25Madison
Venture studioNew York · Pre-Seed–Series A · 43 people tracked
Also known as 25MADISON PROPEL FUND MANAGEMENT COMPANY, LLC · 25MADISON VENTURES MANAGEMENT COMPANY, LLC
Investment thesis
25Madison focuses on harnessing artificial intelligence to modernize legacy businesses across two main strategies. On the early-stage venture side, it incubates and invests in AI-native software and tech-enabled companies through its Studio (incubation) and Ventures (investment) arms. On the buyout side, its Propel strategy acquires and transforms lower-middle market businesses by applying AI. The platform combines company building, direct investment, and transformation buyouts under a unified applied-AI approach.
Source: firm website, verified Aug 25, 2026.
Team · 43 people
from the firm's website & public directoriesFounder mafia
2 people who came through 25Madison went on to found or lead other companies.
What they invest in
from 37 of 57 portfolio companiesHealthtech ×23AI & Machine Learning ×18Digital Health ×18SaaS ×14Enterprise Software ×5HR Tech ×5Data & Infrastructure ×3Future of Work ×3
HQs:United States×20
Who they back
founder profiles across 18 portfolio companiesFounding team size:solo founder×132 founders×23 founders×3
Where their founders studiedfrom 14 founders with education data
Imperial College London ×3Harvard Business School ×2Massachusetts Institute of Technology ×2University of Pennsylvania ×2
Where their founders worked beforefrom 14 founders with career history
Glispa Global Group ×2National Guard of Cyprus ×2
Investments · 57 tracked
founders shown can be your intro pathBy year:2026 · 32025 · 22024 · 12022 · 12021 · 12016 · 19 dated
New York, US
Alexander Toporek(Executive Officer, Director)Daniel Teran(Director)in
Board seatGrant Silow· per SEC Form D · $2.4M raise · filed Jan 2025
Co-investorsGutter CapitalGreen Egg Ventures
New York, US
Keith Cowing(Executive Officer, Director)
BoardJustine Lee(Director)
Board seatGrant Silow· per SEC Form D · filed Jun 2021
New York, US
Paul Tumpowsky(Executive Officer, Director)Michael Greene(Executive Officer, Director)Miles McMullin(Executive Officer)Elie Gordis(Director)
BoardPaul Metselaar(Director)
Board seatKirk Posmantur· per SEC Form D · $1.6M raise · filed Oct 2024
April Health provides mental healthcare integration tools and services for primary care providers, particularly serving underserved and rural communities where psychiatric specialists are scarce.
Digital HealthHealthtechMental Health
Liberty Eberly, D.O. , eMBAin
Co-investorsThe MBA Fund
Basalt is a healthcare software tool that reads incoming patient referral packets—including faxed PDFs, photographs, and scanned handwriting—extracts clinical and payer signals, and checks each referral against a facility's admission criteria, flagging findings as red, yellow, or green with links to the source document.
AI & Machine LearningDigital HealthHealthtech
Co-investorsNew Enterprise Associates (NEA)
Canopy develops an IoT-based wearable safety platform for healthcare organizations to protect workers from safety risks and workplace violence.
Enterprise SoftwareHealthtechIoTPalo Alto, US
Shan Sinha(Co-founder & CEO)inVinay Pulim(Co-founder & Chief Technology Officer)inHemanth Meenakshisundaram(Co-founder & Chief Scientist)in
Co-investorsACME CapitalFounder CollectiveNextView VenturesSpero Ventures
Century Health is an AI company serving the healthcare and life sciences sector, with a stated focus on using data to support patient outcomes and its partners.
AI & Machine LearningDigital HealthHealthtech
Vish Srivastava(Founder)in
Co-investors2048 VenturesLifeX VenturesNext Play VenturesOrigin VenturesAlumni Ventures
Clear Health provides software for healthcare providers that models expected versus actual reimbursement to identify missed payments and revenue leakage across patient-pay and payer-pay claims.
Digital HealthHealthtechSaaS
Co-investorsFortySix Venture Capital
Clearpol provides AI-powered software solutions for post-acute and long-term care providers, including clinical oversight with real-time alerts, automated plan-of-correction generation, and regulatory compliance management.
AI & Machine LearningHealthtechSaaS
Arash Hosseini Jafari M.S.(Founder)in
Co-investorsIA Seed VenturesVertex Ventures
Croissant is a resale app and browser extension that lets consumers see the resale value of fashion and branded items they own, then sell them for cash or store credit by shipping them in.
