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CEO Aaron Klein’s Great Reads of 2021


By: Aaron Klein

CEO & Co-Founder, Riskalyze

The last time I sat down for dinner with a group of advisors, one of them asked me “what books have you been reading lately?” I love that question, because I’ve long believed that reading a broad range of perspectives is the key to becoming a better CEO, a better leader, a better husband, a better dad, and a better person all around.

Financial advisors are among the best “lifelong learners” I’ve ever met, so I hope you find a couple of gems for yourself among the favorite books I had the chance to read in 2021.

Loonshots by Safi Bahcall was really fascinating, talking about the environment you have to create for real innovation to occur.

Amazon Unbound by Brad Stone was a fascinating deep dive into the e-commerce and cloud services behemoth, and how Jeff Bezos has crafted the company into an invention machine.

True Amazon fans have to follow it up with Working Backwards by Colin Bryar and Bill Carr. I asked our entire leadership team to read this book, and it has spawned some fascinating conversations and new practices inside of Riskalyze.

About then, my wife and I left for a trip — celebrating twenty years of her putting up with me — so it was time to hit pause on the serious book tour and pivot to fiction.

Sooley by John Grisham is a heart-warming and shocking novel that feels all too real about the perils of a young immigrant kid getting the chance to leave his hometown in rural Africa, chase his dreams in the United States, and have it turn out to be more than he bargained for.

If you love historical fiction, The Devil May Dance by Jake Tapper transports you back to the 1960s, where a young New York congressman is secretly working on behalf of Attorney General Bobby Kennedy to figure out how deep Frank Sinatra’s mob ties really go.

Then it was back to the grind for me, and Power Play by Tim Higgins had just arrived. This book profiles Elon Musk and the journey to build Tesla into our country’s leading manufacturer of electric vehicles. While presented as a bit of a scandal story — I am shocked, SHOCKED to hear that Elon is demanding of his employees! — the book made me an even bigger fan of Tesla.

The Cult of We by Eliot Brown and Maureen Farrell had the opposite effect, absolutely shredding the reputations of WeWork, Adam Neumann, and Softbank billionaire Masayoshi Son on its pages. You end the book wondering how it was possible that so many people got taken in by Neumann’s charm.

Play Nice But Win by Michael Dell was a fascinating follow-up autobiography to Dell’s first book a couple decades ago. After a long stint as a public company, Dell recounts the story of taking his firm private in a PE-funded recapitalization. (What would I ever find interesting in THAT story? The only difference was a few zeroes!)

Now it was time to prepare for the Fearless Investing Summit in Palm Springs, so what did I pick for my next book? That would be Span of Control by Carey Lohrenz. It’s a relatively quick read but she delves into the science and practicality of how to optimize human thinking for strong decision making under pressure. If you didn’t know, Carey was the first female F-14 Tomcat fighter pilot in the United States Navy, and she did a bang-up job helping to kick off Fearless on opening day! Her book is awesome.

The Wires of War by Jacob Helberg was fascinating. There was much about the author’s presumptions and view of the world I disagreed with, but his core point was hard to argue with: autocratic and authoritarian governments are rapidly taking advantage of the Internet to wage information and cyber warfare against western liberal democracies. This one was a sobering read.

And finally, Three Days at the Brink by Bret Baier was a masterful recounting of the three-way summit in Tehran between US President Franklin Roosevelt, UK Prime Minister Winston Churchill, and Soviet dictator Joseph Stalin, where the three leaders planned what became Operation Overlord to invade Normandy and save the world from Nazi fascism.

I had already read Baier’s Three Days in Moscow that discussed the fateful summit between President Ronald Reagan and General Secretary Mikhail Gorbachev. Now I’m really looking forward to the final book in the series, Three Days in January about President Dwight Eisenhower’s final mission before turning over the Oval Office to JFK.

Happy reading!

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