Pursuing knowledge through understanding

About the club

Jackson Square Ventures is a VC firm leading early stage deals in SaaS and marketplace companies. We select books from all genres that we believe will have an impact on our 250+ constituents: founders, CEOs, LPs, and beyond. Thanks to our partner, Merrill, we're proud to be able to provide free copies of each book to our members.

Currently Reading

William Finnegan

Barbarian Days: A Surfing Life


Barbarian Days is William Finnegan’s memoir of an obsession, a complex enchantment. Surfing only looks like a sport. To initiates, it is something else: a beautiful addiction, a demanding course of study, a morally dangerous pastime, a way of life. Raised in California and Hawaii, Finnegan started surfing as a child. He has chased waves all over the world, wandering for years through the South Pacific, Australia, Asia, Africa. A bookish boy, and then an excessively adventurous young man, he went on to become a distinguished writer and war reporter. Barbarian Days takes us deep into unfamiliar worlds, some of them right under our noses—off the coasts of New York and San Francisco. It immerses the reader in the edgy camaraderie of close male friendships forged in challenging waves. Finnegan shares stories of life in a whites-only gang in a tough school in Honolulu. He shows us a world turned upside down for kids and adults alike by the social upheavals of the 1960s. He details the intricacies of famous waves and his own apprenticeships to them. Youthful folly—he drops LSD while riding huge Honolua Bay, on Maui—is served up with rueful humor. As Finnegan’s travels take him ever farther afield, he discovers the picturesque simplicity of a Samoan fishing village, dissects the sexual politics of Tongan interactions with Americans and Japanese, and navigates the Indonesian black market while nearly succumbing to malaria. Throughout, he surfs, carrying readers with him on rides of harrowing, unprecedented lucidity. Barbarian Days is an old-school adventure story, an intellectual autobiography, a social history, a literary road movie, and an extraordinary exploration of the gradual mastering of an exacting, little-understood art.

Past Reads

Andy Dunn

Burn Rate: Launching a Startup and Losing My Mind


Burn Rate is an unconventional entrepreneurial memoir, a parable for the twenty-first-century economy, and a revelatory look at the prevalence of mental illness in the startup community. With intimate prose, Andy Dunn fearlessly shines a light on the dark side of success and challenges us all to take part in the deepening conversation around creativity, performance, and disorder.


Margaret O'Mara

The Code: Silicon Valley and the Remaking of America


The popular mythology of Silicon Valley tends to focus on the swashbuckling entrepreneur who defies all odds to bend the arc of history to his or her will. Based on a half-decade of pioneering research, The Code reminds us that the true story of Silicon Valley isn’t just about the visionaries, but also the powerful institutions—from The Pentagon to Stanford University—that created the framework for innovation as we know it today.


Geoffrey Moore

Zone to Win


From the critically acclaimed author and speaker, Geoffrey Moore, comes his latest book that explores what it takes for companies to transform themselves in the face of disruptive competition. This book can help any founder better understand the mentality of the incumbents against which they compete.


Bill Walsh, with Steve Jamison and Craig Walsh

The Score Takes Care of Itself


Bill Walsh is a towering figure in the history of the NFL. His advanced leadership transformed the San Francisco 49ers from the worst franchise in sports to a legendary dynasty. In the process, he changed the way football is played. He taught that the requirements of successful leadership are the same whether you run an NFL franchise, a fortune 500 company, or a hardware store with 12 employees. These final words of 'wisdom by Walsh' will inspire, inform, and enlighten leaders in all professions.


Angel Au-Yeung and David Jeans

Wonder Boy: Tony Hsieh, Zappos, and the Myth of Happiness in Silicon Valley


Tony Hsieh revolutionized both the tech world and corporate culture. He was a business visionary. He was also a man in search of happiness. So why did it all go so wrong? At its peak, Zappos’s employee-friendly culture was so famous across the tech industry that it inspired copycats and earned a cult following. Then Hsieh moved the Zappos headquarters to Las Vegas, where he personally funded a nine-figure campaign to revitalize the city’s historic downtown area. But as Hsieh fell deeper into his struggles with mental health and drug addiction, the people making up his inner circle began changing from friends to enablers. Drawing on hundreds of interviews with a wide range of people whose lives Hsieh touched, journalists Angel Au-Yeung and David Jeans craft a rich portrait of a man who was plagued by his eternal search for happiness and ultimately succumbed to his own demons.


Tom Kemp

Containing Big Tech: How to Protect Our Civil Rights, Economy, and Democracy


This richly detailed book exposes the consequences of Big Tech’s digital surveillance, exploitative use of AI, and monopolistic and anticompetitive practices. It offers actionable solutions to these problems and a clear path forward for individuals and policymakers to advocate for change. By containing the excesses of Big Tech, we will ensure our civil rights are respected and preserved, our economy is competitive, and our democracy is protected.


Taylor Branch

Parting the Waters: America in the King Years 1954-1963


In the first of three installments chronicle the history of the civil rights movement, Taylor Branch has created an unparalleled epic of America in the midst of change, poised on the threshold of its most explosive era. Here is a vivid, panoramic portrait of America divided, at war with itself, and finally transformed by a struggle that left no citizen untouched – the civil rights movement, led by Dr. Martin Luther King, Jr., borne by the spirit of a generation of young black leaders determined to seize equality and justice.


