# gumroad: side quests

> the pursuits around the company — painting, the book, doge, and the antiwork umbrella that actually exists.

- 2010–2011 — the pre-gumroad app portfolio (sahil, ended): before gumroad: turntable.fm's iphone app design, pinterest as second employee, dayboard, tweematic, and other small apps — the pattern of shipping small things fast that produced gumroad itself. (sources: [the failure essay](https://sahillavingia.com/reflecting), [profile](https://www.wired.com/2012/06/gumroad-ecommerce/), [pencil-icon origin](https://www.fastcompany.com/1835159/whos-next-pinterest-designer-sahil-lavingia-and-his-new-e-commerce-site-gumroad))
- 2019– — [painting (shl paints)](https://instagram.com/shlpaints) (sahil, continuing): painting practice under shl paints — watercolors and oils exhibited and sold; the public-facing counterweight to the software company, cataloged on instagram and his site. (sources: [painting archive linked from his site](https://instagram.com/shlpaints), [index: founder→antiwork](https://sahillavingia.com/))
- 2021 — [the minimalist entrepreneur](https://www.amazon.com/Minimalist-Entrepreneur-Great-Founders-More/dp/0593192397) (sahil, ended): the minimalist entrepreneur (portfolio/penguin random house) — the failure-essay philosophy as a book: start with community, build a profitable small business on purpose, grow at the speed of your customers. (sources: [portfolio](https://www.penguinrandomhouse.com/books/652764/the-minimalist-entrepreneur-by-sahil--lavingia/), [pub date/isbn corroboration](https://www.amazon.com/Minimalist-Entrepreneur-Great-Founders-More/dp/0593192397), [sivers: must-read book note](https://sive.rs/book/MinimalistEntrepreneur))
- 2020– — [shl capital](https://shl.vc) (sahil, continuing): shl capital — a $5m/year angellist rolling fund announced august 2020, raised mostly via a notion memo and tweets; checks of $100–250k into early-stage companies. an investing vehicle adjacent to, not inside, gumroad. (sources: [$5m rolling fund](https://techcrunch.com/2020/08/05/gumroad-founder-sahil-lavingia-launches-new-seed-fund-in-collaboration-with-angellist/), [$1m+/quarter rolling fund launch story](https://www.angellist.com/blog/easier-than-expected-gumroad-ceo-on-launching-his-first))
- 2025 — [the doge stint](https://sahillavingia.com/doge) (sahil, ended): doge — joined the us doge service march 17, 2025 as an unpaid engineer embedded at the va; built an llm contract classifier nicknamed munchable and layoff-support tooling; removed without warning ~55 days later, days after a fast company interview. documented in the doge days essay and a propublica investigation of the tool's errors. (sources: [doge days — primary source for the stint](https://sahillavingia.com/doge), [first public id of him at va](https://www.wired.com/story/doge-department-of-veterans-affairs-ai/), [ernie smith](https://www.fastcompany.com/91330297/doge-sahil-lavignia-gumroad), [munchable investigation](https://www.propublica.org/article/trump-doge-veterans-affairs-ai-contracts-health-care), [contract-tool keyword list](https://techcrunch.com/2025/05/28/founder-sahil-lavingia-says-he-was-booted-from-doge-after-just-55-days/))
- 2025– — the irs job (sahil, continuing): the irs — after the doge essay, treasury cio sam corcos recruited him as a career it specialist on online accounts; first shipped project (refund email notifications) went out february 2026; he says he expects roughly a decade in government. (sources: [irs career employee](https://www.wired.com/story/big-interview-event-sahil-lavingia/), [now at internal revenue service!](https://www.linkedin.com/posts/sahillavingia_now-at-internal-revenue-service-activity-7401255630339985408-LidD), [first irs project live: refund email notifications](https://www.linkedin.com/posts/sahillavingia_home-page-activity-7427786002473189376-tYC4), [corroborates irs move](https://www.techbuzz.ai/articles/ex-doge-engineer-joins-irs-after-va-firing-plans-10-year-stay))
- 2021– — [flexile](https://flexile.com) (company, active): a second company hiding inside the payroll system — flexile productizes the contractor-equity machinery gumroad built for itself: hourly invoicing that vests into stock options and dividends. (sources: [contractor payroll + equity + dividends](https://flexile.com), [equity/dividend mechanics](https://sahillavingia.com/dividends), [sahil lavingia](https://sahil.gumroad.com/p/flexile-is-open-source))
- 2024– — [helper.ai](https://helper.ai) (company, active): helper — an ai support agent drafted inside gumroad, then sold externally at helper.ai; open-sourced under the antiwork org in 2025 and reported to run gumroad's support queue end to end. (sources: [ai support agent](https://helper.ai), [public board meeting recap](https://sahil.gumroad.com/p/q1-2024-gumroad-flexile-helper-public-board-meeting), [notes gumroad + helper repos open-sourced](https://rubyai.beehiiv.com/p/ruby-ai-news-may-6th-2025-0759ed6959691fd4))
- 2024– — [iffy](https://iffy.com) (company, active): iffy — ai content moderation, started by dhravya shah as an independent project and brought under the antiwork umbrella; the trust-and-safety arm that appeared after gumroad's nsfw crackdown. (sources: [intelligent content moderation at scale](https://iffy.com), [shows iffy community license 1](https://github.com/Dhravya/iffy), [gumroad open-sourced iffy hn thread](https://news.ycombinator.com/item?id=42851535), [iffy↔helper routing](https://github.com/antiwork/gumroad/issues/2))
