Matt Dennis, Austin-based Investor, Shares His Family Book Club’s Top-10 Books

Austin-based investor Matt Dennis has long-strived to perfect work-life balance, filling his days with everything from stretching to cooking to reading, on top of his investment work. For Matt Dennis, life is about much more than corporate earnings reports and portfolio construction; he’s on a quest for lifelong growth and learning, and he’s bringing his family along with him on the journey. 

As a result, Matt Dennis and his family has created their own family book club, delving into both popular titles and self-improvement tomes. Together, they brainstorm the key takeaways that they can learn from some of the world’s greatest scholars and writers. Their book list is full of must-reads, but the top 10 should be required reading for everyone who seeks more from life than just a job and an existence.

The following is an excerpt from a recent interview with Matt Dennis where he shared some of the most influential and impactful books his family has read over the past few years.

Tuesdays with Morrie by Mitch Albom

Author Mitch Albom was blessed with a college professor, Morrie Schwartz, who gave him guidance during his formative years. Over time, they lost touch but reconnected during the final months of Morrie’s life. The two men rekindled their friendship and began to meet in Morrie’s study every Tuesday, just as they had when Mitch was in college. But now, Mitch was attending a class that taught him how to live. Mitch chronicled their time together, and the lessons imparted, in Tuesdays with Morrie.

From this book, we learned to focus on what matters – your relationships (cultivation, repair, renewal, reunion); that love is a choice; the poignant light that death shines on the importance of making the most of the time we have on this earth; the lesson about the value of time versus the limited satiety and value derived from material items; and the importance of being intentional in life, rather than allowing society or culture norms to dictate your priorities if you want to find true happiness.

Ikigai: The Japanese Secret to a Long and Happy Life by Hector Garcia and Francesc Miralles

An ikigai is a reason for living. In the Japanese village with the world’s longest-living people, finding your ikigai leads to a happier and longer life. Your ikigai gives meaning to your days and gives you a reason to get up in the morning; their ikigai is the reason most Japanese never actually retire. 

Your ikigai is a convergence of what you love, what you’re good at, what you can get paid for, and what the world needs.

Ikigai has been one of the most influential books and concepts in my life. Through it, I have learned the power of flow and the importance of its pursuit in everything we do; the importance of microflows, which are daily routines and tasks (such as washing dishes); finding your “moai” or community where you have common interests and take care of one another (friend group); and how to embrace “wabi-sabi,” the Japanese perspective which values the beauty in imperfection and age as well as the impermanence of life.

The Screwtape Letters by C.S. Lewis

Told through a series of letters from a senior demon to a junior demon, this classic book highlights the frailty of humanity while giving powerful insights into human nature. An inability to block out noise undermines our self-awareness, and being intentional about who we spend our time with is incredibly important. Our possession of a moral compass in a world rife with temptations that do not serve us is an absolute necessity. The power of free will and the vulnerability that comes with it. Definitely a book that we will read again and again in order to fully extract the author’s wit and wisdom.

The Ruthless Elimination of Hurry: How to Stay Emotionally Healthy and Spiritually Alive in the Chaos of the Modern World by John Mark Comer

Written by a pastor, this book suggests that “hurry,” or busyness, is the root of much evil and toxicity. Our modern world requires creative solutions to maintain our emotional health and spirituality.

The key takeaways for our family were that today’s culture and societal norms inject too much hurry into our lives, but “More” is oftentimes “Less.” Simplifying your daily routines and limiting the constant pursuit of material things is crucial to our wellbeing. Hurry is the great enemy of a spiritual life and must be ruthlessly eliminated.  We need to make time for silence and solitude. Turning off the phone, the TV, and the social media apps makes space for reflection. We should all be intentional in how we direct our attention in a culture that is geared to disrupt it: the gift of our presence is the greatest gift of all.

Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones by James Clear

Author James Clear is an expert on habit formation, using Atomic Habits to reveal practical strategies on how to form good habits, break bad ones, and master all of the tiny behaviors that lead to real change. With a focus on creating systems that allow for change, Clear helps readers reach new heights.

