The best books for solo founders building businesses to last

Who am I?

Alex Hillman is always thinking about the intersection of people, relationships, trust, and business. He’s an author, educator, and community builder. These days, he splits his time between operating Indy Hall, which is one of the oldest coworking spaces in the world; teaching creative people how to bootstrap their own businesses at Stacking the Bricks; and collaborating with people and organizations towards the goal of helping 10,000 people become sustainably independent by 2029.

I wrote...

The Tiny MBA: 100 Very Short Lessons about the Long Game of Business

By Alex Hillman,

Book cover of The Tiny MBA: 100 Very Short Lessons about the Long Game of Business

What is my book about?

What you really need to know is something that most business people won't say out lou. There is no single right way to do things in business, but there are plenty of avoidable mistakes along the way. The Tiny MBA offers 100 pointed pieces of guidance that will help you begin to think like someone who has started and run their own business for 15 years and intends to keep doing it for a long time. Each page of the book offers ideas and prompts and clues and suggestions and reflections to help you navigate the business in ways that most people only learn the hard way.

Check out the book here.

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The books I picked & why

Book cover of Just Listen: Discover the Secret to Getting Through to Absolutely Anyone

Alex Hillman Why did I love this book?

I’ve recommended this book to people in sales, marketing, copywriting, and management, even though you’d never see it listed as a book about those topics. That’s because the most universal experience that people crave is feeling understood, and this couldn’t be more true for your customers. 

Successful founders know the importance of listening to and understanding their customers, but very few actually approach the act of listening as a practice. Unlike business books that focus on artificial experiences like interviews and focus groups, Just Listen teaches the reader the power of truly listening as a tool and a skill that can be practiced. 

The source of this expertise? A clinical psychologist who also happens to train FBI hostage negotiators. The same techniques apply across the board, and are shared in the book through interesting and surprisingly relatable stories, paired with specific and concrete exercises and techniques that you can try on yourself before trying on other people. I use many of these techniques on a daily basis running my businesses. 

By Mark Goulston,

Why should I read it?

2 authors picked Just Listen as one of their favorite books, and they share why you should read it.

What is this book about?

Getting through to someone is a critical, fine art. Whether you are dealing with a harried colleague, a stressed-out client, or an insecure spouse, things will go from bad to worse if you can't break through emotional barricades and get your message thoroughly communicated and registered.

Drawing on his experience as a psychiatrist, business consultant, and coach, author Mark Goulston combines his background with the latest scientific research to help you turn the "impossible" and "unreachable" people in their lives into allies, devoted customers, loyal colleagues, and lifetime friends.

In Just Listen, Goulston provides simple yet powerful techniques you can…

Book cover of Badass: Making Users Awesome

Alex Hillman Why did I love this book?

Whether you sell products or services, customers don’t really buy either: they buy outcomes. And it’s not enough to understand what people want to accomplish, truly successful businesses deeply understand how customers view their own success, and how to create a path from where they currently are to where they want to be. 

In Badass, Kathy uses her unique and very visual learning style to help you get in the head of your customers and understand the world from their point of view. There’s a shortlist of people who’ve had a huge impact on my career, and Kathy Sierra is at the top of that very shortlist. This book embodies that impact, I consider it required reading.

By Kathy Sierra,

Why should I read it?

1 author picked Badass as one of their favorite books, and they share why you should read it.

What is this book about?

Imagine you're in a game with one objective: a bestselling product or service. The rules? No marketing budget, no PR stunts, and it must be sustainably successful. No short-term fads. This is not a game of chance. It is a game of skill and strategy. And it begins with a single question: given competing products of equal pricing, promotion, and perceived quality, why does one outsell the others? The answer doesn't live in the sustainably successful products or services. The answer lives in those who use them. Our goal is to craft a strategy for creating successful users. And that…

Book cover of The Essential Yoga Sutra: Ancient Wisdom for Your Yoga

Alex Hillman Why did I love this book?

One of the most valuable lessons I’ve learned is how to manage my own fear and excitement. How we react to the world around us is one of the few things we are truly in control of! This is the book that helped me most to shift the way I perceive and react to things, allowing me to live more calmly in my work and my life even in the face of complexity, fear, even success. 

This book is weirdly simple, almost child-like in its cadence, but don’t let the simplicity fool you. I found it valuable to sit with the short parables and examples especially when I’m having an emotional response surrounding a business decision. 

This was the first book based on Buddhist teachings that I ever read and made sense to me in a practical way. The writing style is strange (and the author has a truly bizarre backstory) but this book taught me a lot about how our perception of reality really works and how it holds us back.

By Lama Christie McNally, Geshe Michael Roach,

Why should I read it?

1 author picked The Essential Yoga Sutra as one of their favorite books, and they share why you should read it.

