Summer Reading List Of “Best Books” For Financial Advisors – 2025 Edition

The ONE Thing: The Surprisingly Simple Truth About Extraordinary Results

(Gary Keller and Jay Papasan)

Diversification is a fundamental tenet of investing. With uncertainty about how any particular company will develop – and in the aggregate with uncertainty about how markets and the economy will evolve in the future – the best practice is to avoid putting all your eggs in one basket. Instead, we diversify across multiple investment opportunities – ideally, those that are not correlated (or even negatively correlated) with one another, to increase the likelihood that one will zig while the other is zagging, reducing the overall volatility of the portfolio. And as financial advisors who not only provide portfolio guidance to clients, but also have our own businesses to manage, the diversification approach often extends to our own business strategies; we often seek to reduce risks through diversification of our clientele (by size or generation of client), our marketing sources for new clients (from referrals to digital marketing), and even our service offerings or 'lines of business' (from AUM to alternative fee-for-service models).

Yet while diversification is quite universally accepted as a way to reduce risk in portfolios, there is some debate about whether it is an equally good idea to diversify (as much, or as quickly) when it comes to running a business. As steel magnate Andrew Carnegie once quipped:

And here is the prime condition of success, the great secret – concentrate your energy, thought and capital exclusively upon the business in which you are engaged. Having begun on one line, resolve to fight it out on that line, to lead in it, adopt every improvement, have the best machinery, and know the most about it. The concerns which fail are those which have scattered their capital, which means that they have scattered their brains also. They have investments in this, or that, or the other, here, there and everywhere. "Don't put all your eggs in one basket" is all wrong. I tell you "put all your eggs in one basket, and then watch that basket." Look round you and take notice; men who do that do not often fail. It is easy to watch and carry the one basket. It is trying to carry too many baskets that breaks most eggs in this country.

Accordingly, in their book "The ONE Thing", Jay Papasan and Gary Keller (of Keller Williams Realty, the largest real estate franchise business in the country) explore how business owners can create a similar level of focus in their businesses. As notably, while businesses may often focus down into a specialization over time, they don't necessarily have that level of focus and clarity from the start. In order to find that clarity, the authors recommend starting with a deceptively simple question to ask: "What's the One Thing I can do such that by doing it, everything else will be easier or unnecessary?"

Notably, the wording of this "Focusing Question" is quite intentional. It starts by asking what is the one thing that will create the greatest impact. As a result, it naturally forces a certain level of focus to consider not just "what are all the things that might be done to improve or grow the business", but "what is the one thing" that can have the most impact. The Focusing Question also orients itself heavily toward not just outcomes, but leverage – what is the one thing to do "that will make everything else easier or unnecessary"? Which naturally attenuates the question to find whatever is the biggest blocking point that might be inhibiting the business from getting to its next level of success (such that solving that particular problem 'will make everything else easier or unnecessary').

In turn, Papasan and Keller note that the nature and benefits of having focus aren't unique to just business. Their Focusing Question can be used in a wide range of contexts from personal life ("What's the one thing I can do in 90 days to get into better physical shape?") to family ("What's the one thing I can do this month to improve our marriage?"), and it can span both long-term strategic time horizons to shorter-term tactics (e.g., What's the one thing I want to do someday to achieve my purpose… What's the one thing I can do in the next five years to achieve my someday-goal… What's the one thing I can do this year to achieve my five-year goal… What's the one thing I can do this month, this week, or today…").

Ultimately, then, "The ONE Thing" approach and the Focusing Question provide a pathway to turn long-term goals and vision into short-term practical action steps that can actually lead to achieving that goal, with a framework that naturally creates focus by trying to identify the one thing that can be done next that will have the most impact. It also implicitly recognizes that when we try to do too many things at once, we rarely do any of them well enough to have a truly meaningful impact.

Or as Archimedes famously said, "Give me a lever long enough and I could move the world". "The ONE Thing" is meant to help us all figure out where to put that giant lever and focus our energy enough to actually be able to move it. For many independent advisory firm business owners in particular – who have lots of ideas of things they might do – this can be a highly impactful level of focus to achieve!

Building With The End In Mind: A Complete Succession Guide For Professional Service Owners

Acquiring Your Future Through A Succession Plan: A Primer For Next Generation Professional Service Providers

(David Grau Sr.)

The typical financial advisory firm is built to leverage the time and talents of its founder-owner, who is not only the manager of the practice itself, but also the lead provider of its advice services to clients. In the modern era, the availability of an ever-growing number of advisor technology tools, coupled with the staff leverage we gain by hiring client service administrators and associate advisors in a team around us, make it feasible for any advisor who works with clientele that pay appropriately for their services to create a $1M+ revenue practice over time. However, while technology and teams make it possible to create a financially strong advisory practice that generates very healthy profits, it is a business that will die with its founder (or at least die when its founder is no longer able to deliver advice services themselves).

