My Top Books 2019: Digital Transformation, Entrepreneurship, AI

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 Inspired by Marty Kagan and Blitzscaling 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 StarCIO. 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 including

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.

If you want to recommend books to me or follow my writing, then please sign up for the Driving Digital Newsletter!

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About Isaac Sacolick

Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld,, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.