One of the most frequent questions we hear during our monthly Office Hours is: “When (and how) should I contact an investor?”

We are big fans of lines, not dots. Investors don’t want a snapshot; they want to see your trajectory over time. Here is how to build that momentum.

1. When to reach out: Earlier than you think

The best time to talk to an investor is when you don’t need their money.

• The Strategy: Reach out while you’re still building. Seek their advice on specific industry hurdles or functional expertise.

• The Goal: Share your “next steps.” When you follow up three months later, you can prove you actually executed those steps. This demonstrates coachability and speed—the two things investors crave most.

2. How to reach out: Use the right door

Not all entry points are equal. In order of effectiveness:

• The Warm Intro: A recommendation from a founder they’ve already funded is gold.

• The Event: Meet them in the wild. It’s the easiest way to gauge chemistry and learn in a low-pressure environment.

• Cold Outreach: If you go this route, be brief, data-driven, and specific about why they are a fit for you.

3. The Objective: Build a relationship, not a bank account

Your first goal isn’t a check; it’s a connection.

• Reliability: Do what you say you’re going to do.

• Consistency: Keep them updated on milestones over time.

By the time you’re officially “fundraising,” you won’t be a stranger with a pitch deck—you’ll be a proven founder with a track record they’ve seen with their own eyes. Once you get into fundraising, there are other questions to ask an investor, preparing for the pitch, themes to nail, etc. But first, build the relationship.