Fortunately, in today's environment, it is increasingly feasible for advisory firm owners to sell their practices to another (typically larger) firm, providing not only continuity to clients themselves but a way for the founder to monetize the enterprise value that they've built. Which, given the stability of recurring AUM fees for well-served clients, can be quite a substantial sale value, in many cases adding up to 2–3X the firm's annual revenue (or what might be 6–9+ years' worth of profits). With the caveat that while clients may continue to be served and the founder can be well remunerated, the 'business' itself will still typically die with the founder's exit, assimilated into a larger enterprise that will serve the clients with its own culture and service model. In such scenarios, to the extent that founders want to ensure their clients are served a particular way after they sell, the best they can do is try to be selective about the firm they choose to sell to.

Unless… the founder cultivates their own internal successor, who is brought up and trained in the service philosophy and culture that the founder created in the first place.

Accordingly, in his new book series "Building With The End In Mind" and "Acquiring Your Future Through A Succession Plan", David Grau Sr. (founder of FP Transitions, which itself has helped to facilitate thousands of succession plans and exit sales over the past 25+ years) provides a series of primers for both founders and successors, respectively, about how to approach the goal of creating an internal succession plan.

The key, as Grau frames it, is that succession plans happen gradually, over time. From a training and development perspective, this allows many years for future successors to learn and be trained in the (founder's) way of doing business, and to practice and hone the various skills it takes not only to service clients successfully, but also to manage the business effectively. From a financial perspective, time allows successors to buy in through multiple tranches over the span of more than a decade, which makes it financially feasible for the successor (who uses the profits of the earlier tranches as they grow and are paid off, to afford the subsequent tranches even as the business grows), and provides ongoing upside to the founder (who still participates in the bulk of the equity growth they still own as the succession plan unfolds gradually over the years).

Arguably, the real benefit of reading Grau's new book series, though, is to help both founders and successors (as there is one book written for the perspective of each) think differently about the business itself and what it means to operate as a business that is creating shared enterprise value. For instance, founders often simply focus on how much money they're able to take home after overhead expenses (without much distinction between the income paid for being an advisor in the business, and the profitability for being an owner of the business), but once there's a second (successor) owner in the picture, it matters… in often unintuitive ways. For instance, with multiple owners, it may actually be in the founder's interests (and really, all owners' interests) to take lower salaries for themselves, as the increase in the bottom-line profitability can increase the valuation of the business (when valued as a multiple of earnings) even if the final take-home income is the same. More generally, financial value for owners is really a combination of Wages + Profit Distributions + Stock Appreciation (further increased by the payments for equity purchases in the case of the founder, or reduced by debt service payments in the case of the successor), which means both parties have multiple ways to adjust the financial levers of the business to better optimize the outcome of each over time.

And so for firms that have a 'G1' (first generation) founder and a 'G2' (next generation) successor coming to the table, Grau's series provides a meaningful book for each to read and glean a better mindset about how to approach the conversation and development of the succession plan. Or alternatively, may be an opportunity for one of them to buy the book for themselves, and then order a copy of the other book for their counterparty to learn from as well?

Culture By Design

(David Friedman)

Anyone who has worked in more than one company throughout their career has likely experienced that not all companies go about their business in the same way. To some extent, that's because every business differs in what it does and who it serves. But even among companies that are nominally in the same industry, offering the same kinds of services – like one advisory firm compared to another – there can still be remarkable differences in how they actually go about conducting their business and executing as a team to serve their clients. A phenomenon that is often characterized as the "culture" of the business.

In practice, the culture of most businesses is a reflection of its founder or key leaders. If the CEO is a detail-oriented service-minded person, then employees who share those qualities – who prioritize precision and client service – tend to be recognized and appreciated. This, in turn, results in a detail-oriented client-centric culture. If leadership is focused on growth above all else, the culture tends to reward growth-oriented behaviors (and might ignore – or simply tolerate – other behaviors from anyone who is still bringing in growth results). Notably, though, these 'key behaviors' aren't often explicitly defined. Instead, they're simply woven into the day-to-day fabric of what's recognized and rewarded, through leadership actions, performance reviews, compensation, and other incentives.

In "Culture By Design", successful entrepreneur and now culture consultant David Friedman explores how businesses can more intentionally 'design' and drive their culture, so it's not simply an expression of what senior leadership happens to do or 'seems to' reward, but something overtly stated, taught, reinforced, and celebrated.

At its core, Friedman's approach is adapted from the Ritz-Carlton, famous for its high-touch service culture. Ritz-Carlton propagates its culture across its locations around the world through the teaching of what it calls the "Ritz-Carlton Basics", such as "Any employee who hears a customer complaint owns the complaint", or "Escort guests rather than pointing out directions to another area of the hotel". Formulated as a series of 20 behaviors, these Basics are taught to every team member on an ongoing basis, anchored in a brief 10–12 minute Daily Lineup where each team reviews the day's work and spends a few minutes discussing the "Basic of the Day". This happens across every team, at every property, such that on any given day, tens of thousands of Ritz-Carlton employees are all reinforcing the same behavior. After 20 days to rotate through the 20 Ritz-Carlton Basics, the cycle begins again.

