I've now sent 30+ cold outreaches about failed Stripe payments. Here's what I actually learned.

3 days ago I wrote about sending 10 cold DMs and what happened. Here's the update — with more honest numbers.

What I did:

~10 outreaches on X
~20 outreaches on LinkedIn
Countless hours finding the right people

What happened:

• X: Almost no responses. Doesn't even feel like messages are being seen.
• LinkedIn: A few real conversations started. The platform just works better for this kind of outreach — people check it with a business mindset.
• IH: This is where the most meaningful conversations happened. Not from outreach, but from people finding my posts and self-selecting in.

The biggest thing I learned:

Finding the right person takes longer than writing the message.

"SaaS founder who uses Stripe" describes hundreds of thousands of people. None of them care about your outreach unless they're already feeling the pain right now.

The only outreaches that felt real were the ones where someone had just publicly said "this is costing me money." That's not a demographic. That's a moment.

On using AI for this:

I've been using AI heavily to find and qualify leads. Honest assessment: without it, I'd have sent maybe 1/3 of the outreaches in the same time. It's genuinely useful for the discovery layer.
But there's a step AI can't replace: the judgment call on whether this specific person, right now, is worth reaching out to. That last filter has to be human. Which means I can go from 3 outreaches per hour to maybe 10 — but not 100.

Where I am now:

No paying customers yet. A few real conversations. One person who said "sounds interesting" and went quiet. A handful of IH commenters who clearly understand the problem deeply.

The gap between "this resonates" and "let me connect my Stripe account" is still the hardest part.

Still building. Still sending. Still learning.

Curious :

For those of you who've done early outreach: what finally made someone go from "interested" to "actually trying it"?

(Building DunnAI — free diagnostic that shows your Stripe failure breakdown. getdunnai.com)