Podcast Summary

The Money with Katie Show

Episode: She Retired at 32. Then Came Guilt—and a Moral Crossroads.
Date: December 10, 2025
Host: Katie Gatti Tostain
Guest: Rebecca Herbst (Founder, Yield & Spread)

Main Theme

This episode explores the journey of Rebecca Herbst, who achieved financial independence (FI) and retired at age 32. Katie and Rebecca dive deep into the emotional, ethical, and practical complexities of retiring early in a world full of inequality. They discuss the responsibilities that come with wealth, the “giving back” debate (local vs. global, tactical vs. emotional), and how to integrate philanthropy into the personal finance journey. The conversation moves from philosophical questions about purpose and privilege toward actionable advice on charitable giving.

Key Discussion Points

Rebecca’s Path to Financial Independence and Early Retirement

[03:33–08:22]

• Motivation for FI: Rebecca was less driven by the specifics of her job and more by a misfit with the 9–5 lifestyle. Initially, her self-worth was tied to her corporate identity.
• “Learning about FI was a game-changer. ...I just didn’t realize there was this mathematical equation behind when you can walk away.” (Rebecca, 06:36)
• Rapid Path: Rebecca achieved FI in 4–5 years due to a high savings rate, frugality, no student debt, and a strong career. She didn’t fully prepare emotionally for early retirement, resulting in feelings of disconnection and aimlessness.

The Emotional Fallout and Guilt After Early Retirement

[08:22–12:34]

• Life Transition: Post-retirement, Rebecca experienced a sense of loss and a lack of community.
• Privilege Acknowledgment: COVID and global economic downturn amplified Rebecca’s awareness of her privilege.
• Influence of Peter Singer’s Philosophy: “Affluent people like you and me have a moral obligation to give back...” (Rebecca, 11:11)
• Rebecca struggled to reconcile her ability to retire with knowing that opportunity is not available to most.

Philosophical and Ethical Questions Around Giving

[14:33–20:12]

• Privilege as Luck: Katie notes that accident of birth is most often responsible for life outcomes: “...my soul was born into this body in this country and that has done more to determine the outcome of the life that I get to live than any other single factor.” (Katie, 14:33)
• When to Start Donating: Rebecca argues for early, regular giving, even if small—testing the waters at 1% of income as a habit-forming first step.

Structuring Charitable Giving: The Philant3 Pledge Approach

[16:25–20:12]

• Intentional Giving: Move from reactive donations to systematic, sustainable giving.
• Financial Security Stages & Giving:
  • Instability: No expectation to give if in debt/crisis.
  • Stability: Try giving 1% of income as an experiment.
  • Momentum/Sufficiency: Increase as financial situation improves.
• “If you earn more than $69,000 a year in the US after taxes, you are already in the top 1% of income earners globally.” (Rebecca, 17:37)

Can You Pursue FI and Give Generously?

[20:12–24:15]

• Balancing “Hoarding” and Generosity: Rebecca introduces the “philanthropy calculator” to model the trade-off between donating now and reaching FI.
• Example: Donating 1% of income annually might only delay FI by 6 months; 3% might mean two extra years. Yet, most people end up with more than enough wealth.
• Memorable Exchange:
  • Katie: “Six extra months?” (22:42)
  • Rebecca: “Yeah, no one I know even hits FI and is like, ‘Okay, I hit it today, leaving my job.’” (22:44)

The Psychological Rewards of Giving

[24:15–25:19]

• Emotional Return: Rebecca feels proud, doesn't miss the money, and values feedback from organizations (she’s a top 3% donor at GiveDirectly; 24:53).
• But Also, Guilt: “Sometimes I look at those numbers and I’m like, I could be doing more. ...We all could probably do more.” (Rebecca, 25:19)

The “Right-Hand, Left-Hand” Dilemma: Investing Ethics vs. Giving Effectiveness

[25:33–31:13]

• Question: Should you maximize investing returns (even in questionable industries) to give more, or prioritize ethical/socially-conscious investing?
• ESG Investments: “A lot of greenwashing out there. ...If I took that three-quarters of a million dollars in fees... I could provide safe drinking water to half a million people for a whole year.” (Rebecca, 27:57)
• Wisdom: Passive investing may not be actively good or evil; direct impact comes from choices and active engagement, not just through fund selection.

Local vs. Global Philanthropy

[31:13–35:29]

• Effectiveness Debate: Giving globally often yields greater impact (“giving $100 to someone living on $2 a day is life-changing”).
• Emotional Reality: Supporting local organizations is a powerful emotional motivator.
• Three Buckets Approach: Spread giving among loved ones, local/emotionally-connected charities, and global high-impact organizations for a balanced approach.

Overcoming the Social Stigma of Public Giving

[36:45–40:04]

• Fear of “Do-Gooder” Alienation: “I don’t want to be seen as saintly ... I promise you, they will say I am no Mother Teresa.” (Rebecca, 36:45)
• Promoting Public Pledges: Public giving is vital for cultural normalization, accountability, and creating networks of generosity.

