Founders: how do you know when a problem is painful enough to keep building?

I’ve been thinking a lot about something I suspect many founders here have struggled with:

How do you know when you’re solving a genuinely painful problem versus simply building something people think is interesting?

The problem we’ve been focused on is founder attention overload.

As founders, we can have information coming from everywhere: emails, customers, leads, meetings, follow-ups, opportunities, tasks, and decisions.

The challenge isn’t necessarily getting more information.

It’s knowing what actually deserves your attention right now.

That led us to build FounderFlow, an AI Executive Chief of Staff. The idea is to help founders identify important conversations, revenue opportunities, follow-ups, relationships that may be going cold, and the things that require action instead of making them dig through everything themselves.

But we’re at the stage where I’m questioning our assumptions, and I’d value perspectives from other founders and makers here.

Is attention overload actually a painful enough problem that you would want software actively helping you prioritize your business?

For example, imagine starting your day and having something tell you:

“This opportunity needs attention.”

“You haven’t followed up with this person.”

“This relationship may be going cold.”

“This conversation could affect revenue.”

“These are the three things that deserve your attention today.”

Would that solve a meaningful problem for you, or would it simply become another tool you have to check?

That distinction is what I’m trying to understand.

I’d also love to hear from people who have already gone through product validation:

What ultimately convinced you that you had found a problem worth continuing to build around?

Was it people saying they wanted the product?

Actually using it repeatedly?

Paying for it?

Referring other people?

Or something else?

I’m especially interested in critical feedback. If you think founder attention overload is the wrong problem to focus on, I’d like to understand why.

I’d rather challenge the assumption now than spend months building around the wrong one.