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The official CEO.com podcast featuring unfiltered conversations with the leaders shaping our world.
Clint Betts: Carrie, welcome to the show. Thank you so much for coming on. What an honor to have you. You're the founder and CEO of WorkMoney. I believe you started this in 2020. Is that right?
And it's a nonprofit. The whole idea is to help people with their money. That's probably a terrible explanation, so give me a sense for what WorkMoney is, what it does, and why it was so important to you that you're doing this.
Carrie Joy Grimes: WorkMoney is a nonprofit, kind of like the AARP. You know how the AARP helps folks navigate aging? Well, we help folks navigate money. We don’t send you an envelope when you turn 50 that makes you feel old, but we do have coupons and discounts. We provide information about different programs and services — everything from public sector resources to private sector tools.
Our vision is an America where everybody who wants to contribute and work hard can afford to live a good life. It’s not rocket science. We do everything we can to help people at the individual level navigate financial decisions, but we also think a lot about scale. How big can we get, and how can we use that size to bargain for cheaper things and make sure businesses and government know what people expect from them?
Clint Betts: What you're doing couldn’t feel more necessary right now. The class divide we’re all experiencing, the transfer of wealth over the past few decades — especially since COVID — is staggering. The wealthy are getting wealthier, the middle class feels like it’s shrinking, and it’s harder and harder for people to get by.
I have kids graduating from high school, and I genuinely wonder: how are they ever going to afford a home? Is that even possible anymore? It feels like the next generation can’t fulfill the American Dream the way it was pitched to us. You used to be able to afford a house and raise a family on a middle-class income. We’re clearly not doing enough.
And what you’re doing feels incredibly important.
You have 9 million members, which is unbelievable. Congratulations. That’s enormous. Utah has about 3 million people total, so just to give people perspective — 9 million is massive.
Talk about the power of negotiating on behalf of 9 million people. How does that work?
Carrie Joy Grimes: First of all, it shouldn’t be this hard to get by. And with AI coming — which is going to transform work, jobs, and communication — there’s so much uncertainty.
My daughter is a freshman in college. I dropped her off a few weeks ago and still can’t believe she’s that old. She asks me, “What should I study to get a good job?” And honestly, I don’t know anymore. We used to say “the sciences,” but AI changes everything.
It’s already hard to get by. I couldn’t afford to buy my own house today at current prices, and I barely got in 15 years ago. I couldn’t save 20% down — I had mortgage insurance. I feel like I was part of the last wave of people who could still get in.
Over the last 50 years, it’s gotten harder, not easier, for people to succeed financially. That’s not the promise of the American Dream. The promise was that if you worked hard, you’d have a reasonable shot at financial security and success. I don’t think that feels reasonable anymore.
We’ve built an economy that generates enormous wealth, but more and more of it is captured by fewer and fewer people. I’m all for people getting rich — go build companies, make money, create value. But we can do that without extracting so much from everyone else.
Clint Betts: I couldn’t agree more. We’re living in a new age of monopolies and oligarchies. Elon Musk may become the first trillionaire, and at the same time, something like 80–85% of Americans couldn’t cover a $500 emergency.
Carrie Joy Grimes: Exactly. Capitalism works best when people can participate in it. When people have enough security to take risks, build companies, and try new ideas, markets are stronger.
When fewer companies control more of what happens, capitalism becomes brittle. It’s bad for innovation and bad for stability.
The purpose of this country is life, liberty, and the pursuit of happiness — the ability for many people to thrive. That’s what the American Dream is supposed to be about.
There’s a really interesting RAND Corporation study that found if working- and middle-class people had kept the same share of productivity gains they had in the early 1970s, the average person’s income today would be double what it currently is.
When COVID happened, everyone’s financial life got turned upside down. I built a simple website explaining things like stimulus checks and how programs worked. It exploded because people needed help understanding money.
That’s how WorkMoney started.
Clint Betts: And the need didn’t go away after COVID.
Carrie Joy Grimes: Exactly. People still need help figuring out how to earn more, spend less, and navigate an increasingly difficult economy.
The way out isn’t waiting for someone to save us. No political party or company is coming to rescue people. We have to organize ourselves, decide what we think is reasonable, and demand it.
WorkMoney is meant to be a market where we can bargain for cheaper goods and services. It’s also a way to use collective power to engage with business leaders and policymakers.
And we’re beginning to invent our own products and services too. We’re launching tools to help negotiate lower cell phone, cable, and internet bills for people. That’s just the beginning.
Clint Betts: Why make it a nonprofit instead of a for-profit?
