Sam’s stair-step strategy to indie hacking with confidence

What keeps so many entrepreneur-curious developers from launching a product? In this series, I speak with dev founders to see what inspired them to launch. Email me if you’re a dev-founder interested in sharing your story.

Few people wake up and suddenly quit their job to become first-time founders.

For most, it’s a process of developing skills, saving money and cultivating confidence that their time and resources will bear entrepreneurial fruit.

That journey is different for everyone. Some are quick to take the leap while others waffle in analysis paralysis.

Whatever the case, there are approaches that can stem risk, instill confidence and improve the chances of success.

Before he launched his first product, Sam Schrup was a web app developer for the University of Iowa for 7 years. He always liked the idea of working for himself and was drawn to the freedom and potential financial rewards that indie hacking offered.

But rather than diving in head-first, Schrup employed the stair-step strategy to becoming an entrepreneur. As the name implies, he took iterative steps to gain confidence, improve his odds of success, and minimize risk.

Schrup is now operating his second SaaS, TextRetailer, which recently entered the TinySeed Accelerator program. I chatted with Schrup to learn more about his entrepreneurial journey and what he’s learned.

How’d you enter entrepreneurship?

In college, I started an optical retail store — eyeglasses, contacts, etc. — with my mom who is an optician. I handled the back office financials and marketing while she ran the retail floor and engaged with customers. … I also freelanced building websites for local small businesses. This started me down the technical path.

After a few years, it was clear the freelancing and part-time salary wasn’t enough. I found an application developer job with the University of Iowa. This role gave me the opportunity to further improve my technical skills with a regular paycheck.

How’d the process look for you?

I’ve taken the stair-step approach to minimize risk. When I started building my first successful company — Textiful — I had a full-time job so there was a steady paycheck coming in the door. I quit my day job only after the business had a proven track record and consistent revenue.

When I decided to start building TextRetailer, I was able to rely on the revenue that Textiful generated as a salary. Textiful was at the point where it basically ran itself which gave me the freedom to focus on another project without sacrificing income.

What was the hardest thing to overcome?

I traded fast growth for security which was frustrating at times. The business grew much slower and features took longer to build than if I was devoted to it full time. There is only so much you can accomplish on nights and weekends.

Starting that first company while having a full-time job felt much more comfortable financially. I never had to dip into savings or go without an income. This allowed me to approach it with the attitude of “if it works out, great! If not, then I still have a great addition to my work experience and I haven’t lost much.”

Did you encounter imposter syndrome?

I think taking the stair-step approach like I did helped to reduce that feeling of unworthiness. The stakes were much lower and my goal was more reasonable. I was never trying to build a product that would become a unicorn. I was just looking to replace my current salary so I could work for myself. That goal felt much more achievable to me so it really wasn’t a reason not to start.

What skills did you cultivate to become a well-rounded entrepreneur?

As a technical founder, it's easy to get fixated on the product and your vision. However, there are so many other aspects that need to be addressed as you build your business. You really need to know a little bit about a lot of things. Developing my marketing skills was critical — and I’m still learning! You can have the best product in the world but if no one knows about it, the business probably won’t work out.

Did you experience analysis paralysis?

I’ve always been a believer that inaction is more harmful than taking the wrong action. Even if you choose the wrong action, it can generally be turned into a learning experience. Very few decisions with a business or product are irreversible so defaulting to action has always been my preference.

For me, this usually manifests in a “just build it” attitude. Although this sometimes results in losing time on a feature that is not important to my customers, generally the benefits outweigh the negatives.

Advice for entrepreneur-curious devs

Minimizing the downside can be a big confidence booster. Maybe don’t start with a standalone SaaS app. Instead, look for a smaller solution - like building an app for an existing platform or marketplace. A great directory of B2B SaaS marketplaces is Rocket Gems Building an app in this way can be less time-consuming and you have an easily identifiable customer base through the marketplace. Pursuing this strategy can give you that first win - it may even be enough for you to quit the day job.