Notably, the Ritz-Carlton Basics aren't just general principles like "Integrity" or "Service"; they're concrete, actionable behaviors that team members can do and that the company can teach. In the same spirit, Friedman's book walks business leaders through a process to identify and formulate their own list of 10, 20, 30, or even 40 key culture behaviors. He then outlines how to create rituals around them – whether it's a daily standup like Ritz-Carlton's, or a weekly 'Fundamental of the Week' discussion – and how to communicate, coach, and lead around those behaviors to embed them across the organization.

For business leaders new to an 'intentional culture' approach, thinking about how to institutionalize rituals like daily standups that teach and train the culture behaviors may feel like a lot to bite off. But the core of Friedman's book is simple: Culture is a set of behaviors that a business identifies, teaches, celebrates, and rewards. And defining those behaviors – then weaving them into everyday operations – is how culture becomes a repeatable, scalable asset.

Which arguably is quite valuable for any organization that's growing and wants to maintain a strong culture – especially in an industry like financial services, where most firms now have access to the same products and knowledge to deliver the same recommendations, and where culture of the team itself may soon be the last true differentiator in how service is delivered to clients?

Misbehaving: The Making Of Behavioral Economics

(Richard H. Thaler)

When clients come forward with goals to pursue, there is often a fairly straightforward 'spreadsheet' answer to determine the financially optimal path. However, in practice, clients don't always implement the most 'efficient' answer: Sometimes, people instead act in a seemingly irrational manner. Which means financial advisors either need to be prepared for clients choosing to pursue 'suboptimal' solutions, or need to figure out how to better engage clients to get them to actually take the more optimal (e.g., financial-planner-recommended) path.

In their efforts to understand why and how clients (and consumers more generally) often seem to choose the less-than-rational path, economists have long studied the gaps between what economic theory predicts rational people should do and what they actually do instead. Over time, this body of knowledge has become known as "behavioral economics", a tacit recognition of how an individual's behaviors influence the financial choices they make.

In "Misbehaving", Richard Thaler, one of the early progenitors of behavioral finance research, explores the gradual development and growth of behavioral economics as a way to meld traditional economic analysis with behavioral theory. As Thaler frames it, behavioral economics blends traditional, logic-driven economics with the psychology of decision-making, seeking to explain why people make the (financial) decisions they do.

In the book, Thaler shares a wide array of examples that contrast rational behavior with real-world behavior (he often uses the personas of the Econ and the Human, respectively), from budgeting to willpower to investment decisions. Partly a history of the development of behavioral economics, and partly an analysis of what drives people's quirks and contradictions, Thaler helps to connect the way that human perception drives each component of our actions.

For advisors balancing the logic of spreadsheet answers against the messy reality of human behavior, "Misbehaving" offers a valuable roadmap for understanding why clients don't always act in financially rational ways. When clients make puzzling decisions, insist on suboptimal investment strategies, or hesitate to implement good advice, Thaler's insights can help advisors make sense of those reactions, offering a pathway to more productive conversations about how clients might proceed. While advisors don't necessarily need to name their clients' behavioral biases when they spot them, Thaler provides practical strategies for recognizing and navigating them as needed. And of course, "Misbehaving" can also provide a diagnostic dashboard to help advisors reflect on their own behavioral blind spots, considering whether they might benefit from making personal changes as well!

The Private Equity Playbook

(Adam Coffey)

Like many industries in recent years, the RIA space has been awash in Private Equity (PE) looking to invest in financial advisory firms, buoyed by our strong (often 25%+) profit margins and our sky-high (typically 95%+) retention rates. The potential for many advisors in their later years, who didn't have a clear pathway to succession, to 'suddenly' have a way to monetize their businesses has led to a growing volume of sales. And as organic growth rates of advisory firms have slowed, outside capital has become more appealing as a way to fund acquisitions to fuel growth inorganically. With so many PE firms that still want to invest, though, demand continues to be fierce, such that the ongoing buying power has just steadily driven up the valuation multiples of advisory firms themselves. Which in turn is triggering even more financial advisors to sell or raise capital from PE, given the valuations they can get.

Yet the caveat is that there is perhaps a darker side to the entrance of PE into the advisory business. In some cases, it's the shift to running the firm "more like a business" focused on maximizing shareholder value – a change that may feel jarring to the founder who previously owned the whole firm and was only accountable to themselves. In other cases, it's the realization that growing an advisory business at the pace and in a style that PE wants to grow is quite different from how most advisory firms are accustomed to growing (leading to a substantial level of 'change management' to have to accommodate). And sometimes, it can simply come down to the fact that founders are not accustomed to having a 'boss', but the implementation of PE capital and a Board governance structure where the founder is no longer the sole decision-maker and stakeholder is difficult to adjust to. Whatever the reason, it's crucial to recognize that as PE dollars have flowed in, a stark number of advisory firm founders at PE-funded firms have somehow found their way out in the past few years.

