Hi Reader,

A founder recently asked me:

It’s a fair question. Chasing feels like effort, like we’re “doing something.” But in practice, it erodes connection. Clients can feel the subtle desperation.

Anybody who’s ever dated knows how this works. We see it everywhere, from job interviews to schoolyards. You’re less attractive when you feel the need to chase.

On the other hand, if I have a conversation with someone with the priority of connecting with them, I will always end up finding out what their biggest problems are. My conversations when I was an investor weren’t about “just checking in.” They were direct offers of help with the very problems my clients cared about most. I rarely had to ask for a call, and when I did, I asked for it directly rather than dancing around my wants.

This approach works across industries, from real estate finance to coaching. Why? Because humans are wired to value what helps them move forward.

Here are a few other principles to keep in mind:

1. Teach first, sell second. Marketing isn’t a pitch—it’s the start of the journey. A coach might send an exercise that helps someone taste the work before they commit. An investor might share market context that helps a founder make sharper decisions. Done right, the prospect is more prepared, more confident, and more successful once they say yes.
2. Urgency works—when it’s real. “We’re closing this round” is compelling because it’s true. Real urgency can also look like: “Enrollment closes Friday so the group can begin together,” or “This pricing ends at midnight because we’re locking in next year’s calendar.” Fake urgency (countdown timers that reset, “last chance” emails that appear weekly) erode trust. But when urgency is tied to an actual moment in time, it galvanizes action.
3. Make sure they invest. People value what they invest in. Facebook was free, but it felt exclusive because you needed an invite. The same psychology shows up everywhere: a waitlist for a new product, a screening process for a coaching program, or requiring a short application for a partnership call. When people take a step to earn the interaction, they value it more deeply and show up more committed. Note: Don’t do this as a gimmick. Design their investment so that it screens your clients: You find out who’s actually interested, who they are, and if they’re a good fit for you.

Big Love,

Joe

This newsletter is brought to you by The Council.