Regaining productivity as a bootstrapper

Regaining productivity as a bootstrapper
Photo by Annie Spratt / Unsplash

There's a lot of great advice online to build better software businesses. The common wisdom includes "start marketing before you start building", "build in public", "validate your business idea", and more. And don't get me wrong, this is great advice!

But, I'm going to argue these tips aren't beneficial unless you're already in the habit of shipping product. They're optimizations to a process that you need to have a firm handle on already.

But how do you get started shipping products?

The key is to build the habit. Your brain acts like a muscle and it tends to gravitate towards doing the same things you're currently doing. So if you want to build the habit of shipping, you need to change things up.

Here is a strategy I use to break out of a productivity slump. It’s just one tool among many that I use to build back the habit of shipping software. Got your own tips as-well? I would love to hear them! Share them with me on twitter.

My Solution: Do a 1-day super hackathon

Let me preface by saying this – this is not your typical hackathon. Typically, a hackathon simply involves spending a day programming to create something new. This hackathon will do that too, but it’ll go one step further. During this hackathon you’ll also get into the habit of going from idea to MVP quickly, building in public, limiting scope, and actually launching product.

I belive these skills combined are more valuable for bootstrappers than simply coding.

The secret sauce: What should you build?

Figuring out what to build can be difficult. For this 1-day super hackathon, I provide a simple solution: Build a free tool in your niche.

Building free tools is a extremely powerful. They can create early traction and idea validation which will serve you effectively for future paid offerings. They're also quick to build and launch. Plus, if you already have a paid tool that you're running, it can be a great engineering-as-marketing activity to bring in more traction.

As bootstrappers, I think we naturally gravitate towards writing code. Yet, sometimes it's easy to get into analysis-paralysis where you lose the habit of programming every day. Between all the activities an entrepreneur has to do, this is understandable. But here's where the benefits of building a free tool really shine through.

Free tools can be killer for SEO and lead generation.

Take a look at Maybe, they have an entire "tools" tab on their landing page with free tools. Same with hubspot. And, ahrefs. Some of these businesses are built entirely around creating value with their free tools. Plus, tools rank well in google. It's like writing a blog post, but you get to write code instead!

2. Free tools are a great way to validate a business idea.

I've found it's hard to get people on a call to validate a business idea. But, there's a secret sauce to getting let in the door. Validate yourself to them first, and they'll help you validate your business. If you build a free tool for accountants, you instantly have much more credibility when you reach out.

"Hi, I'm Bob and I make tools for accountants (such as this one). I know you're an expert in the field, so I'm reaching out to see if you could provide some insights into day-to-day problems so it could guide future tools."

3. Free tools are quick to build.

Free tools shouldn't need auth, or a database (beyond airtable), or a monorepo, etc. If you're an experienced developer, it's easy to launch these tools quickly. If you're still learning, even better! Building and launching free tools is a phenominal way to walk yourself into the world of launching software.

4. Free tools can be "launched"

This is the ultimate hack to building free tools. They can be launched on ProductHunt, IndieHackers, twitter, etc. And if they provide value, it's a great way to get early traction. Compared to launching a paid product, people won't be as critical of a free tool. And if it provides value, you'll start building a loyal audience.

Let me provide an example. I run a paid addon tool for Notion called But, before I built it, I built a free site called This site now ranks #3 for the keyword "Notion integrations" and gives traction that I can direct towards Engine if I want to. Also, an early version of the site featured a search bar. I used this to collect data and discover what integrations users wanted to see.

This was key because it let me get a head start on marketing before I ever started coding Engine. It was also a tool I could show to consultants in the space and say “Hey, am I missing any tools on here? Is there other integrations your clients have been requesting”?

How to effectively execute your hackathon

Now that you know what you're planning to build, it's time to learn how to execute this hackathon effectively. The key separating your hackathon from a traditonal hackathon is that you don't want to be working in a vacuum.

It might feel weird, but it's important to get in the habit of sharing your products, not just building them. Here's how I recommend you do this.


Before you start, draft an Indiehackers post sharing your hackathon plans. Invite others to offer suggestions for what they'd like to see. And share that you'll be offering a play-by-play of the progress on your twitter.

Additionally, and this is very important, get a landing page up for your tool!

Start marketing it. This should be your concrete goal: "Before I start building I want to get a link to this landing page existing in at least 10 places on the internet".

Use easy channels such as reddit, facebook groups, indiehackers, hacker news, relevant forums, blog posts, your personal site, etc. Since your tool isn't released yet, you can share something like this:

I'm in the final stages of building a 100% free tool for users to accomplish x. It will be released in the coming days! I'm giving out early access so if you're interested fill out the form here (link).

Then, your link should simply point to where the tool will exist in the future. This will start generating backlinks. Since it's not built yet, just put a quick form or email capture at that link. This will be really helpful for (1) early traffic, (2) a launch list and (3) relevant feedback.

During the hackathon

During the hackathon, it's important not to pick your foot off the gas pedal of marketing. Do the following:

  1. make a tweet every hour sharing an update. This doesn't always need to be an "acheivement", in fact it's better if it isn't. Stuck on centering a div for 2 hours? Share that. Found a neat little bug that you haven't seen before? Share that too.
  2. Go back to those relevant links you made before starting. Did any communities resonate well? Share updates in those communities.

Finally, get to coding! Make sure you set a fixed time limit, but I wouldn't go anything longer than 3 days. The time limit should be short to force you to cut corners and not get too deep into thought. Learning that skill is essential for entrepreneurs as you won't always be able to do things the correct way all the time.

How to finish your Hackathon

As your final day is winding to a close and your tool is almost ready to publish, pat yourself on the back. Congrats! You’re getting yourself into the habit of shipping. Here's what you do next.

First, get your code out into the world. Put it on a personal website, a github repo, or a Vercel instance and get your tool interactable. Does it look ugly? Feel clunky? That's good. In fact, that’s ideal. Because, you'll probably want to come back tomorrow and polish it up, right? Congrats, you’re getting into the habit of shipping product.

Finally, the next day I encourage you to write a recap of your experience. Make a blog post describing the process and what you learned. Also, share the tool in relevant communities. Share a 2 sentence story about the build process and invite feedback to help you iterate on it more.

As a bonus: You can even execute a ProductHunt launch with your new tool. This could be a whole separate blog post in itself, but it's something worth considering if you think people will draw value from it.

Thanks for reading!

On another note, welcome to week 3 of my bootstrapper articles. I’ve been writing these from a neighborhood in Minneapolis called Uptown. It’s the most beautiful place I’ve ever lived. Labelled as the “20-somethings” area of Minneapolis, it boasts the best walkability I’ve ever experienced. I’m gonna miss walking to get food in the morning, riding my bike around the lakes after work, and creating swarms of electric scooters with my friends.

That said, I’ve had multiple doors close in my life: leaving high school, moving to college, leaving college. But, this one feels different. This one is a door that can reopen again. In the first quarter of life you’re “on rails” and can only really experience things once. But, now that’s not the case. I can always move back to Uptown. I can always get the lifestyle back that I enjoy so much. And that’s cool!