In "The Private Equity Playbook", former business leader Adam Coffey (who has nearly two decades of experience as the CEO of three different PE-funded service businesses) shares his perspective on what it's like, as a CEO, to successfully navigate the leadership evolution of a company that takes outside capital from a private equity firm, from preparing the business to take on an investor to navigating the growth phase and ultimately exiting at the other end of the 4–7 year journey.

The starting point is simply to understand the private equity business from the perspective of private equity investors themselves – what their motives and goals (to make money with money by earning a portion of what's made during the growth cycle) and how they measure their own success (e.g., the Multiple On Invested Capital [MOIC] and Internal Rate of Return [IRR], which are very sensitive not only how much the firm grows, but also how quickly the growth happens).

From there, Coffey highlights how founders can evaluate potential private equity investors, what to expect in terms of equity structure and shareholder agreement provisions, and how founders may have the opportunity to roll at least a portion of their equity forward to get what's known as "two bites at the apple" (where the founder monetizes a portion of the business upfront and retains the opportunity to benefit from a second sale when the PE firm exits alongside the remainder of the founder's equity in the future).

Perhaps even more useful for advisory firm founders who might be considering a private equity investment, though, is Coffey's perspective on what it's actually like to run a PE-funded business during the growth phase. He unpacks the core metrics and strategies that founders-turned-CEOs become accountable to in a PE-funded environment, such as driving EBITDA growth (with tactics like hiring consultants whose fees can be treated as 'one-time' expenses added back to future EBITDA, or considered 'below the line' CapEx expenditures that don't count against EBITDA in the first place), investing into technology (especially early on), expanding profit margins (if the business generates more profit on the same revenue, its valuation still increases as a multiple of that higher earnings level), and accelerating growth with M&A (both because acquiring revenue can speed up the pace of revenue growth but also because of the valuation expansion that comes from buying smaller companies at lower multiples to build a larger company that gets a size premium to its own multiple at exit).

As an experienced executive at multiple PE-funded businesses, Coffey provides a good primer for those who have never followed the path, offering insight into what the focus becomes when an advisory firm takes on private equity dollars (growing EBTIDA and enterprise value, and the levers to pull in order to do so). But for many advisory firm owners, it may also offer an interesting perspective on just how differently a private equity firm thinks about the business as a business compared to how most founders run advisory firms today. Which can be helpful context for those considering a private equity investment, as well as for those who don't want to, but still want to gain a better perspective on how to grow their enterprise value without outside capital!

The Pathless Path: Imagining A New Story For Work And Life

(Paul Millerd)

In decades past, it wasn't uncommon for an individual to remain with the same company for their entire career, either becoming a master in their chosen craft, or pursuing a management track and rising up the leadership ranks before eventually retiring. While this career arc is less common today, many individuals still find themselves on a particular path within their field (if not within a single company), with promotions and salary increases on the horizon if they keep their nose to the grindstone. Nevertheless, while such a path might be financially lucrative or carry perceived prestige, it might not necessarily be fulfilling – particularly if the higher-paying roles don't align with the individual's interests and goals.

In "The Pathless Path", Paul Millerd explores how individuals can end up on such a 'default path' and why they might consider stepping off it in order to pursue their own 'pathless path' – one that provides them with greater meaning while still providing sufficient income. Millerd writes from personal experience, as his own default path began at a prestigious consulting firm, working alongside CEOs and earning an attractive salary. However, after a severe health issue temporarily took him away from his work, he took a step back and began questioning whether he wanted to follow his current path for the rest of his career.

Realizing that consulting lacked the meaning – and the flexibility – he was craving, Millerd eventually decided to leave his job and begin working independently as a writer, career coach, and digital creator. The change brought him greater freedom (including the ability to work remotely from locations around the world) while still earning enough to support his lifestyle.

In the financial planning world, there are multiple possible 'default paths' that advisors might find themselves following – often without even realizing it. For instance, an entry-level hire at a large planning firm may assume their career path will progress from paraplanner to associate advisor to lead advisor to firm leadership and eventual partnership. However, somewhere along the way, they might find that their skills and interests don't quite align with this trajectory. Perhaps, after spending time as an associate advisor, they realize they enjoy conducting financial planning analyses and educating others on technical planning topics, but they are less energized by client-facing work. In this case, they might decide to step off the default path and instead join the firm's dedicated financial planning team – or even start their own firm offering outsourced financial planning services!

Default paths can also arise for firm owners in the form of continuous growth – more clients, more revenue, and (hopefully) more profits. However, a founder on this path might wake up one day and realize they've become an 'accidental business owner', spending most of their time managing the business and its employees rather than doing the client-facing work that they once loved. At that point, the founder may decide to take a step back and assess whether their current path is aligned with what brings them the most meaning. That reassessment might lead some founders to abandon the growth path and instead explore how to 'rightsize' their clientele and build a lifestyle practice – one that allows them to prioritize planning work and opens up time for family or for other interests.

