End of Summer Reading List from the Winners Of Wealthtech

“When summer gathers up her robes of glory, And, like a dream, glides away.”

— Sarah Helen Whitman

Now that summer has glided away and left us with only memories of vacations and longer days, I thought this would be an opportune time to share some insights as we all get ready for fall. And what better source of wisdom that our very own Winners of Wealthtech (WoW)?  The WoW include a diverse group of thinkers and leaders who were profiled on my podcast and blog.

Combing back through the interviews, my staff pulled some of their favorite book recommendations.  The end of summer is a terrific time to refocus and energize yourself and a book can be just the thing to kick start your rejuvenation.


Shoe Dog by Phil Knight

A memoir by the co-founder of Nike which chronicles the company’s history was recommended by Sunayna Tuteja, Head of Emerging Technologies at TD Ameritrade. “The thing I take away from this book is a very eloquent quote about solving problems. It’s about making a dent in the world, it’s about making people’s lives just a little bit better…. But the inherent purpose is not innovation for innovation, it’s about giving that dent a purpose.”

It may seem surprising that a wealthtech leader would be recommending a “sports book”, but that’s because Phil Knight’s tome is not a “sports book” at all, but is actually more of an economics textbook. And one that every business person should read. Knight creates page-turning suspense at several junctures and also provides an intimate look at his personal life.

The Intelligent Investor by Benjamin Graham

First published in 1949 by the ‘father of value investing’, David Lyon (CEO of Oranj) recommends this book, “because I think most people believe that investing is some unknown science, that you have to have some advanced degree to know how to invest. Whether you do it yourself or you work with an advisor…you still need to be educated about the general principles and the building blocks of investing. And I think everybody should read that book.”

“You either get the idea in the first five minutes, or you don’t get it at all”, commented Warren Buffet in the epilogue. Other reviewers have offered similar advice to approaching this book. You don’t necessarily need to read all 550 pages, but you should at least skim through the idea of value investing – it could change your way of looking at investing.

New York by Edward Rutherfurd

“I’ve spent so much time in New York, I just found it fascinating how he does a terrific job of describing how the city grew up,” says John Michel, CEO of CircleBlack. “But the other thing I found fascinating is the discussion around father son relationships and how through the book the sons become successful but never quite in the way that the father was. As fathers we sometimes say everybody should do this or that, and I think it’s important to recognize that everyone has their own paths.”

Rutherford’s skillful technique of connecting the history of New York City by tying together generations of the same families will intrigue and surprise you throughout this work of historical fiction. All history should be taught this way! From the Native Americans and trappers through the Revolution to the Great Depression, it will be hard for you to put this book down.

Atlas Shrugged by Ayn Rand

A personal favorite of Cheryl Nash, President of Fiserv Investment Services, Rand’s final novel expresses the importance of reason, individualism and capitalism which would later be developed into her philosophy of Objectivism. Rand stated her goal for writing the novel as “to show how desperately the world needs prime movers and how viciously it treats them,” making this a great gift for the lonely CEO in your life.

“Atlas Shrugged” is a sprawling, dystopian work that combines economics, science fiction, philosophy, and intrigue. The novel is written in a modern popular style and is mostly highly readable.  Rand ridicules inherited wealth, non-profit ventures, and academics in general. Ivory tower self-aggrandizing scholars make inane statements, “the duty of thinkers is not to explain, but to demonstrate that nothing can be explained,” and “how do you know what’s good, anyway? There are no absolutes … Everything is a matter of opinion.” There are straw men philanthropists, like the banker who brags “I can proudly say that in all of my life I have never made a profit!”

Great By Choice: Uncertainty, Chaos, and Luck by Jim Collins

Why do some companies thrive during times of change, and others do not? “What I really love is the fact that there is a choice,” explained Stuart DePina, Chief Executive of Envestnet Data & Analytics. This sequel to Good to Great expands Collins’ research on thriving companies looks at what is needed to prosper in an age of constant tumult and uncertainty.

In Collins’ book he relies on the method seen in previous books like Built to Last and Good to Great. What’s different in this one is he selected companies not just on their status or explosive growth, but because they succeeded in extreme and uncertain environments.  Collins’ explains the term 10Xer, which is a company that beat their industry returns by 10 fold. Just 7 companies were selected as a 10X case out of 20,400 analyzed.

The Seventh Sense by Joshua Cooper Ramo

“It’s about how networks are recreating political, economic and social infrastructure, networks are fundamentally game-changing,” described Bill Crager, Chief Executive of Envestnet Wealth Solutions. “My dad died when he was 50 in Geneva, Switzerland. He was an electrical engineer and worked for ITT. He had patents related to packet switching for fax transmission and predicted that paper would no longer be necessary for communications, which was a crazy idea at the time. This book inspired my passion to look into more of my father’s work.”

