Must Read Leadership Books and the Lessons Learned

Win Make Give with Ben Kinney38mMay 8, 2026

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AI-Generated Summary

In this episode of 'Win Make Give,' host Ben Kinney and co-hosts Chad Himes and Bob Stewart dive into a curated list of six transformative leadership books that have shaped their thinking. The conversation begins with Ben sharing his personal journey with reading—overcoming dyslexia and attention challenges by using audiobooks, paper copies, and short, focused reading sessions at double speed. The core of the episode centers on six must-read leadership books: 'High Output Management' by Andrew Grove, 'Work Like You're Showing Off' by Joe Calloway, 'The Hard Thing About Hard Things' by Ben Horowitz, 'The Five Levels of Leadership' by John Maxwell, 'The Captain's Class' by Sam Walker, and 'Engaged Leadership' by Clint Swindoll. Each book is unpacked for its unique insights—ranging from Grove’s data-driven management philosophy and Calloway’s radical idea of 'showing off' as a mindset of excellence, to Horowitz’s gritty realism about leadership under pressure, Maxwell’s pyramid of influence, Walker’s revelation that team greatness stems from character-driven captains, and Swindoll’s fable-based model for cultivating employee engagement. The hosts emphasize that true leadership isn’t about titles or charisma, but about character, consistency, and the ability to develop others.

Key Takeaways
1

Read in short, focused bursts with dual input (audiobook + physical book) to boost retention and focus.

2

Leadership is influence, not position—true leaders earn respect through character and consistent action.

3

The most impactful leaders are often not the most visible; they’re the 'lunch pail' captains who lead by example.

4

Past success can be the enemy of future growth—challenge old habits to innovate and improve.

5

Engaged leadership requires identifying and empowering 'oh yeah' employees while transforming 'oh no' ones.

…and 3 more takeaways available in PodZeus

Chapters
0:00
5 min

Introduction and the Power of Leadership Books

Ben Kinney welcomes listeners to the podcast and introduces the episode’s focus: a deep dive into the most impactful leadership books. He shares his personal struggle with reading due to dyslexia and attention challenges, setting the stage for how he now approaches books through short, multi-modal sessions.

5:00
5 min

Ben’s Reading Strategy: Overcoming Learning Challenges

I speed it up on Audible. And when you speed it up on Audible, and you're holding the book at the same time, it forces you to go so fast line by line, you can't daydream.

Highlight
10:00
10 min

High Output Management by Andrew Grove: The Leader Who Led by Example

I recently ran out of space on my bookshelf at home, so I was faced with a choice. Either I had to throw away some books or buy a bigger house. Well, that was an easy decision, but which books to throw out? Then I thought the management books...

Highlight
20:00
10 min

Work Like You're Showing Off by Joe Calloway: The Power of Pride in Your Work

If you're not showing off, then what's the point? If you're not showing off, then why even show up? Why go to work? Why play the game? Showing off as I define it is a good thing.

Highlight
30:00
10 min

The Hard Thing About Hard Things by Ben Horowitz: Leadership in the Trenches

The most important thing I learned as an entrepreneur was to focus on what I needed to get right and stop worrying about all the things I did wrong or might do wrong.

Highlight
High-Impact Quotes
If you're not showing off, then what's the point? If you're not showing off, then why even show up? Why go to work? Why play the game? Showing off as I define it is a good thing.
Joe Calloway (via Ben Kinney)10:19
Viral: 90.0
The most crucial ingredient in a team that achieves and sustains historic greatness is the character of the player who leads it.
Sam Walker (via Chad Himes)27:01
Viral: 88.0
I recently ran out of space on my bookshelf at home, so I was faced with a choice. Either I had to throw away some books or buy a bigger house. Well, that was an easy decision, but which books to throw out? Then I thought the management books...
Ben Kinney7:29
Viral: 85.0
Speakers

Hosts

Ben KinneyChad HimesBob Stewart
Topics Discussed
Team Excellence and Captain Class Leadership95%Character Over Charisma in Leadership92%Leadership Mindset90%Employee Engagement and Organizational Culture88%Leadership Development and Mentorship86%Reading Strategies for Busy Leaders85%Practical Leadership Books82%Overcoming Past Success80%
People & Brands

Ben Kinney

person

12xPositive

Chad Himes

person

11xPositive

Joe Calloway

person

10xPositive

Bob Stewart

person

10xPositive

Ben Horowitz

person

9xPositive

Sam Walker

person

9xPositive

John Maxwell

person

8xPositive

Andrew Grove

person

8xPositive

Clint Swindoll

person

6xPositive

Intel

organization

5xPositive

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