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May 29, 2026 · 32m · masters-of-scale

How to get better at money (with Carrie Joy Grimes) | Masters of Scale

CJ Grimes · 22m spoken Jeff Berman · 6m spoken
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In this episode of Masters of Scale, host Jeff Berman interviews Carrie Joy Grimes, Founder and CEO of WorkMoney, about scaling her non-profit organization to serve nine million Americans facing economic challenges. Grimes discusses her transition from union organizing to civic leadership, unpacking the emotional psychology of money, practical budgeting, and building collective middle-class power.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The host holds 22.2% of the talking time here. How this is scored →

The host as informed peer 3.3 Guest teaching 1.9 Guest disagreement 0.4 The host pushing back 0.4
05100:0010:0020:0030:000:32–5:40 · The host as informed peer 3/10 Introducing CJ Grimes and WorkMoney Jeff warmly welcomes CJ as a friend and sets up the scale of WorkMoney's rapid growth from zero to nine million users. CJ explains the origins in COVID and her 20 years in union organizing in an entirely collaborative, conversational exchange.5:40–9:21 · The host as informed peer 2/10 The $100 Loan and Learning to Budget CJ shares the story of borrowing $100 from her union boss and creating her first budget in a motel room. Jeff listens attentively and adds sympathetic color commentary about working-class budgeting.9:21–13:15 · The host as informed peer 3/10 Financial Trauma and CJ's Mother's Story Jeff shares his own early career financial constraints as a public defender, and CJ highlights the structural reality that money struggles are primarily math problems rather than moral failings before recounting her mother's tragic financial avoidance.13:15–15:44 · The host as informed peer 2/10 Math, Feelings, and Overcoming Avoidance Jeff admits to his own financial avoidance tendencies, prompting CJ to explain the psychological equation of money being math plus feelings and how shame drives avoidance.15:44–21:37 · The host as informed peer 4/10 Scaling WorkMoney Post-Pandemic Jeff demonstrates domain knowledge by citing data on the historic divergence between stock market highs and consumer economic sentiment. CJ details how WorkMoney rejected narrow startup playbooks to scale broadly.21:37–23:54 · The host as informed peer 3/10 WorkMoney Partnerships and Value Creation CJ details partnership models like Upside and reading the federal tax bill for members. Jeff summarizes the business model as an AARP-style marketplace.23:54–28:23 · The host as informed peer 5/10 Building Middle-Class Power & Launching Money Finder Jeff delivers a direct counterpoint when CJ claims she does not look to politics for solutions, noting that legislative policy is the direct mechanism creating tax bills and regulatory structures. He also draws on his legal background when discussing bill negotiations.28:23–32:07 · The host as informed peer 4/10 Best Financial Advice & Book Recommendation CJ forcefully rejects shame-based money gurus and cowboy crypto culture, laying out a pragmatic financial checklist. Jeff connects her philosophy to Morgan Housel's The Psychology of Money.0:32–5:40 · Guest teaching 1/10 Introducing CJ Grimes and WorkMoney Jeff warmly welcomes CJ as a friend and sets up the scale of WorkMoney's rapid growth from zero to nine million users. CJ explains the origins in COVID and her 20 years in union organizing in an entirely collaborative, conversational exchange.5:40–9:21 · Guest teaching 1/10 The $100 Loan and Learning to Budget CJ shares the story of borrowing $100 from her union boss and creating her first budget in a motel room. Jeff listens attentively and adds sympathetic color commentary about working-class budgeting.9:21–13:15 · Guest teaching 2/10 Financial Trauma and CJ's Mother's Story Jeff shares his own early career financial constraints as a public defender, and CJ highlights the structural reality that money struggles are primarily math problems rather than moral failings before recounting her mother's tragic financial avoidance.13:15–15:44 · Guest teaching 3/10 Math, Feelings, and Overcoming Avoidance Jeff admits to his own financial avoidance tendencies, prompting CJ to explain the psychological equation of money being math plus feelings and how shame drives avoidance.15:44–21:37 · Guest teaching 2/10 Scaling WorkMoney Post-Pandemic Jeff demonstrates domain knowledge by citing data on the historic divergence between stock market highs and consumer economic sentiment. CJ details how WorkMoney rejected narrow startup playbooks to scale broadly.21:37–23:54 · Guest teaching 1/10 WorkMoney Partnerships and Value Creation CJ details partnership models like Upside and reading the federal tax bill for members. Jeff summarizes the business model as an AARP-style marketplace.23:54–28:23 · Guest teaching 2/10 Building Middle-Class Power & Launching Money Finder Jeff delivers a direct counterpoint when CJ claims she does not look to politics for