There were a lot of great quotes in this book that left a strong impression, including “Habits are the compound interest of self-improvement” and “We don’t rise to the level of our goals, we fall to the level of our systems.” Remember that tiny changes compound over time; your goal should be to try to get better by 1% every day. Your environment is the “invisible hand” that shapes your behavior, so look for prompts that signal potential rewards.

In order to form new habits, make them easy and satisfying (examples include placing the fruit on the kitchen counter and your running shoes beside your bed, or placing a book on your pillow when you make your bed, etc.). To break bad habits, make them invisible or unattractive, i.e. stop buying ice cream at the store.  Habits are not a finish line to be crossed, but instead are a lifestyle to be sustained.

Indistractable: How to Control Your Attention and Choose Your Life by Nir Eyal and Julie Li

We learned that there are two types of people, those who allow their attention to be controlled by others, and those who control their time. In order to be a person who controls your time, you must specifically plan your time or day; consider the “time boxing” hack. Learn to identify and deal with discomfort that often acts as a trigger for distraction and ask yourself: what are your triggers?

Learn to value “time” and make it a part of your identity. Turn off notifications, move time-wasting apps off your home screen, finish meetings on time, etc. “Strive to DO what you say you will DO.” Create and utilize pacts with yourself or others to keep yourself on track.

The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness by Morgan Housel

Told through 19 short stories about the strange ways people think about money, The Psychology of Money examines the various factors that play into how people make financial decisions. Monetary decisions aren’t made just based on data and formulas, but on personal history, unique worldviews, ego, pride, marketing, and odd incentives.

Financial independence is within everyone’s grasp given time, discipline, and thoughtful decisions, and this book helps explain how to set the right priorities.

Financial independence is the greatest dividend you can earn as it leaves you in control of your time. It’s important to be aware that your early experiences with money can color your financial decisions for the rest of your life, but good financial decisions don’t always lead to good financial outcomes; you must consider the role of luck and risk.

When it comes to making financial decisions, focus on what works for a broad group of people or patterns rather than what has worked for an individual (such as Bill Gates).  Remember that getting money and keeping money are different skill sets; one requires taking risks, and the other requires humility and avoiding unnecessary risks.

Most of all, stay optimistic, even when things are bleak (otherwise, you’re likely to miss opportunities). Greed and acting on FOMO can do irreparable harm to your finances, so focus on resilience, not high returns.

The Listening Road: One Man’s Ride Across America to Start Conversations About God by Neil Tomba

The Listening Road inspired us to appreciate the power (and gift) of active listening and the power of connection; that everyone has a story worth hearing, we just have to stop and listen – without judgment; and above all else, Listen, first! 

The Great Mental Models by Rhiannon Beaubien

We learned a lot from this book including the following powerful insights:

• The Map is not the Territory – The map of reality is not reality, but an abstraction…. with even the best maps being imperfect.
• Circle of Competence – Honestly define what you really “know” and play in this sandbox for success.
• First Principles Thinking – Strive to break down problems into the core building blocks and then put them back together to master something – it is the foundation of most great breakthroughs in science.
• Second-Order Thinking – Looking beyond the immediate or obvious implications of a decision to consider the long-term effect(s) of the same decision (think about a chess move and the opportunities/risk associated with subsequent moves). A lack of it is often the cause of many bad decisions.

Socrates Cafe: A Fresh Taste of Philosophy by Christopher Phillips

This book reminded us of the power of using questions to facilitate dialogue and civil discourse (Socratic Method), that listening is a skill that must be refined and practiced and the value of questioning the underlying beliefs that shape one’s views and opinions. 

We should learn to question everything (in a constructive way) and seek answers through conversation to foster critical thinking.

If you’re looking to connect and learn as a family, forming a book club is a fantastic way to both expand your horizons and create an open dialogue about a shared subject. For Matt Dennis and his family in Austin, their family book club has brought them closer together while teaching and reiterating some of life’s most important lessons.