Circular EconomyConsumerMarketplaces
Co-investorsThird Prime
Flourish Health provides psychiatrist-led mental health care for young people ages 8-26 with serious conditions such as bipolar, depressive, anxiety, and trauma-related disorders.
Digital HealthHealthtechMental Health
Co-investorsAV8 VenturesCity LightGreyMatterHypothesisNew Stack VenturesTensility Venture Partners+2 more
Co-investorsBlack Opal VenturesSpringTide VenturesThe Venture Collective
Co-investorsConnecticut InnovationsThe Venture Collective
Gratia Health offers an employee engagement platform for healthcare organizations that uses gamification, smart rewards, and real-time recognition to reinforce behaviors like shift reliability, safety, and patient experience.
HealthtechHR TechSaaS
Co-investorsCity LightHeadwater VenturesJumpstart Capital
Handspring provides virtual mental health therapy for children, teens, and young adults, with insurance coverage and rapid access to care without waitlists.
Digital HealthHealthtechMental Health
Sahil Choudhryin
Co-investorsCobalt VenturesCornucopian Capital ManagementNextView VenturesNVP CapitalRPS VenturesVamosVentures+3 more
Hut 8 operates high-performance computing (HPC) and data center infrastructure, including its Beacon Point data center campus.
Cloud ComputingCrypto & Web3Data & InfrastructureEnergy
Asher Genootin
Co-investorsArchetypeCoatue ManagementFlucas Ventures
Keragon offers a no-code platform for healthcare organizations to build HIPAA-compliant workflow automations, aimed at clinical and operations teams.
AI & Machine LearningDigital HealthHealthtechSaaS
George Eracleous(Founder)inPanos Papageorgiou(Founder)inConno Christou(Founder)in
Co-investorsAfore CapitalFocal VenturesUpfront VenturesFocal
Kouper builds an AI platform that automates patient-facing healthcare workflows — including appointment scheduling, insurance verification, discharge planning, and care coordination — for healthcare organizations.
AI & Machine LearningDigital HealthHealthtech
Co-investorsCVS Health Ventures
Kyra runs influencer marketing programs for global brands, activating creators across TikTok, Instagram, and YouTube and analyzing large volumes of creator video to forecast and measure campaign outcomes.
AdTechAI & Machine LearningCreator EconomyMarketing Tech
Dev Karaca(Founder)inDevran Amaratunga Karaca(CEO & Co-Founder)Nicholas Dart(COO/CTO & Co-Founder)Stewart Rawle(Chief Commercial Officer)inSteph Fadahunsi(Chief People Officer)Ed Galvin(Chief Financial Officer)
Co-investorsGMG VenturesTorch CapitalLionTreeMercuri.vcMetaplanetfirstminute capital+3 more
Kyra is an ICHRA (Individual Coverage Health Reimbursement Arrangement) platform that handles contribution modeling, quoting, enrollment, compliance, and year-round benefits support for employers, brokers, and employees.
HealthtechHR TechInsurTech
Lucas Hearn(Founder)in
Co-investorsDorm RoomFlyover Capital
Ladder Health provides digital health services focused on pediatric care and developmental screening, helping families navigate healthcare options for their children.
Digital HealthHealthtechBoston, US
Elizabeth Kidder
Co-investorsGROOVE CAPITALJumpstart CapitalNina Capital
Lynd Clinical operates a network of clinical research sites in underserved rural and community markets, using technology and local partnerships to expand patient access to clinical trials.
AI & Machine LearningBiotechDigital HealthHealthtech
Matt Ullum(CEO)in
M7 Health builds an AI-powered nurse and staff scheduling platform that forecasts staffing demand, auto-balances schedules, fills open shifts, and provides real-time coverage visibility for hospitals and health systems.
AI & Machine LearningDigital HealthHealthtechSaaS
Ilana Borkenstein(Co-founder)inEric Gruskin(Co-founder)in
Co-investorsJanuary VenturesThreshold VenturesFirst Round CapitalLakehouse Venture Partners
Marit is a free career platform for physicians and advanced practice providers (APPs) that offers crowdsourced, anonymous salary data and aggregated job listings from employers, associations, and job boards.