Ultimately, the key point is that financial advisors (and other professionals) can find themselves on a 'default path' dictated by what others say they should do rather than a 'pathless path' that truly aligns with what truly brings them the most fulfillment (and still allows them to achieve their lifestyle goals). Which suggests that regular check-ins to evaluate whether an advisor's current path is one they're actively choosing could lead to greater career satisfaction and better alignment between professional goals and personal values.

Bittersweet: How Sorrow And Longing Make Us Whole

(Susan Cain)

As the financial planning industry increasingly acknowledges the relevance of financial psychology in building meaningful client relationships, there's a growing focus on enhancing the interpersonal experience advisors have with clients, going beyond money management to understanding and empathizing with their clients' goals, priorities, and pain points. Yet in some cases, getting more personal can open up conversations that advisors themselves may not be accustomed to navigating. And when it comes to difficult transitions like death, divorce, retirement, or illness, the natural impulse may be to sidestep grief altogether, or at least to hand the client a tissue (tacitly suggesting that they should finish crying) and then quickly steer the conversation back to more 'comfortable' territory.

The challenge for clients, though, is that when advisors try to stay 'positive' in the face of genuine sorrow, it can often make people feel more alone – not less – even when it might feel natural to 'respect' the individual's privacy during times of grief. And so in "Bittersweet", the follow-up to her bestselling book "Quiet", Susan Cain makes a powerful case for rethinking how we relate to sadness, grief, and longing – not as problems to fix, but as essential aspects of life that can strengthen human connection.

Accordingly, the book explores how these emotions aren't weaknesses to hide from but tools that help us shape creativity, compassion, and belonging. Often, it's the act of acknowledging pain that allows people to persevere. To this point, Cain cites author Susan McInerny:

What can we do other than try to remind one another that some things can't be fixed, and not all wounds are meant to heal? We need each other to remember, to help each other remember, that grief is this multitasking emotion. That you can and will be sad, and happy; you'll be grieving, and able to love in the same year, or week, the same breath. We need to remember that a grieving person is going to laugh again and smile again... They're going to move forward. But that doesn't mean that they've moved on.

Cain also explores how Western culture – especially American workplaces – tends to suppress emotional honesty in favor of constant optimism and productivity. Yet this behavior has consequences, particularly in a profession like financial planning, where advisors are expected to remain neutral and composed even while witnessing some of the hardest moments of their clients' lives. Yet, as Cain writes, "Sadness is the ultimate bonding agent", suggesting that advisors can actually deepen connections with clients by holding space to explore their grief or emotional transitions. Suppressing those emotions doesn't make them disappear; it just makes them harder to name, and harder to face alone.

Ultimately, "Bittersweet" challenges the idea that grief is something to avoid or ignore. Instead, it frames grief as a bridge – one that, when shared, can make relationships stronger and more resilient. For financial advisors, that message might be subtle but important: Showing up for a client in their grief isn't unprofessional; it's essential. When we don't shy away from those hard moments, we create space for real conversations, more meaningful planning, and a client experience rooted in empathy and trust. While it's not a how-to guide, "Bittersweet" is a helpful read for advisors who want to understand the emotional dynamics that shape meaningful relationships, especially during times of grief or uncertainty.

The Bond King: How One Man Made A Market, Built An Empire, And Lost It All

(Mary Childs)

For most of the 20th century, investing in bonds had one primary goal: to receive steady interest payments over the bond's lifetime until the principal was paid back at maturity. Consequently, bond investors tended to be the types of entities that benefited from the predictability and stability that bonds offered, such as insurance companies (whose actuarial models provided them with a reasonable assumption of their cash flow needs in any given year) and pension funds (which need to fund ongoing guaranteed payments to retirees). Investment managers would put a lot of work into deciding which types of bonds to hold – such as Treasuries versus corporate bonds, and those with long- versus short-term maturities – but once the bonds were actually on their books, there was little to do beyond clipping the quarterly interest coupons to redeem their bonds' interest payments. In the days of paper bonds, this was literally the process: Junior staffers at the institutions that managed bond portfolios were often tasked with cutting the coupon off and taking it to the bank to redeem each interest payment.

One such junior staffer who clipped bond coupons for the Pacific Life Insurance Company in the 1970s was Bill Gross. An MBA and Navy veteran with a brief career as a professional blackjack player, Gross had a keen intuition for gauging risk and distilling a complex web of factors into simple asset valuation models. He used these traits to become one of the first investors to capitalize on the idea that bonds could be traded rather than simply being held to maturity, where the bond's "total return" came from both its nominal interest rate and the fluctuation in price between when it was bought and sold.

Gross eventually became the co-founder and CEO of Pacific Investment Management Company (PIMCO), which started as a unit of the Pacific Life insurance company, where he originally clipped bond coupons. It later spun off as an independent company before being acquired by Allianz. At PIMCO, Gross managed the firm's flagship PIMCO Total Return Fund, amassing an impressive 30-year track record of outperforming the overall bond market from the early 1980s until the early 2010s. The fund grew into a behemoth in the mutual fund industry, becoming a staple for investors ranging from pension plans to charitable endowments to individual retirement savers' 401(k) plan accounts and IRAs. All the while, Gross became a mainstay in the media through TV appearances on financial news channels and his regular monthly Investment Outlook newsletters.

