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The First Step in the Stair Step Approach to Bootstrapping


I've been both an employee and a founder. I've built venture-backed companies, worked for venture-backed companies, built bootstrapped apps, and worked for bootstrapped companies. From all this experience, I can tell you there is no one correct path. Building a business is hard, and sometimes it takes outside investment to get it off the ground. Sometimes, outside investment causes nothing more than distractions. Either way, each founder has to decide which path makes the most sense for them and their business.

In my case, I'm planning for my post-employment future. I won't say I will never start a venture-backed company again (circumstances and opportunities change too frequently to speak in absolutes), but I will say my current plan is for what comes next after Pinata. I plan to be at Pinata through an eventual exit–whether that's an IPO or an acquisition. But what comes after that? Preferably, I will be in a position where I can run a bootstrapped, lifestyle business. A lifestyle business doesn't mean you don't have ambition. It doesn't mean you don't work hard. Instead, it simply means you build the business to match your lifestyle. This is distinctly different from a venture-scale business which is built to return the fund (i.e. ensure investors not only make back their investment in you but make up for the missed bets on other companies in the portfolio).

Knowing that my goal is to build a bootstrapped business, and having taken many half-assed swings at this in the past, I decided to be as pragmatic as possible. Fortunately, there is a pretty solid guide to the pragmaticism necessary called the Stair Step Method to Bootstrapping. This was written originally by Rob Walling and popularized by him through blog posts, talks, and his podcast. Walling is famous in the indiehacker and bootstrapper community for his businesses, his books, and his conferences. Unlike a lot of other famous "indiehackers" Walling has the business success to back up the things he talks about. He bootstrapped and sold multiple companies, including his biggest exit with Drip, an email marketing platform.

Walling's formula for bootstrapping success is built off his own experience, so it's important to consider this when following it. Past performance does not guarantee future outcomes, especially when that performance was from someone who is not you. That said, the approach is sound, easy to follow, and worth considering.

Which is exactly what I'm doing.

Though I've built two startups in the past, one that raised through an accelerator and one that raised from angel investors, and though I've built many side projects, I decided to start at the bottom step of the Stair Step Method. But we should talk about what Step One means before we dive into what I'm building and how I'm approaching step one.

Step one is to build a small app or product that has a built-in distribution mechanism. Some people choose not to make this a SaaS and instead focus on one-time payments, but others attach a subscription fee to the app with built-in distribution. In fact, Walling's original blog post focuses on one-time payments. However, the landscape has changed a lot since 2015, and many app marketplaces support subscription payments and make it easy to implement. Still, the key ingredient is distribution. But where does this distribution come from?

It comes from marketplaces. Think Shopify apps, Slack apps, etc. these have a built-in audience so marketing is not as big a lift. It allows you to focus on the product.

So, this brings us back to my step one.

Some of you know I worked for ClickUp for a short period of time. During that time, I got very familiar with project management software. Coincidentally, my wife’s company started using Monday.com (a ClickUp competitor). Fast forward to now.

ClickUp does not have a third-party developer marketplace but Monday does. So I talked to my wife, I poured over the Monday community forum, and I explored search trends. All of that led me to the idea for my app. Monday does not have native recurring task functionality. You either have to use a difficult combination of automations and manual updates or…you’re out of luck.

So, I decided my step one app would be a Monday app focused on making recurring tasks possible. The beauty of this is I know people are searching for it, competition is low, and distribution is handled by Monday’s app marketplace search.

Building the app was simple and painless. But, even though Monday has an app marketplace with built-in distribution, I started marketing the app through content before I'd written a line of code. Content marketing (i.e. blogging) comes naturally to me. So, it was easy to whip up a few posts to hopefully help rank for some of the keywords I found when doing SEO research. Marketing, more than building, is what makes or breaks an app. But remember, step one is about using built-in distribution, so any boost I get from content marketing is just a bonus.

I just recently submitted the app for review and am going through the approval process. I’ll update here as the journey continues. I'll be working on this nights and weekends and in between other side projects. Pinata is my main focus, and I intend to help make the company a massive success, but I also intend to set myself up for the future. Bootstrapping makes sense. Doing it pragmatically makes even more sense. We'll see where this all leads.

If you use Monday and are interested in my app, sign up for the waitlist here: https://www.tryrecur.com