How to Stress-Test Your Side Business Idea

So you’ve got a few ideas for a side hustle swirling around. That’s the fun part. But how do you figure out which one actually has the legs to become a real, money-making venture? The next step is to take a closer look and see which concept has the most potential before you decide to .

Consider the story of Joe Maiellano. By day, he’s the director of development at a cancer research center in Philadelphia, doing incredibly important work. In his off-hours, he and his friend Jack shared a deep appreciation for cocktail culture. They even created their own homemade gin recipe together.

One day, they had a big idea: “Let’s open our own distillery!”

It seemed brilliant, but the dream quickly ran into reality. When they started looking into the regulations around operating a distillery, they discovered a mountain of red tape. Local, state, and federal agencies all had a say. Beyond the paperwork, the startup costs were staggering—they estimated needing somewhere between one and three million dollars. That idea was dead on arrival.

Disappointed but not defeated, Jack proposed a pivot: what if they sold people the tools to make their own gin at home? This was a fantastic workaround. This new would require far less capital, and because they weren't selling alcohol, they could sidestep most of the legal hurdles. This was one of those that was actually feasible.

They got to work, assembling the first 250 “Homemade Gin Kits” in Joe’s 700-square-foot condo. They had no idea if anyone would buy them. But word spread through friends, family, and a few supportive websites, and sales began to climb. They refined their process, built a better website, and dedicated their nights and weekends to the project, all while and keeping their day jobs.

Within four years, they’d sold 75,000 kits. Major retailers started stocking them, The New York Times gave them a glowing review, and a friend even spotted one in a celebrity’s home. Their security had officially taken off.

Of course, it wasn’t all smooth sailing. Success brought copycats who mimicked their product and branding. But Joe and Jack saw it as a natural consequence of launching a profitable and compelling idea. They started with a love for cocktails and ended up with something much better than a distillery: the security of a successful side project they genuinely enjoyed.

Finding Your Own Obstacles and Opportunities

The story of the Homemade Gin Kit perfectly illustrates the clash between a big idea’s obstacles (massive cost, regulation) and its hidden opportunities. If they had chased the distillery dream, it would have been a high-risk, high-cost gamble. The three-million-dollar price tag was a major obstacle they wisely chose to avoid.

Their brainstorming, however, led them to a much better opportunity with fewer barriers. Your ideas will have a similar mix of pros and cons. You won't see them all at once, but it's crucial to identify as many as you can, as early as you can. This isn’t about immediately discarding any idea with challenges; it’s about weighing those challenges against the potential for profit.

By doing this, you'll not only pick a idea but also understand the hurdles you’ll need to clear to make it work. The gin kit guys used two simple strategies you can use, too: brainstorming and research.

Brainstorming

Just by thinking through your idea logically, you can spot some initial roadblocks and advantages. Ask yourself:

If you want to sell golf carts for astronauts, you can immediately see the constraints: a tiny market, massive production costs, and a tough commute to your storefront on the moon. On the flip side, opportunities are often just as clear. Joe and Jack knew other cocktail lovers would appreciate their kits, and they correctly identified that the kits would make a perfect gift. They were their own target audience, which gave them a huge advantage.

Research

Sometimes you need more than just logic. But research doesn’t have to mean spending weeks in a library. Joe and Jack’s initial research was as simple as asking around and checking a few websites about local alcohol laws. When they pivoted, their research shifted to sourcing costs and marketing ideas for their new kits.

Combining your intuition with a little digging should help you answer critical questions for your :

What do I need to get started, and what will it cost?
What are the biggest potential roadblocks?
How difficult will it be to land my first customer?
Has anyone else tried something like this?
What’s the absolute best-case scenario if things go well?
And what’s the worst-case scenario if it all fails?

The more of these questions you can answer, the more confident you’ll be in the idea you choose to pursue.

Putting It to Work

Let’s apply this thinking to a few other potential ideas by weighing their obstacles and opportunities.

This requires technical skill and can't be automated. It’s also a seasonal business.
The market is recurring. Top photographers are always busy and well-paid, making them likely to outsource this kind of work.

You’re limited by the number of pets in an area and competing with cheap teenage labor.
You aren't doing the actual pet-sitting; you’re a matchmaker. This is far less time-consuming and doesn't involve rainy-day dog walks.

Getting to a critical mass of followers is difficult, and your success is tied to the platform's popularity.
This is one of those you can run from anywhere in the world, and it’s easy to outsource tasks once it grows.

Take your top ideas and make a quick list of the pros and cons for each one. Think about what would be uniquely great or uniquely challenging. Understanding how easy or hard it will be to get an idea off the ground is the key to knowing which projects to put on the back burner and which one to pour your energy into.