Edited by Joshua Brown and Brian Portnoy – How I Invest My Money: Book Review & Audio Summary

Book Info

• Book name: How I Invest My Money
• Author: Edited by Joshua Brown, Brian Portnoy
• Genre: Business & Economics, Self-Help & Personal Development
• Published Year: 2020
• Publisher: Harriman House
• Language: English

Audio Summary

Synopsis

Ever wondered what financial experts actually do with their own money? This refreshingly honest book pulls back the curtain on the personal investment strategies of 25 top finance professionals. Instead of generic advice about asset allocation and retirement planning, editors Joshua Brown and Brian Portnoy asked contributors to reveal their real-world financial decisions and the deeply personal reasons behind them. From billionaire investors to financial advisors, each essay explores the “why” behind investing—showing that money management isn’t just about maximizing returns, but about aligning your finances with your values, goals, and what truly matters in your life.

Key Takeaways

• How you invest should reflect your personal values and life goals, not just follow universal investment rules or maximize returns
• Financial experts often make different investment choices for themselves than what they recommend to clients, and that’s not hypocrisy—it’s recognizing that everyone’s situation is unique
• Dividend-paying stocks can provide both stable income and growth potential, making them ideal for long-term financial independence
• Building an “independence fund” by maintaining your lifestyle while banking raises can create powerful financial freedom over time
• The most successful investors focus on the “why” of investing first, which then clarifies the “how” of specific investment choices

My Summary

When Financial Experts Get Real About Money

I’ll be honest—when I first picked up this book, I was skeptical. Another investment book? Really? But “How I Invest My Money” completely flipped my expectations. Instead of the usual prescriptive advice about index funds and compound interest (though those certainly have their place), this collection does something radical: it asks financial experts to get vulnerable about their actual money decisions.

What struck me immediately was how personal these essays are. We’re not talking about theoretical portfolios or hypothetical scenarios. These are real people—some managing billions, others running boutique advisory firms—explaining where their money actually goes and why. It’s like getting a peek at someone’s bank statement, except with context and meaning attached.

The book features 25 contributors, each offering a chapter about their personal investment philosophy. While the summary I’m working from highlights just a few perspectives, including Morgan Housel and Jenny Harrington, the full book provides an even richer tapestry of approaches. What becomes clear quickly is that there’s no single “right” way to invest—there’s only what’s right for you.

The Doctor Analogy That Changes Everything

Morgan Housel opens with a question that billionaire Sandy Gottesman asks all job candidates at his investment firm: What do you own and why? Not “What stocks look good right now?” or “Where’s the market heading?” but rather, what have you personally chosen to do with your own money?

This might seem like a gotcha question at first. After all, Morningstar found that only half of mutual fund managers invest in their own funds. Doesn’t that smell like hypocrisy? Shouldn’t experts practice what they preach?

But Housel brilliantly dismantles this assumption with an analogy about doctors. He references Ken Murray’s 2011 article “How Doctors Die,” which revealed that physicians with terminal illnesses typically choose far less aggressive end-of-life treatment than they prescribe for patients in similar conditions. Are doctors being hypocritical? Not at all.

Doctors understand their situation completely—they know exactly what aggressive treatment entails, the suffering it causes, and the slim odds of success. Their patients, lacking that expertise, may still hope for miracles and want every possible intervention. Different people, different needs, different choices. All valid.

This really resonated with me because I’ve fallen into that trap of thinking there must be one “optimal” investment strategy. If it’s good enough for Warren Buffett or Ray Dalio, it should be good enough for me, right? But that thinking ignores the most important variable: what I actually want from my money.

A financial advisor might recommend aggressive growth stocks to a young client while keeping their own money in more conservative investments. That’s not dishonest—it reflects different life circumstances, risk tolerances, and goals. The advisor might be nearing retirement or have family obligations that require stability. The client might be 25 with decades to recover from market downturns.

The Independence Fund: Investing in Freedom

Housel’s personal strategy centers on what he calls an “independence fund,” and this concept has stuck with me since reading about it. He and his wife identified their core value: independence. Not luxury, not status, not even traditional wealth—but the freedom to make choices on their own terms.

Here’s what makes their approach so powerful: despite their income rising steadily over more than a decade, they’ve kept their lifestyle essentially frozen at the level it was when they got married. Every raise, every bonus, every increase in income goes straight into savings. Not to buy a bigger house or a nicer car, but to buy something more valuable—optionality.

This flies in the face of lifestyle inflation, which is probably the biggest wealth killer for high earners. Most of us, when we get a raise, immediately adjust our spending upward. We “deserve” that nicer apartment or newer car. Before long, we’re making twice what we made five years ago but somehow still living paycheck to paycheck.

The Housels took a different path. That independence fund isn’t earmarked for retirement at 65 or some distant goal. It’s there to provide freedom now and in the future—freedom to turn down projects that don’t align with their values, freedom to take career risks, freedom to weather unexpected challenges without panic.

