A content strategy reading list for bootstrappers

A content strategy reading list for bootstrappers

It’s not easy to research everything you need to know about content strategy as a founder. I’ve collected the resources that helped me to connect the dots between building bootstrapped businesses and creating a content strategy.

A better starting point

When you start researching content strategy, you’ll get distracted by hundreds of „Ultimate Guides to Content Strategy“ cluttering Google, leaving you with little substance. There aren’t many dedicated (and useful) resources for content strategy for startups, even less so for bootstrapped companies of one.

I would know about that frustration: My solution was to dedicate 2 years of my life to studying content strategy and learn directly from industry professionals. Oh well! But this is my attempt to create a better starting point for you.

I’ll keep the list updated to add more precious finds.
Last updated: May 30, 2020

What is strategy, really?

Understanding what strategy is, and how business strategy and content strategy overlap has been one of the most important things for me. It helped me understand that these strategies don’t live alongside each other, but are sharing their fundamentals.

If you want to create a content strategy, you will inevitably get to the bottom of your business strategy as well. (Don’t let that scare you!)

Content strategy intros

I haven’t got a lot of books on my shortlist that I would recommend you to read about the content strategy in general.

These books often include a lot about stakeholder alignment and how to sell content strategy as a consultant – they’re not written for you and me as indie founders. But they are valuable to get an understanding about what content strategy entails, of course.

How businesses grow (with content)

Growth is a sensible topic for many bootstrapped businesses. While most of us strive for sustainable growth that doesn’t compromise how we want to live our lives, it is a necessity for businesses. A business without growth is a dying business.

Here are some resources that helped me shape my approach while resonating with my values.

  • Product-led Growth: How to Build a Product That Sells Itself
    by Wes Bush
    If your desire for growth roots in the desire to bring more value to people, this book will help you create a framework to do so. I think it’s especially valuable for indie SaaS companies. But no matter what business you build, it gives you a lot to think about. If your product should sell itself, like the title proclaims, your content is a key element to communicate your its value and help people experience it.
  • HubSpot’s Flywheel
    This is an alternative model for the dreaded funnel, and especially valuable for businesses that can’t and won’t just dump money into marketing. It’s a customer-first approach that shows you how making customers happy helps your business grow. It supports HubSpot’s Inbound Marketing approach, where content plays an important role.

Questioning growth for the sake of growth

As I think that topic is important, I’ll recommend some resources that help you reflect what kind of growth you want to 1) being able to shape your own life and 2) be responsible about the finite resources we have in this world.

I know this is not about content strategy per se, but these books helped me shape strategic decisions more than any specific strategy tool.

Understand who you’re writing for

You need to understand your audience and how they think about the world to create a product that is useful for them. It’s just as important as a basis to decide how and where you can communicate to them.

Finding your voice & positioning yourself

The groundwork of a content strategy is to know how to position yourself on the market, and defining how you want your customers to perceive you.

Analyzing content

To make strategic decisions about your content, you will need to know what content you have, and how it performs right now. One of the most important tools to do that are content audits.

You might find this boring as hell if you don’t love Excel sheets, but I promise you’ll discover a lot of insights about your content – even if you work with it every day and think you know it well!

  • Content Audits and Inventories: A Handbook
    by Paula Ladenburg Land
    While audits are mentioned in almost any content strategy book, this is the real deal. It offers a complete process about how to define the criteria and set up your content audit to get the most insights.

Structuring content

Structuring content helps your audience relate to it, and makes it findable. How you organize your content and how you lead people through it is an art and science alike (and I quote this from the first book on the list 👇️).

  • Information Architecture: For the Web and Beyond
    by Louis Rosenfeld, Peter Morville & Jorge Arango
    This book is a classic, and only referred to as The Polar Bear Book in information architecture circles. It’s not something you’ll excitedly read in bed before going to sleep, but it holds so so much value.
  • Everyday Information Architecture
    by Lisa Maria Martin
    If you want to read something a bit more conversational to get an intro, this is a very easy read.
  • The Accidental Taxonomist
    by Heather Hedden
    This book is so great to help you understand how to create reliable categorization systems for your content. Buckle in, as there is a lot of substance in there – but I promise it gives you actionable tools as well.

Creating content systems

As a bootstrapped company, being efficient in your content operations is important. If you want to make the most of your time, you’ll need to create repeatable systems and be smart about reusing your content.

These things tend to get more important as your business grows, but it pays off if you start with the basics early.

Writing better content

Writing consistently

I wrote about why I think that we need to develop good content habits before. These are the two books that helped me do that (and also create a healthier life in general)

SEO – Optimizing content for search

Honestly, I’m not an expert on SEO – but I’ve dug through too many clickbait-y SEO advice articles to count. These two resources are no bullshit, by people I really respect in that space.

I know this is a pretty wide range of topics and books, and it can feel quite overwhelming at first. Content strategy is integrated with every part of your business, so all of these puzzle pieces influence it.

You definitely won’t regret digging down that rabbit hole.

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