The Runway Is Shorter Than It Looks

There’s a specific look founders get when I ask, “What’s your runway?” It’s part shame, part bravado, and part magical thinking. “Maybe a couple of months,” they say, casually, like they’re describing a parking ticket. Sometimes, the answer is worse: “We already ran out, actually.”

In these moments, I resist the urge to applaud. Not because I’m impressed—but because it takes a particular brand of optimistic delusion to mistake desperation for optionality.

Let’s be clear: you are always fundraising. Rounds don’t really “close”—they just rest. Like volcanoes. There is no finish line, no time when capital stops mattering, and no safe zone where you can relax into the fantasy that product-market fit is a force field. The clock is always ticking. And it’s usually faster than you think.

Too often, founders are sheepish in the ask. They request $500,000, thinking it’s frugal, modest, non-threatening. But here’s the dirty secret of early-stage finance: $500,000 is not a round. It’s a quarterly buffer. Maybe. That money disappears the moment you hire a couple of engineers, pay back some legacy debt (read: unpaid advisors), or—heaven forbid—realize you actually need to hire a regulatory consultant. Inflation is real. So are surprises.

That’s why I tell startups to ask for five million. Not because they’ll always get it. But because that’s what durability costs. Real runway—18+ months, real breathing room—costs real money. And if you’re not ready to raise that, then you’re not ready to scale.

More to the point, raising is not just about money. It’s about readiness. Your pitch materials should not be “in progress.” Your data room should not resemble a dropbox folder from 2019. Your cap table should not be a Jackson Pollock painting. If you can’t answer who owns what without squinting, you’re not investable. This isn’t about perfection—it’s about credibility.

I see it constantly: a startup just closed a round. Relief washes over them. “We’re good now,” they say. No, you are not. You are temporarily not dead. This is not the same thing.

Public companies have to justify their existence every 90 days. Earnings calls, investor briefings, shareholder reports. It’s brutal. But it forces rigor. Founders can learn from this—not the burnout, not the bean-counting, but the discipline of constant capital narrative. Storytelling isn’t a luxury. It’s a survival skill.

Of course, this endless performance culture comes with its own dysfunctions. I’m not suggesting that every founder should live like a NASDAQ CEO. But somewhere between quarterly guidance and blind hope lies the golden rule of company-building: cash flow is oxygen. Everything else is noise.

So yes, have the vision. Build the thing. Dream the dream. But don’t forget to raise the money. And then raise it again. Because the runway is always shorter than it looks. And unlike airplanes, startups rarely take off just once.