Startups | 3 min read

Q&A: What books would you recommend to new entrepreneurs?

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This week, our question comes from Gabriele:

“What books would you recommend to an entrepreneur just starting out?”

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. Even though it’s now 10 years old, the key ideas haven’t aged, and they likely never will.

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. You can read a short extract here: The Orange Juice Test.

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. Not necessarily from a creative fiction or fancy words style, just a sharp, concise, and persuasive one. As an example, if you read Steve Jobs’ thoughts on Flash, it’s not beautifully worded. It’s just phenomenally concise and punchy. When you finish that letter, you’re like “Shit, why didn’t they kill Flash earlier? Why is anyone still supporting it?”

Lanham’s book is great because it teaches you how to get messages down to their core parts and share them. The better you can communicate, the better you can lead, persuade, and inspire. You really don’t realize how important that is until you have to write a message to your entire company about something. You soon realize that the conciseness of your message has a multiplicative effect on how well read and understood it is. It’s also pretty indicative of how much you’ve understood and internalized what you’re trying to communicate.

More generally, I think there’s a lot of books in your career that you need to read twice. You need to read it once when you don’t really know what it’s about. Then you need to read it again when you have the experience, when it explains something you can directly relate to.

For example Managing Humans by Rands (Michael Lopp) is a great book on management. The first time I read that, I didn’t manage many humans. Sure, it was fun to have all of these anecdotes, but it didn’t really click. But then the second time I read it, I realized he was right all along.

In general, books are best for a specific person at a very specific time in their life. Occasionally, I find myself reading recommendations I’ve given and I’m like, “Really? I don’t really think that anymore.” But at the time, the particular book meant a lot to me because I needed to get out of a hole, or go in a different direction in my career.

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. 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. So much has to do with the point in time in your career. I’ll hopefully have a whole different set of recommendations in 10 years time.


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