Blog

Dunning thoughts, short and practical

Notes on failed payment recovery, founder-led customer service, and building a SaaS that treats people like humans.

DunningJul 2, 20265 min read

The Real Reason Stripe Payments Fail (And It's Not What You Think)

Most founders blame customers when a payment fails. The truth is more useful—and a lot less personal.

StrategyJul 4, 20266 min read

Manual vs Automated Dunning: What Actually Works in 2026

Automation scales. Manual follow-up converts. Here's how to use both without annoying your customers.

ProductJul 6, 20265 min read

The Founder-in-the-Loop Approach to Failed Payment Recovery

Why I built StayPaid to keep the founder in the conversation—and why that matters more than a 100% recovery rate.

EmailJul 8, 20267 min read

How to Write a Payment Recovery Email That Doesn't Sound Like a Robot

The emails that actually recover payments are short, specific, and human. Here's a framework you can steal.

StrategyJul 10, 20265 min read

When to Write Off a Failed Payment and Move On

Not every failed payment is worth chasing. Knowing when to stop recovering is as important as knowing how to start.