/
© 2026 RiffOn. All rights reserved.

Get your free personalized podcast brief

We scan new podcasts and send you the top 5 insights daily.

  1. Masters of Scale
  2. How to get better at money, with Carrie Joy Grimes
How to get better at money, with Carrie Joy Grimes

How to get better at money, with Carrie Joy Grimes

Masters of Scale · May 28, 2026

Work Money founder CJ Grimes shares how to master personal finance by tackling the feelings, not just the math, and building collective power.

Work Money Grew by Defying Startup Wisdom and Broadening Its Scope

Contrary to the "niche down" mantra, Work Money scaled to 9 million members by acting as a generalist resource. Focusing on quickly solving *any* financial problem for a user, rather than specializing, allowed them to provide immediate value and accelerate growth.

How to get better at money, with Carrie Joy Grimes thumbnail

How to get better at money, with Carrie Joy Grimes

Masters of Scale·2 months ago

A Single Small Financial 'Win' Can Permanently Reshape Your Money Mindset

Work Money founder CJ Grimes transformed her financial behavior after paying back one small but aggravating $100 debt. This single accomplishment changed her self-identity from someone "bad with money" to someone capable, creating a positive feedback loop for all future financial habits.

How to get better at money, with Carrie Joy Grimes thumbnail

How to get better at money, with Carrie Joy Grimes

Masters of Scale·2 months ago

To Create Systemic Change, Treat Politics as an Outcome, Not a Starting Point

Work Money's founder avoids direct political lobbying, instead focusing on building market, constituent, and audience power. She believes politics is the *outcome* of shifts in these other areas, making them more effective primary levers for creating lasting, systemic change.

How to get better at money, with Carrie Joy Grimes thumbnail

How to get better at money, with Carrie Joy Grimes

Masters of Scale·2 months ago

Personal Finance Mastery Hinges More on Feelings Than on Math

Work Money founder Carrie Joy Grimes found that emotions like shame, avoidance, and comfort-seeking are the biggest barriers to financial health. Addressing one's personal "money story" and feelings is more critical for success than simply understanding the numbers.

How to get better at money, with Carrie Joy Grimes thumbnail

How to get better at money, with Carrie Joy Grimes

Masters of Scale·2 months ago

Union Organizing Skills Directly Transfer to Building Mass-Market Communities

Work Money's founder credits her 20 years as a union organizer for her success. The core skills of listening deeply to people's problems, identifying shared needs, and mobilizing collective action were perfectly transferable to building a 9-million-member financial community.

How to get better at money, with Carrie Joy Grimes thumbnail

How to get better at money, with Carrie Joy Grimes

Masters of Scale·2 months ago

Shame-Based Financial Advice Fails Because It Promotes Short-Termism

Founder CJ Grimes argues against financial advice rooted in shame, not just on moral grounds, but because it is ineffective. Shame fails to create sustainable habits, instead encouraging short-term fixes and avoidance that don't address root behavioral issues.

How to get better at money, with Carrie Joy Grimes thumbnail

How to get better at money, with Carrie Joy Grimes

Masters of Scale·2 months ago

A Crisis-Response Website Revealed a Permanent Gap in the Financial Services Market

Work Money began as a simple website to answer urgent questions about stimulus checks during COVID. Its immediate, explosive growth demonstrated that the need for a single, trusted source of financial guidance for everyday Americans was a massive, permanent, and unmet market need.

How to get better at money, with Carrie Joy Grimes thumbnail

How to get better at money, with Carrie Joy Grimes

Masters of Scale·2 months ago