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Getting RealTheir words
The number one book I recommend any entrepreneur to read is Getting Real by Basecamp, named 37 Signals when they published. It is probably the most inspiring book on business I’ve ever read, and it made me realise that small teams can build huge successes.
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The Secrets of ConsultingTheir words
A more left of field one would be The Secrets of Consulting by Gerry Weinberg. It’s not on many “Top 10 books for entrepreneurs” lists, but on an abstract level, consulting explains a lot of things, like interpersonal dynamics, and how larger companies can easily go off track.
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Revising ProseTheir words
I’d also recommend Revising Prose by Richard Lanham. I’ve rarely met a great CEO or founder who isn’t also a great writer.
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Managing HumansTheir words
For example Managing Humans by Rands (Michael Lopp) is a great book on management.
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It’s Not How Good You AreTheir words
For example, when I was starting my career, I definitely took a lot of much-needed motivation from Paul Aarden’s It’s Not How Good You Are, which Eoghan had given me a copy of.
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The Innovator's DilemmaTheir words
A decade later I took a lot of inspiration from The Innovator’s Dilemma for a similar reason – we were about to embark on this crazy Intercom thing and I needed to believe it was possible.