But Gross's fortunes began to change in the early 2010s. A series of bad bets led the PIMCO Total Return Fund to underperform its benchmark for several years. Some investors began to question whether Gross's track record was just a reflection of the long overall bull market in bonds that stemmed from steadily declining interest rates from the 1980s until the 2010s (although subsequent analysis supports the idea that Gross did, in fact, add value with his skills as an investor and trader). At the same time, Gross became increasingly erratic in his writing and public appearances, which further sapped his investors' confidence and led to large-scale outflows from PIMCO. In 2014, Gross preempted the PIMCO board's decision to remove him as CEO by leaving the firm to start a new fund at Janus, which he managed for five years with mixed results before retiring as a professional investor in 2019.

Mary Childs's "The Bond King" offers a deeply reported account of Bill Gross and PIMCO, offering insights into what led to PIMCO's rise (including some nerdy in-depth technical discussions of bond investing, such as Gross's signature 'structural alpha' techniques that helped boost the Total Return Fund's performance even when its underlying investment decisions didn't all pan out), as well as the firm's eventual decline as Gross became increasingly consumed by interpersonal battles with his perceived rivals (including his own handpicked successor).

In all, Childs's book is a balanced portrait of a firm, PIMCO, and investor, Bill Gross, whose names became synonymous with each other, for better or for worse. But perhaps more importantly, it serves as a reminder that, as much as the behaviors of 'eccentric' founders and executives are often widely tolerated when investors and employees are making money, they just as often do little to inspire confidence when business conditions turn south.

The Fund: Ray Dalio, Bridgewater Associates, And The Unraveling Of A Wall Street Legend

(Rob Copeland)

There's a widespread assumption that when a person becomes well-known and successful in a certain field, it's because they've developed a better understanding of how the world works – not just as an expert in their chosen field, but also as an expert in success itself, by mastering a worldview, mindset, or work ethic that can be applied universally. Which is why there's an evergreen industry of biographies, memoirs, and self-help books that examine highly successful people, from Warren Buffett to Steve Jobs to Bill Gates and many, many others. Not because the lives of billionaires are necessarily all that interesting, but because it's easy to sell the hope that, by learning a little about what made one person successful, 'regular' people can apply those same lessons to become more successful in their own lives.

In 2017, Ray Dalio – already well-known within the finance industry as the founder of the hedge fund Bridgewater Associates – achieved much broader fame as the author of the book "Principles: Life and Work". The book's main thesis was that Dalio's success in building Bridgewater could be distilled into a set of foundational concepts – the titular "principles" – that can be applied systematically nearly anywhere in business and in life. In particular, "Principles" espouses the idea of 'radical transparency', where employees are encouraged to give their most candid feedback at all times so that the best ideas are heard out, and employees can rise in the organization based solely on merit (i.e., the quality of their ideas). Most significantly, as Dalio frames it, the concepts laid out in his book are the same as those he himself implemented and systematized at Bridgewater, giving them the imprimatur of the world's largest hedge fund as proof of their validity.

But while Dalio's principles might make sense on paper, the reality of what life was actually like at Bridgewater – at least according to Rob Copeland's well-reported and entertainingly written "The Fund" – was more complicated. In Copeland's telling, what began as an earnest attempt to communicate Bridgewater's core values and encourage the free flow of ideas gradually evolved into a means of elevating Dalio's own ideas, surveilling employees, and stifling dissent – the exact opposite of their stated intention of allowing the best ideas to float to the top, no matter the source.

For example, Copeland recounts how Bridgewater employee input became heavily weighted toward their perceived 'believability', a score based on peer ratings. But when Dalio realized that several employees had believability scores that exceeded his own, he reportedly ordered the score's calculation to be changed so that his own believability served as the "baseline" for others – that is, that his believability was ranked the highest by default.

The book also describes 'show trials' held for senior employees who openly disagreed with Dalio or expressed skepticism of the Principles. These employees would be called in to meetings where they were berated by Dalio in front of a group of their peers, then given the choice to either renounce their views or resign from the firm (with the whole affair being recorded and sent to the whole company afterward for 'training' purposes). And although Dalio has publicly disputed the book's characterization of the environment at Bridgewater, it's worth noting that once Dalio stepped down as Bridgewater's CEO in 2022, the company almost immediately began to roll back many of the most intrusive and constraining elements of the Principles system.

The key point is that while concepts like transparency and meritocracy may be appealing in the context of a book or a TED Talk, the unfortunate reality is that some organizations and leaders tend to deploy them in ways that actually achieve the opposite effect. If candid feedback is encouraged for some employees but not others, or if an employee's 'merit' is determined mainly by their position on the organizational chart, then it's hard to make the claim that truly anyone can deploy those principles to achieve success for themselves. Or in other words, while it's fine (and even desirable) to have a set of organizational values that inform and underlie the decisions of employees, those values can really only serve their purpose if they extend to everyone in the organization.

