Why entrepreneurs should improve their writing

Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes frameworks, analyses, profiles, and musings about building entrepreneurial careers. This isn’t just startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal.

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Why entrepreneurs should improve their writing

If I had to pick one skill to encourage any aspiring entrepreneur to develop, it would be writing.

Good writing helps you to make better decisions, faster. Good writing enables you to test your assumptions as inexpensively as possible. Good writing makes you better at everything else. Good writing can influence others without you in the room. All of these things are essential to having a successful entrepreneurial career.

Good writing helps you make better decisions, faster

In a 2004 memo to his S-Team, Jeff Bezos wrote: 

"The narrative structure of a good memo forces better thought and better understanding of what's more important than what, and how, things are related...PowerPoint-style presentations somehow give permission to gloss over ideas, flatten out any sense of relative importance, and ignore the interconnectedness of ideas.”

A good piece of writing will clarify your own thinking and ensure that the logic is sound. If you make a logical leap while writing in prose, it jumps off the page and forces you to question some of your own reasoning. This process of turning thoughts into prose reinforces sounder decision-making. This post started with an outline, and as I turned it into prose, I ended up throwing away a lot of ideas that didn’t make sense to include.

A good piece of writing will also elicit more valuable input from others when requesting feedback, helping you make better decisions.

When joining Amazon, the Leadership Principle that gave me the most angst was “Are Right, A Lot: “Leaders are right a lot. They have strong judgment and good instincts. They seek diverse perspectives and work to disconfirm their beliefs.”

As a recently failed founder, I didn’t have confidence that I had strong judgement or good instincts. But I found that with writing, you don’t need to be a visionary prophet who is magically right about things. Writing took the pressure off of me being right at the beginning. Through my two years at Amazon, I’ve been right about a lot of things, even though my initial thoughts were usually wrong. I credit that to using writing to get input from others before making decisions.

The quantity of decisions I’m able to make confidently is a function of how much I am writing. While you can’t write out every small decision you need to make, writing for the big ones can make sure you’re practicing good judgement. If building a successful company requires making a lot of big decisions confidently, then good writing is one of the best ways to maximize your chances of success.

Good writing enables you to test your assumptions as inexpensively as possible

Building a startup often boils down to the practice of constantly testing assumptions to de-risk your venture. 

Decades ago, you would need to build software and release it into the market to test your assumptions around a new venture. It was really expensive. Fast forward to the 2020s, and no-code tools make it easier than ever for people to hack together their own products in a weekend without any engineering skills.

As a proud non-technical founder and an evangelist of no-code tools, it pains me to say this: even building MVPs with no-code tools is too expensive of a way to test early assumptions. 

Writing is the cheapest way. Clearly writing out your ideas will reveal your core assumptions, and you’ll be able to get feedback from customers or others on these core assumptions 10x faster than building anything – even if you’re building using no-code tools. Max Nussenbaum summed this up well this week:

Max Nussenbaum @maxnuss

1. For most founders, learning to code is about being able to quickly iterate and test an MVP. But you can often test an idea even faster just by writing about it and observing the feedback. Sometimes, the writing process itself even reveals where your assumptions are wrong.

Max Nussenbaum @maxnuss

I've had the experience of realizing an idea was bad halfway through fleshing it out in writing. I've also had the experience of realizing an idea was bad after working on it for four years, raising $3mm, and hiring 20 people. They both suck, but the latter sucks more!

Often MVPs will show the product, but don’t reveal the underlying assumptions behind the business. Building an MVP might give you good feedback on the usability of your product, but glazes over some of your most fundamental assumptions.

Entrepreneurs who write well will be able to get higher fidelity feedback on their core assumptions from customers, investors, and other stakeholders – faster. They will have a faster rate of learning than entrepreneurs who index towards building something first.

Being a great writer makes you better at everything else

Writing is the common denominator across every function of building a business. Sales, fundraising, marketing, hiring, product management, product design – and everything in between – require clear, concise writing. An entrepreneur who is a great writer will start on second base on all of those functional aspects when building a business. 

Successful entrepreneurs are T-shaped – they’re great generalists with one or two elite skills. One of the most efficient ways to become a great generalist is to become a great writer. If you learn the basics of any skill – like email marketing, recruiting, or product management – and then layer on great writing, you’ll be better than most people at that skill.

Good writing can also be a force multiplier on some of your elite skills. Skeptics of this “writing is important” thing might suggest that being a naturally charismatic seller or being a great engineer are more important skills for aspiring entrepreneurs than writing. 

Why can’t you have both? A naturally charismatic seller who is also able to write persuasively will be a far more effective of a seller. A great storyteller who can also write will be even better at fundraising. A world-class engineer who write will more effectively push back on feature requests and focus on building the right things.

Good writing can influence others without you in the room

Often entrepreneurs may have natural charisma or raw intellect that drives them to become entrepreneurs in the first place. These traits are essential to being able to influencing others – whether it be fundraising, recruiting, selling, or team management.

Relying on this charisma or raw intellect to influence others means you need to be in the room, and entrepreneurs need to scale themselves in order to grow a business. If you have to be in the room every time you need to influence someone, then it’s going to be really difficult to grow anything.

Good writing can scale your influence internally and externally, working around the clock for you. While sales and fundraising may be the “sexy” things that folks think about when it comes to influencing others, it applies to the more operational aspects of building a business too. Leaders who write good documentation or onboarding materials are going to be able to onboard new team members faster and influence team members to adhere to certain processes or cultural principles. Writing scales your influence.

Anyone can improve their writing

Not everyone is well-suited to develop software engineering skills. Not everyone is well-suited to develop sales skills. But everyone could and should develop their writing skills. All it takes is practice. And if you want to build an entrepreneurial career, it’s one of the most important skills you could build.