Weekend Briefing No. 516

Top 10 Books of the Year

Welcome to the last weekend of the year. 

I love reading. To me, it’s such a joy to learn a new concept or see the world from someone else’s perspective or just getting lost in a story. This year I read 58 books. If you want to see the entire list, click here. But in this final briefing of the year, I’ve ranked my top 10 books of 2023. As a bonus I threw in my favorite podcast series as well. 

I’d love to hear your thoughts on these books. Are there any you particularly loved / hated? What are you looking forward to reading? Why? Leave a comment with your thoughts. 

Lastly, I’ve built a framework for end of year reflection. The purpose of this exercise is to create a simple structure that allows you to pause and honestly reflect on the past year as well as set clear intentions for the upcoming year. My hope is that it will help you align your values with your actions. Click here to access my annual reflection framework.

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10. The Order of Time

Why do we remember the past and not the future? What does it mean for time to "flow"? Do we exist in time or does time exist in us? Physicist Carlo Rovelli invites us to reconsider our assumptions about the nature of time, explaining how according to quantum gravity theory, time disappears at the most fundamental level. Rovelli argues that our perception of time flowing steadily forward is subjective, shaped by the structure of our brains and emotions rather than the physical world. Blending philosophy, science and literature, he suggests time is more mysterious than we realize, and our conventional notions of its uniformity and universality do not capture the strange timelessness of reality. Rovelli aims to give new meaning to this extreme landscape where the familiar concepts of past, present and future no longer apply. This book is still blowing my mind. Buy Now

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9. The Tech-wise Family

In his book, Andy Crouch goes beyond limiting screen time and using filters to examine how the choices we make about technology impact our character and family relationships. Drawing on Barna Group research, Crouch challenges us to consider not just what devices we use but who we want to become as people and families. He shows how technology often distracts us and promises instant gratification while moving us away from our goals. Crouch offers wisdom and guidance for anyone who has seen their family connections suffer amidst constant digital distractions, providing a path forward to reclaim real life and develop courage and conscience in our use of technology, rather than passively accepting its control over us. Though Crouch comes from a Christian perspective, I think the message is applicable to any family looking to lead an intentionally brave and beautiful life. Buy Now

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Blast From the Past. 

Spoiler alert—there’s still trouble with impact investing. Too much money chasing returns; too little making a difference. In 2012, Kevin Starr, CEO of Mulago, penned a three-part series in The Stanford Social Innovation Review entitled “The Trouble with Impact Investing.” A decade later, the fascination with impact investing is only stronger, yet achieving true impact, let alone an investment return, is hard to find. Few problems have been truly solved by impact investing, and returns have been nominal at best. In a world with increasing challenges at every level, inequality remains the common denominator. Why? Because the fundamental premise is wrong. Kevin said a decade ago, “Few solutions that meet the fundamental needs of the poor will get you your money back…(and)…overcoming market failure requires subsidy.” These two realities have not changed, and if anything, the cost of solving for inequity has only gotten higher. For impact investors like DRK, we measure return by direct lives impacted, not economic return. For us, a win is sustainable impact first, and second, just getting  our principal back. Time and time again, we see those chasing greater returns invariably seeing diminished social returns. The impact investing ecosystem would be better served by right sizing these expectations so more capital can be unlocked. Impact investing needs to be a tool for solving inequity, not a destination. Kevin’s series is a great reminder that when solving for poverty, market return should be off the table. DRK Foundation (Sponsored)

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8. Number Go Up

In his book Number Go Up, investigative reporter Zeke Faux chronicles the rise and fall of the cryptocurrency frenzy that gripped the world in 2021-2022. Beginning with a nagging question about whether it was all a confidence game, Faux embarks on a globe-spanning quest to understand the players behind this new financial machinery, gaining incredible access to elite crypto parties, personalities, and gatherings. His reporting leads to the schlubby crypto billionaire Sam Bankman-Fried in the Bahamas, who boldly declares he will use his fortune to save the world. When the crypto bubble bursts in 2022, Faux brings readers inside as Bankman-Fried faces arrest. Fueled by absurd details and authoritative reporting, Number Go Up provides an essential, at times harrowing and uproarious account of the $3 trillion crypto delusion and the larger-than-life characters behind it. Buy Now

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7. Meet Me in the Bathroom

Meet Me in the Bathroom is an intriguing oral history chronicling the early 2000s decline of the old music industry and the rebirth of the New York rock scene led by iconoclastic bands like The Strokes, Yeah Yeah Yeahs, LCD Soundsystem, Interpol, and Vampire Weekend. As author Lizzy Goodman recounts through interviews with over 200 musicians, artists and insiders, 9/11 plunged New York into uncertainty just as these bands were honing their signature sounds in relative obscurity. Perfectly capturing the cultural zeitgeist of a young, forward-looking generation in need of an anthem, they became glamorous symbols pushing New York back to the epicenter of rock music and defining a new era as technology was forcing the behemoth music industry into free fall. Goodman offers a fascinating portrait of the explosive transformation of the New York scene and the cultural forces shaping it in the first decade of the 2000s. Buy Now

