Bootstrapping Stories

Learn from founders who navigated bootstrapping challenges. Make the same decisions they faced and understand the outcomes.

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Daniel Vassallo
Small Bets Approach

How Small Bets Led to a $3.6M Exit

Daniel Vassallo left Amazon in 2019 and adopted a small‑bets portfolio: freelance, a fast‑shipped AWS ebook, and a one‑take audience course that each produced early revenue. In 2021 a live cohort evolved into the Small Bets community, later packaged as ‘join the community; course included’. In April 2025 he sold Small Bets to Gumroad for $3.6M on a mixed cash/options structure while continuing to operate it—an outcome consistent with his downside‑aware, audience‑led approach.

Indie Hacking Info Products +8 more
5 decision points
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Danny Postma
HeadshotPro

How HeadshotPro Grew to $300k MRR with Programmatic SEO & Lean Ops

HeadshotPro is Danny Postma’s pivot from avatar novelty to a durable, paid use case: professional AI headshots. He combined programmatic geo pages and targeted blog posts to capture purchase-ready demand, and kept operations lean with one-time purchases and automation. Prior Headlime experience and a build-in-public audience supplied capital, confidence, and backlinks that accelerated traction. As growth outpaced solo capacity, he began hiring selectively to sustain quality and momentum.

Indie Hacking SEO +6 more
4 decision points
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Jon Yongfook
Bannerbear

How Jon Yongfook Grew Bannerbear: Lessons Behind a Bootstrapped $50k MRR Engine

Bannerbear’s growth came from choosing a domain with strong product–founder fit, operating on a strict build–market cadence, and turning free tools into link and traffic engines—while hardening infrastructure after a DDoS. Branding and open updates kept it memorable as an API business matured toward ~$50k MRR over ~3 years.

SaaS Developer Tools +9 more
4 decision points
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Marko Saric & Uku Täht
Plausible Analytics

How Plausible Hit $1M ARR with Open‑Source Trust, Clarity & Calm Content

Plausible Analytics began as Uku Täht’s lightweight, privacy‑focused GA alternative; Marko Saric joined to refine positioning and drive a content‑led go‑to‑market. Public code and transparent messaging built trust, while licensing and self‑host packaging evolved to protect a bootstrapped business. With a simple one‑page dashboard and paid‑only pricing, they reported thousands of paying users and a public $1M ARR milestone, continuing to grow with a lean, independent team.

SaaS Open Source +6 more
4 decision points
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