The American Dream Is Broken. This $50M Bet Could Help Rebuild It

Denver: Jeff, your Stay Gold, America blog tells how you grew up poor in West Virginia, coding on a TI-99/4A, whatever that is, to chase a better life. How did those early struggles spark your drive to give families hope through your $50 million cash payment program?

Jeff:  I was always kind of forced to be the adult in the family, luckily at a later age than many kids are. And my parents, they really loved me, which is the greatest gift. They loved me so much, but they did not have their lives together. So someone had to do it. And it turned out to be me.

And they helped, but like I think that’s where a lot of this comes from… is this desire to continue to build family and relationships and connect with the wider world. I’m very, very mission-driven. I want all of us to succeed, not just some of us, not just the chosen few, not just the lucky, but everyone.

Denver: Yeah.

Jeff: That’s what I want.

Denver: Very much at the heart of everything you do.

Jeff: It’s very difficult to let go of.

Denver: Yeah.

Jeff: I even get complaints– Am I putting the family ahead of everyone else in the world? And I’m like, it’s close, it’s close, but the family will come first for sure. I promise.

“It’s like… we have everything we need; how do we make sure everybody has what they need? Because that’s the basic thing:  Do you have a comfortable place to live? Do you have enough to eat? Do you have healthcare? And if you have the basics, you’re in a good place in life, and everybody should have that opportunity.”

Denver: Well, a lot of what Jeff is talking about was forged in the hills of West Virginia, and your story continues together across the country now in Alameda, California. Betsy, with your remarkable background in biology, you guys are now raising three kids there, and you’re really the heartbeat of this mission, I think. How have your children sparked your passion for guaranteed minimum income, GMI pilots in rural counties across the country?

Betsy: I think it’s just that raising kids obviously has many challenges, and one is: How do you raise your kids to… obviously we’re very comfortable and have been since they were born, and they would have questions like: Are we rich?

And thinking about how to answer those questions, it’s like, “Well, we have everything we need!” And that’s how I’ve always phrased it to them. And that, I think, kind of extends out into the GMI stuff. It’s like… we have everything we need; how do we make sure everybody has what they need? Because that’s the basic thing: Do you have a comfortable place to live? Do you have enough to eat? Do you have healthcare? And if you have the basics, you’re in a good place in life, and everybody should have that opportunity.

Denver: And that’s a wonderful way to explain it, Betsy. I think anytime you can put things in context for children, it’s that comparative which helps them understand.

Betsy: Right.

Denver: Jeff, for listeners who may not be familiar, can you walk us through what a guaranteed minimum income actually is, how it works in practice? What makes it distinct from other forms of economic support?

Jeff: Well, I want to point out that part of my role here is to lift up other organizations and other people, and we’re working with GiveDirectly. And GiveDirectly has the most experience in the United States doing GMI or UBI studies. They’re kind of synonyms– universal basic income and guaranteed minimum income. However, we feel that “guaranteed minimum income” just explains it a little better.

Denver: Yeah.

Jeff: It’s a guarantee, which there’s nothing more American than a guarantee. Minimum… meaning it’s not extravagances, this is just the fundamentals, and then income. And unless you’re opposed to people getting money for any reason, then that’s a whole other discussion, but that’s how we arrived at the name and the general concept.

Denver: And how does it work? I mean, how do you go into a community and select people and the money that they get? And what are the expectations, if any?

Jeff: There’s a couple criteria just to keep it, a couple reasons. I tied it to my mother and father. The counties they’re from– Mercer County, West Virginia and Beaufort County, North Carolina are still in poverty.

Denver: Yeah.

Jeff: If you sort all the counties in those states by poverty level, they’re right in the middle. It’s eerie. West Virginia has more poverty in general, but that was a good place to start.

“The GMI studies will continue until morale and/or the economy approves. That’s the plan.”

Denver: Okay. So let me get back to you here, Jeff. So you’re building something which is grounded in dignity and choice, and that ethos is not new for you. It sounds a lot like Stack Overflow, which was sold for $1.8 billion, which was like a free classroom for coders worldwide. How did that open door spirit guide your cash payment program to create fair opportunities in rural communities?