Value First Prospecting: The Proven System To Attract Ideal Clients

(Sten Morgan)

In the early days of the financial advice industry, compensation was primarily tied to the sale of products, and our value was often defined by the quality of what we sold. As a result, we sought to be affiliated with the companies that had the best products on the shelf in order to provide differentiated value. But as the industry evolved toward providing financial advice, though, the value proposition began to change. Suddenly, we were crafting long-term financial plans to help people achieve multi-decade financial goals… for which clients may thank us for eventually, but which can be remarkably difficult to explain in the present, given that the value of financial planning services might not be fully realized until decades from now.

The challenge is further exacerbated by the fact that finance is an industry filled with jargon and math that is too complex for most people to do in their heads. It's difficult to explain the benefits of diversification to clients who don't understand the difference between stocks and bonds, or to communicate why a single index fund may still be far less risky than five hand-selected stocks. It often takes charts and graphics to demonstrate the long-term return drag of high-cost investments, or how saving an extra $200 – or $2,000 – per month could meaningfully improve their ability to achieve their financial goals (as virtually everyone underestimates the power of long-term compounding!). And if we do too good of a job explaining our recommendations and their value, there's always the fear that clients might just take that information and implement it themselves without hiring us at all.

In his book "Value First Prospecting", financial advisor and Elite Advisor Network coach Sten Morgan highlights a practical approach to explaining the value of what we do as financial advisors in a way that inspires prospects to want to work with us and implement the advice we offer, and not just take the ideas and run.

At its core, Morgan's approach is built around the idea that our primary value is no longer in the products we sell or the portfolios we implement; it's in the ideas that we provide. And if we're thoughtful about how those ideas apply to a prospect's specific situation, we can present and quantify their value in a manner that's immediately compelling.

For instance, rather than saying "I do comprehensive financial planning for small business owners", an advisor might say "I recently helped a business owner implement a strategy to pay their children. As a result, the business owner will save an estimated $120,000 over the next 10 years, and his children will be able to use the funds for college or other expenses". This reframing highlights a particular idea (paying children through the business) and the concrete financial outcome it generated (saving the business $10,000 each year in taxes, amounting to $120,000 over 10 years).

Notably, "Value-First Prospecting" isn't simply about making financial planning ideas more concrete and quantified. Morgan's deeper point is that if the business we're in is about selling valuable 'ideas', then the key to being a successful financial advisor is to have a strong 'quiver' of ideas – ones that can be clearly explained, illustrated, and tailored to the right prospects (who might be interested). Accordingly, the book also explores how to cultivate Center of Influence relationships not just as a source of referrals but as "Idea Partners" who can help identify relevant high-impact strategies that can be brought as ideas to new and existing clients. It also emphasizes using tools like whiteboards to draw and illustrate to get away from confusion industry jargon, how to highlight the cost to the prospect of not moving forward with a proposed idea as a way to create urgency, and how to identify ideal prospects based on who would benefit most from the ideas that we're prepared to offer and communicate.

Ultimately, while it's not the only way to prospect, Sten Morgan's "Value-First Prospecting" provides a strong framework for advisors who are stuck trying to figure out how to explain the value of an intangible service like financial planning. By explaining the value of what we do in concrete ways that resonate, Morgan shows how advisors can position themselves as essential partners so prospects will want to work with us to achieve the results that we've already helped quantify.

How To Know A Person: The Art Of Seeing Others Deeply And Being Seen

(David Brooks)

As Tim Maurer has long said, "Personal finance is more personal than finance", because our financial decisions are often shaped by life events that are deeply personal. Yet at the same time, the emotions that come with these personal experiences can make it difficult for many to open up about money in the first place – it's one of the few subjects that is still often taboo to discuss. Which means financial advisors must be skilled at cultivating deep connections with clients just to make them feel safe enough to share their open up about their money goals, values, and financial preferences.

The challenge, though, is that while some people are naturally charismatic and "easy to talk to", others may have to work harder to build rapport – without seeming artificial or putting someone on the defensive by unwittingly asking too many questions too soon. The good news is that being a good conversationalist isn't just an inborn trait; it turns out that being someone easy to talk to is a skill and, therefore, something that can be learned and mastered.

In "How To Know A Person", David Brooks discusses the art of truly seeing others – and being seen – as a pathway for forming deeper connections. He explores the skills and tactics that can help anyone become a warmer, more receptive conversational partner – even if it doesn't come naturally.

At the core of Brooks' philosophy is the idea that better conversations start with asking better questions. While people are generally advised to ask more questions in general, Brooks goes a layer deeper, offering specific prompts that get people talking more deeply about their background, passions, and purpose. He also shares how to build on points of commonalities while still keeping the conversation centered on the other person.

