Learning From Literature

How I Invest My Money by Joshua Brown and Brian Portnoy

Cover of How I Invest My Money by Joshua Brown and Brian Portnoy

How I Invest My Money: Finance Experts Reveal How They Save, Spend, and Invest by Joshua Brown and Brian Portnoy is a personal finance book published in 2020.

While financial experts often share investment advice, few are asked where they personally invest their own money. For instance, nearly half of U.S. mutual fund portfolio managers don’t even invest in their own funds. 

In this book, 25 financial professionals were asked to share how they manage their finances. Each expert wrote a short chapter (3-10 pages) outlining their mindset on money and investing, making it an easy read. While they all agree on some core principles, there’s no single “right” way to handle money.

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Table of Contents

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Ch 1 – Morgan Housel 
  • Author of The Psychology of Money
  • Independence is about your savings rate, not income. Once you earn enough, controlling lifestyle expectations helps you save more.
  • Despite higher incomes, our lifestyle has stayed the same since most things we enjoy—like walks, reading, and podcasts—are inexpensive.
  • Investors should pick strategies that match their goals. Dollar-cost averaging into low-cost index funds offers the best odds of success.
  • If you can meet your goals without extra risk, why try to outperform the market?
  • My strategy focuses on saving, patience, and trusting in long-term global economic growth, not on picking sectors or timing recessions.
Ch 2 – Christine Benz 
  • A low-cost, simple portfolio lets us focus on what matters: rewarding careers, passions like music and travel, community involvement, and family.
  • Financial compatibility with your partner is key to financial success, but often overlooked.
  • We understand markets move in cycles, so downturns don’t bother us.
  • Success in life is about balance, and my investments reflect that.
Ch 3 – Brian Portnoy
  • True wealth is the ability to fund a life that’s meaningful to me.
  • In a successful money life, investing is easy once you cut through the noise. The real work is in earning, spending, saving, and borrowing.
  • Tracey and I have been disciplined in spending, not because of a strict budget, but because we don’t covet big-ticket items like cars, jewelry, or art.
  • After two decades with top fund managers, my takeaway is: we should all own stock and bond index funds (or ETFs), allocate reasonably, and get on with life.
Ch 4 – Joshua Brown 
  • Almost everything I do has a long-term focus; I don’t day trade or swing trade.
  • When people disagree about a stock or sector bet, the simple resolution is time.
  • A skilled advisor knows not just investments, but their clients well enough to find the right mix of investments for each person.
Ch 5 – Bob Seawright 
  • Humans lack courage more than genius, and persistence most of all. Sticking to financial plans is often harder than creating them.
  • Our decision-making defaults to immediate, tangible rewards, making it easy to short-change and ignore long-term investments.
Ch 6 – Carolyn McClanahan
  • I was taught to invest in myself, and the joy of reading was another gift from my family.
  • Our spending reflects our values—experience, charity, and convenience—with little spent on consumer goods.
  • The key to financial independence isn’t how much you save, but how much you spend.
Ch 7 – Tyrone Ross 
  • I grew up in a financially illiterate home, which led to hard financial lessons.
  • I later emptied my 401k, wasting it on living expenses, buying jewelry, a nice car, destroying my credit, and spending everything I made.
  • When you gain financial knowledge, it’s crucial to pass it on.
  • My investing history can be summed up as: failure pays the best interest.
Ch 8 – Dasarte Yarnway
  • Our values and who we are can be traced through how we choose to invest our money.
  • During the accumulation phase, time is my biggest asset.
  • The intersection of my time and values guides where I invest my money. If I value something or someone, I invest there. If it also buys back time, I’ll invest, as that allows me to reinvest that time into what I value.
Ch 9 – Nina o Neal
  • I see the stock market as a powerful tool for long-term goals, requiring careful management and discipline.
  • I favor dollar-cost averaging through monthly contributions, primarily investing in mutual funds and ETFs.
  • The greatest return on investment is my happiness and the freedom to love what I do without a corporate agenda.
  • We must prepare to live well both in the present and in the future.
Ch 10 – Debbie Freeman
  • Seizing financial opportunities has been key to building my financial independence.
  • I invest every month, regardless of market conditions, with a mix of ETFs and mutual funds.
