I asked over a dozen indie hackers for the one book they each find indispensable to bootstrapping a successful business. Check out their answers below.
This is an odd one but I've found Ernest Hemingway On Writing — an edited collection of excerpts and letters by Ernest Hemingway on doing the work of writing — to be tremendously helpful. Writing a novel and generally being a professional writer seems to have a ton in common with building a great software product/company and being a bootstrapper in general.
My favorite tip is to stop each day when you're going good. Writing a novel and building a business is about maintaining momentum over weeks, months, and years. One way to keep that motivation loop going strong is to find a point when you know exactly what you're going to do next, then stop for the day, get as far away from the work as you can (read, go outside, eat dinner with friends) and then pick up the next day right on that thing. This way you never start your day with "what the heck do I do now?" You always have one high-value thing to kick off the day with.
I learned a ton from the book and collected more of my favorites here.
P.S. Yes, this is why Hemingway is our Twitter avatar. :)
In the early days of Baremetrics I found myself almost self-sabotaging the success it was having. I'd procrastinate the hard things, ignore the obvious moves, and focus on things that didn't matter.
The War of Art by Steven Pressfield talks a lot about overcoming the ways in which we inadvertently and subconsciously work against our own strengths and successes, and lays out how to work on what matters not just to the success of the project but to you as an individual.
Someone once asked Somerset Maugham if he wrote on a schedule or only when struck by inspiration. “I write only when inspiration strikes,” he replied. “Fortunately it strikes every morning at nine o’clock sharp.”
Show up. Do the work. Some days (many? most?) you won't want to. But if you stick with it, the needle will move.
The book I find myself recommending the most often to Indie Hackers is Traction by Justin Mares and Gabriel Weinberg. It's a great high-level take on different strategies for getting traction for your product, framed in a concise, clear, and actionable way. I found it particularly helpful because it provides a framework you can actually execute and follow yourself instead of just discussing ideas.
The biggest thing I took away from Traction was that founders should to try and split their time evenly between building a product and marketing it. For many developers and Indie Hackers this balance gets very skewed towards the building side, which is where most of us are more comfortable. But by trying to achieve a 50/50 split I ended up investing much more thought and energy into promoting my projects, which ultimately led to far more success than I would have achieved if I'd followed my instincts and focused only on building. Now I always categorize the time I spend on projects into these two time buckets and course-correct when I find I've spent too much time building.
The single biggest reason that startups fail is that they don't acquire customers fast enough. Traction explores how to overcome that problem and lays out more than a dozen different channels that startups can use to attract and acquire customers.
Obviously, execution is key. But working from a blank slate is really hard. This book gives you ideas of where to start and provides practical advice to take your first steps in testing each channel to see what will work best for you... and what won't.
How to Win Friends and Influence People by Dale Carnegie. A lot of books come and go for me but this is the one that has a permanent spot on my shelf at all times. As someone who has to spend a lot of time communicating, it's been a crucial resource.
It's caused me to think a lot about potential responses to what I say, and has helped me anticipate responses to statements so I can craft something that works for my audience. I use it a lot when making asks (for instance, in TinySeed I do a LOT of emailing asking mentors for help with our founders — I need to ask for help confidently, but also be deferential to our mentors and their schedules) and I wouldn't be as effective if I hadn't read this book first.
Surprised this one hasn't been mentioned yet, but Antifragile by Nassim Taleb.
It's been useful for forcing me to think about where there might be fragilities in my business. One of the big keys to success, especially in a bootstrapped company, is just not dying, and one of the main ways you die is through unforeseen weaknesses that take you by surprise.
I try to re-read it every year or so, since I usually find something new and relevant to whatever problems I'm grappling with at the time.
When I discovered this book I was amazed and grateful that someone had actually written a textbook for how to run a business!
Scaling Up is extremely practical. The book lays out how often to meet, what your meetings should be about, how to structure your team, how to craft your goals, etc.
After being a business owner for more than ten years I've seen that nothing is one-size-fits-all, and we certainly don't feel like we have to follow every detail of the book. But it's one of those great basics that I can always count on. When I'm feeling lost on how to achieve something, Scaling Up contains the fundamentals I return to on how to make a business work.
Creativity, Inc. The best piece of advice from Ed Catmull, the cofounder of Pixar, is that when you're successful it's easy to think you know what contributed to that success.