Jeff: There were a couple things, and I wanted to mention that the episode you did with the Khan Academy, Sal, was amazing. And he is at the base of what we’re doing, which is really learning at a more specialized level with Stack Overflow.

And it was all about peer-to-peer education. What can we learn from each other? And the process of teaching, become better at it ourselves, and to incentivize that without making it exploitative. And everything on it is creative commons, meaning when you participate, it’s available to the world. Everyone can benefit from the time that you contributed here.

And it works a bit like Wikipedia. You can edit things, vote things up. So it’s a bit more of a living document. It’s what I would describe as the encyclopedia for programmers essentially. And one of the interesting things related to that is I kept seeing there was so much traffic from outside the United States.

Denver: Yeah.

Jeff: There was so much untapped potential in the world. And I think there’s a lot of untapped potential in rural areas in the United States that are being overlooked. And they’re not very happy about it either. Let’s just put it that way. But why shouldn’t all of America be prosperous and beautiful? What’s the problem?

Denver: Yeah, absolutely. Basic question. Nobody’s come up with the answer to it. You’ve got to do something about it.

Jeff: We have the answer.

Denver: Yeah.

Jeff: GMI studies.

Denver: You’re doing it.

Jeff: The GMI studies will continue until morale and/or the economy improves. That’s the plan.

Denver: Betsy, early in 2025, you and Jeff made eight $1 million donations to groups like The Trevor Project, the Children’s Hunger Fund, and it was inspired maybe in part by MacKenzie Scott’s bold giving. In those eight contributions, was there a common thread, maybe a shared mission or impact that tied those choices together?

Betsy: It was mostly… initially I think it started with four and sort of expanded as, you know, I was like, well, what about this? What about this? But…

Jeff: It’s fun to be generous, as it turns out. It’s very satisfying. More rich people should try this.

Betsy: Yeah. It is, it is. And it, I think was just so, you know, trying to be diverse in terms of the types of groups we were trying to target and maybe some that were underserved and some that were more prominent, trying to have a good mix in there of ones that people knew very well, like say Planned Parenthood, and others that maybe people didn’t know as well, like Rubicon and others like that. So just trying to have a good diverse mix of nonprofit groups.

Jeff: And both of my parents, their fathers served in the military. I have immense respect for the American military. I think maybe it could be doing more here with us, with all those skills, but it is considerable. So, yeah, a deep respect for all those. None of those things was chosen out of trying to look good. It was like: this is a diverse set of bets that we think matter, that will really help these people.

Denver: Yeah. And picking up on Team Rubicon, Betsy, that one jumped out to me because it really shows a big faith that both of you have in veterans. How will veterans in counties like Beaufort, North Carolina lead your cash payment pilot to transform lives there?

Betsy: Well, we really do hope to involve the military. If you go to any community, there’s always veterans wherever you go. And so these are people who have lived a life of service and continue to, even when they’re not in the military anymore. And so, let’s harness that power.

These people know how to organize, to bring things together. They’re in their communities already and so people know them and trust them. And so, is that a way to help get communities on board with what we’re trying to do?

One thing we worry about is coming into these communities as outsiders. Are they going to be welcoming of what we’re trying to do? And we’re hoping that veterans can help sort of bridge that gap for people that already know them within the community.

Denver: Yeah, that really makes a lot of sense. Betsy, how are you thinking about success? How you are going to measure success?  A part of it will probably be through the stories of families, maybe OpenResearch data. But how do you know… or how do you look at the impact that you’ve been able to make in these communities over time?

Betsy: I mean, the scientist in me likes to see the data. The OpenResearch data from their studies is just amazing. The level of detail that they were able to uncover there, looking at people’s mental health, and all the different things that they were using their money for. And those kinds of metrics to me, I think, are important.

But also, there’s the things that are harder to measure. Are you bringing a sense of hope to a community that maybe feels like it’s been left behind? And that, to me, as I said, hard to measure, but if we can go to these communities and see those kinds of effects and those kinds of stories, that to me would be really satisfying.