Carrie Joy Grimes: During COVID, it mattered that people trusted the information they were getting. I wanted people to know the mission was the point.
We do have a for-profit subsidiary where we’ll launch products and services, but it’s owned by the nonprofit. The goal is financial security for everyday people. That mission is baked into the organization.
Clint Betts: What does being a member look like?
Carrie Joy Grimes: People usually find us through social media or a friend. They sign up with their phone number, email, and ZIP code so we can personalize help.
We text people, email them, and sometimes call them. Usually people come to us because they care about a specific issue — food costs, debt, Social Security, prescription prices, things like that.
We have about 100 employees now, which is wild to say out loud.
Clint Betts: Is the team remote?
Carrie Joy Grimes: Entirely remote. We started during COVID, so we built the organization that way from day one.
Culture matters enormously, so we do annual in-person gatherings, department meetups, lots of Slack communication, and frankly, an absurd number of Zoom meetings.
But being remote gave us a huge hiring advantage. We can hire great people from anywhere.
Clint Betts: What does a typical day look like for you?
Carrie Joy Grimes: I live on the West Coast, but most Americans don’t, so I start early — usually around 6 a.m.
I drink tea because coffee makes me too intense. I spend some quiet time getting grounded, then I jump straight into Zoom calls.
A lot of my day is spent talking with my team, partners, and figuring out how to scale WorkMoney and launch new products.
I’m usually living one or two years ahead of the organization mentally, trying to solve today’s problems while preparing everyone for what’s coming next.
And somewhere in the day I text my daughter, who mostly ignores me unless she needs money.
Clint Betts: How does someone become a member?
Carrie Joy Grimes: Just go to workmoney.org and sign up. It’s free.
Clint Betts: Tell me more about negotiating on behalf of members.
Carrie Joy Grimes: I think about lowering costs in three ways.
First, we already negotiate discounts and partnerships — prescription savings through GoodRx, insurance deals, phone plans, things like that.
Second, we’re launching a service where we negotiate directly on people’s behalf with cable, internet, and cell phone companies. We know the deals they’ll offer if someone threatens to cancel. We know the market pricing. We’ll do the work for people.
Third, once we scale this, we can negotiate almost anything — insurance, financial services, healthcare. I would love to start arguing with health insurance companies on behalf of members.
As an individual, it’s hard to fight giant corporations. But with 50 million people behind you? That changes the conversation.
Clint Betts: How do you keep the organization afloat financially?
Carrie Joy Grimes: Right now it’s philanthropy. A lot of people believe the economy should work better for working people.
Eventually, our negotiation services will likely involve some type of fee structure where we take a small percentage of the savings we generate for members.
And long term, there are other revenue models. We reach over a billion views annually through our content. There are trustworthy products and companies out there that genuinely help people, and we can help connect people with those.
Clint Betts: How are you thinking about AI?
Carrie Joy Grimes: AI is coming whether people like it or not. The important question is how we shape it.
The service we’re building to negotiate bills will combine humans and AI agents. Right now the technology isn’t fully there yet, despite what people say, but it’s coming quickly.
WorkMoney wants to help shape an economy where people can still thrive in an AI-driven world.
Clint Betts: What are you reading?
Carrie Joy Grimes: Honestly? A lot of fantasy romance novels.
But I’m also reading Reid Hoffman’s Superagency, which has really influenced my thinking about AI.
My daughter and I are reading the Throne of Glass series together. I also love Ilona Andrews’ fantasy books.
And if people haven’t read Robert Caro’s biographies of Lyndon Johnson, they absolutely should. They’re incredible.
Clint Betts: We end every interview with the same question. At CEO.com we believe the chances one gives are just as important as the chances one takes. Who gave you a chance that led to where you are today?
Carrie Joy Grimes: There are a few answers.
First, when I was young and trying to figure out college, there was a woman in the bursar’s office at Northern Illinois University who took the time to explain things to me. I don’t even remember her name, but if she hadn’t answered the phone that day, I wouldn’t be here.
Second, Reid Hoffman. I read Blitzscaling and realized WorkMoney could become something much bigger. Eventually someone on his team gave us an early $50,000 investment that helped get us going.
And third, everyone who has joined WorkMoney — employees, members, supporters. Building something like this requires people willing to believe in the mission before the outcomes are obvious.
Clint Betts: Carrie, what you’ve built is incredible. Thank you for coming on.
Carrie Joy Grimes: Thank you. I really appreciate the chance to talk with you and learn from what you all do at CEO.com.