I’ve tried implementing a version of this in my own life, though I’ll admit it’s harder than it sounds. When Books4soul started generating more revenue, my first instinct was to upgrade my home office setup, maybe take nicer vacations. And I did some of that. But I also started automatically routing a percentage of every increase into a separate account I literally named “Freedom Fund.” Just naming it differently changed how I thought about it.

The psychological shift is real. That money isn’t for retirement (I have other accounts for that). It’s not for emergencies (that’s what an emergency fund is for). It’s specifically for independence—for having the option to say no, to take a sabbatical, to pursue a project that might not be immediately profitable but feels meaningful.

Dividend Stocks: The Overlooked Income Engine

Jenny Harrington’s chapter introduces another compelling strategy that emerged from a specific client need. In 2001, a 55-year-old client was preparing for early retirement. His challenge? He needed income now, but he also needed that income to grow over the next several decades. This is trickier than it sounds.

Traditional fixed-income investments like bonds provide stability but no growth. You get your interest payments like clockwork, but those payments don’t increase with inflation or your changing needs. Meanwhile, growth stocks might appreciate over time, but drawing income from them requires periodically selling shares, which gradually depletes your investment base.

Harrington’s solution was dividend-paying stocks, and her explanation of why they work so well for certain goals is enlightening. When you buy dividend stocks, you’re purchasing ownership in established companies that regularly distribute a portion of their profits to shareholders. Unlike bonds, where you’re a lender receiving fixed interest, you’re a part-owner receiving a share of growing profits.

The magic happens when you invest in mature, stable companies with long histories of consistent revenue. Think AT&T, Verizon, IBM—corporations that aren’t sexy or explosive growth stories, but that generate reliable cash flow year after year. As these companies grow (even modestly), their dividends typically grow too. You get income now, and that income increases over time without selling any shares.

Harrington also highlights more niche opportunities like Douglas Dynamics, a snow plow manufacturer. On the surface, Douglas seems inconsistent—sales fluctuate year to year depending on weather patterns. But zoom out to eight-year cycles, and a clear upward trend emerges. By understanding these longer cycles, Harrington could invest with confidence in the company’s dividend sustainability and growth.

What I appreciate about this strategy is how it aligns investment structure with life goals. If you need income, dividend stocks provide it without the anxiety of timing the market for sales. If you need growth, the right dividend stocks deliver that too. It’s not the flashiest approach—you won’t get rich quick buying AT&T—but for certain life stages and goals, it’s remarkably effective.

I’ve started incorporating more dividend stocks into my own portfolio, not because I need the income right now, but because I like the psychological benefit of seeing those payments arrive. It makes investing feel more tangible and less abstract than just watching account balances fluctuate. Plus, I’m reinvesting those dividends now, which should compound nicely over time.

Why “Why” Matters More Than “How”

The overarching theme that ties these diverse investment approaches together is the primacy of purpose. The financial industry spends enormous energy debating the “how” of investing: Active versus passive management. Growth versus value stocks. Domestic versus international exposure. Real estate versus equities. These questions aren’t unimportant, but they’re secondary.

The primary question is “why?” Why are you investing at all? What do you want your money to do for you? How does your portfolio serve your actual life, not some theoretical optimal outcome?

For Housel, the answer is independence. That clarity makes every financial decision easier. Should he buy a more expensive house? Only if it doesn’t compromise the independence fund. Should he invest in high-risk, high-reward opportunities? Only with money he can afford to lose without impacting his freedom.

For Harrington’s client, the answer was sustainable income for early retirement. That clarity pointed directly toward dividend stocks as the solution. A different goal—say, leaving a large inheritance or funding a business venture—would have suggested entirely different investment strategies.

This perspective has been genuinely transformative for how I think about money. I used to approach investing almost like a video game: maximize returns, beat the market, accumulate the highest score. But that framing was making me miserable. I’d stress over every market downturn, constantly second-guess my allocation, and feel like I was never doing enough.

Now I start with purpose. What do I want? For me, it’s a combination of things: security for my family, freedom to write and create without financial pressure, and the ability to be generous when opportunities arise. With those goals clarified, investment decisions become much simpler. I need some stable, low-risk assets for security. I need some growth investments to maintain purchasing power. And I need sufficient liquidity to act on opportunities without disrupting long-term plans.

None of this requires beating the market or finding the next Amazon. It just requires aligning my portfolio with my actual goals. That’s far less stressful and, ironically, probably more likely to succeed over time because I’m not constantly tinkering or panic-selling during downturns.

Applying These Lessons to Real Life

So how do you actually put these principles into practice? Here are some concrete applications I’ve found helpful:

Start with values clarification. Before you touch your portfolio, spend time identifying what you actually value. Not what you’re supposed to value or what sounds impressive, but what genuinely matters to you. Is it security? Adventure? Family? Independence? Creative freedom? Philanthropy? Write it down. Be specific. This becomes your investment north star.

Resist lifestyle inflation deliberately. The Housel independence fund strategy works because it’s proactive. Don’t wait until you feel like you can afford to save more. Decide now that future raises will go primarily (or entirely) to savings. Your current lifestyle is clearly sustainable—you’re living it. Lock it in and bank the growth.

