The Red-Eye Over Nebraska

The tray table is rattling against my knees, vibrating at that specific, jarring frequency that makes the plastic feel like it’s about to disintegrate into a thousand tiny shards. I’m somewhere over Nebraska, or maybe it’s Kansas-the darkness outside the window is absolute, save for the faint, rhythmic red glow of the wingtip light. My eyes are stinging from the recycled cabin air, and my skin feels two sizes too small for my face. But the blue light of the laptop screen is the only thing keeping me pinned to reality. I just refreshed my inbox for the 14th time since we leveled off at cruising altitude.

There are 204 unread messages. A Slack thread about a database migration that went sideways. A resignation from a lead designer who feels “unsupported” and “directionless.” A passive-aggressive note from the Head of Product asking if I’ve had a chance to look at the roadmap for the next 4 months. And here I am, clutching a pitch deck that I’ve edited 44 times in the last week, wondering if I even remember how to be a CEO anymore. I’m not running a company. I’m running a marathon of rejection, and the company I built is slowly starving for attention in my absence.

The Aggressive Emptiness

I met a man once named Jamie M.-C., a water sommelier with a penchant for expensive scarves and a deep, almost spiritual understanding of mineral content. We were at a sterile VC dinner in London… Jamie spent 14 minutes explaining to me that the quality of water isn’t defined by its purity, but by its “Total Dissolved Solids.” He told me that if you strip away all the minerals, the water becomes aggressive. It actually leaches minerals from your body to find balance.

I had turned myself off and on again so many times trying to reset my pitch that I’d forgotten to stay plugged into the product.

The Vacuum Effect

When the CEO disappears into the fundraising tunnel, a leadership vacuum forms. It’s not just that the emails don’t get answered. It’s that the subtle, high-frequency decisions-the ones that define the culture-stop being made. Your VP of Engineering is suddenly 14% less certain about the tech stack. Your marketing lead starts hedging their bets. The momentum, that fragile, shimmering thing that took you 1,004 days to build, begins to evaporate.

You’re on a red-eye back from San Francisco, or London, or Singapore, and you realize that you’ve spent the last 4 weeks talking about the company instead of actually building it. You’ve become a storyteller, a narrator of a fictional future, while the present is quietly burning. I once spent 24 consecutive hours preparing for a meeting with a partner who didn’t even show up. I sat in a lobby for 44 minutes past the scheduled time, staring at a ficus plant, calculating the burn rate of my own dignity. Meanwhile, back at the office, the team was waiting for me to sign off on a pivot that would have saved us 4 months of wasted development time. I wasn’t there. I was in a lobby with a plant.

Hazing Ritual Disguised as Finance

There’s a fundamental contradiction in the venture model. They want to invest in “visionary leaders” who are “obsessed with the product,” but the process of getting that investment requires those same leaders to abandon the product for 4 to 6 months. It’s a hazing ritual disguised as a financial transaction. I’ve made the mistake of thinking I could do both. I thought I could pitch all day and lead all night. But you can’t. You end up doing both poorly. You give a 4-out-of-10 pitch and you provide 4-out-of-10 leadership.

I remember looking at a spreadsheet of potential investors-234 names, most of whom would never reply. Each name represented a potential 14-minute conversation that would lead to a “let’s keep in touch.” It’s a volume game that scales poorly with the human soul. I’ve seen founders lose their minds in this process… By the time the check for $4 million clears, the person who earned it is often a ghost of the person who started the journey.

Automating the Hunt, Regaining Minerals

We need to stop pretending that this is a healthy way to build things. If you have a car that requires you to stop driving and stand in the middle of the road for 4 hours every time you need to refuel, you’d call it a broken car. Yet, that is exactly how we’ve structured the startup ecosystem.

Closing the Laptop

I think back to that red-eye flight. I remember the moment I decided to stop trying to be everything to everyone. I was staring at a slide about “market expansion” and I realized I didn’t care about the slide. I cared about the fact that my Lead Engineer hadn’t laughed in 14 days. I cared that our customer churn had ticked up by 4% because I wasn’t there to hear the feedback. I closed the laptop. I didn’t send the 204 emails. I slept.

The next morning, I didn’t start by pitching. I started by listening. I sat in on the stand-up. I asked about the designer’s kids. I looked at the code. The business started to breathe again. The irony is, when I finally did get back on the fundraising trail, I was better at it. I wasn’t desperate. I wasn’t hollowed out. I had the “dissolved solids” of a real, functioning company behind me, rather than just a collection of polished slides.

Protecting Your Presence

Fundraising will always be part of the game. It’s the gravity of the startup world. But you don’t have to let it crush your bones. You can choose to protect your time. You can choose to be the CEO who actually runs the company, rather than the CEO who just spends their life on a red-eye, refreshing an inbox over Nebraska at 2:04 AM.

I still think about Jamie M.-C. sometimes when I drink a glass of water… Anything worth building takes time, and anything worth leading takes presence. Don’t trade your presence for a pile of cash that you’re too exhausted to spend. The vacuum you leave behind is far more expensive than any equity you’ll ever give away. Just turn it off and on again-the way you think about your role-and see if the signal finally clears up.