Writing as an onramp to building a startup

Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes essays, interviews, and more about building entrepreneurial careers. This isn’t 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. I’m a former startup founder, the co-author of a book on seed fundraising, and am on the Early Stage Startup team at AWS.

If you’re in the middle of en entrepreneurial career or want to start something down the road, consider subscribing below!


Writing as an onramp to building a startup

If I were forced to predict who would start their first startup in the future, I would look at who is currently writing and publishing content. 

Writing helps you start exercising the muscles that are required to be a good startup founder, helps you figure out what your startup will be, accelerates your path towards starting a startup, and stacks the deck in your favor so that you have a better chance at success when you launch your startup.

one of my motivations behind starting this newsletter is that I know I want to start another startup in the future, yet I have no idea what I’m going to start or when. But I know that writing consistently will keep me on a path to starting something down the line and will increase my chances of success.

Starting a startup is a huge leap, but writing can be a smooth onramp.

Why is that the case?

Developing the intellectual honesty to navigate product-market fit

The most simple answer to “how do I build a startup?” is to make something people want. As a writer, you’re trying to create a piece of content that readers want. Aren’t they basically the same thing?

As I’m typing this, I’m trying to make a piece of content that people want – that answers some of the big questions aspiring founders have around how to position themselves to start a startup in the future.

One of the most important skills that founders can have is the ability to be intellectually honest with themselves about their ideas and if people actually want what they’re building. Founders who are able to be skeptical of their own ideas and challenge their own assumptions find product-market fit faster (AKA building something people want).

Writing something that your target audience wants to read requires a similar level of self-awareness and self-scrutiny. For example, as I was sitting down to write this, I almost wrote a post about how writing a book accelerated my career. But as I thought about the target readers of this newsletter and what they wanted, I realized that while that post may have been good, it ultimately does not address some of the biggest questions my ideal readers have. 

At the end of the day, if you’re able to figure out how to write things that people want to read, you’ll have a lot of the skills required to build something that people want. 

Getting comfortable with shipping early and often

“If you are not embarrassed by the first version of your product, you've launched too late” - Reid Hoffman

Building a startup requires that you ship products uncomfortably early and open yourself up to scrutiny. Founders who are comfortable doing this ship early and often, allowing them to get feedback from the market and keep improving towards making something that people want (and that works). 

Consistently publishing writing requires that you get comfortable with shipping uncomfortably early the possibility that something you ship might not be great, or that an opinion you have might be wrong. As I’m writing this article, I think it’s going to be good! But I know that there’s a distinct possibility that it might not be as good as I hope. Writing a newsletter means I need to ship it regardless rather than spending weeks agonizing about making it perfect. In the future, based on feedback I get, I can always crystallize some of the concepts in this post in other ways. Writing this newsletter is a forcing function, getting me back into the mentality of shipping early and often.

Getting comfortable with shipping writing to readers will help you be more comfortable with shipping other things (like products) to customers. 

Building a relevant network of mentors, peers, and audience

Starting a startup involves many chicken-and-egg challenges and leaps of faith. Founders need to attract early adopters for products that are barely working. They need to attract investors, co-founders, and early employees for ideas that are incredibly risky.

When starting from zero, looking ahead to some of these challenges is incredibly daunting. Even as a former founder myself with a pretty good network, when I look ahead into the possibility of starting another startup down the road, I wonder if I’ll be able to do it again.

One way to make these down-the-road challenges easier is by building a relevant network of mentors, peers, and who share your interests in something. If you’re able to do that, then you’ll have a network of investors, teammates, and early customers/users who are interested in whatever you build down the road and will give you their attention.

Alex Taub’s story is a great example. Alex’s Tech Thoughts (which he started in 2010) included blog posts on Business Development, tech startups that he liked, and other various tech-related topics. Not many of his posts went viral and Alex didn’t necessarily become a prolific tech writer, but his writing made him a magnet for people in tech who were looking to level up their careers. I came across Alex as a college senior looking to break into startups in 2012 and started following his writing and engaging with him on Twitter. There are many people like me who first engaged with Alex through his articles or tweets.

A year ago, he started working on a new startup, Upstream, a new social professional network. Kickstarting a social professional network is a huge challenge. But because of Alex’s writing, he had an audience of similarly-minded ambitious tech folks who followed him. This gave him a huge advantage in starting a social professional network, and he’s been able to quickly overcome some of the early chicken-and-egg problems that have killed countless social professional networks before Upstream. 

