side quests
the pursuits around the company — painting, the book, doge, and the antiwork umbrella that actually exists.
sahil's quests
- 2010–2011the pre-gumroad app portfolio · endedbefore 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.
- 2019–painting (shl paints) · continuingpainting practice under shl paints — watercolors and oils exhibited and sold; the public-facing counterweight to the software company, cataloged on instagram and his site.
- 2021the minimalist entrepreneur · endedthe 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.
- 2020–shl capital · continuingshl 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.
- 2025the doge stint · endeddoge — 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.
- 2025–the irs job · continuingthe 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.
- 2019–fiction and the newsletter · continuingfiction 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.
the umbrella
- 2021–flexile · activea 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.
- 2024–helper.ai · activehelper — 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.
- 2024–iffy · activeiffy — 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.
- 2024–shortest · activeshortest — 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.
- 2025gum.new · activegum.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.
- 2025–small bets · activesmall 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.
- 2025–the open-source stable · activeopen-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.
- 2015small product lab · endedsmall 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.
- 2019–public board meetings · continuingopen 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.
- 2018–2024public monthly financials · endedpublic 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.
the ecosystem's quests
- 2021–the contractor orbit · continuingthe 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.
AI-drafted at Ben Guo's direct request and credited to Hraness; every claim links to its cataloged source.