Historian and investor Joseph Moore, PhD, spent over a decade digging through 300 years of American financial advice to find out what actually worked, and what everyday people, not just the Rockefellers of the world, were told to do with their money.

In this conversation with Melissa Joy, CFP®, Joseph explains why Americans used to say “go ahead” instead of “get ahead,” what that shift in language reveals about self-reliance and the American dream, and why perspective on how hard life used to be (one and a half shirts per person in 1870, no flush toilets well into the twentieth century) can reframe how we think about today's challenges.

They also dig into a subject close to Melissa's heart: the long, well-documented history of women managing, investing, and building wealth, from Ladies' Home Journal financial columns to Abigail Adams quietly out-investing John Adams. Joseph shares what his own real estate investing taught him about the myths of passive income, makes an unlikely defense of personal finance gurus, and reflects on how his working-class upbringing in rural South Carolina shaped a book that became a national bestseller.

What You'll Learn

• Why Americans historically said “go ahead” instead of “get ahead,” and what that language reveals about self-reliance versus collective pessimism
• How dramatically material life has improved in the last 150 years, and why that context matters when comparing today's challenges to the past
• Why the idea of a long history of stay-at-home moms is a myth, and how women's self-employment and part-time income kept most American families afloat
• The overlooked history of women investing in mortgages, securities, and real estate going back to the 1700s, including Abigail Adams's investment returns
• Why real estate is not always a passive investment, and what it actually takes to make money owning it
• A historian's case for what personal finance gurus get right, and where their advice tends to fall short
• Why saving a percentage of every paycheck in the stock market is newer advice than most people realize
• The power of living on one income and investing the other, a strategy with roots stretching back generations

Guest Bio

Joseph Moore, PhD, is a national bestselling author, historian, and investor whose self-experimentation with history's wildest financial strategies made him financially independent in his mid-40s. His writing has appeared in The New York Times and through HarperCollins and Oxford University Press. His new book, How to Get Rich in American History: 300 Years of Financial Advice That Worked (and Didn't), is an instant USA Today bestseller. You can find his free newsletter and more of his writing at josephmoorebooks.com, and follow him on Instagram.

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Retirement talk tends to fixate on a magic number, but Melissa Joy, CFP®, and fellow financial planner and podcaster Stephanie McCullough argue the real work happens well before and long after that number is reached. In this candid conversation, the two planners compare notes on what they see in their own practices: clients who retire on a fixed rule of thumb only to discover it doesn't flex with real life, retirees who under-spend out of fear even when the plan says they can afford more, and families quietly overwhelmed by aging parents' finances, unspoken inheritances, and adult children who haven't yet launched.

Melissa and Stephanie also dig into the myths that shape how people think about retirement long before they get there, from the outdated idea that retirement equals age sixty-five, to the belief that a portfolio should get more conservative simply because a client is getting older.

They close with a rapid-fire round covering the most overrated retirement rule of thumb, the most underestimated expense, and what people should and shouldn't be losing sleep over, before reflecting on how their own work with retirees has shaped how they each plan to retire themselves.

What You'll Learn

• Why the idea that retirement equals age sixty-five is outdated, and how ageism, layoffs, and longer lifespans complicate that math
• Why Melissa and Stephanie now encourage many clients to spend more, not less, in the early years of retirement
• The difference between a plan “failing” and a plan needing adjustment, and why that framing matters
• Why the four percent rule and age-based portfolio allocation are two of the most overrated pieces of retirement conventional wisdom
• The most underestimated retirement expenses, including Medicare surcharges (IRMAA) and dental care
• How to navigate family conversations about aging parents' finances, inheritance, and adult children who still rely on financial support
• Why having a plan for aging in place, or choosing not to, is one of the most overlooked parts of retirement planning
• Why even confident self-managed investors need a transition plan for handing off financial management as they age

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

What is money actually for? On this episode of Women's Money Wisdom, Melissa Joy, CFP®, welcomes Shanna Due, CFP®, founder of Due Financial and editor of the book series More Than Money and Even More Than Money, back to the podcast to talk about her newest project.