Digital HealthHealthtechHR Tech
Rob Anderson(Co-founder)
Co-investorsDefine Ventures
Virtual women's health clinic offering insurance-covered perimenopause, menopause and midlife care in all 50 U.S. states.
Joanna Strober(Founder)in
Co-investorsFelicis VenturesIcon VenturesSteelSky VenturesGingerbread Capital
MIDI develops digital health solutions for patients and clinicians to improve access to and delivery of care across diverse populations.
Digital HealthHealthtechLos Altos Hills, US
Joanna Stober(Executive Officer, Director)Sharon Meers(Executive Officer, Director)inJoanna Strober(Founder)in
BoardAllison Gates(Director)in
Co-investors1843 CapitalAble PartnersAdvance Venture PartnersCity Lightf7 VenturesFelicis Ventures+13 more
Miravoice uses natural language processing to conduct automated voice interviews and surveys, capturing structured data, transcripts, and recordings.
AI & Machine LearningData & InfrastructureMarketing TechSaaSSan Francisco, US
Shreyas Tirumala(Founder)inNishant Jain(Founder)in
Co-investorsStartXUnusual Ventures
AI-powered sales intelligence platform analyzing body language and verbal communication from virtual meetings using NLP and non-verbal language processing.
Co-investorsSixth Millennium Venture Partners Management, Llc
Offload is an AI-powered platform for oversized and overweight freight operations that digitizes permits, maps route restrictions into compliant navigation, and connects dispatchers and drivers.
AI & Machine LearningLogistics & Supply ChainSaaS
Co-investorsMarket Square VenturesCERVIN VENTURES
Opsera is an AI-powered software development lifecycle platform that automates application development, governance, and deployment across enterprise organizations.
AI & Machine LearningDeveloper ToolsEnterprise Software
Co-investorsProsperity7 VenturesAlumni VenturesClear VenturesFelicis VenturesHitachi VenturesTaiwania Capital
Paxton AI is a legal AI assistant for attorneys, law firms, and legal professionals that automates tasks such as contract review, case law research, document drafting, and analysis of medical or billing records.
AI & Machine LearningDigital HealthHealthtechLegalTechSaaS
Co-investorsFlori VenturesKyber Knight CapitalUnusual VenturesVoyager CapitalIdentity.vc
Quantivly provides data liquidity and analytics tools for radiology providers, converting heterogeneous and legacy imaging data into usable insights about radiology operations.
AI & Machine LearningData & InfrastructureDigital HealthHealthtechSaaS
Robert MacDougall(Founder)in
Co-investorsLair East LabsNina CapitalNovaCapitalOne Way VenturesWalnut Venture AssociatesBoxOne Ventures
New York, US
James Zhan(Executive Officer)Sanford Spivey(Executive Officer, Director)
BoardTyler Churchill(Director)in
Co-investorsBonfire VenturesInovia CapitalPanache Ventures
Ranger provides an AI platform that connects industrial teams, workflows, and documents across an operation, mapping workflows to reduce time spent searching, drafting, and reviewing.
AI & Machine LearningEnterprise SoftwareSaaS
Co-investorsNorthside VenturesPanache Ventures
Sift Search is a recruiting service that helps early-stage, venture-backed startups make foundational hires across engineering, product, and go-to-market roles, from founding engineers to first sales leads.
Future of WorkHR Tech
Silkline provides supply chain orchestration software for advanced manufacturers, automating procurement workflows and enabling supplier collaboration to reduce time to revenue and improve operational efficiency.
Advanced ManufacturingEnterprise SoftwareLogistics & Supply ChainSaaS
Brent Shulman(Founder)in
Co-investorsBarrel VenturesOrigin VenturesValia VenturesForward Deployed VCMatchstick VenturesPlow Ventures
Swap Health connects patients with registered dietitians for evidence-based, personalized nutrition care and lifestyle coaching.
Digital HealthHealthtechWellness & FitnessGrove City, US
Syndicate provides infrastructure to scale the Ethereum blockchain, supporting staking and development operations on the network.
Crypto & Web3Mountain View, US
William Raphael Papper(Executive Officer, Director)Ian John Lee(Executive Officer, Director)ian //(Founder)in
Co-investorsA.Capital Venturesa16z cryptoAndreessen HorowitzArchetypeAtelierBlueYard Capital+12 more
TCARE provides a clinical protocol combining data-driven risk algorithms and dedicated specialists to assess and reduce burnout among family caregivers.
