Bio
Bootstrapped operator. Founded or involved with 75 businesses across nearly every business model. Built MetaLab, then assembled Tiny — a holding-company-of-bootstrapped-cash-flow-businesses including Letterboxd, Dribbble, Serato, and others. Vocal counter-narrative to venture-backed startup orthodoxy: pick boring undermonetized niches, delegate ruthlessly, and stay private long enough to compound.
Operating themes
- Fish where the fish are. Boring markets with willing buyers beat sexy markets with chewed-up incumbents.
- Lazy leadership. Delegate every task you hate; fight the Protestant work ethic.
- Willingness to pay tracks buyer economics. Same service, different segment, very different price.
Cards
- Pick a niche where the fish are; do not deadlift 300 pounds on day one — Pick boring niches with willing buyers; don't deadlift 300 pounds on day one [Tier A]
- Same service, different segment, 5x price — the variable is buyer economics, not effort — Same service, different segment, 5x price [Tier B]
Sources captured
- 2026-04-28 — Lenny's Podcast, "Niche Markets, Lazy Leadership, and AI Automation" (
raw/podcasts/andrew-wilkinson--niche-markets-lazy-leadership--2026-04-28.md)