Michael Segal
CEO of Skylight, the bootstrapped, profitable family-tech company behind the Skylight frame and calendar (~2M households). Ex-Bessemer VC. Added a subscription in 2018 and later doubled the calendar subscription from $39 to $79/year. (Transcript renders the surname “Siegel”; episode title says “Segal”.)
Strong on: emotional/values test for paywall lines, growth vs profit trade-offs (IAP vs web), day-zero payback, inventory financing, retail.
Bias to keep in mind: hardware buyers already paid $300+, so subscription behaviour differs from software-only apps; Skylight admits light experimentation (no growth PM yet).
Sources: sources/youtube/sub-club-by-revenuecat/2026-02-18-*.
Notes citing Michael Segal
- External payment links vs in-app purchase (US, 2025+)RevenueCat's Dipsea test after the 2025 US ruling — web-only checkout earned $1.96/user vs $2.09 for IAP at a 30% fee (≈ a wash), fewer trials but higher trial conversion and far lower auto-renew-off (3.5% vs 19%); at the 15% fee IAP wins; Skylight saw +100% conversion moving a QR flow from web to Apple.
- Raising subscription prices (Skylight $39 → $79)How Skylight doubled its subscription from $39 to $79/year with minimal loss of attach or retention — price tests (incl. hardware discount), choosing below the ARPU-max $99, grandfathering existing subscribers, honouring the old price on request.
- Removing the free trial (pay-up-front plans)When dropping the free trial wins — Natal's no-trial monthly grew monthly subs 2,000% (quarterly +46%, annual +21%), Claim went paid-only after 34% trial starts and 50–55% trial-to-paid — and the prerequisites, plus counter-cases (Ladder, Skylight).
- Tiered subscriptions plus consumables (fitting the demand curve)Tinder's model — 2–3 subscription tiers (Plus, Gold, Platinum) with à-la-carte consumables (Super Likes, Boosts) layered on top to capture both low and high willingness to pay; subscriptions act as a force multiplier for consumables, which free users rarely buy.
- Weekly vs monthly vs yearly plans — and which plan gets the trialMonthly plans usually underperform; test weekly vs yearly per category, and put the free trial on the plan with the highest LTV — moving it from yearly to a 3-day weekly tripled sales in one app.
- What to put behind the paywall (drawing the free/paid line)How to decide which features are free vs paid — keep the core promise free, gate new self-explanatory features, start things behind the paywall (moving out is easy, moving in is painful), meter usage visibly, and watch for "disgust" reactions, not just A/B lifts.