Third Time’s the Charm: Why You Shouldn’t Ditch a New Marketing Strategy Too Soon

Trying a new marketing strategy is a little like starting a new workout routine. You don't wake up the next day with six-pack abs (unfortunately). You wake up sore, cranky, and questioning all your life choices. But if you keep showing up… things start to change.

The same goes for marketing—especially handwritten mail.

We had a client (we’ll call them "The Determined Deal Hunter") who gave us permission to share their story anonymously. They were new to using handwritten direct mail. They sent their first campaign with high hopes and crisp new lists. You know what happened?

Crickets.

Few calls, no leads, no deals. Just the echo of their own optimism bouncing back at them.

Now, most people would’ve stopped right there. Said something like, “I tried mail once, didn’t work.” And gone back to cold calling or yelling into the internet void. But not this investor.

They regrouped. Tweaked the message. Sent a second campaign.

Still nothing.

But here’s the thing—this was the second touch on the list. Relationships (and deals) aren’t always love at first sight. Sometimes it takes a few hellos before someone says, “Okay, fine. I’ll talk to you.”

So they mailed a third time.

Same list. Third touch. And boom—a deal. A real one. Like “this pays for all three campaigns and then some” kind of deal.

Why? Because marketing, especially direct mail, isn’t about getting lucky. It’s about building familiarity, trust, and timing. Sometimes the seller isn’t ready yet. Sometimes they haven’t seen your name enough times. And sometimes they’re just waiting for the right moment to say yes.

If they had quit after one or two tries, they would’ve missed it.

Moral of the story?

Marketing is a long game. You can’t expect a new strategy to hand you a win on the first try. Keep showing up. Keep sending value. Keep building that recognition.

The third time just might be your charm, too.

Need help getting started with consistent, targeted campaigns that build seller trust over time? That’s kind of our thing. 😉

📬 Reach out to our team or check out our mailers here.