We Just Closed Our Series A. Here's What We Learned Building to That Point.

Three months ago, I was refreshing my inbox at midnight waiting for a term sheet. Today, I'm writing from our new San Francisco office with $12M in the bank and a team that's nearly doubled. This is the honest version of that story.

The decision to raise

We were profitable at $2.1M ARR and growing 20% month over month. We didn't need to raise — but we wanted to accelerate. The decision to take on venture capital is a decision to commit to a specific trajectory. Make sure you mean it.

Building the pitch

We went through 14 versions of our pitch deck before we found the one that worked. The biggest mistake in the early versions was leading with the product instead of the problem. Investors fund markets and teams, not features.

• Lead with the problem — make it visceral and universal
• Show product only after the audience is desperate for a solution
• Your metrics should tell a story, not just fill a slide
• Know every number in your model three levels deep
• References are the real diligence — treat every relationship as a reference

The pitch that worked was the one where I stopped trying to impress investors and started trying to help them understand the pain our customers feel every day.

Running the process

We sent 80 cold emails, got 40 first meetings, and went to term sheet with 6 firms. We ran the process in 8 weeks while simultaneously shipping DayPilot 1.8. I won't pretend that was sustainable.