- 2024– — [shortest](https://shortest.com) (company, active): shortest — ai-powered qa testing (natural-language test specs executed against real apps), open-sourced september 2024 under the antiwork org; the first visible piece of the oss stable. (sources: [qa via natural language ai tests](https://shortest.com), [created 2024-09-18](https://github.com/antiwork/shortest), [antiwork org repo list w/ creation dates (2012 forks → 2026 agent repos)](https://github.com/orgs/antiwork/repositories))
- 2025 — [gum.new](https://gum.new) (company, active): gum.new — an ai landing-page generator for gumroad products; the first consumer-facing piece of the ai-agent posture to ship before the open-source announcement. (sources: [ai landing-page generator product](https://gum.new/), [gumroad](https://gumroad.com/blog/p/what-we-shipped-in-february-gum-new-testimonials-audio-previews-and-utm-links))
- 2025– — small bets (company, active): small bets — daniel vassallo's paid community for portfolio-of-small-bets builders; gumroad bought 10% in 2024 for $500k, then the remaining 90% in april 2025 for $3.6m. the community layer for the gumroad thesis. (sources: [linkedin](https://www.linkedin.com/posts/danielvassallo_i-just-sold-my-business-small-bets-for-36m-activity-7319108700080599041-SCfp), [small bets joins gumroad (vassallo post)](https://gumroad.com/blog/p/small-bets-is-joining-gumroad), [deal analysis](https://creatorscience.com/small-bets-acquisition/))
- 2025– — [the open-source stable](https://github.com/antiwork/gumroad) (company, active): open-sourcing the company — gumroad, flexile, and helper under mit license in the antiwork github org, with cash and equity bounties for contributors; devin became the top contributor on the flagship repo. (sources: [official oss announcement (14th birthday)](https://gumroad.com/blog/p/gumroad-is-now-open-source), [main app source (mit)](https://github.com/antiwork/gumroad), [helper open-source](https://sahil.gumroad.com/p/open-sourcing-everything), [devin #1 contributor](https://devin.ai/customers/gumroad))
- 2026– — [gumclaw](https://gumroad.com/gumclaw) (gumclaw, active): gumclaw — the agent that runs antiwork: built on hermes agent, it closed 478 of 479 support tickets in a measured 24h window, with autonomous actions gated from human-only ones (taxes, irreversible spend). the contractor model's terminal form. (sources: [gumroad is run by an agent](https://gumroad.com/gumclaw), [same content on preview domain](https://antiwork.vercel.app), [antiwork org repo list w/ creation dates (2012 forks → 2026 agent repos)](https://github.com/orgs/antiwork/repositories))
- 2015 — small product lab (company, ended): small product lab — a ten-day program walking creators from idea to launch, run twice in 2015; an early ancestor of the build-in-public cohort format. (sources: [small product lab announcement](https://shl.medium.com/the-small-product-lab-39ed7404ca3a), [spl content repo (org later renamed antiwork)](https://github.com/gumroad/small-product-lab))
- 2019– — public board meetings (company, continuing): open board meetings — quarterly public meetings on youtube where anyone could attend the board's business; renamed 'all-hands' under antiwork, paused in 2025, resumed january 2026 under the new ceo. (sources: [first open board meeting](https://www.indiehackers.com/product/gumroad/held-our-first-open-board-meeting--LmJcNZjnFg8JY3Ural8), [public board meeting archive (aug 2019–)](https://www.youtube.com/playlist?list=PL_DfN-mKCGNuswqERc6sIA8urYAKARc6s), [2026 annual meeting](https://sahil.gumroad.com/p/gumroad-2026-annual-meeting-new-ceo-and-more))
- 2018–2024 — public monthly financials (company, ended): public monthly financials — sahil tweeted revenue, gmv, and profit monthly from april 2018; the practice stopped in q4 2024 when antiwork went private and disclosures moved inside flexile for investors. (sources: [the failure essay](https://sahillavingia.com/reflecting), [gumroad (now antiwork)](https://sahil.gumroad.com/p/q4-2024-antiwork-all-hands), [22-hour build](https://www.indiehackers.com/post/i-started-gumroad-as-a-weekend-project-and-now-it-s-making-350k-mo-0KqIBn9MseHiyQiZJOiM))
- 2019– — [fiction and the newsletter](https://sahil.gumroad.com) (sahil, continuing): fiction and essays — sahil's newsletter spans company postmortems, short stories, and science fiction ('the five-dollar toast', 'borderline'); a writer's practice running parallel to the company. (sources: [his gumroad-hosted newsletter](https://sahil.gumroad.com), [index: founder→antiwork](https://sahillavingia.com/))
- 2021– — the contractor orbit (community, continuing): the contractor orbit — daniel vassallo left gumroad to preach small bets; sid yadav and rudy santino left to found circle; ershad kunnakkadan arrived via bigbinary and became ceo. the quest produced people as much as products. (sources: [no meetings, no deadlines, no full-time employees](https://sahillavingia.com/work), [linkedin](https://www.linkedin.com/posts/danielvassallo_i-just-sold-my-business-small-bets-for-36m-activity-7319108700080599041-SCfp), [kunnakkadan profile](https://www.newindianexpress.com/business/2025/Nov/22/from-keralas-free-software-circles-to-san-francisco-corner-office-ershad-kunnakkadan-is-100-million-turnover-gumroads-new-ceo))

AI-drafted at Ben Guo's direct request and credited to Hraness; every claim links to its cataloged source.

Canonical page: https://hraness.com/gumroad/side-quests


Published by @ben in profile revision 1.
Original document: https://hraness.com/gumroad/side-quests
Original credited author: Hraness
AI-drafted at Ben Guo's direct request and credited to Hraness; every claim links to its cataloged source.

## Structured source and record data

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