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5 posts tagged.
A composite founder diary (2026): the month I rebuilt my pricing page around annual billing at $32K MRR. Why monthly billing was quietly leaking customers, what ChartMogul's 2024 data shows about annual retention (62% versus 41% for monthly), the discount and cash-timing tradeoffs, and why I defaulted new signups to annual instead of forcing everyone onto it.
A composite founder diary (2026): the month I deleted two of my four pricing plans at $37K MRR. Why a 'Business' tier only 6% of customers ever chose was taxing everyone, what the research says about three tiers (and why I went to two), the scary first-week conversion dip, and how simplifying took trial-to-paid from 3.1% to 4.4% and MRR from $37K to $40K without new traffic.
At $42K MRR I finally added up what an AppSumo lifetime deal I ran years earlier was really costing me: about 1,150 active lifetime accounts paying $0 a month while eating support and server costs. A 2026 founder diary on the long tail of a lifetime deal, and how I cleaned it up.
A bootstrapped founder removed a freemium tier at about $16,200 MRR in 2026. The honest 90-day ledger: signups halved, support fell ~38%, and MRR grew ~21%.
A bootstrapped founder raised prices at ~$18k MRR in 2026. The real 90-day ledger: who churned, who stayed, and the segmented plan that lifted MRR 16%.
