One of my 2019 new year resolutions was to read more books.

I signed up for GoodReads

and stated a reading challenge with a modest goal of finishing twelve books. I finished twenty-four, and many of these books are great reads for entrepreneurs, CIOs, and other digital transformation leaders.

What makes a good book? My favorites have a strong focus, come from a unique perspective, are easy to read/listen, deliver a clear message, back their hypotheses with data or testimonials, tell personal stories, and are concise.

Here are my favorites in three topics: (i) digital transformation leaders, (ii) startup founders and entrepreneurs, and (iii) AI and data.

My Top Books for Digital Transformation Leaders

Two books really stand out from my list for those leading digital transformation programs. I spent my earlier years working in the newspaper and magazine industry, including three years as CIO of Businessweek. I had a front-row seat to the publishing industry’s digital disruption and really enjoyed Ruth Reichl’s perspectives in her book,

Save Me The Plums

. Reichl was the last editor of Gourmet Magazine and tells the story of the magazine’s heyday and its demise, partially due to digital disruption.

Then read Bob Iger’s book,

The Ride of a Lifetime

, where he tells the story of driving Disney through a fast-paced digital transformation from its acquisition of Pixar through Marvel, Star Wars, and 21st Century Fox. He tells the top-down story, which is unique and especially important for leaders executing a digital M&A strategy.

Other notable reads


Ninja Future

by Gary Shapiro about innovation’s digital ninjas,

The Technology Fallacy

by Gerald C. Kane, Anh Nguyen Phillips, Jonathan R. Copulsky, and Garth R. Andrus about the people/human/cultural side of transformation, and

The Black Swan

by Nassim Nicholas Taleb about chasing after significant, disruptive innovations.

My Top Books for Startups and Entrepreneurs

I have several excellent reads in this category to recommend. My absolute favorite read this year was

Lost and Founder

by Rand Fishkin that tells his authentic story of starting and growing Moz, the SEO and data company. This book is packed with useful insights on developing great products, sharing personal vulnerabilities, and understanding startup economics.

Speaking of startup economics,

Sand Hill Road

by Scott Kupor is

the bible

to best understand VC funding. It is a must read for startup founders, CFOs, CIOs, and anyone thinking of raising venture capital.

Two other essential reads for startups building digital products are


by Marty Kagan and


by Reid Hoffman and Chris Yeh. Both cover a lot of ground with Inspired being one of the best books I’ve read on digital product management.

If you are an entrepreneur running a small business, then I’d recommend several books that have been very helpful in how I think about my business



Building a Story Brand

by Donald Miller is a highly resourceful book on marketing, and I’m sure you’ll learn a thing or two on negotiation from

Never Split the Difference

by Chris Ross and Tahl Raz. If professional services or consulting is part of your business model, then

Book Yourself Solid

by Michael Port will help you rethink your lead generation and nurturing strategy.

Other notable reads


The Culture Code

by Daniel Coyle (some excellent details and stories in this book on assembling and managing great teams),

Steal the Show

by Michael Port (very good for those of you keynoting and speaking at conferences) and

Business Secrets from the Bible

by Rabbi Daniel Lapin (a biblical historical perspective and origin to business thinking and ethics).

My Top Books on AI and Big Data

I’ve already

written a review of three outstanding books covering AI


After publishing the reviews, I went looking for more technical books on artificial intelligence for leaders that don’t go into the implementation weeds. I found one in

Applied Artificial Intelligence

by Mariya Yao, Adelyn Zhou, and Marlene Jiawhich. The book provides a full background on AI experimentation, including a review of machine learning approaches, s summary of data requirements, and an overview of talent considerations.

Other notable reads


Prediction machines

by Ajay Agrawal, Joshua Gans, and Avi Goldfarb (more great reading on AI) and

Storytelling with Data

by Cole Nussbaumer Knaflic (best practices in data visualization).

Driving Digital Still Strong in 2019

I still get a lot of very positive feedback on my book, Driving Digital. The need for organizations to drive digital transformation and implement business-IT-Data collaborative practices including agile management, product management, DevOps, data-driven practices, and proactive data governance. Businesses need to operate smarter and faster and drive significant culture change. If you haven’t done so already, I hope you’ll read

Driving Digital


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