Written By: Marc Halpin
“I learned one of my biggest venture fundraising lessons by accident — on a flight from NYC to Chicago back in 2015.”
It was late September, and I was flying back on the 8pm flight from LGA after pitching a venture investment committee on my Series C — 35 people in the room (yep, it was for a big check), real IC vibes, high-stakes energy. I was traveling with my CFO, debriefing the meeting and, of course, thinking about what I could have done better.
As we boarded the flight home to Chicago, we spotted a familiar face — a fellow Chicago founder, a prolific fundraising CEO known for his ability to raise strong venture rounds. He had his CFO with him too, which told you everything about the purpose of his trip.
Just six months earlier, he had closed a massive round.
So when he mentioned he’d been in New York pitching the same investor we had just met with, my CFO and I looked at each other. We finally asked:
“You’re raising again? You just closed a round. Surely you don’t need the cash?”
He smiled and said these words that have stuck with me ever since:
“I’m not raising because I need the cash, I’m raising because I can raise the cash”.
That sentence replayed in my head the entire flight back to Chicago and completely reframed how I think about timing a round. (it also challenged a lot of conventional thinking about raising capital)
As founders, we spend so much time thinking about when to raise venture capital — runway, burn, milestones, time of year, market conditions etc.
But here’s the part many miss:
Your ability to raise — the strength of your story, traction, and momentum — matters far more than your need to raise.
Raise on Leverage, Not on Lifeline
In venture, your best fundraising window is when things are going really well in your business:
- Customers are adopting fast
- Retention is strong
- Growth is compounding
- Investors are leaning in and asking for updates
- You’re getting inbound interest from more than one fund at the same time
- Investors are starting to reference each other on calls (“We’ve heard good things from ABC.”)
That’s when you and you have real leverage — you control the story, the valuation, and who joins your cap table.
Wait until you need the money — when burn is biting and momentum has slowed — and suddenly you’re negotiating from a position of weakness, not strength.
The Lesson for Venture-Backed Founders
Raising venture capital isn’t just about extending runway — it’s a strategic move about timing, leverage, and ambition.
The best founders don’t raise because they have to.
They raise because they can — when the story is sharp, the metrics are working, and the market is listening.
This is exactly how I now help founders think about their rounds: not as emergency lifelines, but as strategic moments to upgrade their investor base, valuation, and options.
So the next time your business is humming — product is working, customers are happy, metrics are trending up, and investors are circling — don’t just celebrate. Consider whether that’s exactly when you should raise your next venture round – Irrespective of how long your runway is!
That 2‑hour flight in 2015, with two CEOs and two CFOs trading notes at 30,000 feet, permanently changed how I think about raising venture capital.
If you’re a founder (building a software business) wondering when to raise — or whether you can raise from a position of strength — send me a message (marc@kerosene.vc), and I’ll share how I’d approach your specific situation.
Kerosene Ventures: Helping Great Founders Raise Capital