All Of It with Alison Stewart: "How to Be a Rich Old Lady"

Air Date: January 12, 2026
Host: Alison Stewart (WNYC)
Guest: Amanda Holden, financial expert and author of How to Be a Rich Old Lady

Episode Overview

This episode centers around financial literacy, particularly for women, and demystifying the path to financial independence regardless of age or circumstance. Amanda Holden, a former Wall Street banker and now an educator and author, shares her philosophy and practical guidance for building wealth. The conversation covers the historical difficulties women have faced, the psychological and systemic barriers to investing, actionable steps towards financial security, and answers to listeners’ real-life financial dilemmas.

Key Discussion Points & Insights

1. Amanda’s Journey from Wall Street to Financial Educator

• Amanda’s Background:

  • Worked in finance starting in 2008 (financial crash) where she “helped rich men get richer” ([04:26]).
  • Realized the lack of accessible financial education for women and decided to democratize the knowledge she acquired ([04:22], [06:05]).
  • Her pivotal moment: fielding basic finance questions from women during a Reno birthday trip ([03:15]).

  Quote:

  • “I have been in the rooms where wealth is being discussed and those people don’t look like us. And these are tools of power. So what I wanted to do was democratize this information and get these tools...to folks like our friends.” – Amanda Holden ([06:05])

2. Structural Barriers and Historical Context

• Systemic Obstacles for Women:
  • Money is harder for women to accumulate due to “centuries of economic design,” e.g., as recently as the 1980s, many women still needed a male signature for credit or loans ([00:38]).
  • Amanda advocates for acknowledging these structural inequities, not just individual shortcomings ([10:40]).

3. Actions for Building Wealth

• Setting up Beneficiaries:

  • First step for passing on assets is to set beneficiaries on retirement accounts ([07:37]).

• Emergency Funds & Debt:

  • Build an emergency fund before investing. Keep enough cash to leave a “bad situation.”
  • High-interest debt (especially credit cards) should be addressed early; “You cannot invest your way out of credit card debt” ([11:42]).

  Quote:

  • “Don’t let the finance bros tell you there is not power in having cash available to leave a bad situation.” – Amanda Holden ([11:42])

• Getting Started with Retirement Accounts:

  • After savings and debt, learn about and open retirement accounts (Roth IRA, etc.).
  • Understand that accounts (401k, IRA) are “vessels,” but you must invest inside them; they do not grow on their own ([15:25]).

  Quote:

  • “We hear retirement plan like a 401k is a retirement plan, and it leads us to believe that somebody’s got a plan for us, when in reality, it is simply a vessel for investing.” – Amanda Holden ([16:26])

4. Financial Nihilism Among Young People

• Gen Z’s Skepticism:

  • Listener Sana, 26, voices the futility of saving for retirement given economic and societal instability ([08:09]).
  • Amanda acknowledges “apocalypse financial planning” is a real sentiment, but hedging bets with some savings and investment is still worthwhile ([08:51]).

  Quote:

  • “Whole scale systems collapse is not outside the realm of possibility, but I do not necessarily think it is likely...” – Amanda Holden ([08:51])

5. System Critique vs. Agency

• Playing and Changing the System:

  • Amanda is a strong critic of the current financial system, calling for collective solutions, but also recommends working for one’s own agency within it until broader changes occur ([10:40], [11:26]).

  Quote:

  • “I also want us to have some agency within this system before the revolution comes.” – Amanda Holden ([11:26])

6. Negotiating (While Female)

• Common Mistake:

  • Women often appeal to a boss’s sense of fairness when negotiating salary; instead, they should use data and demonstrate tangible value ([17:25]).

  Quote:

  • “The biggest mistake...is probably appealing to someone’s sense of fairness... Instead, come in with facts and figures about the value that you provide.” – Amanda Holden ([17:25])

7. Advice on Real-Life Listener Scenarios

• Gen X and Boomer Concerns:

  • Diversification is key, especially for those with pensions (e.g., city workers, teachers). Social Security likely still present, but don’t rely on a single stream ([15:25]).

• Credit Card Debt:

  • For those struggling post-unemployment, consider a 0% balance transfer card, but read fine print and avoid accruing new debt ([21:34]).
  • Call credit card companies to negotiate a lower rate; focus incomes on eliminating this debt once re-employed.

• Self-Employed/Artists:

  • Start with a Roth IRA, upgrade to SEP IRA or Solo 401(k) as earnings grow ([25:24]).

• Tracking Spending:

  • Before investing, get to know your spending habits. Print statements, categorize spending, and find your “savings opportunity” ([26:44]).

  Quote:

  • “It is this know-thyself situation.” – Amanda Holden ([26:44])

• Social Security and Retirement Transitions:

  • If possible, delay collecting Social Security until “full” or even “late withdrawal” age for a higher payout ([28:36]).

• Required Minimum Distributions (RMDs):

  • RMDs from traditional IRAs/401ks are taxable as income; know your tax bracket and set aside for taxes accordingly. Consider withholdings ([30:09]).

Notable Quotes & Memorable Moments

• “The next time someone waxes a tad too nostalgic about the good old days...remind them grandma didn’t have a bank account.” – Alison Stewart ([00:38])
• “[Learning to invest] gives you a psychological benefit of just knowing you’re doing something for yourself right now.” – Amanda Holden ([09:50])
• “You cannot invest your way out of credit card debt.” – Amanda Holden ([11:42])

Key Timestamps for Segments

• Introduction and Historical Context for Women & Money: [00:38] – [02:35]
• Amanda’s Reno Moment & Financial Education Origins: [03:15] – [05:49]
• Structural Barriers and Systemic Critique: [06:05] – [06:58]; [10:40] – [11:26]
• Listener Questions & Advice:
  • Beneficiaries/Legacy: [07:37]
  • Gen Z Nihilism: [08:09]; Amanda's response: [08:51]
  • Settlement/Emergency Funds: [11:26]
  • Pensions and Diversification: [14:04]; Amanda's response: [15:25]
  • Salary Negotiation: [17:03]
  • Credit Card Debt (Post-Unemployment): [20:45]; Amanda's advice: [21:34]
  • Self-Employed/Artists: [25:07]
  • Spending Tracker Basics: [26:44]
  • Social Security Question: [27:53]; Amanda’s advice: [28:36]
  • Required Minimum Distributions (RMDs) & Taxes: [29:45]; Amanda's advice: [30:09]

Tone & Style

Amanda maintains an empathetic, frank, and often gently humorous tone, balancing systemic critique with pragmatic advice. She is clear about the imperfect nature of the system and the need for personal agency and planning within it.

Conclusion

This episode offers sobering context about the long road to financial parity for women, encouragement to take charge where possible, and actionable steps for listeners at every life stage and financial disposition. Through real listener calls and direct, unvarnished advice, Amanda Holden demystifies finance, offering both optimism and realism in the journey toward becoming a “rich old lady”—or simply financially empowered.

End of summary.