Writing for Founders — The Bootstrapped Founder

Founders should write. And it's not just for "building an audience" — it has internal business benefits too. Here's why writing matters.  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌

Dear founder,

Earlier this week, I talked to Hassan Osman. He shared his insights from writing 17 books while being a full-time employee. If you want to write your own, you'll find all the steps needed to get started.

Now, let's talk why founders should write.

Wait, one more thing to do? Aren’t founders busy enough trying to build a business?

I get it. The founder’s life could use fewer commitments, nor additional ones. Self-funded entrepreneurs already wear too many hats and juggle dozens of tasks at any given moment. But what if I told you that taking up writing could be the missing piece of the puzzle that brings all of your efforts together?

Writing is a skill that, when honed, is immediately applicable to every single thing you do, which is why it should be a part of your business strategy. I’ll share a few great examples from the bootstrapped entrepreneurship space to clarify how much writing can help entrepreneurs grow their businesses.

Communication and Clarity

Communication is critical in business, and writing helps you to communicate your ideas and thoughts clearly. It allows you to express yourself in a concise and meaningful way, making your message more impactful.

And that’s not just in emails to your employees or customers. The better you get at expressing yourself clearly, the more precise your process documentation will get. Too often, we think that writing is just for educational or entertainment consumption. But writing your business manual is a critical task to keep everyone marching in the same direction.

When I look into the Standard Operating Procedures written by founders who don’t regularly write, I understand why their operations leave a lot to be desired: I often find mentions of things that are never defined, important steps being omitted, and a lack of structure both in thought and in the presentation.

Getting used to writing to be read by others is a great exercise to write more clearly. I recommend starting with a topic you know a lot about: the reason why you started your business in the first place. People can benefit indefinitely from a well-written mission/vision document in which you lay out the “why” behind your business. This can live in an internal document — or even be turned into something very public.

Take Basecamp, for example. The project management software company is known for its clear and concise communication style, much of which can be attributed to its founder, Jason Fried. Fried is a strong advocate for writing and has written several books on the subject, including “Rework” and “It Doesn’t Have to Be Crazy at Work.” Notice how Fried takes the internal DNA of the business and externalizes it into books that will still be around no matter what happens to the software. Basecamp has started and dropped several products in its lifetime, but the principles that Fried and his co-founder write about at length remain.

That’s what writing can do: it calcifies your vision into a tangible form that leaves traces of your ambition for others to find.

Attracting Attention

And in a world of digital media, this level of discoverability turns writing into an excellent marketing tool. You can use it to promote your products or services and reach a wider audience than what paid advertising could ever accomplish. If people read your work because it’s intrinsically helpful, they will think the same about your products or services.

Writing provides a platform for you to showcase your professionalism and attract potential customers or partners. For instance, Buffer, the social media management tool, has built a massive following through its blog. The company regularly publishes articles on social media, marketing, and entrepreneurship, positioning itself as a thought leader in the industry.

You’ll find that most software companies that engineers actually want to work for have an engineering blog. That spirit alone is something that attracts software talent. If you’re a technical founder and want to find your first developer hires, talking about the interesting challenges of your product-building journey might just be the right thing.

And here's a company that runs precisely such a blog. Let's take a quick look at this issue's sponsor, Drata.

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Writing about your area of expertise is a wonderful process: you win twice. First, you really have to understand what you’re writing about. There is no pretense when you have to explain the details of a complicated process to people who are ready to understand it. Either you know it, or you don’t. In addition to this, you end up with a digital artifact —a blog post, a tutorial video, a white paper— that you can re-use forever. Double value, right here.

Fostering Relationships

Networking is also a critical component of building a successful business. Writing can help you build relationships with potential customers or partners. Whether it’s through blog posts, email newsletters, or social media, writing allows you to connect with others and establish yourself as a thought leader in your field. For example, Pat Flynn, founder of Smart Passive Income, has built a thriving online business through his blog and podcast. Flynn regularly shares his knowledge and experiences with his audience, helping him to build relationships and grow his business.

Introspection and Reflection

Reflection is an essential aspect of personal and business growth. Writing provides a tool for reflection, helping you to clarify your thoughts and goals. It enables you to take a step back, evaluate your progress, and make informed decisions. One entrepreneur who embodies this is Brennan Dunn, founder of Double Your Freelancing. Dunn is a strong advocate for reflection and journaling and has written extensively on the subject, including in his newsletter Create & Sell. Through writing, he’s been able to reflect on his journey and make important decisions that have helped him grow his business.

Building a Personal Brand

Thought leadership is also a key component of building a successful business. Writing allows you to establish yourself as an expert in your field and generate credibility. Whether it’s through thought-provoking blog posts or insightful articles, writing can help you position yourself as a trusted authority in your industry. For instance, Noah Kagan, founder of AppSumo, has built a massive following through his blog, podcast, and online courses. Kagan regularly shares his knowledge and experiences with his audience, positioning himself as a thought leader in the entrepreneurship and marketing space.

This is likely the kind of writing that comes to mind when founders are told “they should write.” But it’s by far not the only kind — or the most important one! I’d wager that writing for your own internal clarity and documentation is more powerful in itself than any externalized content you might produce. Go for becoming a recognized expert in your field by any means, but don’t underestimate the power of writing within the business.

Sellability

Finally, writing can have a significant impact on the sellability of your business. By writing about your business, you can increase its perceived value and make it more attractive to potential buyers or investors. For example, Brian Casel, founder of ZipMessage & Restaurant Engine, wrote extensively about his experiences building and growing his business. Through writing, he established himself as an expert in the restaurant industry and made his business more attractive to potential buyers.

I experienced that myself when we were selling our SaaS business. I hadn’t written anything in public at that point, but our internal documentation was incredibly thorough. I had spent weeks making sure our docs and processes were as expansive as they could be, and our would-be-acquirer loved that. In the end, this got us a nice premium on the sale price because it allowed our buyer to transition the work over to their team immediately.

While it may seem daunting at first, the benefits of writing are worth the effort. Start small by writing for yourself, then look into a blog post or newsletter, and work your way up from there. You don’t need to be a professional writer to get started – just be clear, concise, and true to your voice. And remember, writing is a journey; the more you practice, the better you will become.

Writing As a Legacy

In the end, writing is an essential tool for self-funded entrepreneurs looking to build successful and impactful businesses. So why not take the time to start writing today? You never know where it may take you.

Examples of successful self-funded entrepreneurs who have leveraged writing to grow their businesses include Jason Fried of Basecamp, Pat Flynn of Smart Passive Income, Brennan Dunn of Double Your Freelancing, Noah Kagan of AppSumo, and Brian Casel of Restaurant Engine. By taking the time to write and share their experiences and insights, these entrepreneurs have established themselves as thought leaders in their fields and built thriving businesses.

So, if you’re a self-funded entrepreneur, don’t be afraid to add writing to your list of business strategies. The benefits are numerous, and the impact can be significant. Happy writing!

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