Finding problems is not hard. Everyone has a wide range of problems. Generally, the goal of the exercise is to identify specific problems worth solving for a specific group of people.

Usually, this comes from observing problems or actively seeking problems through conversations or user interviews. There is a good guide on how to conduct user interviews widely used by founders called The Mom Test.

In the discovery phase, avoid dismissing problems on half-baked evaluation criteria. Using simplified phrases like “painkillers, not vitamins” might cross out potentially good problems to solve before evaluating them fully.

When you start problem discovery in practice, you’ll notice that it quickly becomes a mess. It becomes way too broad to become specific at all. For example, my spreadsheet of problems had everything from under-utilization of inventory for used-car dealerships to finding funeral home availability and prices for families after a recent death.

Set boundaries by keeping all variables locked in to minimize this paradox of choice problem. Start with a single variable as the starting point: Users.

Users as the starting point

Okay, so I don’t like using the term “user”. After all, you don’t even know who will be “usingwhat and why. It also creates this weird, formalized, commercial distance between you and the users.

Think of “users” as people you actually like.

Ask your simple questions like “Do I like these people?” “Do I enjoy conversing with them?” “Do I empathize with them”?

You’d be surprised how many founders are indifferent about users — or even worse, dislike them. If you don’t like talking about fantasy football all day, maybe don’t choose fantasy football players as your users.

Another way to test if you like users is the “airport test”. If you were stuck at the airport due to a delay, would you like to spend a few hours with your users?

I’ve observed that people aren’t great at choosing users, which is why there is advice like “start with solving a problem for yourself”. You know yourself well, and you probably like yourself too. The criteria below helped me find my general user group:

  1. You enjoy being around them.
  2. You understand them.
  3. You can easily talk to them.

Once you have a broad user group, you want to narrow down that user group and then specific problems. For example, let’s say your target users are “venture capital investors”. You might think it is narrow enough, but it’s only a starting point.

It turns out that venture capital investors have several workflows, from company prospecting to due diligence, internal reporting, LP reporting, and portfolio management. And for every title — analyst to partner — the importance and process of workflows will be vastly different. Add to that the stage, sector, and geography of the fund, and you have an infinite number of potential workflows and problems.

Benefits of starting with the right user group

Starting with users has at least three benefits in short-circuiting the ideation process.

  1. It’s easy. Mathematically and anecdotally, optimizing a single variable is easier than multiple variables at once. Other variables will come into play in later stages of the PESE process anyway.
  2. It’s enjoyable. In the early days, your job is to find out what to build, build it, and then sell it. To use the lingo, it’s product, engineering, and sales. 2/3 of those things require talking with users. If you don’t enjoy working with users, you’ll hate most of the startup work.
  3. It embeds advantages. Advantages that maximize the chances of getting to a good idea:

Fast iteration cycles. Who do you think learns and iterates faster? Someone who can text and call dozens of users a day to ask specific questions to test hypotheses on problems they know of already, or someone who struggles to get 1–2 formalized video interviews to start understanding the user’s day-to-day?

If it takes you days and weeks to get to user interviews, this is probably a sign that you’re choosing the wrong group.

High quality, minimum quantity. If you are already familiar with users and problems, you can get down to a good set of problems to test during user interviews. You start with good intuition. If not, you have to take a more methodological way, similar to a MECE approach used by consultants. The most useful book for these user interviews was “The Mom Test”.

I’m not saying the latter won’t work, but it will take you many more interactions to get a sense of the universe of workflows, problems, and motivations of users. And speed is the lifeline of startups.

Founder market fit: This is a term thrown around a lot. It’s a loaded term that serves as a catch-all, including the founders understanding of the market and users and the domain expertise to build the solution. In the context of problem discovery, it goes beyond analytically understanding the problem but embeds the emotional states of users, which are often the drivers of decisions.

What I liked about Jack Conte’s reason for building Patreon is that he understood the emotional component of the problem. It wasn’t “I saw problem x, and solved it”. It was “no, I emotionally felt the pain as a creator of giving my hard work to YouTube for maybe a few cents for views.”

Liking your users is the cheat code to finding good problems

Each interview should be positioned to learn something new, not used to confirm what you already know.



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