186 Ventures is a pre-seed and seed-stage venture capital firm based in Boston, founded by DraftKings alumni Giuseppe Stuto and Michael Fialkow. The firm invests across consumer, enterprise, and disruptive tech, leveraging deep operational and founder experience to back impact-obsessed founders.
Average disclosed round size is $16.9M (across 15 rounds with reported amounts).
Portfolio
12
Fund Size
$37M
Top Stage
Seed
Last 12 Mo
1
Team
Giuseppe Stuto
Co-Founder, Managing Partner
Julian Fialkow
Co-Founder, Managing Partner
Kendall Hope Trucker
Founder & CEO @ Stealth company, 186 Ventures Founder Partner, 2 time 186 portfolio founder
John Capodilupo
Co-Founder & CTO @ Whoop, 186 LP
David Lebow
Chief of Staff @ Draftkings, 186 LP
Sophie Panarese
Operations Manager
Portfolio Breakdown
Stage Distribution
Sector Distribution
Investment Activity
Portfolio
| Company | Round | Amount | Date |
|---|---|---|---|
 Flagler Health | Series B | $50M | Aug 2026 |
| Flagler Health | Series B | $50M | Jan 2026 |
| FFlagler | Unknown | $50M | Jan 2026 |
 Wingspan | Series B | $24M | Jul 2025 |
| Wingspan | Series B | $24M | Jan 2025 |
| IIPX | Unknown | $3M | May 2023 |
 Integrated Projects | Seed | $3M | May 2023 |
 Onyx Private | Unknown | $4.1M | Jan 2023 |
| IIPX | Seed | $3M | Jan 2023 |
| Wingspan | Series A | $14M | Jan 2023 |
 Mural | Seed | $5.6M | Aug 2022 |
| NNeighborSchools | Seed | $5M | Jan 2022 |
 Tappity | Seed | $1.3M | Dec 2020 |
 Moni | Growth | — | — |
 Sourgum | Series A | $12.5M | — |
 Beluga | Seed | $4M | — |
Top Co-Investors
Last updated: 20 October 2026