The Saga of the "Maybe": Where Startups Go to Die

Startups rarely die from bad ideas alone. Or even from a lack of talent.   Most often, they die slowly—in the murky middle called a “Maybe.”

• Maybe is the customer who’s “interested” but can’t commit.  

• Maybe is the investor who wants another meeting.  

• Maybe is the pilot that goes live but never expands.  

• It’s the opportunity that seems promising—until you realize it’s not moving.

Maybe is Seductive.  

It gives just enough hope to keep going.   But behind the scenes, it quietly drains your most precious resource: time.

Because startups are a game of speed. The only question on every board deck, pitch, and planning doc is some version of:   “When do we run out of money?”

Burn rate is the clock. And clarity is your most valuable asset.

• Yes gives you customers, momentum, energy.

• No gives you signal, direction, focus.

• But Maybe? Maybe gives you meetings, delays, and false hope.

Founders—emotionally invested in the vision—can chase Maybes far too long. We tweak decks, shift roadmaps, and add features. We sell. Investors, on the other hand, are trained to collapse the middle. They want a signal. They want resolution. Yes or No.

And they’re right.

💥 Why Are Maybes So Hard to Spot?

Because they look like traction. A signed pilot. A demo request. A name-brand logo on your deck.  All of it feels like progress—but none of it means commitment.

Especially in the enterprise market, where customers may half-deploy your tool and never speak up again. Why? Because admitting failure means someone has to raise their hand and say, “I made a bad decision.” No one wants to do that. So instead of a clean No, you get lingering silence—a zombie customer that quietly stalls your roadmap.

It’s not just enterprise either. Founders are especially vulnerable to false traction. You’re closing some deals, but only through grinding outbound. You’re chasing meetings. You can’t get to a decision-maker. You’re always pushing—never being pulled.

Contrast that with real market pull:

• Your inbox fills with inbound demo requests.

• Prospects escalate you internally.

• People you didn’t pitch are reaching out.

Fake traction is friction. Real traction is lift.  

Fake traction is draining. Real traction is energy.

🎯 How to Discover Real Needs - Ask Better Questions

Another common trap? We ask the wrong questions. We commonly ask, “Is this a problem?”  And sure—most people will say yes.

But the better question is:

✅ “Is this a problem worth solving?”  

✅ “Is it painful enough to bump a currently budgeted initiative?”  

✅ “Will someone fight to make this happen?”

That’s where the truth lives.

Product discovery isn’t just about identifying pain—it’s about validating urgency.  

• Is this problem meaningful enough to trigger change?  

• Is there internal alignment?  

Would someone risk political capital to champion your product? The answer to that is the difference between true product market fit and a slow fade-out.

🧭 Maybes Are the Real Risk

Founders love to iterate. Investors love to eliminate. Founders try to fix Maybes—by tweaking the UI, adjusting pricing, changing positioning. Investors want clarity—because Maybe wastes cycles and obscures the truth.

The best founders learn to do both.   They build discovery processes that uncover not just need—but priority.   They ask better questions, measure real engagement, and treat ambiguity as the enemy.

In other words: they learn to shoot the Maybes. Not recklessly, but deliberately.   Not to be cynical, but to make space for the Yes. Because that’s where real traction lives—and startup survival depends on it.