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    Positive Sum

    Greenwich, Connecticut, United StatesFounded 2020
    positivesum.comLinkedIn
    AIFintechHealthcareEnterprise SoftwareData & Analytics

    Positive Sum is an early-stage venture capital firm co-founded by Patrick O'Shaughnessy and Sam Cates. The firm backs founders pursuing their life's work across technology sectors including AI, fintech, healthcare, and enterprise software.

    Deal activity increased 400% year-over-year (5 deals in the last 12 months). Average disclosed round size is $140.9M (across 23 rounds with reported amounts).

    Find people at Positive Sum on Goldilocks AI

    Portfolio

    17

    Fund Size

    —

    Top Stage

    Series A

    Last 12 Mo

    5

    Team

    AD

    Alison Davis Riddell

    AR

    Avidan Rudansky

    BW

    Brie Wolfson

    DC

    Dom Cooke

    DL

    Donald Lee-Brown

    EJ

    Eric Jasinski

    GM

    Gabi Marques

    JS

    Jeremy Stern

    JB

    Joe Berg

    JP

    Joe Parker

    JH

    Julia Hitchins

    MD

    Michael Douglass

    Portfolio Breakdown

    Stage Distribution

    Sector Distribution

    Investment Activity

    DealsAvg Round Size

    Portfolio

    25 investments
    CompanyRoundAmountDate
    LLone Palm LabsSeries A$21MAug 2026
    Neko Health logoNeko HealthSeries C$700MJul 2026
    Rogo logoRogoSeries D$160MApr 2026
    Skyryse logoSkyryseSeries C$300MFeb 2026
    Retro logoRetroSeries A$21MJan 2026
    LLone Palm LabsSeries A$21MJan 2026
    Base Power Company logoBase Power CompanySeries C$1BOct 2025
    ID.me logoID.meSeries E$340MSep 2025
    ID.me logoID.meSeries E$65MJan 2025
    Neko Health logoNeko HealthSeries B$260MJan 2024
    Candidate logoCandidatePre-Seed$4MOct 2023
    Neko Health logoNeko HealthSeries C$65MJul 2023
    Passthrough logoPassthroughSeries A$10MFeb 2023
    Blues Wireless logoBlues WirelessSeed$11MJan 2023
    Curebase logoCurebaseSeries B$40MMay 2022
    Curebase logoCurebaseSeries B$40MJan 2022
    Curebase logoCurebaseSeries A—Jan 2022
    Prefect logoPrefectSeries B$32MJun 2021
    Prefect logoPrefectSeries A$11.5MFeb 2021
    Alpaca logoAlpacaSeries B$50MJan 2021
    Casa logoCasaSeries A$21M—
    HourWork logoHourWorkSeries A$10M—
    Witan Labs logoWitan LabsSeed$7.4M—
    Rogo logoRogoSeries B$50M—
    Alt logoAltGrowth——

    Top Co-Investors

    BoxGroup8 shared
    Thrive Capital7 shared
    Tiger Global Management, LLC4 shared
    Acrew Capital4 shared
    Lightspeed Venture Partners4 shared
    Industry Ventures3 shared
    GGV Capital3 shared
    Stanford's StartX Fund3 shared
    Gilead Sciences3 shared
    Xfund3 shared
    Bold Capital Partners3 shared
    World Innovation Lab3 shared
    Ribbit Capital3 shared
    Khosla Ventures3 shared
    Sequoia Capital3 shared
    Scribble Ventures3 shared
    Imaginary Ventures3 shared
    Copper3 shared
    Conviction Partners3 shared
    BDT & MSD Partners3 shared

    Last updated: 20 October 2026