11 Books to Read Before You Quit Your Job (From a Founder Who Did)

In this video, I go over my top 11 books that made it possible to build not just one, but two businesses. These are life-changing books!

I read most of these before leaving my architecture job to go full-time on my first product business. Some I’ve re-read multiple times since. Here’s the full list with what I actually took from each one.

1. The 4-Hour Workweek — Tim Ferriss

This was the book that broke my brain in the best way. I read it while I was still working as an architect, and it completely reframed what was possible. The idea that you could design a business around your life instead of the other way around felt radical at the time. What stuck with me most wasn’t the lifestyle design stuff — it was the concept of testing ideas cheaply before going all-in. That thinking directly influenced how I approached my first Kickstarter. If you only read one book on this list, make it this one.

2. The $100 Startup — Chris Guillebeau

I picked this up right after The 4-Hour Workweek, and it was the perfect follow-up. Where Tim’s book was about rethinking the structure of work, Chris’s book was about the mechanics of actually starting something with almost no money. The case studies of people who launched real businesses for under $100 made it feel achievable, not theoretical. I kept coming back to his framework for finding the intersection of what you’re good at and what people will pay for. It helped me narrow down my first product idea.

3. Crushing It — Gary Vaynerchuk

I know Gary isn’t for everyone, but this book came at exactly the right time for me. I was figuring out how to build an audience around a product that didn’t exist yet, and his emphasis on documenting the journey rather than waiting until you have something polished to show was freeing. The practical breakdowns of how to use each platform were genuinely useful back when I was starting from zero followers. It gave me permission to start before I was ready.

4. The Lean Startup — Eric Ries

This changed how I thought about product development. Before reading this, I would have spent months perfecting something before putting it in front of anyone. Eric’s build-measure-learn loop became how I approached everything from product design to marketing experiments. The concept of the minimum viable product saved me from over-engineering my early products. I still use validated learning as a framework when deciding what to build next.

5. Start with Why — Simon Sinek

I’ll be honest — I resisted this one for a while because it felt like a TED talk stretched into a book. But the core idea genuinely changed how I talked about my business. Once I could articulate why I was building BestSelf (not just what we sold), everything from marketing copy to hiring decisions got easier. It forced me to go deeper than “we make planners” and get to the real reason the company existed. That clarity showed up in everything we put out.

6. Zero to One — Peter Thiel

This is the most intellectually challenging book on the list, and I loved it for that. Peter’s argument that the best businesses create something genuinely new rather than competing in existing categories stuck with me. It pushed me to think about what we could do that nobody else was doing, rather than just making a slightly better version of what already existed. The contrarian thinking framework — asking “what important truth do very few people agree with you on?” — is one I still use regularly.

7. The E-Myth Revisited — Michael Gerber

I wish I’d read this earlier. Michael’s distinction between working in your business versus working on your business hit hard. I was doing everything myself — packing orders, answering emails, designing products — and this book made me realize I’d just created a job, not a business. The systems-first thinking it teaches is what eventually allowed me to step back from day-to-day operations. If you’re drowning in tasks, this is the one to read first.

8. Rich Dad Poor Dad — Robert Kiyosaki

This was one of the first books that shifted my relationship with money. The idea that assets put money in your pocket and liabilities take money out — and that most people confuse the two — was a lightbulb moment for me. It didn’t teach me how to run a business, but it rewired how I thought about building wealth and financial independence. That mindset shift was foundational to everything that came after. I think of it as the prerequisite book.

9. Think and Grow Rich — Napoleon Hill

I almost didn’t include this because it’s from 1937 and some of it feels dated. But the core principles — having a definite chief aim, the power of focused intention, the mastermind concept — those are timeless. I read this during a period when I was struggling with confidence about whether I could actually pull off leaving my career, and it helped me take the mental game seriously. The practical takeaway: write down what you want and read it every day. Sounds simple. It works.

10. Rework — Jason Fried & DHH

This is the anti-startup book, and I mean that as the highest compliment. Jason and David’s argument that you don’t need investors, you don’t need an office, and you don’t need to work 80-hour weeks was exactly what I needed to hear. It validated the kind of business I wanted to build — profitable, lean, and designed around my life rather than optimized for a fundraising narrative. I’ve probably gifted this book more than any other on the list.

11. The Hard Thing About Hard Things — Ben Horowitz

I saved this for last because it’s the one that matters most once you’re actually in it. Ben doesn’t sugarcoat anything. The chapters on firing people, managing your own psychology, and making decisions with incomplete information are brutally honest. I read this after we’d been running BestSelf for a couple of years, and it helped me navigate some of the hardest moments — including dealing with the kind of personnel issues I’ve written about elsewhere on this site. Essential reading for anyone past the honeymoon phase.

These books won’t do the work for you. But they’ll rewire how you think about the work — and that’s what made the difference for me.

If you’re ready to take the leap, here’s how I went from nothing to a Kickstarter success.