E. Keller Fitzsimmons

Lost in Startuplandia


As investors, we know better than most that the thrilling adventure of entrepreneurship never goes exactly as planned. In this brave account of her personal entrepreneurial journey, E. Keller Fitzsimmons shares the dark side of running a company. What many founders experience, and few openly discuss, is the anguish and in some cases, depression that running a startup feeds.


Alex Honnold

Alone on the Wall


The book chronicles Alex Honnold's path to the legendary accomplishment of being the first person to free-solo El Capitan in Yosemite, detailing the seven most astonishing achievements of his life and career. In this new edition, Alex tells, for the first time in his own words, the story of his 3 hours and 56 minutes on the sheer face of El Cap. As the New York Times put it, Alex’s accomplishment is “one of the great athletic feats of any kind, ever.” We all strive to make our mark on the world. Alex has done it in the field of rock climbing. It is an inspirational feat that we can all apply to our own fields of work


Robert Kurson

Rocket Men


In 1968, the United States, fractured by setbacks in the Vietnam War and the aftermath of Martin Luther King Jr's assassination, found itself falling behind in the space race. The Soviet Union became the first nation to loop around the moon with an unmanned spacecraft. Rocket Men tells the heroic story of the men and women of Apollo 8, who pulled off the seemingly insurmountable: sending three astronauts, Jim Lovell, Bill Anders, and Frank Borman, on a mission around the moon without ever having sent an unmanned spacecraft to prepare. Apollo 8 solidified our place in history as the winners of the space race and healed the spirit of a broken nation. This fascinating tale weaves together lessons for anyone who dares to tackle the impossible.


Kevin Horsley

Unlimited Memory


Memory Grandmaster Kevin Horsley shares the techniques he's used to break world records for human recollection. This book helps people break through the preconceived notion that they have "bad memories" to create better recall and live more efficient lives.


David Kushner

Masters of Doom


Masters of Doom is the amazing true story of the Lennon and McCartney of video games: John Carmack and John Romero. Together, they ruled big business. They transformed popular culture. And they provoked a national controversy. More than anything, they lived a unique and rollicking American Dream, escaping the broken homes of their youth to produce the most notoriously successful game franchises in history—Doom and Quake—until the games they made tore them apart. This is a story of friendship and betrayal, commerce and artistry—a powerful and compassionate account of what it's like to be young, driven, and wildly creative.


Dan Ariely

Dollars and Sense


Blending humor and behavioral economics, New York Times bestselling author and world renowned economist Dan Ariely delves into the truly illogical world of personal finance to help people better understand why they make bad financial decisions, and gives them the knowledge they need to make better ones. In Dollars and Sense, Ariely tackles questions like: - Why does paying for things often feel like it causes physical pain? - Why does it cost you money to act as your own real estate agent? - Why are we comfortable overpaying for something now just because we’ve overpaid for it before?


Jocko Willink and Leif Babin

Extreme Ownership


In Extreme Ownership, authors Babin and Willink share the leadership lessons they learned during their time as commanders of SEAL Team Three’s Task Unit Bruiser in the Battle of Ramadi. In battle, they learned that leadership—at every level—is the most important factor in whether a team succeeds or fails. Post-deployment and after departing the SEAL teams, Willink and Babin have helped scores of clients across a broad range of industries build their own high-performance teams and dominate their battlefields. And now, they share their secrets with us in their New York Times #1 Bestselling book.


Robert Wachter

The Digital Doctor


Written with a rare combination of compelling stories and hard-hitting analysis by one of the nation’s most thoughtful physicians, The Digital Doctor examines healthcare at the dawn of its computer age. It tackles the hard questions, from how technology is changing care at the bedside to whether government intervention has been useful or destructive. And it does so with clarity, insight, humor, and compassion. Ultimately, it is a hopeful story. This riveting book offers the prescription for getting it right, making it essential reading for everyone—patient and provider alike—who cares about our healthcare system.


Phil Knight

Shoe Dog


In Shoe Dog, Nike founder and board chairman Phil Knight illuminates his company’s early days as an intrepid start-up and its evolution into one of the world’s most iconic, game-changing, and profitable brands. Fresh out of business school, Phil Knight borrowed fifty dollars from his father and launched a company with one simple mission: import high-quality, low-cost running shoes from Japan. Selling the shoes from the trunk of his car in 1963, Knight grossed eight thousand dollars that first year. Today, Nike’s annual sales top $30 billion. In this age of start-ups, Knight’s Nike is the gold standard, and its swoosh is one of the few icons instantly recognized in every corner of the world. But Knight, the man behind the swoosh, has always been a mystery. In Shoe Dog, he tells his story at last.


Frans Johansson

The Medici Effect


Frans Johansson's The Medici Effect shows how breakthrough ideas most often occur in 'The Intersection'—the place where where ideas and concepts from diverse industries, cultures, and disciplines collide. The book offers concrete examples of how we can turn the ideas we discover into path-breaking innovations and is considered the definitive book on how diversity drives innovation.