A lot of founders jump straight to trying to sound impressive in a pitch. That usually backfires. In this episode of Back Channel, I break down the step most people skip, getting the investor to actually care before you show them anything clever.

I talk through why context matters more than complexity, how to think about an ideal investor who already “gets it,” and how to reverse-engineer what you need to explain so someone can lean in instead of getting lost. We cover opportunity size, credibility, unfair advantages, and why your real goal early in a raise is just to keep the page turning.

If you’ve ever felt like your pitch makes sense to you but not to the room, this one’s for you.

I want to walk through a real example of a founder who is doing the fundraising work the right way. Not theory. Not vibes. Actual behavior that leads to calendar density.

I talk a lot about calendar density as the punchline, and I’ve realized that for a lot of founders the obvious follow-up is, okay, but how do I get there. This episode is my answer to that question.

I break down what I saw this founder do before he ever “started” his fundraise. Starting earlier than feels comfortable, making warm intros incredibly easy for busy people, following up the right way, and treating fundraising like a written process instead of a handful of one-off asks.

If you’ve heard me say “get to calendar density” and felt a little stuck on the mechanics, this is the episode to copy.

I’ve been thinking about a fundraising idea that keeps showing up once you’ve pitched enough rooms. I call it the resonant frequency of investors. It’s that moment in a pitch when someone stops evaluating you and starts dreaming alongside you.

In this episode, I break down what that state actually looks like, how it feels when an investor is nowhere near it, and why the difference matters more than most founders realize. We talk about the myth of only pitching people who “already get it” and why that mindset leaves money on the table.

I share how narrative, framing, and a few small changes can move someone from skeptical to fully bought in. There’s a real example from a founder I’ve worked with where a single shift in context changed everything for me personally. One and a half slides in and it all clicked.

If you’re raising and wondering why some investors poke holes and others fill them in for you, this episode is for you.