With Black Friday happening today and many founders ready to make their libraries a little less incomplete, I will share with you the books that helped me on my own founder journey in the hopes that your Black Friday budget has room for a few of these books.
Welcome to the Bootstrapped Founder. This episode is sponsored by the folks over at acquire.com, more on that later. Let’s walk through my bookshelf now.
I’ll share my library grouped into broad categories —Entrepreneurship, Business Strategy, Marketing, and Customer Interaction— and I’ll say what each book has brought to my own journey.
You will find that I will omit the books that everybody else recommends all the time. No “Lean Startup,” no “Zero to One,” no “Hard thing about hard things.” These books are great, but they’re not as instructive for indie founders and creators as they are for people who follow the venture capital route.
The books I will talk about today are books that I have actually read and found to be useful for someone who wants to build a self-funded, self-controlled, and ultimately self-empowering business. That’s my experience, and it can be yours as well.
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Let’s dive into the most important category first.
Entrepreneurship
- Let’s start with “Company of One” by Paul Jarvis. Paul, ironically, is running a company of two with Jack Ellis at the moment. Their privacy-focused Fathom Analytics SaaS is a spectacular example of staying small and doing big things. That’s what this book is about, and I loved listening to Paul narrating his own audiobook. That’s the way an indie founder does it. In this book, you’ll find a lot knowledge from Paul’s personal founder experience. Those books are the best.
- The same goes for “The Four Hour Workweek” by Tim Ferriss: it’s half manual and half memoir. And that makes it somewhat outdated. The version I read a few years ago already contained many recommendations and links to products and websites that have long since vanished. But it’s worth looking beyond that because if you’re new to indie hacking, this book will reliably blow your mind. It did for me: after reading The Four-Hour Workweek, I finally understood just how powerful owning your time is. And Ferriss doesn’t hold back in the book: he offers concepts on outsourcing, automating, and pragmatic problem-solving, all of which are pivotal for new entrepreneurs. This is probably one of the first books you should read as a founder. I did, and it opened up completely new paradigms for me.
- “Life Profitability” by Adii Pienaar is another book that did just that. He explores the balance between life needs and business goals, which is a core activity for lifestyle entrepreneurs. I remember having a physical response to this book when I read it. What Adii lays out in the book is a completely re-imagined way of prioritizing goals. What is enough? What do you want, what do you need, and is it aligned? That’s the kind of thinking you’re going to do as you read this book. And it comes with templates, too. It’s a really important read for founders who are taking their destiny into their own hands.
- Part of this reprioritizing is actively reducing complexity. “The Minimalist Entrepreneur” by Sahil Lavingia will help you with that. Sahil has been building sizable software businesses in the past, and they were not without controversy. I had him on the podcast when Gumroad did a massive price change, and the whole creator community complained. But look at where he is now: Gumroad is profitable, people have returned after seeking supposedly greener pastures, and Sahil’s building a strong business in public. He knows what few things matter, and he explains it all in the book. It’s a short read with significant lessons.
These books are overall “lifestyle” books, more focused on the founder than the business. Let’s dive into the ones that affect how you run your operation.
Business Strategy
- “Built to Sell” by John Warrillow: Easily my #1 book in this category. This is one of those where I have a “before the book” and an “after the book” life. When I read Built to Sell, I knew what I had done wrong in all my prior attempts to build a business. And the fun thing is: Warrillow doesn’t even talk about software businesses — and yet any software founder will find massive value in this book. It teaches what you need to know about structuring your business and your goals. I attribute my life-changing exit to the framework presented in this book.
- Which is why I started reading all of Warrillow’s other books. “The Automatic Customer” by John Warrillow is equally impactful: it focuses on subscription business models. And again, not just the boring old SaaS monthly fee kind of model. In this book, you’ll find nine ways to monetize whatever kind of business you’re building on a recurring basis. It’s super helpful if you want to be inspired by other industries. One of the models in there is “the insurance,” which I rarely ever see used in SaaS, but it works. People pay for not having to think about things. This is the kind of well-exemplified insight you’ll find in this book.
