<?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>12-31-2023</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</com:street1>
          <com:street2>#41309</com:street2>
          <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>1</currentEmployees>
      <totalAssetMostRecentFiscalYear>18336708.44</totalAssetMostRecentFiscalYear>
      <totalAssetPriorFiscalYear>11370873.71</totalAssetPriorFiscalYear>
      <cashEquiMostRecentFiscalYear>16100625.66</cashEquiMostRecentFiscalYear>
      <cashEquiPriorFiscalYear>8810331.19</cashEquiPriorFiscalYear>
      <actReceivedMostRecentFiscalYear>0.00</actReceivedMostRecentFiscalYear>
      <actReceivedPriorFiscalYear>0.00</actReceivedPriorFiscalYear>
      <shortTermDebtMostRecentFiscalYear>4735255.46</shortTermDebtMostRecentFiscalYear>
      <shortTermDebtPriorFiscalYear>5779542.07</shortTermDebtPriorFiscalYear>
      <longTermDebtMostRecentFiscalYear>0.00</longTermDebtMostRecentFiscalYear>
      <longTermDebtPriorFiscalYear>0.00</longTermDebtPriorFiscalYear>
      <revenueMostRecentFiscalYear>20738506.09</revenueMostRecentFiscalYear>
      <revenuePriorFiscalYear>10562408.54</revenuePriorFiscalYear>
      <costGoodsSoldMostRecentFiscalYear>6498316.20</costGoodsSoldMostRecentFiscalYear>
      <costGoodsSoldPriorFiscalYear>6785047.87</costGoodsSoldPriorFiscalYear>
      <taxPaidMostRecentFiscalYear>67574.26</taxPaidMostRecentFiscalYear>
      <taxPaidPriorFiscalYear>27542.62</taxPaidPriorFiscalYear>
      <netIncomeMostRecentFiscalYear>8911462.37</netIncomeMostRecentFiscalYear>
      <netIncomePriorFiscalYear>-1240819.49</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>05-14-2024</signatureDate>
        </signaturePerson>
      </signaturePersons>
    </signatureInfo>
  </formData>
</edgarSubmission>