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6. Trust

Set in 1920s New York, Hernan Diaz's Pulitzer Prize winning novel Trust centers around wealthy couple Benjamin and Helen Rask, legendary fixtures in Manhattan's financial elite. While all of New York seems to have read the bestselling 1937 novel Bonds about the Rask's world of privilege won through deceit, Diaz presents competing narratives that call "facts" into question. Trust elegantly weaves these contradictory versions together through a woman determined to unravel fiction from truth. Diaz crafts an exhilarating literary puzzle spanning a century, immersing readers in a quest for the heart of the Rasks' relationship and the realities of how capital and power can deceptively warp facts. As much a brilliant story as a meta-commentary, Trust confronts the ease of manipulation in personal bonds and at society's highest echelons. Buy Now

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5. Demon Copperhead

Set in Appalachia, Barbara Kingsolver's Pulitzer Prize winning Demon Copperhead is the raw coming-of-age story of a boy named Demon born to a single teen mom in a trailer. With only his dead father's looks, wit, and talent for survival, Demon navigates modern threats like foster care, dangerous jobs, addiction, and more. In his own voice, Demon reckons with rural invisibility. Inspired by Dickens' David Copperfield, Kingsolver transposes that Victorian epic to contemporary rural America, adopting Dickens' anger and compassion for the institutional damages still imposed on children like Demon. As a new generation's invisible boy, Demon speaks for all those born into the beauty and curse of a place they can't imagine leaving behind. Demon Copperfield gives voice to the forgotten. Buy Now

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4. Unfollow

In her memoir Unfollow, Megan Phelps-Roper recounts her journey escaping the extremism of the Westboro Baptist Church, the infamous hate group consisting almost entirely of her extended family. As the church's prominent Twitter spokesperson, Phelps-Roper was an accomplished debater but started doubting their absolutist beliefs after engaging in dialogue on Twitter. A gripping narrative of moral awakening, Phelps-Roper relates how conversations online led her to question the church's confidence in its own fallible, sinful members, ultimately finding connection with someone who would help her depart Westboro. Rejecting the black-and-white thinking of her youth, she found new forms of community and warmth outside the church. Unfollow exposes the dangers of absolutism and the power of humility in an age of polarization. Buy Now

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3. The Creative Act

In The Creative Act, iconic music producer Rick Rubin shares the wisdom gleaned from his storied career on unlocking creativity. Rather than a book on producing great art, Rubin reveals how his practice helps artists of all genres reconnect with an innocent, fearless state to access the surprising. He argues creativity is not about output but one's relationship to the world, and the artist's path is one we can all follow to transcend self-limitations. Distilling a lifetime of learning into a luminous reading experience, The Creative Act illuminates how we can make space for creativity in our lives, take responsibility for it, and follow the road of the artist to find exhilarating moments of transcendence. For Rubin, creativity has a place in everyone's life. Surprisingly, this may be one of the most spiritual books I’ve read this year (and I read a lot of spiritual books.) Buy Now

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2. The Canceling of the American Mind

In The Canceling of the American Mind, the authors who brought you The Coddling of the American Mind present the first full examination of cancel culture, backed by extensive data and research. They argue cancel culture is not a moral panic but rather a dysfunctional battle for power and status, where cheap rhetorical tactics "win" arguments by simply silencing opponents. The book offers hundreds of new examples showing both left and right working to cancel enemies, and concrete solutions to reclaim free speech, tailored for parents, teachers, business leaders, and social media users. With intellectual humility, resilience, and openness, we can counter cancel culture's threat to democracy and promote essential American principles of individuality and open-mindedness. This vital book sounds the alarm on a new phenomenon and provides hope to restore a culture of free speech. Buy Now

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1. The Coming Wave

In The Coming Wave, AI pioneer Mustafa Suleyman argues we are approaching a critical threshold as powerful new technologies like AI, quantum computing, robotics and synthetic biology rapidly proliferate, profoundly disrupting society. Suleyman shows how these forces, which governments are sleepwalking into, will create immense prosperity but also threaten the nation-state and global order. We face an existential dilemma between unprecedented harms and overbearing surveillance. Drawing on his insider experience co-founding DeepMind/Google, Suleyman establishes "the containment problem" - maintaining control over these technologies - as the defining challenge of our age. This groundbreaking book from an AI insider sounds an urgent alarm while laying out solutions to forge a path between catastrophe and dystopia. The coming wave of technological change will redefine the next decade - we must prepare. Buy Now

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Best Podcast Series: The Witch Trials of J.K. Rowling

The Witch Trials of J.K. Rowling is an audio documentary that examines some of today's most divisive conflicts through the life and career of the world's most successful author. In candid conversations with host Megan Phelps-Roper, J.K. Rowling speaks openly about the controversies surrounding her, from book bans to debates on gender and sex. The series also analyzes the historical forces propelling this cultural moment through interviews with supporters, critics, journalists, clinicians and more. While providing a human look at issues like trans rights and cancel culture from opposing sides, the documentary ultimately offers a thought-provoking masterclass in engaging with those we disagree with, modeling civil discourse in an age of division. Listen Now  

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Should We Work Together?

Hi! I’m Kyle. This newsletter is my passion project. When I’m not writing, I run a law firm that helps startups move fast without breaking things. Most founders want a trusted legal partner, but they hate surprise legal bills. At Westaway, we take care of your startup’s legal needs for a flat, monthly fee so you can control your costs and focus on scaling your business. If you’re interested, let’s jump on a call to see if you’re a good fit for the firm. Click here to schedule a one-on-one call with me.

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Founder Fridays

Check out my other email, Founder Fridays — a Friday morning briefing helping startup founders and operators scale smarter.

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Weekend Wisdom

If you want to see the true measure of a man, watch how he treats his inferiors, not his equals. -J.K. Rowling