Guiding Principles for a Bootstrapped Side Project

I’ve got this site, PlaidMaker, that lets people make plaid patterns online for free. I started it as a side project just because I thought it was cool and I wanted to test the metaphor that threads are like pixels. Throughout the project, there have been some principles that have guided my decisions. Here they are.

Make It Ugly

I’d like to write more about this topic in the future, but when you’re building the very first version of an app, it should be ugly. The focus of your efforts should be more on the user interaction and interface. Why? I’m not saying aesthetics aren’t important, it’s just that interaction is more important to get right and it’s harder change. If it turns out you didn’t nail the interaction you’ll find out quicker because the aesthetics won’t be hiding any glaring usability issues.

UI frameworks like Bootstrap give you a solid (albeit somewhat boring and ubiquitous) baseline for a simple aesthetic. But Bootstrap is only meant to be a starting point. Once you have a wireframe-like site that is answering user needs, then make it stunningly gorgeous! Unfortunately PlaidMaker has not made it to this phase yet.

Try It Before You Buy It

People on the web are impatient and fickle. They want what they want right now. They are inundated with constant alerts and feeds from multiple devices. Your site needs to deliver something to the user before they get distracted by the next shiny object. It should also deliver value before it asks for anything in return (like a contact point, an app download, payment info). These things are real hurdles for the user, especially when trust has not been established between the site and visitor. And what better way to establish trust than by giving the user—at no strings attached—a real sample of what your site has to offer? Sites that ask for your contact info too soon or ask you to share them too soon are being selfish. As a site, you don’t want people to sign up because you begged them to, you want them to beg you for the privilege of signing up.

I wanted PlaidMaker to let people use the site without creating a user account for the above reasons. It’s a simple enough tool and nothing about the problem that it’s solving (creating a pattern) requires there to be user accounts. However, there are problems that user accounts can solve (once trust has been established) like saving private content and sharing content with attribution.

Set It and Forget It

I learned a lot from the entrepreneur Pud at my first startup job, at AdBrite. Pud has a lot of great ideas and he turns them into sites. Some are really successful (TinyLetter, DistroKid) and some are not (Blippy, AdBrite). Prior to AdBrite, he started a site called Mobog. It was a mobile photo sharing site which was innovative at the time. While working on AdBrite, he had zero time to work on Mobog. Yet it kept chugging along. It had a community of users and it had traffic that was generating income from AdBrite ads. After the initial investment of creating the site, it continued to provide value for both the users and its creator without active investment.

Getting started on my side project, I knew that my enthusiasm and resources would fluctuate. I wanted to build something such that it would be OK if I wasn’t investing in it. I wanted to be able to set it and forget it. And that I’ve done. My last commit to PlaidMaker was 2014.

I don’t think this is a great strategy for building a lasting business but it’s a great strategy for the given circumstances and it helps you focus on building the right things.

UGC and Web 2.0

While these concepts are taken for granted today, they were revolutionary around the dawn of YouTube, Facebook and Wikipedia. Before then, regular people didn’t publish things online. The content that was found online was either professionally developed or published by geeks with an understanding web design.

UGC stands for user-generated content. It’s people creating things on the Internet and other people looking at those things. Content can be photos, text, videos, audio. Or it can be plaid patterns. I knew that if I was going to be able to “set it and forget it” there had to be an element of UGC. To date, users have saved 23,641 different patterns. PlaidMaker even lets people copy and edit existing patterns.

It’s the Data, Dummy

The Internet is a medium for sharing and manipulating data. It cannot do anything else. Lots of startups offer services but as far as the Internet is concerned, it’s just transmitting data to aid people in accomplishing some other thing like hailing a ride, watching a movie, buying a shirt or finding someone to date.

PlaidMaker isn’t a tangible service because there isn’t anything to it beyond just data. Really, it’s a software service. But software, like the Internet, is just data too. I knew that if I couldn’t provide a real service, I needed to provide enticing data. And that data comes from users. It feels like I’ve created something from nothing but really I just created a tool and the crowd has created lots of patterns.

SEO and Sharing

There’s a website or an app, but how are people going to get there? This is the field of marketing and there are many different techniques for creating an audience online. The most tried and true techniques for unestablished brands with no budget are social sharing and SEO. The majority of PlaidMaker’s audience has come from organic search with a sprinkle of social sharing and backlinks. After saving a pattern, users are prompted to share it. There are also share buttons on every plaid page but it still hasn’t been as effective as SEO.

When non-industry people ask me about SEO (“how do you get to the top of Google?”) I usually tell them that the best things they can do are get backlinks to their site. This can be accomplished by reaching out to publishers of any size. LifeHaker has a “Wallpaper Wednesday” feature and I emailed the author to tell them that plaids make for great desktop backgrounds. Eventually he included it. Likewise, I found an independent blog post about a competitor. I merely commented on that post and 6 days later she wrote one about PlaidMaker. Publishers are just as hungry for fresh content as a service is for getting noticed.


WYSIWYG: What You See Is What You Get. This one is pretty simple. The editor lets someone tweak a design to get instant feedback. This makes the art of making a pattern quicker and quite satisfying.

Test for Demand

If you’re going to invest in something, spend time figuring out if real people would pay real money for it. Is PlaidMaker something people will pay for? One good way to find out is to put up the concept and see if there is interest. I put up a page with an email address to find out. I’ve named the product PlaidMaker Plus and I’ve gotten some feedback that indicates that there is some definite potential. Of course this creates a whole new set of questions like how much should it cost? Exactly how much demand could there be? How big is the market? Etc. Hopefully I’ll sort these questions out in the future.

So there you have it. A couple of principles that have guided me on my side project.

Written 27 February 2017