solutions, noting that legislative policy is the direct mechanism creating tax bills and regulatory structures. He also draws on his legal background when discussing bill negotiations.28:23–32:07 · Guest teaching 3/10 Best Financial Advice & Book Recommendation CJ forcefully rejects shame-based money gurus and cowboy crypto culture, laying out a pragmatic financial checklist. Jeff connects her philosophy to Morgan Housel's The Psychology of Money.0:32–5:40 · Guest disagreement 0/10 Introducing CJ Grimes and WorkMoney Jeff warmly welcomes CJ as a friend and sets up the scale of WorkMoney's rapid growth from zero to nine million users. CJ explains the origins in COVID and her 20 years in union organizing in an entirely collaborative, conversational exchange.5:40–9:21 · Guest disagreement 0/10 The $100 Loan and Learning to Budget CJ shares the story of borrowing $100 from her union boss and creating her first budget in a motel room. Jeff listens attentively and adds sympathetic color commentary about working-class budgeting.9:21–13:15 · Guest disagreement 0/10 Financial Trauma and CJ's Mother's Story Jeff shares his own early career financial constraints as a public defender, and CJ highlights the structural reality that money struggles are primarily math problems rather than moral failings before recounting her mother's tragic financial avoidance.13:15–15:44 · Guest disagreement 0/10 Math, Feelings, and Overcoming Avoidance Jeff admits to his own financial avoidance tendencies, prompting CJ to explain the psychological equation of money being math plus feelings and how shame drives avoidance.15:44–21:37 · Guest disagreement 1/10 Scaling WorkMoney Post-Pandemic Jeff demonstrates domain knowledge by citing data on the historic divergence between stock market highs and consumer economic sentiment. CJ details how WorkMoney rejected narrow startup playbooks to scale broadly.21:37–23:54 · Guest disagreement 0/10 WorkMoney Partnerships and Value Creation CJ details partnership models like Upside and reading the federal tax bill for members. Jeff summarizes the business model as an AARP-style marketplace.23:54–28:23 · Guest disagreement 1/10 Building Middle-Class Power & Launching Money Finder Jeff delivers a direct counterpoint when CJ claims she does not look to politics for solutions, noting that legislative policy is the direct mechanism creating tax bills and regulatory structures. He also draws on his legal background when discussing bill negotiations.28:23–32:07 · Guest disagreement 1/10 Best Financial Advice & Book Recommendation CJ forcefully rejects shame-based money gurus and cowboy crypto culture, laying out a pragmatic financial checklist. Jeff connects her philosophy to Morgan Housel's The Psychology of Money.0:32–5:40 · The host pushing back 0/10 Introducing CJ Grimes and WorkMoney Jeff warmly welcomes CJ as a friend and sets up the scale of WorkMoney's rapid growth from zero to nine million users. CJ explains the origins in COVID and her 20 years in union organizing in an entirely collaborative, conversational exchange.5:40–9:21 · The host pushing back 0/10 The $100 Loan and Learning to Budget CJ shares the story of borrowing $100 from her union boss and creating her first budget in a motel room. Jeff listens attentively and adds sympathetic color commentary about working-class budgeting.9:21–13:15 · The host pushing back 0/10 Financial Trauma and CJ's Mother's Story Jeff shares his own early career financial constraints as a public defender, and CJ highlights the structural reality that money struggles are primarily math problems rather than moral failings before recounting her mother's tragic financial avoidance.13:15–15:44 · The host pushing back 0/10 Math, Feelings, and Overcoming Avoidance Jeff admits to his own financial avoidance tendencies, prompting CJ to explain the psychological equation of money being math plus feelings and how shame drives avoidance.15:44–21:37 · The host pushing back 0/10 Scaling WorkMoney Post-Pandemic Jeff demonstrates domain knowledge by citing data on the historic divergence between stock market highs and consumer economic sentiment. CJ details how WorkMoney rejected narrow startup playbooks to scale broadly.21:37–23:54 · The host pushing back 0/10 WorkMoney Partnerships and Value Creation CJ details partnership models like Upside and reading the federal tax bill for members. Jeff summarizes the business model as an AARP-style marketplace.23:54–28:23 · The host pushing back 3/10 Building Middle-Class Power & Launching Money Finder Jeff delivers a direct counterpoint when CJ claims she does not look to politics for solutions, noting that legislative policy is the direct mechanism creating tax bills and regulatory structures. He also draws on his legal background when discussing bill negotiations.28:23–32:07 · The host pushing back 0/10 Best Financial Advice & Book Recommendation CJ forcefully rejects shame-based money gurus and cowboy crypto culture, laying out a pragmatic financial checklist. Jeff connects her philosophy to Morgan Housel's The Psychology of Money.

