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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.
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