Personally, I don’t know what startup I’m going to start down the line. But part of my motivation for writing is that it will help me start to find the areas I’m most interested in, help me meet people with similar interests who could be future collaborators, and build an audience of people who care about the topics I’m writing about. Today, writing is one of the best things I can do to de-risk my future startup, whatever and whenever that is. 

Developing clarity of thought and unique points of view

One of the biggest things investors look for in early stage investments is if the founders have a unique insight about what they’re building. If founders have a unique insight on the product or market, then perhaps they can be successful where others have failed. When I think about what I need in order to start my next startup, one of my prerequisites is a unique, contrarian insight that would enable me to build something unique and different. How do develop unique insights? One way is by writing. 

Before sitting down to write this, I had some loose thoughts around how writing is generally a good thing for aspiring founders to do. But through the process of writing this, I’ve developed clarity and conviction that writing is an ideal onramp to starting a startup. It started as an idea, and through writing this post, that idea turned into a non-obvious insight that is now one of my firmly held beliefs.

Writing – especially long form writing and not just tweets – forces you to have clarity of thought and form strong, supported points of view. These points of view can turn into the theses behind future startups.

Establishing credibility and expertise

Establishing credibility on a topic results in people trusting you as an expert. When you’re a trusted expert, people are more willing to give you their attention, time, or ideas. 

Ryan Hoover founded Product Hunt, a site to discover or launch new products. But what did Ryan do before Product Hunt? 

He wrote essays about building habit-forming products, product design, and breakdowns of some of the most popular products like Snapchat. All this culminated in Ryan writing a book with Nir Eyal about habit-forming products.

By the time that Ryan was tinkering around with the idea for Product Hunt, he already had credibility as a product expert through his writing, and he was the perfect person to launch an idea like Product Hunt. When Ryan reached out to his friend Nathan Baschez about the idea, Nathan was happy to spend some time building the MVP. When Ryan debuted Product Hunt as an email list, people who knew Ryan were eager to sign up. When new people who didn’t know Ryan saw that a guy who’d written essays and a book about products was launching something called Product Hunt, it seemed like real deal. Ryan’s credibility as a product expert helped him get Product Hunt off the ground. 

But what if you don’t have expertise? Write. 

Back in 2018 after I wound down my startup, I by no means considered myself an expert on seed stage fundraising – I’d only raised $1M in funding and hadn’t raised from top-tier VCs. But I ended up writing a guide to fundraising in a Google Doc which I shared with some friends. That Google Doc started getting longer and longer, and I looped in my friend Max as a co-author to turn the growing Google Doc into a book. I developed expertise on fundraising through the process of writing the book and writing a newsletter about fundraising. The fact that I wrote a book and a bunch of essays about fundraising has given me credibility as a fundraising “expert.”

Expertise isn’t a prerequisite for writing about a topic – it’s the result. 

Frankly, that’s part of why I’m writing this newsletter. I want to write my way into becoming an expert on entrepreneurial careers.

Writing is a more accessible onramp that preserves optionality

Not everyone can quit their job and go full-time on side projects that they want to turn into startups. Not everyone can spend 10-15 hours per week working on a side project. But everyone can carve out a few hours per week to write if they prioritize it. 

Actually, this newsletter for me is a more minimal version of a side project I was working on a few months ago: a non-profit which helped founders move on from their startups and figure out the next chapter of their entrepreneurial careers. After working on it for a few months and struggling to give it the time it needed, I decided that a newsletter would be a smaller, better place to start. 

The other important benefit of writing is that the stakes are low, which gives you more freedom to explore and less pressure to figure something out. You can pivot topics, pause, or stop writing altogether – without consequence.

However, If you quit your job try to turn side projects or ideas into a full-time startup, the clock starts ticking. You eat into your savings, your friends and family know that you started working on something, and you’ll start feeling pressure to make progress. In other words, the stakes are high. 

But with writing, you can start positioning yourself well to start a startup in the future, keep the stakes low so you can feel free to explore. 

I didn’t have this strong of an opinion when I started writing this post but now I do: when aspiring founders tell me that they want to start a company but don’t know where to start, I will tell them to start writing.