25madison is a New York-based venture platform that builds and invests in businesses through studio, venture, and buyout strategies, focused on AI modernization of legacy industries. Its venture fund invests pre-seed to Series A in category-defining B2B software and healthcare startups.
Deal activity increased 200% year-over-year (3 deals in the last 12 months). Their most common stage is seed (68% of deals). Average disclosed round size is $7.8M (across 19 rounds with reported amounts).
Portfolio
17
Fund Size
$60M
Top Stage
Seed
Last 12 Mo
3
Team
Portfolio Breakdown
Stage Distribution
Sector Distribution
Investment Activity
DealsAvg Round Size
Portfolio
19 investments
| Company | Round | Amount | Date |
|---|---|---|---|
 Century Health | Seed | $5M | May 2026 |
 Ranger | Seed | $8.4M | May 2026 |
 Miravoice | Seed | $6.3M | Apr 2026 |
 Handspring Health Inc. | Series A | $12M | Jul 2025 |
 Kouper Health | Unknown | $10M | May 2025 |
 Wilya | Seed | $4M | Jun 2024 |
 Gig and Take | Seed | $4M | Jun 2024 |
 Wilya | Seed | $4M | Jun 2024 |
 Paxton.ai | Seed | $6M | Jan 2023 |
| DDemoleap | Seed | $4.4M | Aug 2022 |
 Handspring | Seed | $6.2M | May 2022 |
 TCARE Inc. | Series A | $17M | Jan 2022 |
| DDemoleap | Seed | $4.4M | Jan 2022 |
 Skylark Travel | Seed | $4M | May 2019 |
| Paxton.ai | Series A | $22M | — |
 VineSight | Seed | $4M | — |
| KKouper | Unknown | $10M | — |
 Ranger AI | Seed | $8.4M | — |
 Steady | Series A | $9M | — |
Top Co-Investors
Plug and Play Tech Center4 shared
Plug&Play4 shared
Bonfire Ventures4 shared
Iron Prairie Ventures3 shared
Schematic Ventures3 shared
Motivate Venture Capital3 shared
Ironspring Ventures3 shared
NextView Ventures2 shared
nvp capital2 shared
Arkitekt Ventures2 shared
Unusual Ventures2 shared
Inovia Capital2 shared
WVV Capital2 shared
Ground Up Ventures2 shared
CVS Health2 shared
General Catalyst2 shared
Clarim Ventures1 shared
Verve Ventures1 shared
Arm Holdings1 shared
Bessemer Venture Partners1 shared
Last updated: 27 September 2026