Published text

Structured research records

1. the pre-gumroad app portfolio · gumroad-quests · 2010–2011 (approximate)

   Original location · source-3de0ac36492861c1d08b · source-b69610c04d856e7c8037 · source-439603b680c9bf9c5f41

   Original structured fields

   {
     "dates": "2010–2011",
     "detail": "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.",
     "id": "qst-early-apps",
     "owner": "sahil",
     "sourceIds": [
       "src-p-reflecting",
       "src-h-wired-2012",
       "src-h-fastco-2012"
     ],
     "status": "ended",
     "title": "the pre-gumroad app portfolio",
     "url": null
   }

2. painting (shl paints) · gumroad-quests · 2019– (approximate)

   Original location · source-c36111d760a70aa95a86 · source-e25a0bde58e2cefd5280

   Original structured fields

   {
     "dates": "2019–",
     "detail": "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.",
     "id": "qst-painting",
     "owner": "sahil",
     "sourceIds": [
       "src-p-shlpaints",
       "src-p-site"
     ],
     "status": "continuing",
     "title": "painting (shl paints)",
     "url": "https://instagram.com/shlpaints"
   }

3. the minimalist entrepreneur · gumroad-quests · 2021 (year)

   Original location · source-e2f210bb072a34f64a09 · source-fe0ea0ce8ee59af83e57 · source-9fcc08b217a72a7194c5

   Original structured fields

   {
     "dates": "2021",
     "detail": "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.",
     "id": "qst-minimalist-entrepreneur",
     "owner": "sahil",
     "sourceIds": [
       "src-p-penguin",
       "src-p-amazon-book",
       "src-c-sivers-tme"
     ],
     "status": "ended",
     "title": "the minimalist entrepreneur",
     "url": "https://www.amazon.com/Minimalist-Entrepreneur-Great-Founders-More/dp/0593192397"
   }

4. shl capital · gumroad-quests · 2020– (approximate)

   Original location · source-20685682b47f2b40b692 · source-212c3a208ab3f10d5746

   Original structured fields

   {
     "dates": "2020–",
     "detail": "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.",
     "id": "qst-shl-capital",
     "owner": "sahil",
     "sourceIds": [
       "src-p-tc-fund",
       "src-h-angellist"
     ],
     "status": "continuing",
     "title": "shl capital",
     "url": "https://shl.vc"
   }

5. the doge stint · gumroad-quests · 2025 (year)

   Original location · source-7f1e2a5f6b783d0c97d7 · source-05e87de84c5e8ea6cd58 · source-564973a40beb0f48bcb5 · source-5d000923ff85053c933d · source-62f43ca782e03d09740b

   Original structured fields

   {
     "dates": "2025",
     "detail": "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.",
     "id": "qst-doge",
     "owner": "sahil",
     "sourceIds": [
       "src-p-doge-days",
       "src-p-wired-va",
       "src-p-fastco",
       "src-h-propublica",
       "src-p-tc-doge"
     ],
     "status": "ended",
     "title": "the doge stint",
     "url": "https://sahillavingia.com/doge"
   }

6. the irs job · gumroad-quests · 2025– (approximate)

   Original location · source-f45237c33c1996a8b18c · source-a4823e15624ec18478a3 · source-adce79c571466968cf9c · source-0d945fecb3e46d381854

   Original structured fields

   {
     "dates": "2025–",
     "detail": "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.",
     "id": "qst-irs",
     "owner": "sahil",
     "sourceIds": [
       "src-h-wired-big-interview",
       "src-p-linkedin-irs-post",
       "src-p-linkedin-irs-project",
       "src-p-techbuzz-irs"
     ],
     "status": "continuing",
     "title": "the irs job",
     "url": null
   }

7. flexile · gumroad-quests · 2021– (approximate)

   Original location · source-b3e78184dbf099621fec · source-cccb70faf0d25c620217 · source-50954a783564baeeb76b

   Original structured fields

   {
     "dates": "2021–",
     "detail": "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.",
     "id": "qst-flexile",
     "owner": "company",
     "sourceIds": [
       "src-p-flexile",
       "src-p-dividends",
       "src-p-flexile-oss-post"
     ],
     "status": "active",
     "title": "flexile",
     "url": "https://flexile.com"
   }

8. helper.ai · gumroad-quests · 2024– (approximate)

   Original location · source-b21f5d7343d2208a13a3 · source-86714885fa68a6d8eb6a · source-54528a29e00819acf5f8

   Original structured fields

   {
     "dates": "2024–",
     "detail": "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.",
     "id": "qst-helper",
     "owner": "company",
     "sourceIds": [
       "src-p-helper",
       "src-p-q1-2024-board",
       "src-h-rubyai"
     ],
     "status": "active",
     "title": "helper.ai",
     "url": "https://helper.ai"
   }

9. iffy · gumroad-quests · 2024– (approximate)

   Original location · source-e61131ed363ca0b314d3 · source-583dec61cd5ff5f59727 · source-03b4c5efcbf8ef1327fe · source-ed92f2fb732f95d96b06

   Original structured fields

   {
     "dates": "2024–",
     "detail": "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.",
     "id": "qst-iffy",
     "owner": "company",
     "sourceIds": [
       "src-p-iffy",
       "src-p-dhravya-iffy",
       "src-p-hn-iffy",
       "src-p-gh-issue-iffy"
     ],
     "status": "active",
     "title": "iffy",
     "url": "https://iffy.com"
   }

10. shortest · gumroad-quests · 2024– (approximate)