In reality, there are way too many factors to know which ones actually mattered. To make a great movie, studios have to start from scratch every time. Every movie starts terrible, then they make it great over time through constant improvement!
I think one of the most underrated business books is Give and Take by Adam Grant. The book paints a picture of three types of individuals: givers, takers, and matchers. Takers visualize life as a zero-sum game and prioritize getting more value out of exchanges. Givers see the world differently and believe in mutually beneficial situations. Finally, matchers fall somewhere in between, with the key differentiator being that they expect reciprocity and operate in a domain of “fairness”. Grant found that the most successful leaders are givers, across every industry that he studied.
It's extremely freeing to recognize that in order for you to be successful, you don't need to take an opportunity away from someone else. There's room at "the top". That's why I've chosen to model my projects and approach to entrepreneurship as an open book, hoping to help as many others along the way. Give and Take also encourages me to think more long term, instead of focusing on the immediate future.
For additional book suggestions, I've compiled my favourites here.
I read Four Steps to the Epiphany right out of college and it completely changed how I thought about entrepreneurship. I grew up in a conservative town without a ton of exposure to entrepreneurs. So to me the idea of starting a business seemed like an act of wizardry.
Four Steps gave me a framework for thinking about validating ideas and how to work your way to an idea that could be the foundation for a business. It gave me a lot of confidence to try and give the entrepreneurship thing a try.
The 7 Habits of Highly Effective People is a classic for a reason. It basically starts with "You are the author of your life." And once you believe that, it tells you how to write the best damn life possible.
If you're a founder you probably already believe that premise, but it's a good reminder that the point of life isn't where you end up or where you start, but what you do with whatever cards you're given.
The critical message for founders is that you should only think about and work on your "circle of influence," i.e. what you can actually change.
Founders constantly run in to shit they can't control. By fanatically focusing on what you can control, you'll dramatically improve your odds of succeeding, and IMO live a much happier life overall.
About four years ago when I was struggling with how to take Ministry of Testing forward, Derek Sivers recommended The E-Myth Revisited by Michael E. Gerber. It struck a chord with me at the time as I was trying to figure out what to do next and how to grow my business without it relying on me. The book focuses in on ideas around franchises. Not that you have to franchise, but it was more a way of saying get processes and people in place so that the machine can work itself.
From that day on, every time I did something I had the idea in my head about how it would work without me. I'd ask, "What things should I be doing? Who should I hire to help me? What processes should I log? If someone else will be helping me in the future, am I charging enough to afford it?"
It's funny looking back, as I've now more or less managed to free myself from the day-to-day, and the ideas behind The E-Myth definitely influenced my direction, even if it was just the constant thoughts in my head.
Reboot by Jerry Colonna. To be good leaders, we have to unpack and understand ourselves better. Much of work is relationships, so learning and knowing how to navigate those ultimately help us do better work.
Jerry is the real deal. Part pragmatic, part Eastern Philosophy, the book is a nice mix of stories and clear actions to work on in your life.
Work does not have to destroy us. Jerry firmly believes work can be the way to achieve our fullest selves. What we need, sometimes, is a chance to reset our goals and to reconnect with our deepest selves and with one another. Reboot moves and empowers us to begin this journey.
My "indispensable life-changing book" list is so long, if you sliced me open I’m pretty sure ITC Garamond would pour out. But I'm actually going to break the mold here and nominate a blog: Kathy Sierra’s Creating Passionate Users, which is still online. She poured a lot of her best work into the book Badass, which I was fortunate enough to help edit. I recommend it to everyone. But it was her blog that got me.
Kathy taught me to focus on people. Understanding them, serving them, and making them better. (Which doesn’t mean "asking them what they want and giving it to them!") The design details she talks about are also great!
But really, it was the philosophy of "people first" — explored from every possible angle — that shaped not only who I am as a person, but who I am in business.
Although I didn't read it until after I had launched my first product, Authority by Nathan Barry is the book I'm always recommending to people who want to write a book or launch a course.
I studied Nathan's work meticulously by reading all of his blog posts, listening to all of his podcast episodes, then listening to more interviews and watching talks from other creators I learned about through his work, and I can say with confidence that there is basically no way I'd be a full-time creator right now without the things I learned from those resources. I've now earned over $2 million selling my own products and have all the time and freedom I could ask for to explore new ideas and start building whatever is going to come next.
