Jordan DiPietro: Personal Blog

Top 25 Business Books That Helped Shape the Way I Think

photo of 25 business books stacked next to each other

A shelf-tested list split between the real-deal memoirs and the timeless business bibles.

Over the last 20+ years, I’ve read a mountain of business books — some great, many forgettable.

These 25 or so have stuck with me. They taught me how to lead, how to market a product, how to obsess over your customer, how to think better.

Some I’ve re-read multiple times. Others hit me like a truck once and I never needed to pick them up again.

I’ve split the list into two parts:

  1. Memoirs & Bios: founder stories, personal arcs, rise-and-fall tales.
  2. General Biz Books: frameworks, strategy, skill-building, data, customer thinking.

Top 10 Business Bios & Memoirs

Real people. Real stories.

1. Shoe Dog by Phil Knight
Reads like a novel, not a business book. It’s scrappy, honest, and full of doubt — a blueprint for grit.

2. Steve Jobs by Walter Isaacson
Brilliant and maddening — like the man himself. You finish it feeling like you’ve been in the room with him.

3. Made in America by Sam Walton
Surprisingly humble for one of the most powerful retailers in history. It’s filled with down-home tactics and old-school charm.

4. Call Me Ted by Ted Turner
Wild, weird, and unfiltered. This one reads like a campfire story from a billionaire pirate.

5. Amazon Unbound by Brad Stone
Less origin story, more empire building. A sharp look at Bezos 2.0 — richer, more ruthless, and more ambitious.

6. The Everything Store by Brad Stone
The definitive account of Amazon’s chaotic rise. You’ll understand how obsession scales.

7. The Four Seasons by Isadore Sharp
A masterclass in hospitality and consistency. Understated but deeply thoughtful.

8. Burn Rate by Andy Dunn
Founders rarely talk this openly about mental illness. It’s a gripping, brutally honest account of bipolar disorder in the startup world.

9. Barbarians at the Gate by Bryan Burrough & John Helyar
Reads like a thriller. It’s about greed, ego, and the wild west of leveraged buyouts.

10. Delivering Happiness by Tony Hsieh
Whimsical and weird in the best way. Full of heart and offbeat lessons that still hold up.

Top 15 General Business Books

Frameworks, data, strategy, and customer obsession.

11. Zero to One by Peter Thiel
Philosophical, sharp, and confidently contrarian. Even if you disagree with parts, it’ll rewire your thinking.

12. The Signal and the Noise by Nate Silver
A dense but essential book about prediction and probabilistic thinking. It’s helped me see patterns more clearly — and ignore the wrong ones.

13. Measure What Matters by John Doerr
The go-to book for understanding OKRs. It’s more than theory — it’s packed with company stories and lessons from the trenches.

14. Predictable Success by Les McKeown
If you’re scaling a company, this is your map. It nails the emotional reality of different growth stages.

15. Customer Winback by Griffin & Lowenstein
Nobody talks about this topic — and they should. Reviving past customers might be your easiest win, and this book shows you how.

16. Customer Retention by Griffin & Lowenstein
Less flashy than acquisition books, but arguably more important. This is foundational if you’re in recurring revenue.

17. Don’t Make Me Think by Steve Krug
Technically about UX, but really about human behavior. Quick read, massive impact.

18. Web Analytics 2.0 by Avinash Kaushik
More than charts and dashboards — this book teaches data thinking. It helps you stop measuring noise and start tracking real impact.

19. Successful Direct Marketing Methods by Bob Stone & Ron Jacobs
Thick, dry, and incredibly useful. If you sell anything online, this book is full of time-tested tactics that still work.

20. Direct Marketing by Edward Baier
An old-school classic with persuasion fundamentals that haven’t aged a day. Think Mad Men with spreadsheets.

21. Rules for Revolutionaries by Guy Kawasaki
Quick, sharp advice from one of Apple’s early evangelists. Think “startup inspiration meets practical momentum.”

22. Platform Revolution by Parker, Van Alstyne, & Choudary
Breaks down the science behind platform-based businesses. You’ll finally understand why Uber, Airbnb, and Amazon dominate.

23. I Love You More Than My Dog by Jeanne Bliss
It’s about how beloved companies build loyalty through emotional decisions. Not your typical “CX” book.

24. The Honest Truth About Dishonesty by Dan Ariely
A fascinating tour of why people lie, cheat, and bend rules. Critical reading if you manage people or build products.

25. Fooled by Randomness by Nassim Nicholas Taleb
Will absolutely humble your ego. Makes you question every success, failure, and signal you think you understand.

Summing It Up

That’s the list. Some are evergreen. Some are snapshots of a moment. But every one of them helped me level up.

You’ll see books on leadership, strategy, customer retention, UX, decision-making, and pattern recognition. That’s intentional. In my opinion, the best founders and CEOs are like Swiss Army knives — they can hire a VP of Engineering, write great content, and sit with the data team without getting lost.

If you’re wondering where the copywriting, persuasion, or direct marketing classics are — don’t worry. They’re getting their own post. Stay tuned.

Got any favorites that I missed? Let me know – I’m always up for adding new ones to the stack!

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