Match investment vehicles to specific goals. Stop thinking about your money as one undifferentiated pile. You have different goals with different timelines. Short-term security might call for high-yield savings or short-term bonds. Long-term growth might suggest index funds. Income needs might point toward dividend stocks or real estate. Different money, different jobs.

Embrace boring when appropriate. The dividend stock strategy isn’t exciting. You won’t have cocktail party stories about your prescient investment in a snow plow company. But if it serves your goals, who cares? The best investment is often the one you can stick with through market cycles without panicking, and boring tends to be easier to hold.

Regularly reassess alignment. Your goals will evolve. The investment strategy that served you at 25 probably won’t be optimal at 45 or 65. Set an annual or semi-annual reminder to revisit your “why” and make sure your portfolio still reflects it. This isn’t market timing—it’s life timing.

What This Book Gets Right (and Where It Has Limitations)

The greatest strength of “How I Invest My Money” is its radical honesty. These aren’t sanitized case studies or hypothetical examples. These are real people with real money making real decisions and explaining their reasoning. That authenticity is rare in financial writing, which tends toward either academic abstraction or salesy prescriptions.

The diversity of perspectives is also valuable. With 25 contributors, you get exposure to approaches you might never have considered. Some contributors prioritize charitable giving. Others focus on real estate. Some are aggressive risk-takers; others are deeply conservative. This variety reinforces the book’s central message: there’s no one right answer.

The book also succeeds in making investing feel more human and less mechanical. Money isn’t just math—it’s psychology, values, relationships, and meaning. By grounding investment decisions in personal context, the book makes finance more accessible and less intimidating.

That said, the book has some limitations worth noting. First, all the contributors are already financially successful. While their insights are valuable, someone struggling with debt or living paycheck to paycheck might find limited immediate applicability. The problems of how to invest surplus wealth are good problems to have, but they’re not everyone’s problems.

Second, the book is light on specific how-to guidance. If you’re looking for detailed instructions on opening a brokerage account, calculating asset allocation, or understanding tax implications, you’ll need other resources. This book is about philosophy and purpose, not mechanics.

Third, some readers might find the personal essay format uneven. Not every contributor is an equally engaging writer, and some chapters will resonate more than others depending on your situation and preferences. That’s somewhat inevitable with an anthology format, but it’s worth knowing going in.

How This Compares to Other Investment Books

The investment book landscape is crowded, so it’s worth situating “How I Invest My Money” among its peers. Traditional classics like Benjamin Graham’s “The Intelligent Investor” or Burton Malkiel’s “A Random Walk Down Wall Street” provide comprehensive frameworks for investment strategy. They’re invaluable for understanding market mechanics and investment theory.

More recent popular books like “The Simple Path to Wealth” by JL Collins or “The Little Book of Common Sense Investing” by John Bogle offer clear, actionable advice for building wealth through low-cost index funds. These are fantastic resources for the “how” of investing.

Where “How I Invest My Money” distinguishes itself is in the “why.” It’s less concerned with optimal asset allocation percentages and more interested in the human dimension of financial decision-making. In that sense, it’s more similar to Morgan Housel’s other work, “The Psychology of Money,” which explores behavioral finance and the emotional aspects of wealth.

If I were building a personal finance reading list, I’d include this book alongside, not instead of, the classics. Read Bogle to understand why index funds make sense. Read Graham to understand value investing principles. Then read “How I Invest My Money” to figure out how those tools might serve your specific life goals.

Questions Worth Pondering

As I finished this book, I found myself sitting with some questions that don’t have easy answers. What would you be willing to sacrifice financially to gain more independence or freedom? How much of your investment strategy is driven by genuine personal goals versus social comparison or vague anxiety about the future?

If you had to explain your current investment approach to someone like Sandy Gottesman—what you own and why—would your answer reveal a coherent philosophy, or would it expose some uncomfortable inconsistencies? And perhaps most importantly: if money is a tool for building the life you want, what life are you actually trying to build?

These aren’t rhetorical questions. I genuinely encourage you to think about them, maybe even write out your answers. The clarity that comes from wrestling with these questions can be more valuable than any specific investment tip.

Join the Conversation

I’d love to hear your thoughts on this book and these ideas. Have you read “How I Invest My Money”? Did any particular contributor’s approach resonate with you? More broadly, how do you think about the “why” of your own investing?

Here at Books4soul, we’re building a community of thoughtful readers who want to go beyond surface-level summaries and really engage with ideas. Drop a comment below sharing your perspective, or if you’ve implemented any strategies inspired by this book, tell us how it’s going. The best insights often come from the conversation, not just the original text.

And if you found this summary helpful, consider checking out the full book. While I’ve covered some key concepts here, the complete collection of 25 essays offers far more depth and variety than any summary can capture. Each contributor brings unique wisdom worth exploring.

Thanks for reading, and here’s to investing with purpose—whatever that means for you.