What is this book about?

The Yoga Sutra of Patanjali is a classic Sanskrit treatise consisting of 195 “threads,” or aphorisms, describing the process of liberation through yoga. Although little is known about Patanjali (most scholars estimate that he lived in India circa 200–300 B.C.), his writings have long been recognized as a vital contribution to the philosophy and practice of yoga. This new, expert translation of the original Sanskrit text of Patanjali’s best-known work presents his seminal ideas and methods in accessible, plain-language English.

Patanjali organized the sutra into four parts: Samadhi (absorption), Sadhana (practice), Vibhuti (supernatural powers), and Kaivalya (liberation). Each represents a…

Book cover of How to Fight a Hydra: Face Your Fears, Pursue Your Ambitions, and Become the Hero You Are Destined to Be

Alex Hillman Why did I love this book?

This book is not at all what it seems. If you’ve ever struggled with a project or idea, especially as it grows in complexity, the metaphor of the mythical Hydra may have come to mind. In the myths, the Hydra is especially dangerous because every time you cut off one of its heads, two more grow back in its place. 

Kinda like a project or business that seems impossible to finish. 

Unlike most business books that beat you over the head with case studies, this book uses a single short story styled as a fairytale to unlock and teach dozens of valuable business lessons from across dozens of fields of study: psychology, planning, marketing, negotiation, and more. Half of the fun of reading this book is realizing each time the story is teaching you something useful. It’s like a little treasure hunt of business knowledge all on its own!

By Josh Kaufman,

Why should I read it?

1 author picked How to Fight a Hydra as one of their favorite books, and they share why you should read it.

What is this book about?

A survival manual for ambitious artists entrepreneurs ADVENTURERS

You have a Hydra: a grand, ambitious project you’ve always wanted to tackle. It feels overwhelming, unconquerable. Chop off one of a Hydra’s heads, and two more grow in its place.

How will you ever defeat such a terrifying monstrosity – and live to tell the tale?
In this illuminating fable, productivity expert Josh Kaufman explores the uncertainty and fear inherent in facing down any ambitious challenge, from starting a new business to completing a work of art.

The risks involved can never be eliminated, but they can be understood, anticipated, and…

Book cover of Design for Cognitive Bias

Alex Hillman Why did I love this book?

The most insidious mistakes we make are the ones we didn’t even realize we were making. This short book brilliantly shines a light on the thousands of “invisible” choices that we make in our work and our lives, but more importantly, the author guides us on how to begin correcting them.

Using examples and case studies, author David Dylan Thomas helps you bring awareness to three lenses of bias that are guaranteed to be affecting your work: how biases impact our own individual experiences and choices, how they wiggle their way into our teams and leadership structures, and how they get wired directly into the products and services we deliver. 

If you care about creating long-lasting and equitable results with your work, you need to read this book.

By David Dylan Thomas,

Why should I read it?

1 author picked Design for Cognitive Bias as one of their favorite books, and they share why you should read it.

What is this book about?

We humans are messy, illogical creatures who like to imagine we’re in control—but we blithely let our biases lead us astray. In Design for Cognitive Bias, David Dylan Thomas lays bare the irrational forces that shape our everyday decisions and, inevitably, inform the experiences we craft. Once we grasp the logic powering these forces, we stand a fighting chance of confronting them, tempering them, and even harnessing them for good. Come along on a whirlwind tour of the cognitive biases that encroach on our lives and our work, and learn to start designing more consciously.

You might also like...

Currently Away: How Two Disenchanted People Traveled the Great Loop for Nine Months and Returned to the Start, Energized and Optimistic

By Bruce Tate,

Book cover of Currently Away: How Two Disenchanted People Traveled the Great Loop for Nine Months and Returned to the Start, Energized and Optimistic

Bruce Tate

New book alert!

What is my book about?

The plan was insane. The trap seemed to snap shut on Bruce and Maggie Tate, an isolation forced on them by the pandemic and America's growing political factionalism. Something had to change.

Maggie's surprising answer: buy a boat, learn to pilot it, and embark on the Great Loop. With no experience, and knowing little about seafaring, diesel motors, or navigation, Maggie, Bruce, and the family dog decided to take on the six-thousand-mile journey down inland rivers, around the Gulf and Atlantic coasts, and across the Great Lakes. They would have to navigate canals, rivers, seas, and locks. But along the way, they made new lifelong friends and were forever changed.

For nine months, Bruce and Maggie navigated shallow rivers, bottomless lakes, joy, and loss. Against all odds, they conquered the Great Loop, and along the way, found common cause across political divides with new friends while blowing the walls off their world.

Currently Away: How Two Disenchanted People Traveled the Great Loop for Nine Months and Returned to the Start, Energized and Optimistic

By Bruce Tate,

  • Coming soon!

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