10 Books That Helped Me Build a Scalable Business
Learn about the systems that will help you succeed
I’m not a big fan of business books that purport to give you everything you need to succeed as there’s a fair sprinkling of survivorship bias in these books. But synthesizing ideas that resonate with you can save you time by learning from others.
Business books I don’t like
First of all… Shoe Dog often appears on these lists but it’s an autobiography - not a business book - and it’s about a boomer apparently drifting through lucky breaks… as a millennial, it is impossible to relate to and as a business person has no practical use. Having said that, I only read the first 100 pages.
Also you often see Start with Why mentioned in these lists - this is a book for zombie executives that think they are having an epiphany when they read it. It massively simplifies Apple’s success into an easily packaged concept that is more useful to the author’s speaking and consulting career than it is to anyone else.
Peter Thiel’s Zero to One I liked but is more aimed at VC-backed ‘disruptive’ startups looking for unicorn exits and I haven’t run one of those (see why), I have only invested in them.
Books I do like
The 7 Habits of Highly Effective People and How to Win Friends & Influence People were important books to me because my Dad made me read them at a young age (mid-teens). I haven’t read them since (though I plan to) but it had a big effect on me not just being an “effective” person but also a good person, I hope.
For anyone running a company or seeking to be a more effective operator, read these and learn on the job and you’re good.
The Lean Startup
Eric Ries’ classic on how to build a new business that is lean enough to last until product/market fit, essential for anyone with a young (especially pre-revenue) business with a new offering.
The E myth
The original take on how to work ‘on’ your business and not in it, I recommend to anyone running a business of any size. The idea that you have to improve your process and structure so that your business thrives without you is drummed in steadily throughout.
Built to sell
This one is agency-specific but plenty of general lessons that can be applied generally.
If I started a business again I would use this ‘operating system’ in its entirety, which lays out how meetings should work, company structure, strategy is communicated etc. Quote: Above all else, your leaders need to be able to simplify, delegate, predict, systemize, and structure.
The Great CEO Within
Similar to EOS… I wish I’d read this book before I became a CEO, rather than having had to learn it all through hard experience. Matt Mochary uses his extensive career and role as CEO coach to summarise tactically how to be an effective CEO, but I think anyone managing a team can learn from this pithy book.
Measure What Matters - the original intro to OKRs
The original introduction to OKRs, which are an effective way to communicate and deliver on strategic initiatives. OKRs are used by most tech companies you know and respect.
This is my all time fave book on management, I love the caustic tone and it has some of the most down to earth advice I’ve ever seen. Recommended to me by JML when he was CTO at Shopify, it definitely has a software engineering angle but again the advice is invaluable to any manager and will save you from learning some lessons the hard way.
Anti fragile by NNT (and also The Black Swan)
Nassim Nicholas Taleb was a pivotal influence on my thinking. It sounds abstract… but his statistical observations on the world will help you understand how complex systems like the economy (and your business) work. His thinking helped me understand the GFC and the nature of the world we live in. Anti-fragile is a sort of manifesto on making systems that are flexible enough to absorb chaos. Be warned the tone is a bit like being stuck at a hotel bar with a drunk professor.
More than a book about habits… more a book about being more effective as a person, including as an operator.
Principles: Life and Work
I was torn on which book to put last on this list but I chose Ray Dalio’s principles, partly because I do like a lot of his philosophies (though at times it makes the firm he founded sound like a cult) but also because I think he neatly touches on some good rules for life from someone that has obviously experienced a lot. The death of his son in an accident at the start of 2021 really shocked me and I truly hope that Ray and his family were able to get through it, his book certainly suggests he’s a man of fortitude.
OK that’s it - hit me up with your recs!