  • Higher education was the best investment I ever made.
  • Life isn’t just about big milestones; it’s about enjoying the moments in between.
  • Be consistent and disciplined with your long-term goals.
Ch 11 – Shirl Penney
  • We have four broad categories of capital: personal capital (Mary Anne and myself), family capital (our daughters, nieces, and nephews), philanthropic capital (focused on education, ALS, and supporting military families), and fun capital (assets for enjoyment, not financial return).
  • We invest in a diversified portfolio, primarily consisting of index funds in the core.
Ch 12 – Ted Seides
  • My childhood was secure, stable, and worry-free, which I associate with contentment.
  • The loss of that stability shook me emotionally and financially; I was ill-prepared.
  • I didn’t have a financial plan back then, and I now realize it would have provided peace of mind and better decision-making.
  • When my cash flow is positive and I maintain a buffer for lean years, I feel stable and can invest long-term.
  • I’m comfortable with equity market volatility and avoid market timing, staying fully invested.
Ch 13 – Ashby Daniels
  • Excess often complicates life instead of making it more fulfilling; I don’t want things to own me.
  • Lifestyle choices will likely determine 80% of our financial future, yet few discuss their impact.
  • Reducing short-term volatility also reduces long-term return, so equities are logical if we can handle long-term thinking.
  • Chasing a few extra basis points of return is a waste of time for most investors, including me.
  • Trying to beat the market introduces the risk of underperforming. If we don’t need to beat the market, why take that risk?
  • If our goals require beating the market, we should reconsider those goals rather than risking a detour.
  • Sticking to a diversified portfolio of index funds is the closest thing to an investing superpower today. Patience is a simpler, more satisfying path.
  • Insurance is vital—it protects us from what can go wrong, enabling us to invest in what can go right.
Ch 14 – Blair duQuesnay
  • Early money memories form “money scripts”—deeply ingrained beliefs about money, like “Hard work earns money” or “Poor people are lazy.” Understanding these can help remove barriers to financial success.
  • Trying to beat the market is a losing game. In golf, par is good; avoiding bogeys matters more than making birdies. Very few professionals beat the market consistently after costs. The market return is solid, and low-cost index funds make it easy to capture if we accept it. I haven’t purchased an individual stock since.
  • As a financial advisor, I’ve learned that the “why” of investing is more important than the “how.” My goals are far more important than the returns of my portfolio. By focusing on avoiding mistakes, I trust my investments will meet my needs.
Ch 15 – Leighann Miko
  • We can only take meaningful action when we discover what truly matters to us. It’s okay to make decisions that don’t always make sense on paper.
  • Future me will thank present me for resisting instant gratification, especially when my values don’t align with the purchase.
  • Understanding what truly matters has given me more control over how I spend my money—or choose not to spend it.
Ch 16 – Perth Tolle
  • I view my personal investments as tools to serve my mission.
  • I focus on low-maintenance instruments like ETFs and index mutual funds.
  • My investable assets are divided into four goals/buckets with specific asset allocations:
    • Short-term/emergency funds: 100% money market
    • General investing and cash for opportunities: 50% stocks, 50% cash
    • Retirement: 90% stocks, 10% bonds
    • Charitable giving: 20% stocks, 80% bonds
  • Investing can also be a form of expression.
Ch 17 – Joshua Rogers
  • Overobsession with personal investments (e.g., checking portfolios too often) may yield short-term gains, but long-term, it can lead to emotional decisions and poor results.
  • Everyone should have a financial advisor as a sounding board to provide objective advice.
  • Avoid loss avoidance. When facing a loss, consider the opportunity cost of holding onto it. Good traders move on quickly from losses to refocus on better investments.
Ch 18 – Jenny Harrington
  • I don’t own shares in my brother’s successful ice cream company to avoid risking our personal relationship over money.
  • I grew up in a financially volatile household and saw the downsides of living above our means, relying on potential big wins.
  • I invest heavily in myself and my business.
Ch 19 – Michael Underhill
  • I learned early on the immense value of hard work, grit, and being self-sufficient by living on cash flow.
  • The performance of individual securities is unpredictable, and so is the performance of portfolios in the short term.
