How to Money – Episode #1049

"Money Truths You Won’t Hear Anywhere Else" with Len Penzo

Release Date: October 15, 2025
Host: Joel (iHeartPodcasts)
Guest: Len Penzo, veteran personal finance blogger and author of "True Money Stories"

Episode Overview

Joel sits down with Len Penzo, a long-time personal finance blogger known for his "offbeat" approach and story-driven lessons, which blend humor, candor, and practical advice. The conversation centers on hard truths about money, lessons learned from family and personal experience, the importance of responsibility and sacrifice, and the ways personal finance has changed over the years. The episode pulls lessons from Len’s new book, "True Money Stories," and reflects on how economic realities have shifted for younger generations.

Key Discussion Points & Insights

Len’s Unconventional Splurge: Model Railroading

• 03:06 – Len admits to being a model train (N scale) enthusiast:

  "I'm a model train buff...I have a weakness for buying anything related to the N scale model railroad hobby. So I'm always, always splurging on that." — Len Penzo

• 03:59 – The financial reality: each locomotive can cost over $200, and a collection easily grows into thousands of dollars.

Origins of the Blog and Offbeat Style

• 05:35 – Len started his personal finance blog in 2008, seeking a hobby after heavily volunteering in Little League. Blogging, then an "ascending medium," quickly became popular as he used storytelling to make finance engaging.
• 08:15 – "There were years where I would get up to 2 million views a year...I treated it almost like a sitcom or a show. I had my family...as characters, and I always tried to end with a lesson on personal finance." — Len
• 09:39 – Joel observes the power of stories in teaching financial lessons.

Intelligence vs. Organization in Personal Finance

• 10:25 – Intelligence is largely irrelevant to personal finance success:

  "I know very smart, intelligent people whose personal finances are a mess...It's really your organizational skills. That makes the difference." — Len (11:07)

Running Household Finances Like a Business

• 13:45 – In the Penzo household, Len is the CEO (long-term planning, investments) while his wife ("the Honeybee") is CFO (tracking, expenses):

  "We meet once a month and go over the household budget...If there's a problem, that's my job to figure out what we need to change." — Len (14:00)

The Personal in Personal Finance

• 15:57 – Every household handles finances differently based on personalities (e.g., spender vs. saver couples). There’s no universal method, but joint involvement is key for success.

On Financial Honesty and Letting Kids Fail

• 17:24 – Len laments a trend of being "too nice":

  "You've got to face reality...If you're not willing to say some difficult things, nothing's going to get fixed."

• 18:24 – He shares a story from the book about his son, who spent his brake repair money on a BB gun and had to learn the hard way about consequences (19:57).

Spending Habits as Windows to Priorities

• 22:37 – Spending habits reflect priorities, and many people simply don’t value financial freedom as much as instant gratification or consumer comforts:

  “Debt is financial slavery. You're putting chains on yourself every time you take a loan out.” — Len, 23:01

Cultural Shifts: Instant Gratification & Normalizing Spending

• 23:51 – The "buy now, pay later" culture is normalized—Len calls himself "old school" for resisting it, but warns against the difficulties it causes (24:31).

The Impact of Circumstance on Financial Success

• 30:27 – A nuanced view:

  "There are cases where people run into difficulties through no fault of their own...but there's still an obligation to save for emergencies if at all possible."

• 32:37 – Sacrifice is essential; sometimes people simply refuse to forego wants for needs (33:32).

Is Financial Independence Universally Achievable?

• 34:29 – For young people, achieving FI is harder than for previous generations, largely due to systemic issues (Nixon’s gold standard abandonment, etc.) and elevated costs. Gen Z and Millennials face a "rigged game," especially with housing.

Advice for Younger Generations

• 36:00 – Required to "work harder, save more, invest more, and maybe take bigger risks"—especially when young, as time is available to recover from mistakes.

Young Investors: Take More Risk (But Not Crypto)

• 37:31 – Len encourages aggressive (stock-heavy) investments and avoiding bonds or stable funds in early years. He’s skeptical of crypto, but says precious metals have value.