    Original location · source-c1b4771f6dcd81d529dc · source-6a2b81002bdd731e6b18 · source-3a9dce4208c3eaba3c0c

    Original structured fields

    {
      "dates": "2024–",
      "detail": "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.",
      "id": "qst-shortest",
      "owner": "company",
      "sourceIds": [
        "src-p-shortest",
        "src-p-shortest-gh",
        "src-h-github-org"
      ],
      "status": "active",
      "title": "shortest",
      "url": "https://shortest.com"
    }

11. gum.new · gumroad-quests · 2025 (year)

    Original location · source-70ae6185b738ef78140c · source-9fb557f3fbf16a1a1d20

    Original structured fields

    {
      "dates": "2025",
      "detail": "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.",
      "id": "qst-gum-new",
      "owner": "company",
      "sourceIds": [
        "src-h-gumnew",
        "src-h-blog-feb2025"
      ],
      "status": "active",
      "title": "gum.new",
      "url": "https://gum.new"
    }

12. small bets · gumroad-quests · 2025– (approximate)

    Original location · source-d363517d794737e8841a · source-875167caa247f22d8837 · source-2660f63f4af840253cff

    Original structured fields

    {
      "dates": "2025–",
      "detail": "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.",
      "id": "qst-small-bets",
      "owner": "company",
      "sourceIds": [
        "src-h-li-vassallo",
        "src-h-blog-smallbets",
        "src-h-creatorscience"
      ],
      "status": "active",
      "title": "small bets",
      "url": null
    }

13. the open-source stable · gumroad-quests · 2025– (approximate)

    Original location · source-173f521cd3a62f48b3ca · source-617be5c4d73f9c0b02b6 · source-b4121e80dfa2835009ca · source-4207319ca91e94302267

    Original structured fields

    {
      "dates": "2025–",
      "detail": "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.",
      "id": "qst-open-source-gumroad",
      "owner": "company",
      "sourceIds": [
        "src-h-blog-oss",
        "src-h-github-gumroad",
        "src-p-open-sourcing",
        "src-h-devin-case"
      ],
      "status": "active",
      "title": "the open-source stable",
      "url": "https://github.com/antiwork/gumroad"
    }

14. gumclaw · gumroad-quests · 2026– (approximate)

    Original location · source-612fb8173be1cdc2f235 · source-0ff81dab0d4fee466547 · source-3a9dce4208c3eaba3c0c

    Original structured fields

    {
      "dates": "2026–",
      "detail": "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.",
      "id": "qst-gumclaw",
      "owner": "gumclaw",
      "sourceIds": [
        "src-i-gumclaw-page",
        "src-p-antiwork-vercel",
        "src-h-github-org"
      ],
      "status": "active",
      "title": "gumclaw",
      "url": "https://gumroad.com/gumclaw"
    }

15. small product lab · gumroad-quests · 2015 (year)

    Original location · source-f261f4950cef6f70476c · source-d58423dd096ff3874e40

    Original structured fields

    {
      "dates": "2015",
      "detail": "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.",
      "id": "qst-small-product-lab",
      "owner": "company",
      "sourceIds": [
        "src-h-medium-spl",
        "src-h-github-spl"
      ],
      "status": "ended",
      "title": "small product lab",
      "url": null
    }

16. public board meetings · gumroad-quests · 2019– (approximate)

    Original location · source-c6d1967cd10c2c50ce6b · source-79cf8acc8a657230d9be · source-64958770874cc701b8c8

    Original structured fields

    {
      "dates": "2019–",
      "detail": "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.",
      "id": "qst-open-board-meetings",
      "owner": "company",
      "sourceIds": [
        "src-h-ih-boardmeeting",
        "src-h-yt-playlist",
        "src-h-sahil-2026-meeting"
      ],
      "status": "continuing",
      "title": "public board meetings",
      "url": null
    }

17. public monthly financials · gumroad-quests · 2018–2024 (approximate)

    Original location · source-3de0ac36492861c1d08b · source-8560adbe66759e43c8fe · source-a02639e7a5c5e79ca2a0

    Original structured fields

    {
      "dates": "2018–2024",
      "detail": "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.",
      "id": "qst-public-financials",
      "owner": "company",
      "sourceIds": [
        "src-p-reflecting",
        "src-p-q4-antiwork-allhands",
        "src-p-ih-350k"
      ],
      "status": "ended",
      "title": "public monthly financials",
      "url": null
    }

18. fiction and the newsletter · gumroad-quests · 2019– (approximate)

    Original location · source-475e65c8b9db58a97029 · source-e25a0bde58e2cefd5280

    Original structured fields

    {
      "dates": "2019–",
      "detail": "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.",
      "id": "qst-fiction",
      "owner": "sahil",
      "sourceIds": [
        "src-p-newsletter-index",
        "src-p-site"
      ],
      "status": "continuing",
      "title": "fiction and the newsletter",
      "url": "https://sahil.gumroad.com"
    }

19. the contractor orbit · gumroad-quests · 2021– (approximate)

    Original location · source-ddb50a3e4b694c36ecfa · source-d363517d794737e8841a · source-e8d1e54d3784bb1237eb

    Original structured fields

    {
      "dates": "2021–",
      "detail": "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.",
      "id": "qst-contractor-orbit",
      "owner": "community",
      "sourceIds": [
        "src-p-work",
        "src-h-li-vassallo",
        "src-h-newindianexpress"
      ],
      "status": "continuing",
      "title": "the contractor orbit",
      "url": null
    }