Denver: Yeah, I agree with you. I like the hard data too, but I don’t think we do nearly enough in measuring the soft data and how people feel about their lives, and that’s equally important.

Betsy: Yeah.

Denver: Jeff, you’ve connected cash payments to Thomas Paine’s 1797 pension idea, and Martin Luther King’s 1967 call for aid. What makes 2025 the perfect time to revive this mission?

Jeff: Well, per the economics data, that’s when we entered the Second Gilded Age in the United States, as I was writing the blog post. Because believe me, I was looking at it. Writing that blog post was excruciating. It took me three months.

Denver: Yeah.

Jeff: And during that time, I was thinking, yeah, this is the problem. There’s just too much wealth concentration. And what do you even do? What’s the purpose of that much wealth? What do you do with it? I mean, go to Mars, really? I mean, it becomes pointless. It’s like, when is enough? It raises all these questions.

And then having wealth dumped on me, and then as much as we have, believe me, we’re just a blip. Like we’re nothing relative to where everyone else is, which is why we can get away with some of the nonsense that we’re doing now, by the way, because they’re not paying attention to us, but they will.

And this vast amount of wealth concentration, I talked to Cecilia Conrad. I got introduced by Jeff Ubois, who’s a great person, MacArthur Lever for Change is the program in particular. It’s very innovative. It was that…

Denver: It was great.

Jeff: Yeah, great. And was introduced to her, an economist, and told her about this. And she’s just nodding. Yeah, yep, yep. That’s pretty much, yeah, just too much wealth in the hands of too few people. That’s the problem.

So how do we fix that? Well, I mean, we could tax them. I mean, if they’ll let us, I guess.

Denver: Yep.

Jeff: And then the other way is to let some chop off some of the massive wealth and just let people have money to live their lives. And again, a guaranteed minimum, not anything special. No Lamborghinis, no jet skis, just the freedom to pursue happiness, maybe even the American Dream. That would be nice.

Denver: Yeah. Give me your vision, or your rundown, or your observations about the American Dream in 2025?

Jeff: What do you think, Betsy?

Betsy: I think it feels like people have lost, like I said, that sense of hope that I can, if I’m in a situation, economically, that I can change that. I get the sense that a lot of people feel like they’re very stuck where they are. And for me growing up, my father was the first in his family to go to college, and then he got a PhD and moved across the country, and that was our family’s origin story.

And he had this dream since he was a kid, and he went and he did it against a lot of odds. And to me, that was always ingrained in us. And so to the idea that people don’t feel like they can change their station in life is just sad. People should be able… we’re supposed to be the land of opportunity. Where are those opportunities?

I think a lot of them have gone away, and we’ve tried to make things accessible, like having more people go to college and things. But then you have people that are weighed down by all this debt from college, but they can’t get a job to balance that. And I don’t know, it just feels like people have really lost hope that they can build a life for themselves and have those dreams and be able to attain them.

Denver: Yeah, I hear exactly what you’re saying. When I was young, I would look at data about social mobility and the US was always right near the top, if not at the top, in the top 10. And now, today you just keep on scrolling down and down and down, and it just seems like your station in life is where you started. And it’s very difficult to move from that, and that is a tragedy.

Betsy: Yeah.

Denver: What are the thoughts you have on the American Dream, Jeff?

Jeff: Well, similarly to Betsy, thinking about it. My father, John, was the only person in his family to go to college at all also, so that’s notable. And thinking about the American Dream and where we want to go with it and what we want to do is just: the world is more interesting with other people succeeding.

I want to help other people succeed. That’s interesting because: Do you really want to live in a world full of angry, pissed off people because they have to work five jobs and can barely even have time to think about voting or anything? Or just have a happier world to interact with by sharing? And half seemed fair for what we were doing. Although by the way, I got in trouble because I did more than half and I’m sorry.