speaking balance: gold is the host, purple is the guest (3 minute bins)

0:00 · the host 26.4% · guest 73.6%0:00 · the host 26.4% · guest 73.6%3:00 · the host 39.1% · guest 60.9%3:00 · the host 39.1% · guest 60.9%6:00 · the host 9.5% · guest 90.5%6:00 · the host 9.5% · guest 90.5%9:00 · the host 34.8% · guest 65.2%9:00 · the host 34.8% · guest 65.2%12:00 · the host 26.7% · guest 73.3%12:00 · the host 26.7% · guest 73.3%15:00 · the host 17% · guest 83%15:00 · the host 17% · guest 83%18:00 · the host 5.3% · guest 94.7%18:00 · the host 5.3% · guest 94.7%21:00 · the host 11% · guest 89%21:00 · the host 11% · guest 89%24:00 · the host 23.1% · guest 76.9%24:00 · the host 23.1% · guest 76.9%27:00 · the host 35.1% · guest 64.9%27:00 · the host 35.1% · guest 64.9%30:00 · the host 14.6% · guest 85.4%30:00 · the host 14.6% · guest 85.4%
Sharpest disagreement ▶ 28:41 Rejecting shame-based gurus

CJ emphatically denounces shame-driven financial advice and gurus on the internet, dismissing them as harmful and counterproductive.

 Hardest push from the host ▶ 24:33 Challenging the dismissal of politics

Jeff refuses CJ's framing that politics is only an outcome rather than a solution, pointing out that legislation and policy are the direct result of political processes.

 Biggest teaching moment ▶ 30:35 Clear financial priorities playbook

CJ cuts through market noise and crypto trends to lay out an exact four-step hierarchy for personal financial health.