Authority is basically all of that knowledge packaged up in one comprehensive read, and absolutely worth checking out if you want to build an audience and release your first product.
Hooked by Nir Eyal has been the most indispensable for me. Lots of books have excellent general advice for founders, but Hooked provided me with knowledge that's specifically been useful for building Indie Hackers.
The core of the book is a model for building products that people are willing to invest in and return to. It's based on lots of psychological research around novelty, habit formation, and human relationships. I think it's need-to-know information for anyone working on a B2C product, especially a social one.
Crucially, I used it to tweak the mechanics of the Indie Hackers forum early on to make it a place worth checking out often, even when there were very few posts. I'm also returning to it today, to help design features that make it worthwhile for founders to continually share their experiences and post about their learnings.
I re-read, reference, and recommend Just Listen by Mark Goulston a lot. The author is a clinical psychiatrist who became famous as a lead trainer in hostage negotiation for the FBI. It's not explicitly about business (even though it has clear themes around negotiation), but it is about human psychology in the context of why we don't really listen, even when we think we do.
One of my favorite things about Just Listen is the way it's structured. It teaches a conflict scale Goulston calls "from Oh Fuck to Okay." He basically illustrates through stories and examples how when you're at the "Oh fuck" end of the conflict scale from a physiological perspective, you can't listen. At the same time, you can't simply jump from "Oh Fuck" directly to "Okay" — there are stages in between. Then he teaches exercises to move from each step to the next.
I use and think about the frameworks and techniques in this book almost every day, whether to check my own reactivity to something and realize I need to de-escalate myself to make a clear-headed decision, or to try to figure out where someone else is and what I might need to do before I (unsuccessfully) try to get through to them with something they aren't ready to hear yet. These skills translate to sales, customer support, management, leadership, and of course my own mental clarity and calm that's helped me understand myself and other people so much better.
I found 4-Hour Work Week by Timothy Ferriss indispensable for several reasons. For example, the book taught me that it's important to choose a scalable business model that fits your desired lifestyle, which is one reason why we made the switch from designing websites (i.e. providing services) at Barn2 to selling WordPress plugins (i.e. selling products), which is much more repeatable and scalable. We realised that the work we were doing would never meet our goals.
Another good tip is that you can build an effective team without having to follow the traditional business model of getting premises and hiring in-house staff. When I first read the 4-Hour Work Week, I was skeptical that you could get a good personal assistant in a non-native-English-speaking country, but Ferriss convinced me to give it a try. I now have a team of fantastic remote colleagues around the world, including three in the Philippines.
The main flaw in the concept of the 4-Hour Work Week is that if you love what you do, minimising work shouldn't be your goal. To me, that suggests that you're doing the wrong thing!
As founders of a bootstrapped company that was constrained in cash, especially during the early stages, Ryan Holiday's Growth Hacker Marketing was helpful in helping us be scrappy while gaining traction. Here's one of many memorable lines I've written down:
Forget the conventional wisdom that says if a company lacks growth, it should invest more in sales and marketing. Instead, it should invest in refining and improving the service itself until users are so happy that they can’t stop using the service (and their friends come along with them).
So many venture-backed startups dump money into PR and marketing to essentially force their growth, but organic growth through an amazing service/product is more sustainable and rewarding. Referrals and loyalty marketing continue to be the biggest sources of growth for us, as we focus on offering best-in-class customer experience and refining the quality of our products. We now have 1,200+ active monthly paid subscribers, and quite a lot of them have been convinced to try us out from friends and family.
It is hard to pick just one, but the book How to Get Rich by Felix Dennis helped me to get rich :). I read the book years ago when it was first published, and then I started re-reading it again. He's completely wrong with some things in retrospect (e.g. he thought Steve Jobs would ruin Apple).
But one takeaway that stuck with me from the first time I read it was how much he stresses holding onto equity. I didn't realize how important it is to make it a goal to never give any equity away. It really helped me — I remained a solo founder for a while because of this advice. It made me work harder, I think, because I knew the company was mine and I was 100% responsible for it.
We'll be aggregating knowledge from from successful indie hackers once a week on all sorts of topics, like:
👉 Click here to subscribe.