Shanna walks through how a group of advisors turned an idea into a traditionally published book, why the follow-up book needed to go further than the first, and how the five-purposes framework, living, changing, dreaming, giving, and enduring, reframes money as a tool for a meaningful life rather than an end in itself.

The conversation also digs into how readers can use the book to find and vet a financial advisor, from understanding the alphabet soup of credentials to knowing what questions to ask and what a real advisor relationship looks like over time.

Melissa and Shanna talk candidly about permission to spend versus permission to save, giving during your lifetime, and why finding an advisor you genuinely like and trust matters just as much as their credentials. All proceeds from the book benefit Third Decade, a nonprofit that provides long-term financial coaching to people rebuilding their financial lives.

What You'll Learn

• How a group of financial advisors turned an idea into a traditionally published book, twice
• Why Even More Than Money was built around a five-purposes framework: living, changing, dreaming, giving, and enduring
• The difference between a must-save mindset and giving yourself permission to spend
• Why giving during your lifetime can be as meaningful as giving through an estate
• How to decode financial advisor credentials and know what questions to ask before hiring one
• What a real financial advisor relationship looks like, from one-time projects to ongoing partnerships
• Why liking and trusting your advisor matters as much as their technical expertise
• How the book's proceeds support Third Decade, a nonprofit providing long-term financial coaching

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Real estate decisions carry enormous financial weight, and yet many people navigate them with a realtor who treats the work as a side hustle rather than a true advisory relationship. Melissa Joy, CFP® sits down with Donna Castillo, a top 1% producer realtor with Intero Real Estate Services in Silicon Valley, to talk about what separates a transactional agent from a real financial partner. Donna shares how she works with clients neighborhood by neighborhood, weighing schools, square footage, and competitive dynamics so buyers can win a home without overpaying by six figures.

The conversation turns to Donna's R.E.A.L. Method, a framework she created specifically for homeowners over 55 who are weighing whether to stay put, downsize, or explore new options like an ADU or a 55-plus community. Melissa and Donna cover capital gains exposure on long-held homes, the role of a good lender in structuring financing around equity compensation and investment portfolios, and why having candid family conversations about aging in place, trusts, and estate plans is one of the most generous things a person can do for the people they love.

What You'll Learn

• Why working with a realtor who treats real estate as a true advisory relationship, not a side hustle, matters most on high-value transactions
• How hyper-local market knowledge, down to the specific street, shapes a competitive offer strategy
• The R.E.A.L. Method: a framework built for homeowners 55-plus to evaluate reality, equity, available options, and lifestyle impact
• How capital gains exclusions work for primary residences, and why the math differs for single versus married homeowners
• How a 1031 exchange can defer capital gains on rental property, and why the full proceeds need to stay in real estate
• Why using investment portfolios, RSUs, and other equity compensation to finance a home purchase requires careful tax planning with the right lender
• The importance of having proactive conversations with family about aging in place, trusts, and estate plans before a crisis forces the decision

Connect with Donna:

Website: donnacastillo.com

Facebook: facebook.com/gotodonna

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Most investors assume the key to building wealth is picking the right stock. Melissa Joy, CFP®, says the far more important decision is how you structure your portfolio in the first place, and how much risk you choose to take on. In this solo episode, Melissa breaks down asset allocation, the mix of cash, bonds and stocks that make up an investment portfolio, in plain language, without requiring a finance degree to follow along.

Melissa walks through the fundamentals of stock and bond investing, explains the common shorthand investors use to describe their portfolios (like 60-40 or 80-20), and shares how she helps clients think through allocation decisions using broader, 15 to 20 percent notches rather than micromanaging every 5 percent. She also digs into the questions that matter most when setting your own mix: your time horizon, your investing psychology, your tax situation, and how you would actually feel if your portfolio dropped 20 to 30 percent for an extended period. The goal, she says, is not the perfect allocation. It is one that helps you stay invested through both difficult and exuberant markets.

