My nose is currently the size of a small, angry plum. I walked into a glass door this morning-one of those floor-to-ceiling sheets of architectural hubris that are so clean they cease to exist. There was no warning. One second I was walking toward the sunlight, and the next, I was flat on the floor, the sound of my own skull vibrating against safety glass ringing in my ears. It was a binary event. The glass was either open or shut, and it was definitively shut. It hurt, but the clarity was immediate. I knew exactly where I stood: on the floor, bleeding slightly, with a very clear understanding that I would not be entering that building through that specific meridian.

We are obsessed with being polite. In the venture world, this politeness has mutated into a terminal condition. An investor doesn’t want to say no because they are terrified of the 16 percent chance that you might actually be the next unicorn and they’ll look like the fool who passed on the ground floor. So, they give you a soft pass. They give you the “maybe.” They tell you to keep them updated on your progress, which is essentially asking you to do free labor for their future optionality. They want the right to say yes later without the commitment of saying anything meaningful now.

Sarah’s email is a masterpiece of desperation and forced optimism. She’s detailing her latest 46 percent growth in user retention, her new hires, and her refined roadmap. She thinks she’s building a relationship. In reality, she’s shouting into a void that only echoes when the market turns. This is the great lie of the “keep us in the loop” crowd: they aren’t waiting for more data; they are waiting for more certainty. And by the time you have the certainty they require, you won’t need their money, or at the very least, you’ll have 106 other people clamoring to give you better terms.

I think about Jasper K.L. sometimes. Jasper is a foley artist I met a few years back while working on a short film that never went anywhere. He was a man obsessed with the literal sound of truth. He once spent 36 hours trying to record the sound of a “hesitant checkbook.” He eventually got it by rubbing a piece of vintage leather against a damp sponge. To Jasper, a “maybe” had a specific sound-a wet, sucking thud that lacked the resonance of a real decision. He told me once that the hardest sound to recreate wasn’t an explosion or a gunshot, but the sound of a person who is trying to say no without moving their lips. It’s a sound of friction without movement.

Founders think a “maybe” is a lead. It’s not. A lead is someone who is moving through a process with a timeline. A “maybe” is a anchor. If you have a pipeline full of 56 investors who are “really interested” but won’t commit to a second meeting or a term sheet, you don’t have a full pipeline; you have a graveyard of indecision. You are wasting your most finite resource-time-on people who are biologically incapable of delivering the one thing you need: a verdict.

I’ve made this mistake myself. Not just with glass doors. I once spent 26 weeks chasing a partnership that was “96 percent there.” I ignored other opportunities because I didn’t want to jeopardize the big one. I kept the loop going. I sent the updates. I did the extra demos. At the end of it, they didn’t even say no; they just stopped responding. The silence was the eventual answer, but I had paid for that silence with half a year of my life. If they had just hit me in the face with a glass door in week one, I could have spent the next 25 weeks building something that actually mattered.

To break this cycle, you have to force the binary. You have to be willing to break the glass. This means creating a structured process that doesn’t allow for the “loop” to exist. You set the timeline. You create the urgency. You don’t ask for feedback; you ask for a decision. When an investor says, “Keep us in the loop,” your response shouldn’t be “Will do!” It should be, “I’d love to, but we’re moving quickly and I need to prioritize the firms that are ready to engage now. Is there a specific milestone you need to see before you can make a clear yes/no decision, or should we just touch base during our next round?”

It sounds aggressive. It feels like you’re closing doors. But you’re not closing doors; you’re just acknowledging that the door was never open to begin with. You are removing the mirage. This is the philosophy behind a truly professional approach to market engagement. Companies like investor matching service understand this visceral need for a process that actually produces results rather than just busywork. If you don’t control the rhythm of the conversation, the “maybe” will consume you. It will eat your 16-hour workdays and leave you with nothing but a high-quality PDF of updates that nobody read.