- And finally, “The Art of Selling Your Business” by John Warrillow. Yeah, I’m a fan. John’s third book is an amazing guide for any founder looking into selling their business. Which, if you ask me, is something you should do from day one, and particularly when you don’t have to sell. Preparing and executing a successful business exit are things best learned earlier than at the last minute.
- And since we’re talking overall strategy here: “The E-Myth Revisited” by Michael E. Gerber is another one of these “read before you start” books. It explains the myth of technical skills being sufficient to build a business. You know… the thing we all believe: if you’re a good developer, you can build a software business. Well, it turns out that’s not enough, and Gerber has many intriguing stories that show processes that we implemented in our SaaS on our way to $55k MRR. This is, yet again, not about SaaS. It’s about building a functional business of any kind.
- But a book that is totally about SaaS is “The SaaS Playbook” by Rob Walling (who was on the podcast this week), and it’s the most recent one on this list. Rob’s insight into numerous cohorts in TinySeed, his accelerator, has given him something a lot of founders would love to have: data. Rob has the numbers, and his advice in this book is built upon that. If you want to start an indie-funded business with potential, this is the book. And you might want to look into Start Small, Stay Small by Rob as well.
Let’s jump into marketing real quick.
Marketing
- The most important book to read here is “Obviously Awesome” by April Dunford. More than anything, fresh founders mess up their positioning by not even knowing what positioning is. April is the expert in this field, and she’ll make sure you start your marketing efforts right. As more and more indie businesses proliferate, you benefit from being clear about who your product is for and who it’s not.
- With real human beings at the center of most indie marketing —be it word of mouth, referrals, or just “mindshare” strategies— you will benefit immensely from**”Permission Marketing” by Seth Godin.** In fact, buy all his marketing books if you can. Seth has been sharing insights into online digital marketing for decades; he even invented the field. So, if you need a primer on why and how we market, read Seth Godin.
- Another one of these “before I read it” and “after I read it” books was “Hooked” by Nir Eyal. It teaches you how to build habit-forming products. It’s a bit of a controversial read, as the techniques described in this book have been used to addict a significant number of people to all kinds of unhealthy products, but you can and should use it for good. The Hook Cycle is a framework I am using in all my products now that I know its power. You’ll create high-retention products with happy customers with it.
Which brings us to dealing with customers.
Customer Interaction
- A rarely recommended book is “Farm Don’t Hunt” by Guy Nirpaz, and I think that’s a shame. Value nurturing is a concept every founder should understand, and who would want to be ignorant of nourishing customer relationships? Well, that’s what this thin but powerful book will teach you. When you have a solid product that can really help your customers, this is how you show up with extra impact.
- And before you get to that point, you have to learn a lot from your customers. “Deploy Empathy” by Michelle Hansen is my favorite book for customer discovery and exploration. This great little gem offers actual scripts for customer interviews, which I love. It doesn’t just tell you the why; it guides you through the how.
- Finally, read “The Mom Test” by Rob Fitzpatrick. It won’t take you more than an hour, and it’s worth it. Rob wrote a guide on communicating effectively with customers without falling into the traps of asking the wrong people the wrong questions. A lot of founders ask their customers if they want new features. Of course, they do, why wouldn’t they? That’s not how you learn what they need; it’s how you ruin your product! Rob teaches you how to ask better questions.
And that’s it, my top 15. There are dozens, if not hundreds, of other books that founders can learn from, but you’d never get through that list before the AI singularity takes over the world.
I will tell you about two more books. My books. I wrote Zero to Sold as a compendium, a guide through every stage of starting, running, and selling a SaaS business. You’ll find this rather sizeable book to be a great manual that you can reference while you build your own thing. It contains my experiences and many anecdotes from failing a lot until I had my breakthrough and a life-changing software business exit. My second book, The Embedded Entrepreneur, dives into a smaller part of this journey: starting a business by understanding the needs and desires of a community you’re part of. If you want to build an audience and a legacy while building impactful products, The Embedded Entrepreneur is for you.
Ultimately, you could start and eventually sell a business without ever having read any of these books. But why play the game on hard mode when dozens of people have shared their hard-earned lessons in easily consumed books, right?
Enjoy your Black Friday book-purchasing frenzy!
