Postmark Startups

Garrett Diamond built Sifter, a bug tracking SaaS for small teams that prioritized simplicity and non-technical user adoption over feature richness. Launched in 2008 after 6 months of development, Sifter grew through word-of-mouth and targeted advertising (notably a $2,500 Daring Fireball ad that brought 30-35 customers). The business generated healthy recurring revenue over 8 years and sold for low six figures in part because recurring revenue allowed Garrett to maintain the business through significant health challenges.