I am trying to keep it within limits. But to me, that’s one of the best ways to spend money. I mean, once you have enough, whatever you classify that as. Have trips, go on trips. Those are amazing. Spend time with your family. Do things like that. Do the things you love. I’m not going to take that away from you. Why would I? But when is enough?

And then it’s just more interesting for other people to succeed. It’s so… their happiness, it’s even better than my own.

Denver: Yeah. I don’t know if people realize that though until they’ve done it. You were even talking about the joy of giving, and I think we’ve all… you experience it, but you don’t realize it in terms of the gratification and satisfaction that you get when you do it.

And you just think it’s a finite pie, and I’m going from my piece of the pie, and we just never seem to look up from that pie to a grander vision.

Jeff: I think isolation is a big problem as you become wealthy. And it’s just sort of this trope that, well, you get a big mansion and you go hang out with all these other rich people, and it just isolates you. I mean, even accidentally. We almost bought this enormous property that would’ve been a massive mistake for us because we couldn’t have had like a normal Halloween, because the street was so long on it.

It was really nice, but luckily the offer got turned down which did us a favor. And it’s just I like to live on a normal street with normal neighbors. I mean, the house is a little fancy, yes, but not exceptionally. I just like well-made things. And we started Stack Overflow, my co-founder, Joel Spolsky— great, great, great man. Love this man. He said to me,” Jeff, if this turns into something big, what do you want?” And I said, “Joel, all I want is to own a house. That’s all I want. That’s really it.”

Denver: That’s what I need.

Jeff: And then you have vacation now and then, although I’m an indoor enthusiast, you kind of drag me out. Betsy does a good job with this, by the way.

Betsy: Yes. Well, I thought it was very telling too, like when Stack Overflow first sold, our first big splurge was a new minivan.

Denver: Wow.

Jeff: Yes. And I love that minivan.

Betsy: Not a sports car.

Jeff: That thing was great. Sienna’s even better though.

Betsy: That’s a great van.

Jeff: Oh my God. Look, the minivan is awesome. People who think it isn’t awesome, they were just wrong. Wrong.

Denver: There you go.

Betsy: Yes.

Jeff: A better vehicle.

Denver: Well, I haven’t seen it, Jeff, and I think it’s awesome. So there you go. I had…

Jeff: You should visit, I’ll show you.

Denver: Hey, I’ll take a look.

Betsy, I had Victoria Vrana of GlobalGiving on the show recently, and we were talking about community-led aid. And how are you thinking of teaming up with rural churches and local businesses in these rural communities to make your cash payments thrive and to have them be walking alongside of you, if not in front of you, in how this thing gets done?

Betsy: Right. Well, a lot of it is listening to what GiveDirectly is expert at. They know how to go into communities, and the main thing is building trust within those communities. And so, again, it’s not wanting to come in and be this outsider.. “I know the right thing to do!”… but really embedding yourself there.

And who knows these communities better than the people that live there, the people who go to church there, the people who work at the grocery store, veterans, any… all these people try to build this sense of: Okay, we want to work with you and help you build your community up, not just us coming in and dumping this stuff on top of you.

So it really is just about building that trust. And I think GiveDirectly is really… they know what they’re doing in that regard.

Denver:  Yeah, they’ve been on the program as well, and they do know what they’re doing. And they punctured a lot of the myths that people had about what happens when you give them unbridled income… and it turns out they just try to make a better life for themselves in almost every case.

Let’s talk a little bit about storytelling. I know you are big supporters of 404 Media, and there are documentaries like Basic that you’ve embraced. I can’t imagine storytelling isn’t going to be a big piece of getting the word out. What is your thinking on that, either one of you?

Jeff: Well, I’ll start. ITSA Foundation… has a really exciting documentary. Betsy, what’s the title? It’s a docuseries, and it’s amazing. And it really gets to the personal side of this. There’s the policy side, which is: we need to figure this out at the government level, but for now, let’s just get it done and get the data and do it scientifically.

But these human stories are so compelling. I mean, I watched their sizzle reel and honestly, I cried. These people, just for someone to see them and say, we care.

Betsy: This is Bootstraps, right?