Family Values, Frugality, and Role Models

• 39:34 – Family played a major role; cousin Kevin framed debt as "financial slavery." Aunt Doris, though frugal, had a rich life and demonstrated you can enjoy life without overspending.

Connecting Money to Values

• 41:09 – Many people aren't clear on their core values and thus misalign their spending; it's key to examine what matters most and fit financial habits to it.

Retirement Realities and Popular Misconceptions

• 43:25 – Commercials about needing “$3.2 million to retire” are overblown; satisfaction in retirement depends on your lifestyle, not your net worth.

  "We're modest spenders...you'd be surprised how little you can get by on as you get older." — Len, 43:48

The Famous Sandwich Survey

• 48:03 – Len’s "Annual Sandwich Survey" has tracked the cost of homemade sandwiches for 17 years, showing it’s almost always cheaper and healthier than school lunches.

  “Every year...the price of a sandwich in a brown bag lunch is always far less than a school lunch.” — Len, 48:25

Staying Motivated After 3,000+ Blog Posts

• 51:43 – Len admits he's less excited after so many years, but still enjoys the community and publishes a weekly "Black Coffee" roundup focusing on macro topics and humor (53:10).

The Realities of Retirement

• 53:10 – Biggest retirement concern is the threat of huge long-term care expenses, for which insurance is costly and not always worth it. Personal finance after retirement is as much about ongoing risk management as accumulation.

Joys and Pitfalls of Early Retirement (FIRE Movement)

• 55:55 – Len cautions young retirees (FIRE adherents) about having enough to do; happiness in retirement relies on having meaningful pursuits, not just financial security:

  "How much tennis can you play? How much golf can you play? Life is long...you need to figure out a way to fill that time."

Notable Quotes

• On the value of organization over intellect:

  “Intelligence has nothing to do with personal finance management...it’s your organizational skills that make the difference.” — Len, (11:07)

• On the need for honest advice in finance:

  “You’ve got to face reality…If you’re not willing to say some difficult things, nothing’s going to get fixed.” — Len, (17:24)

• On debt and spending:

  “Debt is financial slavery. You’re putting chains on yourself every time you take a loan out.” — Len, (23:01)

• On personal responsibility amid tough circumstances:

  "That doesn't absolve people of the obligation...to save up for emergencies if you can." — Len, (30:27)

• On retirement savings goals:

  "You'd be surprised how little you can get by on as you get older...Those commercials are totally overblown." — Len, (43:34)

Timestamps for Key Segments

• 03:06 — Model train hobby, the costs of passion spending
• 05:35 — Blogging origins and unique storytelling approach
• 10:25 — Intellect vs. organization in money management
• 13:45 — Running household finances "like a business"
• 17:24 — Honesty in financial education; letting kids learn hard lessons
• 22:37 — How spending reflects life priorities; why people stay stuck
• 30:27 — Systemic barriers vs. personal responsibility
• 36:00 — Young generations: working harder, saving, and investing
• 39:34 — The influence of family on money values
• 43:25 — Retirement cost myths; living below your means
• 48:03 — Annual Sandwich Survey: lessons from tracking grocery inflation
• 53:10 — Main risks and fears in retirement; decision on long-term care
• 55:55 — The necessity of meaningful activity in early and late retirement

Final Thoughts

This episode blends humor and homey wisdom with hard truths, tackling uncomfortable realities about personal responsibility, generational change, and the cultural shift toward instant gratification. Len encourages listeners to confront the realities of their circumstances, embrace sacrifice, and carefully assess risk—not just in finances, but in life choices and retirement. Family stories, relatable analogies (like sandwich prices), and a clear-eyed take on how financial guidance has changed make this episode essential listening for anyone frustrated by "too nice" or generic personal finance advice.

Find Len Penzo:

• lenpenzo.com
• Twitter: @lenpenzo
• "True Money Stories" available on Amazon

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