  • Inflation of 2% annually for 30 years reduces purchasing power by 45%, introducing “longevity risk” — the risk of outliving one’s financial resources in retirement.
Ch 20 – Dan Egan
  • I save to afford future expenses and have a buffer for the unexpected.
  • Since starting work at 16, my hourly rate has grown nearly 10-fold, thanks to reinvesting in myself.
  • My biggest asset is myself—my time and effort—and I focus most of my attention here.
  • I invest in a low-cost, globally diversified portfolio of ETFs.
  • People can become owned by their money and possessions, spending their lives managing them instead of enjoying freedom. Money should be a servant, not a master; it should only be valued for the joy it brings or the pain it removes. Otherwise, give it as little attention as possible.
Ch 21 – Howard Lindzon
  • Charlie is my financial advisor when it comes to market asset allocation. 
  • We talk as business partners at least once a week about the markets and about allocations once a month.
  • Charlie uses low cost ETFs (Vanguard, Schwab) for building client portfolios
Ch 22 – Ryan Krueger
  • The greatest trick the devil played on investors is making them think investing matters most; the working part—both the deposits and the discipline—moves the needle more.
  • A good partner can improve anyone’s approach to investing.
  • The most important piece of my life wasn’t planned, but pure luck—my wife agreeing to marry me. She’s not focused on money; she’s fully invested in raising our five kids.
Ch 23 – Lazetta Rainey Braxton 
  • My first investment was in myself. Building my human capital as a high school student paid off.
  • I strongly believe in index investing as the core, with satellite investments like real estate, stocks, and business ownership.
  • Connecting human capital and financial capital reveals that my career and my husband’s serve different purposes. He’s the bond investment, with steady income and low risk, while I’m the equity investment, taking on higher risk as an entrepreneur.
  • We’re grateful that our values align and that we laid the foundation for financial flexibility early on.
Ch 24 – Marguerita Cheng 
  • The best advice my dad gave me was not to define myself by possessions, but by my accomplishments and education.
  • Money shouldn’t be the sole factor in life decisions.
  • While money doesn’t buy happiness, it provides peace of mind, freedom, and flexibility.
  • Money means different things to different people, shaped by experiences and values.
  • “What if” scenarios will happen, even if you don’t prepare for them.
  • My philosophy on money shapes my investment approach: I focus on flexibility and discipline.
  • I prefer simplicity, avoiding over-optimism or pessimism, which my clients value. My approach is a trifecta of dollar-cost averaging, tax-free growth, and time value.
  • Just as we wouldn’t raise illiterate children, financial literacy should be taught in schools.
Ch 25 – Alex Chalekian
  • To understand why people invest the way they do, it’s crucial to know their background and first experiences with money. It’s important to understand what money means to them and how early experiences shaped their views on wealth.
  • Wealth means different things to different people. For me, after seeing my family struggle, it means financial independence, health, time, and options.
  • Dollar-cost averaging may be boring, but it works.
  • I prefer passive investments like ETFs and index funds in my retirement accounts.
  • Money is simply a means to an end.
  • Take the time to discover what wealth means to you. Once you understand this, build the foundation for a happier future.
Conclusion – Main Ideas to Remember
  • Money scripts, or unconscious beliefs about money, often influence decisions more than mathematical analysis.
  • There are many ways to invest and build wealth, but key principles include saving smartly, borrowing wisely, and spending prudently.
  • If you can meet your goals without taking extra risk, there’s no need to introduce risk unnecessarily. If your goals require beating the market, revise your goals instead of taking on excess risk.
  • Money can buy happiness by creating opportunities and providing financial flexibility.
  • Money reflects our values and identity, with saving and spending habits showing who we are.
  • Investing in human capital (yourself and others) is often the most fulfilling investment.
  • Teaching your children financial literacy is a valuable gift.
  • You don’t have to solve financial problems alone—meet with a professional for guidance.
  • Even financial experts have advisors.
  • Keeping lifestyle expectations in check is key to building wealth faster.
  • Money is a tool to meet personal goals.
  • Define your goals and values, allocate your money accordingly, and invest mainly in index funds or ETFs.

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