Jeff: It’s called Bootstraps.

Betsy: Yeah.

Jeff: And Deia is the director. She’s an award-winning director, and it is incredible. I sincerely hope this gets picked up.

Denver: Yeah.

Jeff: This needs to get picked up because just this effect this little amount of money can have on these people transforms them and makes the world better for them and for all of us, versus being trapped on this treadmill or… and one of the major findings from some of the data, Betsy, that we saw in the OpenResearch, that’s the biggest UBI study it done in the United States. It was a massive study. It cost $60 million.

And one of the biggest findings was two that we really liked. Betsy and I, and Betsy being a scientist, she’s like, this is a great set of results presented well. That 26% of the people that you gave this guaranteed minimum income to shared it with other people. They were so generous because they understood struggle and their friends.

Denver: Yeah.

Jeff: And at that point, honestly, I was sold. I was like: this is the way we have to do this, but it gets a little bit better. We drilled into the data a little bit more recently, and there was a big decrease in alcohol and opioid use. Like large numbers, I want to say 20%, 30% because… Yeah, because you’re no longer stressed out by having to just barely survive.

Betsy: Yeah.

Denver: I would imagine you got something to do the next day. You can build a business, you can do something, and you’re going someplace. So just…

Jeff: Absolutely.

Denver: …The despair that you were talking about a moment ago has dissipated because I can make something here with this money.

Jeff: And they do. I forget the term we had to come up with was business opportunities, but they come with all these interesting ways to make and sell things, like on the internet or ad hoc, or there is a lot of little small business stuff happening, and the internet makes it easier for them to do that.

So yeah, they’re actually very entrepreneurial. That’s not… this a fancy word for saying it, but Americans, we’re good at doing that sort of thing. The whole capitalism thing.

Denver: Yeah.

Jeff: Within reason, but the capitalism, yes.

“…I think there’s also a lot of misinformation about, Oh, people just get money. They’re just going to buy alcohol and sit around all day. And being able to tell those stories of those people and showing them the data that these stereotypes aren’t true, is really, I think, the key to making bigger change here, whether eventually that leads to policy changes where we have guaranteed minimum income from our government.”

Denver: Not the Gilded Age capitalism… the bad capitalism, but the good capitalism.

Well, I have always noticed in philanthropy, emotion does lead information and data. And every time I’ve tried to get a gift, I’ve touched people emotionally or told them a story just the way that you two guys have described. And then the data actually just becomes the justification for them to make the decision that they’ve already made anyway.

So I’ve always looked at the head, the brain, as being the PR agency for the heart that’s already decided. Just give me some info now so I can tell the boss that we’re making this grant type of thing. And that is absolutely the flow that you have really nailed.

Jeff: Well, thank you.

Betsy: Well, I think that the storytelling is so key because when we first started talking about this, just even with friends, we knew people that were like, “Well, what’s UBI?”  Like they hadn’t even heard of it. And so I think there is…

Jeff: There’s a lot to learn.

Betsy: There’s a lot of people that don’t even know what this means. And then I think there’s also a lot of misinformation about, Oh, people just get money. They’re just going to buy alcohol and sit around all day.

And being able to tell those stories of those people and showing them the data that these stereotypes aren’t true, is really, I think, the key to making bigger change here, whether eventually that leads to policy changes where we have guaranteed minimum income from our government…something like that.

I think there’s a lot of minds that need to change and the stories are what is going to do that.

Denver: And you’re really… that’s the heart of it because we do in this country have many preconceived notions about these people.

Betsy: Yes.

Denver: They don’t have the right stuff. If you gave them the money, they don’t have the right stuff inside to do something about it. And they put themselves in this predicament; it’s their own fault. And nothing could be further from the truth. Because I had some people on from Bard, and these guys were in detention from murder and all these other things, and they started a debate team.

And these are just the hopeless of the most hopeless of society. They got onto the debate team, and they took on the Harvard debate team, and they whipped them. You know what I mean? And you begin to say…

Jeff: That does not surprise me, actually.