What You'll Learn

• What asset allocation actually means, and why it matters more than picking individual stocks
• The differences between cash, bonds and stocks, and the pros and cons of each
• How to read portfolio shorthand like 60-40 or 80-20
• Why Melissa builds portfolios in 15 to 20 percent notches instead of fine-tuning by 5 percent increments
• How time horizon, investing psychology and tax considerations shape the right mix for you
• Why the first days of retirement can be the riskiest, and how allocation needs can shift over time
• How to check your current asset allocation and decide whether it needs adjusting

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

AI has made everyday life more convenient, but it has also given scammers a powerful new set of tools. In this episode, Melissa Joy, CFP®, is joined by Patrick Coughlin, CEO of Savi Security and author of the new book The Dark Side of the Boom: How Scammers Hijacked the AI Revolution. After building and selling a cybersecurity company to Splunk, Patrick shifted his focus to protecting everyday families following a deeply personal experience: a sophisticated AI voice cloning scam that targeted his own mother.

Patrick walks through how AI tools are supercharging scam operations around the world, why imposter scams have become the most reported fraud type in the country, and the practical habits families can build to protect themselves, from creating a family code word to running a second channel check before sending money. Melissa and Patrick also discuss the role financial advisors and trusted contacts can play in catching fraud early, and how parents can talk to kids and teens about digital safety without shame.

What You'll Learn

• How an AI voice cloning scam targeted Patrick Coughlin's mother, and what helped her recognize it in time
• Why digital fraud now costs Americans almost $200 billion a year and has grown eightfold since the launch of ChatGPT
• The "five families of fraud" and how scam organizations around the world specialize like businesses
• Why imposter scams are now the number one reported fraud type, making up 33 percent of all scams in 2025
• What a "hot zone" moment looks like, and the three ingredients scammers rely on to pressure victims
• How a family code word and a second channel check can stop a scam before money changes hands
• Why caller ID can be faked, and what to do instead if you get a call from your bank's fraud department
• The role trusted contacts and financial advisors can play in catching fraud early
• How to talk with teens and aging parents about scams without shame, and why younger generations are targeted more often than they realize
• How free tools like ScamWise can give you a fast second opinion on a suspicious text, email, or piece of mail

Download the Digital Fraud Protection Guide

Connect with Patrick: LinkedIn

Follow Patrick: Instagram

Savi Security: Website

Savi Security LinkedIn: LinkedIn

Savi Security Instagram: Instagram

The Dark Side of the Boom: Book

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

What would it look like if your financial plan actually included a line item for aesthetics? Melissa Joy, CFP®, sits down with Stephanie Stewart, PA-C, founder of The Aesthetic Method, an award-winning medical spa in Ferndale, Michigan, to have the honest conversation that most financial planners and patients avoid entirely. From the secret dollars women squirrel away for skincare to the emotional weight of wanting to invest in how you look and feel, this episode brings a private topic into the open where it belongs.

Stephanie shares her remarkable path from emergency medicine to entrepreneurship, sparked by a car accident at 15 that required years of facial reconstructive surgeries. She opens up about the real cost of injectable treatments, what a full face assessment actually looks like, and how to find a provider you can trust. Melissa and Stephanie also explore the parallel between financial planning and aesthetic medicine, two fields built on transparency, trust, and the courage to say no when it is not the right fit.

What You'll Learn

• How burnout in the emergency department led Stephanie to found The Aesthetic Method in 2018
• Why women often keep aesthetic spending secret, and how to change that conversation
• What happens during a full face assessment and how a personalized treatment plan is built
• The difference between neuromodulators, bio-stimulators, and filler, and how long each lasts
• Real cost ranges for common injectable treatments, from 500 dollar Botox sessions to 3,500 dollar Sculptra plans
• Green flags and red flags to look for when choosing a med spa provider
• Why a provider willing to say no is a sign of someone looking out for you
• How financial planners and aesthetic professionals share a standard of care worth seeking out

Connect with Stephanie

theaestheticmethod.com

Instagram: The Aesthetic Method

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...