Productive Difficulty: How Choosing Hard Creates Unfair Advantage (and) The CEO’s Framework for Building Competitive Moats

by Joshua Waldron

295 pages, Kindle Edition

Published September 22, 2026

About the author

I spent five years in a wheelchair after a spinal cord injury at fifteen. The doctors said it was permanent. Five years of physical therapy proved them wrong, and most of what I write about now I learned on that floor.

Later I co-founded a manufacturing company in a hostile political environment, in a market no investor would touch, and built it from a side project into the largest firearm suppressor company in the world (SilencerCo, Inc. 500 several years running). After that I served as president of Vista Outdoor, a publicly traded portfolio of forty brands. Today I'm Senior Director of Revenue at Angled Spade Technologies, working in additive manufacturing for defense, and I sit on the board of Ball & Buck. I also run a real estate firm with my brother and work with a small number of founder-operators each year.

I've written and released three studio albums, which I mention because the music was the first hard thing I chose on purpose, and it's given me a lifetime of joy.

Hard is Fun is the family code. My four kids each wear it on a dog tag. Productive Difficulty is the first book in that body of work: a practical framework for choosing the right hard things, written from the shop floor rather than the lectern. I live in Virginia Beach with my wife and our four children.

Reviews

[Jill Rey]

In “Productive Difficulty,” author Joshua Waldron blends his own business successes and failures with the lessons he learned the hard way, offering readers a framework to avoid unnecessary pain while embracing the challenges that create lasting advantages. His central premise – front-load the pain to back-load the power – anchors the book, but Waldron is careful to distinguish between productive difficulty and pointless suffering. The difference, he argues, is the foundation of any true moat.

Waldron begins with his own story: a teenager told he would never walk again, who deliberately damaged his wheelchair to force himself into the harder path. That instinct to choose meaningful difficulty shapes the way he builds companies, having lived his life proving the doctors wrong, it only makes sense he would lead businesses by doing the same.

“Productive Difficulty” breaks down how to select the right hard thing: capabilities that compound, solutions that address both present and future problems, and moats that competitors cannot cross. Waldron’s guidance is practical, structured, and immediately applicable.

As “Productive Difficulty” shifts to part two the focus becomes on culture. Outlining traits that define high-performance teams – unjaded outlooks, intrinsic motivation, low ego paired with high confidence, and pattern recognition rather than credentials, Waldron argues culture is truly revealed in what leader’s signal when they believe no one is watching.

Moving then to mapping the emotional terrain of hard things Waldron recounts the excitement of beginnings, the fatigue of the middle, and the discipline required to reach the end. Using milestones, team rituals, accountability, and evidence collection, readers are armed with the tools for persistence.

Where many business books stop at theory, Waldron closes with execution. Delivering in part four a roadmap to ensure “Productive Difficulty” becomes not just a concept but a stainable practice.

[Cheri Farnsworth]

Thoughtfully written by someone who has lived and learned. Joshua provides solid and practical steps to choose hard over comfort. I have already applied many of the suggested methods of evaluating situations in life and in business.