Denver: Not at all. They were in…

Jeff: They have better survival skills than the people at Harvard.

Denver: They were…

Jeff: For sure.

Denver: You’re absolutely right. And they were taking a…

Jeff: No contest.

Denver: They were taking Philosophy.

Jeff: I wish I could have bet on that.

Denver: Yeah, it would’ve been good. Well, they’ve beaten the Navy and a bunch of other places since. I think they were taking philosophy, and they were reading Kant… or somebody.  They go to their professor and they make a request. They request to see if they could get the books in the original German, because they would understand it better if it wasn’t translated.

And you say to yourself, what are we in society?   How have we depicted them? And oh my goodness, who they are. It couldn’t be anything further from the truth.

Jeff: And Denver, I want to emphasize on the website that we’re going to put out.. we did a three-part history series on like all direct cash transfer type programs in the United States. And there’s actually a rich, long history of this that I was not aware of.

And the beauty of this is I got to work with two guys I graduated from Thomas Dale High School with, who wanted to be historians. And it’s great because one is sort of center-left, and one is center-right. Both very relatable, very funny guys. I love them to this day. I have signed pictures of them in the yearbook over here.  

But working with them has been an absolute joy. And I’m good at the words, yes, but they know the history. I mean, Sanders has published… he worked for the U.S. Army as a historian. I didn’t even know this. My man, Sanders, is out there making names for himself and so was Marston, right? But anyway, it’s just amazing to come back and tell the story of how we got here.

And it does make sense. If you read the history… the Huey Long stuff is crazy. Like he was putting caps on how much money millionaires could have. We’re not even talking about that.

Denver: No.

Jeff: That’s not even possible to talk about, my friend. Like Huey Long was doing it. I mean, maybe not for the right reasons, but the people liked it. One wonders why they liked it and perhaps maybe… but other politicians wouldn’t adopt this for better reasons.

“And I think there’s a lot of good answers, but I think guaranteed minimum income, if you look at the end of Martin Luther King’s life, at the end he realized it was all about the money. The only way you achieve equality, the only true equality, is economic equality. And that’s the work that we want to continue with GMI studies.”

Denver: Jeff, you have said the American Dream is incomplete until it is shared. What’s your call to action for tech entrepreneurs to fuel the American Dream at this moment?

Jeff: Well, look, I’m not here to tell anyone what to do with their money, but I think we’re certainly facing a lot of issues right now as a country. I mean, look around. And I think there’s a lot of good answers, but I think guaranteed minimum income, if you look at the end of Martin Luther King’s life, at the end he realized it was all about the money.

The only way you achieve equality, the only true equality, is economic equality. And that’s the work that we want to continue with GMI studies. Just for every year like clockwork, we want people to come in and sponsor counties and have fewer rural in poverty,  just to keep our focus narrow so we stay on target.

But we’re certainly… all the data will be open and the programs we run well, like GiveDirectly, with participation, and as Betsy mentioned, in harmony with the structures of the counties that are there. And every county is a little bit different, too. So as time goes on, we’ll have a playbook of how this works. And we want to reach all 50 states because I guarantee you, there’s poverty everywhere in the richest country in the world.

Denver: Yeah.

Jeff: But should there be? That’s the question.

Denver:  Well, as you state, economic equality is the floor. And if people are given that, it is unimaginable what they would be able to do from there, but they need to get to there to reach even higher rungs.

And Betsy, there are a lot of people who are listening– nonprofit leaders, donors, everyday folks like me.

Jeff: Just average people like you, Denver.

Denver: What’s your call to them? What do you want them to do? And how can they learn more about this?

Betsy: I think we’re still learning a lot about philanthropy and how oftentimes groups will amass a lot of money, but then kind of get stuck on how and where to put that money. And that it’s becoming more clear that there are things about just the philanthropy world that need to change… and being more proactive and just getting the money out there and helping people.

And we’re hoping that this inspires not only donors, but also these groups that have the power… they have the money… and just getting out there and doing it with less barriers in the way of actually getting help to people that need it.