AI & Machine LearningDigital HealthHealthtechWellness & FitnessSt.Louis, US
Mohammad Ali Ahmadi(Executive Officer, Director)Vijay Anand(Executive Officer)Mike Mings(Executive Officer)Bikram Bakshi(Director)in
Co-investorsAmerican Family VenturesClaritas CapitalConnetic Ventures
Thrive Mobile provides affordable wireless plans through the Lifeline program, powered by SafetyNet Wireless, with plans starting at $0/month and integrated health resources for low-income users.
ConsumerHealthtechSaaS
Co-investorsPrimetime PartnersCVS Health VenturesFrist Cressey VenturesWinter Street Ventures
Truehold Financial provides financing for real estate investors, including long-term loans for rental properties qualified on property cash flow and short-term loans covering purchase and renovation costs.
FintechPropTechSt. Louis, US
Azat Tulegenov(Founder)inConnie Adams(CEO)
Co-investorsBAM VenturesClocktower VenturesGreat Wave VenturesHabitat PartnersLaunchpad CapitalSamsung Next+3 more
Vinesight offers an AI-driven platform that detects disinformation and toxic narratives in real time, providing evidence-backed alerts to help organizations respond quickly.
AI & Machine LearningCybersecuritySaaSNew York City, US
Nir Hauser(Founder)
Co-investorsAnD Ventures
A scheduling and workforce management platform for frontline workers in manufacturing that enables flexible work arrangements and skill-based assignment matching.
Advanced ManufacturingFuture of WorkHR TechSaaS
Rahil Siddiqui
Co-investorsIron PrairieSchematic VenturesMotivate Venture Capital
Rows marked “SEC filing” are inferred from directors named on the company's SEC Form D — public regulatory data, not a portfolio list published by the firm.
Exits · 1
IPOs and acquisitions across the tracked portfolioHut 8NASDAQ: HUT
Portfolio news
latest coverage across their companies
April · local21news.com · Aug 20, 2026


Syndicate · tekedia.com · Jul 18, 2026
Kyra · today.com · Jun 26, 2026
Century Health · trysignalbase.com · May 21, 2026
Ranger RFX · thesaasnews.com · May 15, 2026
Kyra Health · kyra.health · Apr 8, 2026
Frequently asked questions
- How many investments has 25Madison made?
- 25Madison has 50 tracked investments, including 1 dated in the last 24 months.
- What stage does 25Madison invest at?
- 25Madison invests at the Pre-Seed, Seed, Series A stages.
- What sectors does 25Madison focus on?
- 25Madison focuses on AI & Machine Learning, Enterprise Software, Fintech, Healthtech, Retail Tech, SaaS.
- Where is 25Madison located?
- 25Madison is headquartered in New York, US.
- Who does 25Madison co-invest with?
- 25Madison most often shares deals with City Light, Felicis Ventures, Icon Ventures, among 86 tracked co-investors.
Media · Podcasts & interviews
featuring the team#21 - Jaja Liao, Principal at 25Madison
Nick's Notes · Jaja Liao
Images
Co-investors · 7
Founder Collective is a seed and pre-seed stage venture capital firm that invests across sectors, describing itself as sector agnostic and anti-thematic.
Slow Ventures is a generalist early-stage venture capital firm founded in 2011, with offices in San Francisco, Boston, and New York, investing in the earliest rounds of companies across many sectors.
The General Partnership (thegp) is a venture firm that supports founders with hiring, product execution, and go-to-market help to close the execution gaps that can undermine growing companies.
23andMe Research Institute is a genetic research organization that unites a community of 11 million members to advance health discoveries and deepen understanding of human DNA through collaborative research. The institute operates a cycle where members contribute genetic data that fuels research, which produces insights and breakthroughs that flow back to members and society.
XFactor Ventures is an early-stage venture firm affiliated with the broader Flybridge community, giving portfolio founders access to a network of founders, builders, and mentors.
An investment firm focused on entrepreneurs who translate cutting-edge science and technology into solutions that advance human health.
Stage 2 Capital is a venture capital firm backed by a network of go-to-market and revenue executives, focused on helping B2B software companies scale their revenue.
Firms observed investing alongside 25Madison, from public investor directories. Shared companies are the overlap with 25Madison's recorded portfolio.
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