This is especially relevant in financial planning, where advisors often help clients navigate challenging life events that can lead to emotionally charged conversations. Brooks shares advice on how to talk about hard subjects while staying focused on the client. In many cases, the client may simply need space to talk through the situation they're experiencing before moving into problem-solving. Taking the conversation slowly and staying fully present can help forge difficult conversations into defining moments that strengthen the relationship between the advisor and client.

The reality is that when advisors can honor the emotional vulnerability inherent in financial planning, they lay the groundwork for more meaningful engagement. And over time, this becomes a positive cycle as trust deepens and a stronger sense of rapport is created. Of course, these principles aren't just useful in client meetings; they're also relevant in leadership, networking, and collaboration. Ultimately, learning how to talk to people and help them feel seen can be a crucial skill in the long term!

How To Win Friends And Influence People

(Dale Carnegie)

While the financial planning profession is nominally one of financial numbers and quantitative analysis, it is arguably more a profession of influence and persuasion in the long run. After all, it doesn't really matter how smart you are about finances if you can't convince anyone to hire you, and it doesn't matter how good your financial planning recommendations are if you can't persuade anyone to actually implement them. Simply put, our financial planning impact will always be limited by how effective we are (or are not) at communicating our advice in a manner that clients are ready and willing to hear and accept. (After all, if it were easy to just 'get the answer' and implement it themselves, most clients could simply look up on the internet what to do and wouldn't need to hire a financial advisor at all!)

Yet unfortunately, the reality is that very little is taught in financial planning programs (or beyond) in the techniques of persuasion – not in a negative or manipulative manner (e.g., sales techniques to take advantage of someone), but simply in the positive manner of helping people agree to implement what they perhaps know they should implement but still struggle to do so. After all, the domain of behavioral economics teaches about the various biases and heuristics that clients may have that cause them to behave 'irrationally', but prescribes very little about how advisors might communicate with their clients differently to help them implement. Instead, it's the realm of financial psychology – still not widely adopted in financial planning circles yet – that provides more tools and approaches for actually convincing clients to implement the advice we provide.

However, books on how to more effectively influence and persuade others have been around for a long time – albeit not specific to financial planning – and there are few out there better than the nearly century-old classic "How To Win Friends and Influence People" by Dale Carnegie.

Ultimately, the advice in Carnegie's book is rather straightforward – criticizing others just makes them defensive, so you may as well approach with kindness and forgiveness; it's easier to get other people to do things by appealing to what motivates them so they want to do it; you make more friends by getting interested in other people rather than trying to get them interested in you, and especially if you can learn more about what really interests them; take a few moments to learn and remember other people's names, because people stay much more engaged when you actually use their name; and so forth. Except the lessons are taught in a remarkably engaging way, as a series of stories that remain incredibly understandable and relatable, even though Carnegie cites 'examples of the time' from the late 1800s and early 1900s. Which is perhaps itself a powerful reminder of how timeless the techniques of persuasion are.

While the book is nominally about winning friends and influencing people, its lessons are highly relevant to what we do as financial planners. For instance, applying Carnegie's principles to a client who is nervous about current market volatility, we might start by showing genuine interest in the client themselves (it's easier for clients to take our advice when they believe we care about them personally and not 'just' their portfolios), talking in terms of their interests (e.g., frame around their financial planning goals, such as "selling now might impair your ability to pursue that sabbatical you wanted!"), avoid saying "you're wrong" or stoking an argument (instead, start with "I understand that it feels scary right now" and then introduce "here's how we've planned for environments like this"), appealing to nobler motives (e.g., "You've always said you want to model financial resilience for your kids. Holding steady now would set a powerful example for them!"), and so forth.

And of course, the underlying premise of the book itself – literally, how to win friends and influence people – can have applications far beyond clients and their financial planning recommendations, from prospecting and expanding our social circles to applying the same positive principles in our own relationships with friends and family, too!

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If you're still looking for more book ideas, be certain to also check out our prior summer reading lists, along with our overall list of recommended books for financial advisors. They may be lists we've published in the past, but if you haven't read the books yet, they're still new to you! 🙂

Top Must-Read Books for Financial Planners

2024 Summer Reading List of "Best Books" For Financial Advisors
2023 Summer Reading List of "Best Books" For Financial Advisors
2022 Summer Reading List of "Best Books" For Financial Advisors
2021 Summer Reading List of "Best Books" For Financial Advisors
2020 Summer Reading List of "Best Books" For Financial Advisors
2019 Summer Reading List of "Best Books" For Financial Advisors
2018 Summer Reading List of "Best Books" For Financial Advisors
2017 Summer Reading List of "Best Books" For Financial Advisors
2016 Summer Reading List of "Best Books" For Financial Advisors
2015 Summer Book List For Financial Advisors
2014 Summer Reading List Of Best Books For Financial Advisors
2013 Summer Reading List Of Top Financial Advisor Books

So what do you think? Will you be reading any of these books over the summer? Do you have any suggestions of your own that you're willing to share? Please share your own great reads in the comments below!