Overview of How to get better at money, with Carrie Joy Grimes
This episode of Masters of Scale features Carrie Joy Grimes (often called C.J.), founder of WorkMoney, a nonprofit that helps millions of Americans earn more, save more, and spend less. The conversation blends personal story, practical money advice, and a broader vision for how ordinary people can gain leverage in a tough economy. C.J. argues that money is not just math—it’s also emotion, identity, and fear—and that lasting financial progress starts by changing your relationship to money, not just your spreadsheet.
What WorkMoney Does
WorkMoney is a nonprofit and growing membership community that now reaches 9 million+ people. Its mission is to help everyday Americans:
- Find ways to earn more
- Save more and spend less
- Access discounts, coupons, and practical services
- Use collective scale to bargain for better prices
- Understand the economy and money policy in plain language
C.J. describes WorkMoney as the thing she wished existed when she was struggling to figure out money herself: a trusted place to go for straightforward help.
C.J. Grimes’ Background and Origin Story
C.J.’s path to founding WorkMoney came through nearly 20 years as a union organizer. That work taught her to listen closely to working people and understand the realities of paycheck-to-paycheck life.
Key formative lessons from that period:
- Most people were never taught basic money skills
- Many people feel alone in their financial struggles
- Real organizing means listening first
- Collective action can improve people’s economic power
She also shares a personal story from her early organizing days: broke, underpaid, and living with almost no cushion, she was helped by a union colleague who paid for dinner and gave her $100. That moment led her to create her first real budget—and it became the foundation for her current approach to money.
Money Is “Math and Feelings”
One of the episode’s core ideas is that:
Money is math and feelings.
C.J. says the math part matters, but what most often holds people back is the emotional side:
- Shame about spending
- Avoidance of bank statements or bills
- Fear of making mistakes
- The feeling that you’re “bad at money”
She explains that when people believe they’re bad at money, they tend to behave that way—and the belief becomes self-reinforcing. Her solution is to treat money as something people can learn, not a fixed personality trait.
The Personal Story Behind Her Book
C.J. discusses how her mother’s later life deeply shaped her thinking. Her mother lived in severe scarcity, was afraid to seek care or spend money on herself, and became increasingly isolated and unsafe as a result. That experience reinforced C.J.’s belief that financial fear can shrink a person’s life dramatically.
Her goal with WorkMoney and her book is to help people avoid reaching that point by making money feel more manageable earlier.
How WorkMoney Scaled So Quickly
The organization’s growth was not driven by a traditional startup strategy. It started during COVID as a practical response to urgent questions about stimulus checks, unemployment, and PPP loans.
Why it kept growing after the pandemic:
- The economic pressure didn’t go away
- Middle-class families are still squeezed by:
- housing
- healthcare
- childcare
- education
- gas and utilities
- People wanted a trusted, nonjudgmental resource
C.J. says the pandemic exposed a permanent need: people want a civic institution that helps them navigate money and use collective power.
How WorkMoney Thinks About Power
C.J. frames WorkMoney’s strategy around several forms of power:
- Market power — bargaining for better prices
- Constituent power — making demands of politicians and regulators
- Audience power — shaping what people know and trust
- Entrepreneurial power — helping people launch ideas and businesses
The goal is not just individual savings, but also helping members influence the economy more broadly.
The New Bill-Negotiation Service
One major example of WorkMoney’s scaling strategy is Money Finder, a bill negotiation service.
It currently helps members negotiate:
- cable
- internet
- cell phone bills
How it works:
- Users upload a bill
- WorkMoney analyzes it
- Negotiators try to get a better rate
- Members pay only if money is saved
Reported results:
- Average savings of around $400 per person
C.J. says the service is nonprofit-backed and built to be trusted, with plans to expand into more categories like health care and insurance.
C.J.’s Best Personal Finance Advice
C.J. pushes back against common bad money advice, especially advice that relies on shame.
1. Avoid shame-based financial advice
If advice makes you feel bad about yourself, it probably won’t help you change your habits.
2. Max out tax-advantaged retirement accounts before chasing flashy investments
Her advice is to prioritize:
- emergency fund
- paying off credit card debt
- 401(k), 403(b), or IRA contributions
- then broader investing
She warns against getting distracted by “cowboy” investing trends like crypto speculation or trading culture unless someone truly has the expertise and interest to do it well.
3. Don’t let other people define what money is for
C.J. strongly argues that financial success should be self-defined:
- You don’t have to buy a house
- You don’t have to follow someone else’s life script
- The point of money is joy, not status
Key Takeaways
- Money struggles are often emotional, not just mathematical
- Most people need basic, trustworthy financial guidance
- Collective bargaining can reduce everyday costs
- Shame is a terrible financial motivator
- Simple financial fundamentals beat trendy investing
- The purpose of money is to support the life you want
Bottom Line
C.J. Grimes presents money as something that can be learned, improved, and reclaimed. Her work with WorkMoney is both practical and political: help people save money today, while building collective power to reshape the economy over time. The episode’s central message is clear: you are not broken if money feels hard—and better money habits start with compassion, clarity, and a little more control.