affordable for these people.
You know, there’s a lot of things can go wrong. And you got to be willing to take that risk. And so, for us is faith. Like I just God’s got my back 100%. He knows I’m doing the right thing for the right reasons. My entire team is right, and we’re all in on this. This will be the one thing that I think that will make more people happy and less stressed.
And then I think through that, that’s going to open up a lot of doors spiritually. And I think there needs to be, you know, with all these things and people paying attention to things on their phone and stuff, I think we’ve lost a lot of connection with people. You know, I think you need that connection with people in order to have a very good spiritual life.
So as an investor and as a homebuilder and a developer, I can’t solve their income problem. But what can I do? Can I build them an amazing house, an amazing community, things that they would all want to live in. So that’s what Upward Communities is. Upward Communities is we’re trying to provide essential houses to keep our essential staff.
Otherwise, they’re going to leave. They are leaving. They’re going at rapid rates. They don’t see the reason other than sense of duty to do this job anymore, because it’s just kill them.
Mark Estrada: It’s more than just the benefits of having a two-minute commute. You know, it’s about being a part of the community, getting to know the people in it better than you would get if you didn’t live here.
Jason Roberts: We’ve only sent out one email to the staff, and we have 650 on like the waiting list. So, like, they haven’t even seen a countertop. They haven’t seen a front door, a fitness center, or a pool. So, what that tells you is we’re just seeing more of the demand for this product was so high.
Keely Hennig: We want them to be, you know, top tier communities that anyone would want to live in. It’s not a matter of, oh, you’re teachers. Therefore, we’re just giving you the bare minimum, like we want to have the amenities, the walking trail, hike, bike trails, pool. The good thing with Jason is everything is a possibility. As long as it’s feasible, everything’s a possibility.
Jason Roberts: From an investment standpoint, I’ve never seen anything this emotionally beneficial. Not even close. This is the Mona Lisa of businesses we’ve ever created. Like nothing has ever been this perfect or this… pure. And so, super excited about that.

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