Three Fatal Mistakes Entrepreneurs Make When Scratching Their Own Itch

Have you heard the advice to Scratch your own itch?

On first consideration the advice sounds like a reasonable idea. You might also recall stories of entrepreneurs who were successful by simply looking for ‘a better way'. Failures may not come to mind.

Let’s get one thing straight. When such advice is directed towards dreamy-eyed wantrepreneurs who have yet another idea for the next app, blog, restaurant, and seminar series (all at the same time!), a bit of personal focus would be the appropriate advice.

Assuming you are not a wantrepreneur, there are (at least) three fatal mistakes every seasoned (read as: screwed up plenty of times) entrepreneur has fallen into when trying to scratch their own itch. Fall for one of these and you’re very likely to fail. Failure doesn’t mean your entrepreneurship journey is over, but this failure won’t teach you anything you can’t learn in the next 5 minutes.

Pay attention, reflect and learn.

You are the easiest person to fool

The first principle is that you must not fool yourself and you are the easiest person to fool.

– Richard Feynman

You will fail when you arrogantly assume everyone has your problem.

Even if you are the target customer of your product, your arrogance may also make you fail. It’s too easy to get caught up in how smart, or how uniquely positioned you are to solve the problem. And because the problem is vivid, it might even feel like you’re already successful.

Big mistake.

Every entrepreneur I know has been in this situation at least once or twice, including me of course. We get excited and dive deep into solving the problem with (what seems as) perfect timing to a market waiting for us to show up. We are convinced that our product has become the category killer or market standard before we make our first customer pitch.

If the problem is real, your target customers are solving it one way or another today. As in, right now. If people aren’t currently solving the problem, they likely don’t care enough about any solution, let alone your solution.

Your job is to understand how they are solving the problem today and whether they care about improving their current solution (better/cheaper/easier to use etc).

Don’t build better if they want cheaper.

Especially don’t build better because you want better.

Never invest in solving a problem that people aren’t trying to solve today. Convincing people they have a problem is harder than addressing the one that frustrates them right now.

When you’re holding a hammer, everything looks like a nail

You will undoubtedly discover that customers have more problems than the one you are solving for them today. What typically happens is the ‘We can do that too' pitch.

Finding more products for your current customers is a good strategy. In fact, because it’s cheaper to sell to existing customers, it’s a brilliant strategy. Here’s the concern: looking at a customer’s new problem as an extension of their first problem may result in a shallow understanding of the market.

For example, let’s say that you have helped a client with their social media strategy. The client wants a CRM and your reaction is: ‘Hey, we can do that!’. Because they love you, they accept your offer and you get to work building a CRM.

The better option would be to see what off-the-shelf products solve 80-90% of their requirements and help them navigate through the process, looking for what problems come up. It’s likely that you won this project because of your trust, emotional labour, and honesty.

If this is a product area you were considering, take the consulting and implementation gig. Implementing your competitor’s product will teach you a lot about how to position your own product. Or maybe you’ll realise that it’s not the market you want to be in.

Just because you know how to solve a problem doesn’t mean you should. Commit and own the relationship, not the product.

Smarter than you doesn’t mean smartest in the world

My guess is, you know people. We all do. Just because you know someone, and they are smarter than you, it doesn’t mean they are the best fit for your team.

The right people for your team depends on what you’re trying to build. Their relative smartness to you never matters. A great working relationship between two people is much more valuable than two amazing people who work against each other.

Hiring someone just because you know them is always a terrible strategy. It’s just lazy. Even if it is a good decision, you failed as an entrepreneur.

I’ve seen countless technology companies base their product around the limited knowledge of the first ‘technical’ cofounder, simply because they didn’t have the cash to hire the right person for the job. That’s simply conflating a financing problem with a talent/leadership problem.

I’ve also seen service companies waste a quarter-million dollars on salespeople who they hired because they were too scared to sell their own product.

Don’t hire someone who impresses you because they’re smarter than you.