2020 was a big reading year for me (a positive COVID-era side effect). Here are my recommendations for excellent business / startup / marketing books, loosely arranged by topic, with an eye towards founder and CEO readers. Most were published in 2020, and a few are older classics.

My top four 2020 reads

All revolve around company culture, told from the perspective of the CEO.

Billion Dollar Loser: The Epic Rise and Spectacular Fall of Adam Neumann and WeWork – Reeves Wiedeman. If there’s a story that illustrates the past decade in startup land – complete with frothy valuations, VCs spewing money, pathological company growth, and outrageous excess – it’s WeWork’s. Wideman is an editor at New York Magazine, so this is phenomenally written and reads like a thriller. My 2020 favorite.

No Rules Rules: Netflix and the Culture of Reinvention – Reed Hastings. In the year when Netflix continued its explosive growth, this book is an extremely thought-provoking read for any founder. Some of the recommendations may seem extreme (e.g. pay whatever amount of money you need to get the best people), but there’s no arguing they lead to results.

Lights Out – Thomas Gryta and Ted Mann. The story of GE’s downfall, focusing on Jeff Immelt’s tenure, but providing an in-depth walk-through of the shortcomings (to put it mildly) of the Jack Welch era. Follow this one with Winning Now, Winning Later: How Companies Can Succeed in the Short Term While Investing for the Long Term by David M. Cote – the exact opposite to Lights Out. It’s written by the former CEO of Honeywell (a fierce GE competitor).

These two books provide valuable insights into not only huge enterprises, but also into startups (and really any company) looking to balance short- and long-term priorities. It’s also a great insider view into the workings of Fortune 100 companies, and helpful for any startup selling to their ilk.

Excellent food business books – with useful lessons for tech founders

I love a good food non-fiction book, and often find applicable lessons to tech startups and entrepreneurs.

Eat a Peach: A Memoir – David Chang and Gabe Ulla. I fell in love with this one from the first page. Dave Chang is the founder of Momofuku (and its associated restaurant group) and has such a bright and unique voice. The book also brought back many fond memories of pre-COVID NYC dining. I’m sure many founders will identify with the self-doubt and mental health challenges Chang has faced in his career, while experiencing tremendous growth and business success.

Rebel Chef: In Search of What Matters – Dominique Crenn. A fascinating life story. Crenn doggedly worked her way to become the first woman in the US with three Michelin stars. No overnight success story here—slow and steady wins the race.

CEO reference books

The Five Dysfunctions of a Team: A Leadership Fable – Patrick M. Lencioni. I love the “business fiction” genre and quickly read through this and The Five Temptations of a CEO. Both do a good job pinpointing common CEO / executive team challenges and possible ways to address them.

The Great CEO Within: The Tactical Guide to Company Building – Matt Mochary. What it says on the tin. From Inbox Zero to running meetings to OKRs, this book is full of tangible advice and how-to’s.

The Psychology of Money: Timeless lessons on wealth, greed, and happiness – Morgan Housel. What makes people (employees, consumers, customers, family) tick when it comes to money. Especially useful for technical founders who tend to view the world through a perfectly rational spreadsheet. Plus a lot of useful, non-trivial personal finance advice.

Fiction about the world of tech

Self Care: A Novel – Leigh Stein. Influencer marketing meets Gen Z NYC startup culture. Insanity ensues.

Uncommon Stock: Version 1.0 – Eliot Peper. Thriller with a tech startup as the backdrop? Sign me up please.

The Phoenix Project: A Novel about IT, DevOps, and Helping Your Business Win – Gene Kim. It’s been a decade or two since my coding days, but I loved this one. A solid read for anyone wishing to understand large corporations and why it’s so hard for them to innovate. It’s also really funny.

Uncanny Valley – Anna Weiner. This is a memoir but reads like fiction. An insider view of working at two hot Silicon Valley startups written by a NYC publishing transplant. The good, the bad, the ridiculous.


Great by Choice: Uncertainty, Chaos, and Luck -Why Some Thrive Despite Them All – Jim Collins. I’m a big Jim Collins fan (Good to Great is a must-read for any CEO). This book riffs on the same ideas, but was especially relevant in the craziness called the year 2020.

The First 90 Days, Updated and Expanded: Proven Strategies for Getting Up to Speed Faster and Smarter – Michael Watkins. Went back to this classic this year as we were starting to work with new big clients. I would recommend it to any senior leader starting at a new place, and to founders welcoming these leaders.

Grit: The Power of Passion and Perseverance – Angela Duckworth. I love the premise of this book and think it should be required reading for every high school student (and their parents). The same premise applies to startup founders and their companies.

Gutenberg the Geek – Jeff Jarvis. Johannes Gutenberg: The OG entrepreneur. The first geek. Made the world a better place. Short & fun read.

Sales, marketing, writing

Obsessed: Building a Brand People Love from Day One – Emily Heyward. Emily is the founder of Red Antler, perhaps the world’s most prominent D2C (direct-to-consumer) creative agency (Casper, AllBirds, Foursquare, Birchbox are some of their clients). This book is a good overview of how Red Antler goes about crafting a compelling consumer brand.

The Introvert’s Edge: How the Quiet and Shy Can Outsell Anyone – Matthew Pollard. Especially recommended for introverted technical CEOs who cringe at the thought of selling. This book shows how you can leverage your perceived weaknesses to actually become a better salesperson than the stereotypical extrovert, bigger-than-life salesperson.

Is This Anything? – Jerry Seinfeld. Seinfeld documented all of his sketches for the 40+ years he’s been doing stand up. The writing and storytelling in these vignettes are simply phenomenal. Seinfeld tells a complete story in three sentences, and makes it funny to boot.

Even more book recommendations