<?xml version="1.0" encoding="UTF-8"?>
<edgarSubmission xmlns="http://www.sec.gov/edgar/formc" xmlns:com="http://www.sec.gov/edgar/common">
  <headerData>
    <submissionType>C-AR</submissionType>
    <filerInfo>
      <filer>
        <filerCredentials>
          <filerCik>0001532978</filerCik>
          <filerCcc>XXXXXXXX</filerCcc>
        </filerCredentials>
        <fileNumber>020-27789</fileNumber>
      </filer>
      <period>12-31-2025</period>
      <liveTestFlag>LIVE</liveTestFlag>
      <flags>
        <confirmingCopyFlag>true</confirmingCopyFlag>
        <returnCopyFlag>true</returnCopyFlag>
        <overrideInternetFlag>false</overrideInternetFlag>
      </flags>
    </filerInfo>
  </headerData>
  <formData>
    <issuerInformation>
      <issuerInfo>
        <nameOfIssuer>Gumroad, Inc.</nameOfIssuer>
        <legalStatus>
          <legalStatusForm>Corporation</legalStatusForm>
          <jurisdictionOrganization>DE</jurisdictionOrganization>
          <dateIncorporation>09-22-2011</dateIncorporation>
        </legalStatus>
        <issuerAddress>
          <com:street1>548 Market St, #41309</com:street1>
          <com:city>San Francisco</com:city>
          <com:stateOrCountry>CA</com:stateOrCountry>
          <com:zipCode>94104</com:zipCode>
        </issuerAddress>
        <issuerWebsite>https://gumroad.com/</issuerWebsite>
      </issuerInfo>
      <isCoIssuer>N</isCoIssuer>
    </issuerInformation>
    <offeringInformation>
    </offeringInformation>
    <annualReportDisclosureRequirements>
      <currentEmployees>2</currentEmployees>
      <totalAssetMostRecentFiscalYear>11948947.05</totalAssetMostRecentFiscalYear>
      <totalAssetPriorFiscalYear>16720734.62</totalAssetPriorFiscalYear>
      <cashEquiMostRecentFiscalYear>6153268.63</cashEquiMostRecentFiscalYear>
      <cashEquiPriorFiscalYear>13821885.61</cashEquiPriorFiscalYear>
      <actReceivedMostRecentFiscalYear>0.00</actReceivedMostRecentFiscalYear>
      <actReceivedPriorFiscalYear>0.00</actReceivedPriorFiscalYear>
      <shortTermDebtMostRecentFiscalYear>4191955.58</shortTermDebtMostRecentFiscalYear>
      <shortTermDebtPriorFiscalYear>4635820.52</shortTermDebtPriorFiscalYear>
      <longTermDebtMostRecentFiscalYear>0.00</longTermDebtMostRecentFiscalYear>
      <longTermDebtPriorFiscalYear>0.00</longTermDebtPriorFiscalYear>
      <revenueMostRecentFiscalYear>17785730.09</revenueMostRecentFiscalYear>
      <revenuePriorFiscalYear>18951308.03</revenuePriorFiscalYear>
      <costGoodsSoldMostRecentFiscalYear>6078822.25</costGoodsSoldMostRecentFiscalYear>
      <costGoodsSoldPriorFiscalYear>5923421.20</costGoodsSoldPriorFiscalYear>
      <taxPaidMostRecentFiscalYear>1815741.46</taxPaidMostRecentFiscalYear>
      <taxPaidPriorFiscalYear>354538.04</taxPaidPriorFiscalYear>
      <netIncomeMostRecentFiscalYear>3792179.17</netIncomeMostRecentFiscalYear>
      <netIncomePriorFiscalYear>4290423.04</netIncomePriorFiscalYear>
    </annualReportDisclosureRequirements>
    <signatureInfo>
      <issuerSignature>
        <issuer>Gumroad, Inc.</issuer>
        <issuerSignature>Sahil Lavingia </issuerSignature>
        <issuerTitle>CEO and Director</issuerTitle>
      </issuerSignature>
      <signaturePersons>
        <signaturePerson>
          <personSignature>Sahil Lavingia</personSignature>
          <personTitle>CEO and Director</personTitle>
          <signatureDate>04-08-2026</signatureDate>
        </signaturePerson>
      </signaturePersons>
    </signatureInfo>
  </formData>
</edgarSubmission>
