Dmytro Krasun
Dmytro Krasun: From Repeated Failures to $25K a Month with One Boring API
ScreenshotOne founder · 800+ paying customers · $25K+ MRR · bootstrapped, no outside funding · built January–May 2022
Dmytro Krasun spent more than a decade as a backend engineer and failed at product after product. Then he shrank his ambition, picked the most boring problem he actually knew how to solve, and built ScreenshotOne — a screenshot API now used by 800+ paying customers at $25K+ a month.
Maria Rubtsova
Maria Rubtsova: From Spare-Hour AI Experiments to 50+ Brand Campaigns
Dreamfall Art Studio founder · 50+ brand campaigns · 1.5M+ Instagram followers · 30+ video lessons · Skool community from $27/month · annual revenue estimated $500K–$1.5M (unverified)
Maria Rubtsova started Dreamfall Art with no roadmap, just spare hours testing generative AI tools. She turned cinematic AI visuals into 50+ brand campaigns, an audience of over two million, and a Skool education business — by selling taste, not prompts.
Nathan Barry
Nathan Barry: The Failed $5,000 Challenge That Built a $33M-a-Year Email Business
ConvertKit founded 2013 · $5,000 challenge failed at ~$2,100 MRR · $50K all-in bet · $33.4M ARR reported by 2022 · bootstrapped, rebranded as Kit in 2024
Nathan Barry gave himself six months, $5,000, and 20 hours a week to build a web app to $5,000 a month. He failed — then bet his last $50,000, did his customers' migrations himself, and turned ConvertKit (now Kit) into a bootstrapped email platform doing a reported $33.4M in annual revenue.
00後東北小伙
A Post-00s Kid from Northeast China: One Person, Zero Filming Experience, ¥450K from a Pure-AI Comic Drama
Pure AI production · ¥200–400K per film · record ¥450K · contracts signed before production finished
A post-2000s kid from Northeast China has never shot a single frame of film — yet his one-person AI comic-drama studio sells each title for ¥200K–400K, up to ¥450K (about $63K). His playbook: pre-sell the unfinished, ride a platform tailwind, and run on zero filming costs.
Derek Sivers
Derek Sivers: $22M Exit, Then He Gave It All Away
CD Baby sold 2008 · reported $22M · proceeds in charitable trust for music education · bootstrapped, 100% owned
Derek Sivers built CD Baby into the world's largest indie-music distributor, sold it for a reported $22M — and put it all into a charitable trust for music education. The story, and the operating system behind it.
Damon Chen
Damon Chen: Four Failed Products, Then a $1M-a-Year SaaS Portfolio
$1.3M/yr portfolio · Testimonial.to $840K ARR · solo, bootstrapped
Damon Chen quit his eight-year Cisco job in 2020, failed four products in a row, then built Testimonial.to into a bootstrapped SaaS portfolio reportedly moving $1M+ a year — solo, no funding, two kids at home.