Tactical Giving: Methods and Best Practices

The 10% Pledge—History and Application

[43:22–46:00]

• Rooted in Tithing: 10% practice is historic (tithing), achievable, and significant. Most high-income countries give less than 1% on average (45:16).
• Rebecca: “Moving the needle from 0.7% to 10% ...is greater than 10 times the impact than our typical rate of giving.” (44:06)

How to Calculate Your Pledge

[45:31–48:00]

• Standard is 10% of post-tax income.
• For FI individuals, pledging by wealth percentage (e.g., 0.5% of net worth) is valid. Don't stress about edge cases — keep it simple and adjust as needed.

Frequency and Habit Formation

[51:35–53:02]

• Preferred Cadence: Set target annually, donate monthly.
• Consistency matters more than precision. Tie giving to recurring finance routines (e.g., monthly budget review).

Picking Charities: What to Look For

[54:13–57:33]

• “I personally feel very emotionally connected to the high impact charities I donate to...” (Rebecca, 54:49)
• Rebecca recommends GiveDirectly (cash transfers to people living in poverty)—direct, research-backed, and transparent.
• Use charity evaluators: The Life You Can Save, GiveWell, Giving Green.

Donating Cash vs. Appreciated Stock

[57:33–61:21]

• Rebecca donates appreciated stock:
  • “You can avoid the 15% capital gains tax ...I choose the shares with the largest gains.” (57:39)
• In 2026, a new tax deduction allows even those taking the standard deduction to deduct $1,000 (single)/$2,000 (married) in cash donations.

How to Donate Stock: Step by Step

[59:38–61:21]

• Find cost basis (“tax lot”) of your shares.
• Complete “partial asset gifting” form from your broker, specifying the asset and charity info.
• Process is manual for most brokerages unless using a donor-advised fund (DAF).

Donor-Advised Funds (DAFs): Pros and Cons

[61:49–65:31]

• Benefits:
  • Simplify donations, especially to multiple charities.
  • Allow front-loading donations (useful in high-income years).
  • Automate and spread grants throughout the year.
• Common Misconceptions:
  • DAFs aren’t necessary for tax deductions or avoiding capital gains tax.
  • You must itemize deductions to benefit (most Americans take the standard deduction and don't itemize).
• Limitation: Only qualified 501(c)(3) charities can receive funds from DAFs.

Bunching/Bundling Donations for Tax Savings

[66:50–68:59]

• “Bunching” several years’ donations into one for tax efficiency can help with deductions, but may undermine regular giving habits and charities’ cash flow predictability.

Notable Quotes & Memorable Moments

• Rebecca, on the paradox of privilege:
  “For so many people, it doesn't matter how hard they try or ...how badly they wanna make a better life for themselves, they don't live within an economic environment or circumstances to allow them to achieve what I did.” (12:01)

• Rebecca, on emotional adaptation:
  “I was just supposed to wake up and feel happy and feel proud... but emotionally, I think it took a really long time to catch up.” (06:36–08:22)

• Katie, on accident of birth:
  “That has done more to determine the outcome of the life that I get to live than any other single factor.” (14:33)

• Rebecca, on ‘do-gooder’ syndrome:
  “The whole good person thing makes me uncomfortable... I don’t want to be seen as saintly when I come on, you know, a podcast like this.” (36:45)

• Rebecca, on building a culture of giving:
  “If your five best friends are donating regularly to charity, the chances are you will probably have an increased inclination to donate...” (40:04)

Timestamps for Important Segments

• 03:33–08:22: Rebecca’s unexpected path to early FI and the personal challenges that followed.
• 08:22–12:34: Processing privilege and navigating guilt during Covid and post-retirement.
• 14:33–20:12: Big-picture questions: moral obligations of the affluent and the psychology of giving.
• 25:33–31:13: Investing ethics—should you maximize returns or invest for social good?
• 31:13–35:29: Local versus global giving; “three buckets” philosophy.
• 43:22–46:00: The rationale for the 10% giving pledge.
• 51:35–53:02: Habit-building and optimal cadence for philanthropic giving.
• 57:33–61:21: Tactical guide to donating appreciated stock.
• 61:49–65:31: Donor-advised funds: what they are, who should use them, and common misconceptions.
• 66:50–68:59: Pros and cons of bunching donations for tax purposes.

Takeaways for Listeners

• Emotional and moral fallout from achieving FI is real. Anticipate and normalize adjustment periods.
• Start giving sooner, even if at a small percentage. Build the habit before you “have enough.”
• Diversify giving: Blend heart-connection (local/known) and high-impact (global/evaluated) causes.
• Structure and automate: Use pledges and regular giving routines; monthly cadence is ideal.
• Donor-Advised Funds are helpful for volume and automation, but not required for most.
• No single “right” answer—personal values, circumstances, and philosophies influence best practices.

This detailed roadmap should equip listeners—or non-listeners—with the philosophical frameworks and practical playbooks needed to integrate impactful giving into any financial journey.