Luke Shepard

I use data to tell stories.


I’ve been reading a lot in the last few years, and I’ve come to really admire books in a variety of categories. I want to share them here for your benefit and to accept more recommendations in a similar vein.


I love reading history. I’ve been particularly thrilled to learn about Roman history (into the Byzantine era) as well as the two World Wars. History repeats itself and we must learn from what has come before.

  • Guns, Germs, and Steel
  • 1491
  • 1493
  • Justinian’s Flea
  • Genghis Khan and the Making of the Modern World
  • Rocket Men: The Epic Story of Apollo Program
  • Lords of Finance: The Bankers Who Broke the World
  • Sapiens
  • Civilization: The West and the Rest
  • Hidden Figures
  • Team of Rivals: The Political Genius of Abraham Lincoln
  • The Clockwork Universe
  • Empire of the Summer Moon (Comanche Indians)
  • The Somme

History Podcasts

  • The History of Rome
  • Revolutions
  • History of Byzantium
  • Hardcore History

Business & Management

These are the books that I have found most helpful as a CTO of a small startup. They are roughly in order of the recommendation that I would give to a new manager.

  • Making of a Manager
  • Deep Work
  • Good Strategy, Bad Strategy
  • It Doesn’t Have To Be Crazy At Work
  • Work Rules
  • Difficult Conversations
  • Debugging Teams
  • Bad Blood: Secrets and Lies at Theranos
  • Good To Great
  • Managing Humans
  • The Five Dysfunctions of a Team
  • Possibilities of Organization
  • Hard thing about Hard Things
  • On Writing Well
  • Truth, Lies, and O-Rings
  • Who: The A Guide to Hiring
  • Running Lean

Science Fiction

I love scifi as it helps me imagine what the future could hold. Of all the authors, my favorite is Neal Stephenson. I have given copies of The Diamond Age to many as The Young Lady’s Illustrated Primer encapsulates the vision of what personalized education could become.

  • Reamde by Neal Stephenson
  • Rise and Fall of DODO by Neal Stephenson
  • Seveneves by Neal Stephenson
  • The Diamond Age by Neal Stephenson
  • We Are Legion, We Are Bob (The Bobiverse)
  • The Three Body Problem
  • Lock In
  • NeuroMancer
  • Permutation City
  • The Long Earth
  • The Day of the Triffids
  • Dimension of Miracles (narrated John Hodgman) - best in audiobook
  • A Deepness in the Sky (Vernor Vinge) & sequels
  • 11-22-63 A Novel by Stephen King
  • The End of Eternity by Isaac Asimov
  • Ready Player One


  • Sailing to Byzantium
  • Little Fires Everywhere
  • Cutting for Stone
  • Artemis by Andy Weir
  • Handmaid’s Tale
  • Women of Brewster Place
  • Fear and Loathing in Las Vegas
  • Their Eyes Were Watching God
  • Man Called OVe
  • Animal Farm
  • the Martian, by Andy Weir
  • Complete Sherlock Holmes
  • The Argonautica, Appolonius Rhodus
  • Adequate Yearly Progress

Chicago & Social Justice

I love Chicago. The city can be beautiful and has many wonderful people, but it also has a severe ugly side of injustice and racism that defines its entire past. I think it’s worth learning about all sides of the city so that I can best work towards a solution.

These books are either primarily about Chicago, or mention the types of injustices that the city faces in the context of the whole country.

  • There Are No Children Here, Alex Kotlowitz
  • Color of Law: A forgotten history of How Our Government Segregated America
  • Evicted
  • Hillbilly Elegy
  • $2 a Day: Living on Almost Nothing in America
  • The New Jim Crow
  • Work Hard, Be Nice
  • Ghosts in the Schoolyard, Eve Ewing
  • The War on Neighborhoods
  • American Pharaoh
  • Boss by Mike Royko
  • Mayor 1% (Rahm Bigraphy)
  • Battle for Lincoln Park
  • Crook County

Memoir & Biography

I love learning from other’s experiences and in particular to witness the life of another person. These are a few of the many biographies that I’ve enjoyed.

  • Trevor Noah, Born a Crime (best in audiobook - Trevor does fantastic voices)
  • Long Walk to Freedom, Nelson Mandela
  • The Boy Who Harnessed the Wind
  • I am Malala
  • Titan (Rockefeller)
  • The Good Neighbor

Recent Past and Near Future

I have enjoyed books that predict the future or describe recent events, that may not be described as “history” but are more likely to appear on a best-selling list or similar.

  • I’ll Be Gone In The Dark by Michelle McNamara
  • What Happened by Hillary Clinton
  • The Next Hundred Years, George Friedman

Technology & EdTech

I’ve consumed a lot of technology books, but some of these are resources I go to over and over again.

  • The Master Algorithm
  • Drawdown, the Most Comprehensive Plan Ever Proposed to Reverse Global Warming
  • Hands-On Machine Learning
  • Python for Data Analysis
  • Disrupting Class
  • Mindset: The New Psychology of Success Carol Dweck
  • Growing Object Oriented Software, Guided By Tests

Special Needs Parenting

Finally, as a parent of a child with special needs, I’ve really needed some of these books to help me navigate that journey.

  • No-Drama Discipline
  • How To Talk So Kids Can Learn
  • Positive Discipline
  • Kids Beyond Limits
  • Long Term Outcomes of Epilepsy Surgery in Children And Adults
  • Effective Literacy Instruction for Learners with Complex Support Needs
  • WrightsLaw: all about IEPs