Product-market fit: Why selling your product is SO hard

Last week, we talked about product-founder (or founder-product fit) over on the newsletter. The concept where a founder self-reflects and finds true alignment with their product. Measuring that you are, for certain, the right founder to sell this product.

Today, I want you to think about the challenges you’re having finding the right customer for your product. Determine if the struggles you might have closing a sale stems from product problems or market problems.

Let’s dig in.

Pushing vs Pulling

While it’s not a novel concept, push vs pull is how I distill down the basic challenges a product might have — mine included.

Often times we get caught up in the design and creativity of building a product. Entrepreneurs love the process of creating something new and making it our own. The problem is, the more we make it unique, the more it moves away from commonality. Customers have to think harder and longer to understand your unique product.

This puts you on the path of “pushing” your product on to customers.

That same unique property — that you thought gave you an advantage — has become the property that works against you. You have to push the idea or concept on to new customers. It’s not something they can easily compare to another product or replace a current solution they are using with yours.

It make your sales and marketing more complex and costly to own the sale. At the end of the day, product market fit becomes a lot harder to measure or even accomplish, when you find yourself pushing product too hard.

Iterations and pivots

The good news is, especially early on, this is the thread in the fabric that makes up your business. All too often, new business builders are just looking for a blueprint: “Give me the answers and I’ll be good.”


Making tiny iterations or pivots — read: failures — is what you learn from and reinvest into your business. It becomes a fingerprint that makes up your brand. You might not see it yet, but it will eventually materialize.

The number one way to deal with this is to talk to your customers or incoming leads:

  • Why didn’t they buy?
  • Why did the cancel?
  • What alternatives were they looking at?
  • Who were they using before you?
  • What was the friction to sign on the dotted line?
  • Why did they say yes?
  • What successes have they had?
  • Why would they refer you?

You must take action against this feedback and then pour it back into your product to align with the market you want to be in.

Pulling in customers

Once a product has been refined to a point where it solves a problem for a market; Say hello to product market fit.

You graduate from pushing product onto customers to pulling customers into your product. You have found the market you can provide value in!

There is a chance, however, that maybe when you were spending all of that time pushing, you were just addressing the wrong market. If you have a luxury product or service, for example, you shouldn’t be marketing to cash-strapped small business owners.

Sure, this type of market needs help — but that’s because they have few funds and little time. You need to move up market and into a segment that has money to spend on your luxury service, as a basic example.

It’s a little bit of product refinement and messaging adjustment. You slowly chip away at uncovering product market fit the more you stretch the muscles that make up the entire process.

And here’s a tip about talking to customers: It doesn’t always have to be during a sales cycle. It could be from the content you’re putting out, like, starting a podcast.


There’s a concept called Minimal Viable Product (MVP) where a business creates a tiny version of their product and pitches it to a market. It’s far from a finished product, but should illustrate what a complete solution might look like one day.

You could get early buy-in, commitment letters, or free beta customers to help improve the product down the road.

Surprise! You can do the same thing with content. You can talk or write about an idea you have, release it out onto the world, and let the comments pour in.

Crickets? Maybe it’s not the best idea. Getting people jumping at you saying, “YASSS! We want this!”, now you have some acknowledgement to pursue a new iteration on your product.

You didn’t spend time spinning your wheels working in the dark, you got the idea out in public and received that feedback out in the open. It helps serve as product development AND promotion — two birds with one stone.

Let me know how you gauge product market fit in the comments. Maybe you want me to review your website, I can do that too.

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