The power and impact of networks is great and growing exponentially. We can’t or at least shouldn’t dismiss or run from them. Doing so may potentially be catastrophic.

The Seventh Sense is not just understanding and embracing these realities but developing intuition about what they all mean and how to make best use of them. In my mind, the book offers few answers so much as it identifies and poses the essential questions which may well lead to insight. Along the way are recountings of historical events illustrating key concepts and the effects thereof.

Extreme Ownership by Jocko Willink

“Right now, I have five copies of this book sitting here on my credenza and I give them to any employee who agrees to read it and send me back a paragraph on what they love the most about it. We’ve almost turned it into a book club,” said Aaron Klein, founder and CEO of Riskalyze. “He’s amazing guy. Navy SEAL. I think most business books are just B.S.. but this book is incredible. The principles that Navy SEALs use to execute their missions have such applications to our world in business. I’m a huge fan of of Extreme Ownership and I’ve been gifting it a ton.”

This isn’t a self-help book from a “guru” and it doesn’t provide an ideology for how to approach all your problems. Extreme Ownership is a mindset which applies to everything you do. Authors Jocko Willink and Leif Babin have crafted a guidebook for success in all ventures of life. They explain hard-learned principles of leadership, which they experienced first-hand as US Navy SEALs, specifically in and around their 2006 deployment to Ramadi, Iraq, one of the most dangerous places and times in the war. These principles can be applied to any relationships or walks of life; they are simple enough for anyone to understand, and broad enough to use in any situation.

The Heart of Change by Dan Cohen

“It’s a great framework for people to use around a transformation they might be embarking on and really leading organizational change,” explained Angela Pecoraro, CEO of Advicent. “Particularly when the changed leader doesn’t have the positional authority to make that change happen but has to leverage influence. Thinking what type of business you want to be running tomorrow rather than at one point in time.”

Excellent book for any organization that’s going through major transformations and all the steps listed can assist with those changes and help them to be successful. It’s painfully clear from reading this book that positive change takes time and Cohen gives a step by step process on how to make those changes happen.

Essentialism: The Disciplined Pursuit of Less by Greg McKeown

“I try to live by essentialism.” Bill Capuzzi, CEO of Apex Clearing, described. “I’ve been working over the last year to focus on the most important things in both my personal and professional life. It requires learning how to say no to the non-essentials, which sounds so obvious. But when you think about your life, how many things in your life do you do because you just feel like you should? How many things in your life do you do that are nonessential to what you’re trying to accomplish?”

Technology was supposed to make our working lives easier, and our workdays shorter. Two decades later, we are still waiting for promised spare time.  If you do not prioritize your life, someone else will.

The Art of the Start by Guy Kawasaki 

Eric Clarke, CEO of Orion Advisor Services described this book as  “a great framework for people to use around a transformation they might be embarking on and really leading organizational change. Particularly when the changed leader doesn’t have the positional authority to make that change happen but has to leverage influence. Thinking what type of business you want to be running tomorrow rather than at one point in time.”

A few takeaway quotes from the book:

“You can’t build a reputation on what you’re going to do.” — Henry Ford

“The whole problem with the world is that fools and fanatics are always so certain of themselves, but wiser people are so full of doubts.” — Bertrand Russell

“Socialism never took root in America because the poor see themselves not as an exploited proletariat but as temporarily embarrassed millionaires.” — John Steinbeck

First, Break All the Rules: What the World’s Greatest Managers Do Differently by Marcus Buckingham

“Somebody gave it to me when I first became a manager, and I’ve given it to everybody else who’s started being a manager,” said Catherine Flax, CEO of Pefin. Detailing studies done by Gallup, this book investigates what makes a strong manager, what kind of people they hire, and how they keep them motivated, as well as the twelve statements produced by the research that distinguish the strongest teams from the rest.

Here are the top three ideas from this book:

1. People don’t quit their companies, they quit their bosses.
2. Define the right outcomes and then let each person find his own route toward those outcomes.
3. The most efficient route that nature has found from point A to point B is rarely a straight line. It is always the path of least resistance.

Wealthtech Trends Through Books

Most of these recommendations are business or investing related books. From the power of networks to the effect of strong leadership to how to best survive in times of economic upheaval, these volumes provide a wonderful resource for anyone looking for ideas to improve their careers or their lives in general.

I hope you got a few good ideas from this list and that you read at least one of these books before the end of the year. If you, please post a comment about which book you chose and why. I’d love to hear from you!



The Wealth Tech Today blog is published by Craig Iskowitz, founder and CEO of Ezra Group, a boutique consulting firm that caters to banks, broker-dealers, RIA’s, asset managers and the leading vendors in the surrounding #fintech space. He can be reached at craig@ezragroupllc.com