 The host holds their own ▶ 24:33 Policy and lobbying reality check

Jeff demonstrates structural expertise by reminding CJ that the tax legislation she helps users parse is forged through political negotiation and lobbying.
the scores for every segment, with the reasoning behind each
ChapterTopicThe host as informed peerGuest teachingGuest disagreementThe host pushing backWhy
Introducing CJ Grimes and WorkMoney 3100 Jeff warmly welcomes CJ as a friend and sets up the scale of WorkMoney's rapid growth from zero to nine million users. CJ explains the origins in COVID and her 20 years in union organizing in an entirely collaborative, conversational exchange.
The $100 Loan and Learning to Budget 2100 CJ shares the story of borrowing $100 from her union boss and creating her first budget in a motel room. Jeff listens attentively and adds sympathetic color commentary about working-class budgeting.
Financial Trauma and CJ's Mother's Story 3200 Jeff shares his own early career financial constraints as a public defender, and CJ highlights the structural reality that money struggles are primarily math problems rather than moral failings before recounting her mother's tragic financial avoidance.
Math, Feelings, and Overcoming Avoidance 2300 Jeff admits to his own financial avoidance tendencies, prompting CJ to explain the psychological equation of money being math plus feelings and how shame drives avoidance.
Scaling WorkMoney Post-Pandemic 4210 Jeff demonstrates domain knowledge by citing data on the historic divergence between stock market highs and consumer economic sentiment. CJ details how WorkMoney rejected narrow startup playbooks to scale broadly.
WorkMoney Partnerships and Value Creation 3100 CJ details partnership models like Upside and reading the federal tax bill for members. Jeff summarizes the business model as an AARP-style marketplace.
Building Middle-Class Power & Launching Money Finder 5213 Jeff delivers a direct counterpoint when CJ claims she does not look to politics for solutions, noting that legislative policy is the direct mechanism creating tax bills and regulatory structures. He also draws on his legal background when discussing bill negotiations.
Best Financial Advice & Book Recommendation 4310 CJ forcefully rejects shame-based money gurus and cowboy crypto culture, laying out a pragmatic financial checklist. Jeff connects her philosophy to Morgan Housel's The Psychology of Money.

Statements from this episode (8)

Assertion Supported
Grimes: WorkMoney operates as a non-profit with nine million members
“It is a nonprofit. We've got nine million members, and we help people figure out how to earn more and save more and spend less, and we do that through programs and services and coupons and discounts, kind of like the AARP.”
CJ Grimes May 29, 2026 ▶ 1:09
Assertion Supported
Berman: WorkMoney scaled to nine million SMS members in five years
“Zero to nine million in, in five years basically is a pretty impressive number, and these are people who have a text relationship, an SMS relationship with not just people like nine million visitors to a website or, you know, an Instagram or something”
Jeff Berman May 29, 2026 ▶ 3:19
Insight
Grimes: Believing you are bad at money drives self-defeating financial habits
“When I thought I was bad at money, then I behaved like somebody who was bad at money, and I kept behaving like somebody who was bad at money.”
CJ Grimes May 29, 2026 ▶ 8:41
Insight
Grimes: Most people's core problem is an income deficit, not mismanagement
“Most people, the problem they have is that they don't have enough money. It's not, it is that, I just want to say that plainly.”
CJ Grimes May 29, 2026 ▶ 10:06
Assertion Supported
Berman: The gap between stock market and consumer sentiment is historically high
“There was a chart that you and I were looking at this weekend that showed, like, basically the delta between where the stock market is and where Americans, how they feel about the economy has literally never been larger since they've been measuring this.”
Jeff Berman May 29, 2026 ▶ 16:52
Assertion Not checkable as stated
Grimes: WorkMoney user signups accelerated after the COVID-19 pandemic ended
“When the pandemic ended and our signups be went just as fast, if not faster. And right now we're seeing a lot of signups because middle-class families are stretched.”
CJ Grimes May 29, 2026 ▶ 17:46
Insight
Grimes: Rapid scaling required breaking startup rules to offer broad financial help
“What became really clear is that being able to scale fast meant how quickly could we talk to anyone and figure out what kind of money help they needed, and then deliver the best version of that. So we kind of broke some of the startup-y rules, where we didn't …”
CJ Grimes May 29, 2026 ▶ 20:55
Assertion Not checkable as stated
Grimes: Money Finder saves users an average of $400 per bill
“And so you go to it and upload a bill, we analyze it, and then our negotiators get to work and we've saved, so far, an average of 400 bucks a pop.”
CJ Grimes May 29, 2026 ▶ 26:30
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