Small Bets

Online community and class library for independent entrepreneurs.

CommunityOnline coursesCreator economy

Acquired^{Source [2]}^{Source [3]}Last verified Oct 2, 2026

About Small Bets

Small Bets is a community and course library for small-time entrepreneurs such as creators, digital product sellers and indie hackers. Members could connect with experts, get feedback on projects and list themselves in a member directory.^{Source [1]}^{Source [3]}

It grew out of a $375, six-session cohort course that Vassallo ran 29 times; the accompanying Discord became the main product, and from July 2022 people could join the community without taking the course.^{Source [1]}

At the April 2025 sale Vassallo reported 6,692 lifetime members, 41 consecutive cash-flow positive months and almost $500,000 profit in 2024, excluding Gumroad fees (self-reported).^{Source [2]}

Its site now lists 54 recorded classes from practitioners including Arvid Kahl, Justin Welsh, Steph Smith and Sahil Lavingia, plus occasional emails.^{Source [4]}

What happened

Daniel Vassallo started Small Bets in November 2021 from the Discord attached to his small bets cohort course, and ran it with Louie Bacaj as partner from July 2023. Gumroad bought 10% in 2024 and the remaining 90% in April 2025 for $3.6 million, with Vassallo staying on to run it. As of October 2026 its website presents a library of 54 recorded expert-led classes and an email list.^{Source [1]}^{Source [5]}^{Source [2]}^{Source [3]}^{Source [4]}

Timeline

2025-04Gumroad acquired the remaining 90% for $3.6 million, 50% cash and 50% stock options.^{Source [2]}^{Source [3]}
2024-05Gumroad acquired 10% in a $500,000 share exchange.^{Source [5]}
2023-07Louie Bacaj joined as partner.^{Source [1]}
2022-07Community opened to sign-ups without the course.^{Source [1]}
2021-11Community started.^{Source [1]}

Products and brands

Small Bets community: Paid Discord-based community for independent entrepreneurs.^{Source [1]}
Class library: 54 recorded expert-led classes (as of October 2026).^{Source [4]}
Small Bets cohort course: Six-session Zoom course on the small bets approach; ended after 29 cohorts.^{Source [1]}

How it makes money: Sold community membership and courses to individuals; Community Inc. reported over $400,000 a year in revenue and more than 4,500 members at the time of its profile.^{Source [1]}

Leadership

Daniel Vassallo	Runs the business as a Gumroad subsidiary^{Source [2]}^{Source [3]}	Since 2021
Louie Bacaj	Partner and co-owner^{Source [1]}^{Source [5]}	2023 to 2025

Funding and financials

Profit: Almost $500,000 in 2024, excluding Gumroad fees (self-reported on X, April 2025)^{Source [2]}
Sale price: $3.6 million for 90%, implying a $4 million valuation (April 2025; per Vassallo and Who's Who Malta)^{Source [2]}^{Source [3]}

People on Founded, and where they went next

1 person on record, connected to 4 other companies.

Person	Here	Also built
Daniel Vassallo	Founder and co-owner, Operator under Gumroad ownership2021 to now	FULL SEND2026 to nowActiveGumroadActiveUserbase2019 to nowActiveAmazon2019IPO

Sources

How Daniel Vassallo Grew a Group of Small-Time Entrepreneurs to $1M, Community Inc.. Accessed Oct 2, 2026.
Small Bets is joining Gumroad!, X (Daniel Vassallo), 2025-04-16. Accessed Oct 2, 2026.
Maltese Founder Daniel Vassallo closes $3.6 million company sale, Who's Who Malta, 2025-04-22. Accessed Oct 2, 2026.
Small Bets: Expert-Led Classes for Entrepreneurs, Small Bets. Accessed Oct 2, 2026.
Gumroad now owns 10% of Small Bets, LLC, X (Daniel Vassallo), 2024-05-03. Accessed Oct 2, 2026.

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