BiggerPockets Money Podcast: "Does Money Buy Happiness? What the FIRE Community Gets Wrong"

Date: November 28, 2025
Hosts: Mindy Jensen & Scott Trench
Guest: Paul Ollinger (ex-Facebook, host of Reasonably Happy podcast, stand-up comedian)

Overview

This episode challenges and reframes fundamental assumptions of the FIRE (Financial Independence, Retire Early) movement, focusing on the question: Does money actually buy happiness? The hosts are joined by Paul Ollinger, a financially independent early ex-Facebook employee-turned-comedian, who shares how hitting his "number" didn't bring him lasting happiness. The discussion interweaves research on happiness, personal stories, and hard truths about life after financial independence, offering a nuanced—sometimes critical—perspective on FIRE dogma.

Key Discussion Points

1. Rethinking FIRE: It's Not All About Early Retirement

• Paul's Big Critique: He loves the idea of financial independence but dislikes the "retire early" aspect, viewing retirement as "death's waiting room."

  • "[Financial independence] has given me a great deal of joy in my life... But the richest I've ever felt is the day I paid off my student loans.” (Paul, 01:01)
  • "Retirement is death’s waiting room...” (Paul, 02:09)

• Walking Away VS Running Toward: Paul admits leaving Facebook was more about escaping a stressful job than actively pursuing a passion—a mistake, he warns.

  • "I walked away. I didn't walk toward anything. And that's lesson number one. You should always be walking towards something. Don't just bail on your job without a plan." (Paul, 04:41)

2. The Purity Paradox in FIRE

• FIRE Purism Called Out: Scott and Mindy critique a vocal minority in the FIRE world that insists on never earning money post-retirement, regarding any income as a betrayal.

  • "There's this fringe contingent that's very loud, that's purist and kind of annoying, frankly... That's not really representative." (Scott, 12:23)

• Purpose and Identity Beyond Work: Both Paul and the hosts stress the importance of continuing to build identity, purpose, and community after leaving a career.

  • "Everybody's going to have this inflection point... where you have to decide, well, what are you besides your job?" (Paul, 25:04)

3. Money, Happiness, and Diminishing Returns

• Famous Research Referenced: Discussion centers on studies by Kahneman, Deaton, and Killingsworth on how happiness increases with income—but only up to a point.

  • “The purpose of money goes from being a painkiller to a vitamin. Every additional dollar I made...was a painkiller...Once you get to the point where...that stuff doesn’t bother you anymore, your life is better.” (Paul, 20:31)
  • "[After a certain point] every additional dollar does correlate with this concept of overall life satisfaction, but the returns begin to diminish greatly." (Scott, 19:03)

• The Danger of Constant Comparison: Building wealth tends to shift one's sense of “enough” ever upward—Paul warns the goalposts always move.

  • “You start hanging out with people who have a lot of money...and then you start thinking, 100 million. And it never stops.” (Paul, 07:34)

4. Lessons Learned: The Scarcity Mindset, ‘Enough,’ and Trade-offs

• From Scarcity to ‘Enough’: Both Paul and Mindy discuss growing up with financial insecurity and how difficult it is to know when to stop hustling.

  • "I was the kid who was going to be successful in business...If I have more money then I'll be happy. That was the mindset." (Paul, 02:56)
  • “You think you know what a lot of money is until you make it...And it never stops.” (Paul, 07:34)

• Sacrifice and Regret: Paul recounts major life trade-offs (leaving Facebook, moving to Atlanta, spending time with dying parents) and doesn't regret his choices.

  • “Regretting decisions...that are irreversible is not a very productive use of energy or time...I've sort of lived my life in a mode of minimizing deathbed regrets.” (Paul, 16:47)

5. Practical FIRE Strategies: Investing, Risk, and the Real World

• Don’t Wait to Live: Paul urges listeners not to postpone hobbies, relationships, or dreams until “after FI.”

  • "If there's things that you want to do with your life, you shouldn't wait until some period at X years in the future to start doing them." (Paul, 13:51)

• Investment Caution: Discussion of the risks of heavily concentrated portfolios and the importance of diversification.

  • “My financial advisors asked me what my goal was, and I said it was to sleep at night. And so we started a methodical drawdown of Facebook...” (Paul, 34:42)
  • “A huge percentage of the FIRE community has all of their wealth, effectively all of their liquid wealth in S&P 500 index fund portfolios. That is not a good place to have all of your wealth…” (Scott, 30:51)

• Withdrawal Anxiety: The hosts note the FIRE community’s sometimes extreme caution—often oversaving, endlessly worrying about safe withdrawal rates, and planning to keep earning.

  • "How many times, Mindy, have we discussed the 4% rule? We've had endless, endless debates..." (Scott, 30:51)

6. Location, Lifestyle Inflation, and Cost of Happiness

• Cost of Living Matters: “Money happiness” numbers differ radically between places. Private school in NYC: $70K+, making FIRE far harder there than in, say, Colorado.

  • “If you're in the FIRE movement, you probably don't want to live in New York City. You certainly don't want to send your kid to private school.” (Paul, 43:37)

• Lifestyle Creep: Comparing self to ever-wealthier peers can diminish contentment post-FI.

  • “Your peers keep working and moving on, and your peer that was a vice president becomes the CEO...the bar keeps moving.” (Paul, 28:17)

Notable Quotes & Memorable Moments

• On retiring ‘early’:

  "Retirement is death's waiting room... people who retire early die earlier than people who keep working." (Paul, 02:09)

• On reaching your 'number':

  "I quit. I walked away. I didn't walk toward anything. And that's lesson number one. You should always be walking towards something." (Paul, 04:41)

• On money as ‘painkiller vs. vitamin’:

  "The purpose of money goes from being a painkiller to a vitamin." (Paul, 20:31)

• On purpose after FI:

  "Everybody's going to have this inflection point where you have to decide, well, what are you besides your job?" (Paul, 25:04)

• On comparison & ‘enough’:

  "You think you know what a lot of money is until you make it... And then it never stops." (Paul, 07:34)

• On money and personal change:

  "Money amplifies who you are. It doesn’t change you." (Paul, 42:55)

Timestamps for Key Segments

• Opening Critique of FIRE: 00:00–02:09
• Paul's Backstory & Money Mindset: 02:56–06:56
• Sacrifice, Scarcity, and 'Enough': 07:34–09:02
• Purist FIRE & Core Community Debate: 12:23–13:51
• Diminishing Returns of Wealth Research: 18:21–20:31
• Identity, Purpose & Life Phases Post-FI: 25:02–25:55
• Investment Strategy & Portfolio Management: 34:42–36:29
• Cost of Living & FIRE in NYC vs. Colorado: 43:36–47:48

Conclusion

This episode is a must-listen for anyone in, near, or even skeptical of the FIRE community. Paul Ollinger’s experience—having succeeded spectacularly by one set of metrics, but finding contentment only when reconnecting with meaning, purpose, and community—serves as a caution and a guide. The general takeaway is not to idolize "the number," but to focus on what kind of life you actually want, before and after FI. Don’t delay living, and don’t confuse financial metrics with life satisfaction.

Find Paul Ollinger

• Substack: words.paulollinger.com
• Podcast: Reasonably Happy (formerly “Crazy Money”)

Curious about FIRE strategies, pitfalls, or thriving post-FI—especially outside the usual blogs? This episode brings the real talk.