ManchesterStory Group is a venture capital firm based in West Des Moines, Iowa, founded in 2016 by Dave Miles and Matt Kinley. The firm partners with early-to-growth-stage companies transforming the insurance, financial services, and healthcare sectors.
36% of their portfolio is in Insurance. Deal activity increased 200% year-over-year (3 deals in the last 12 months). Their most common stage is series-a (59% of deals). Average disclosed round size is $10.1M (across 42 rounds with reported amounts).
Portfolio
37
Fund Size
$125M
Top Stage
Series A
Last 12 Mo
3
Team
Portfolio Breakdown
Stage Distribution
Sector Distribution
Investment Activity
DealsAvg Round Size
Portfolio
44 investments
| Company | Round | Amount | Date |
|---|---|---|---|
 XCaliber Health | Seed | $6.5M | May 2026 |
 Trussed AI | Seed | — | Feb 2026 |
 Salvo Health | Series A | $8.5M | Jan 2026 |
 Penguin AI | Series A | $29.7M | Sep 2025 |
 XP Health | Series B | $33.2M | Sep 2024 |
 Rainwalk Pet Insurance | Seed | $4M | Jan 2024 |
| Penguin AI | Seed | — | Jan 2024 |
 Open Loop | Series A | $15M | Mar 2023 |
| JJoyn Insurance | Series A | $17.7M | Jan 2023 |
 Joyn | Series A | $17.7M | Jan 2023 |
 Better.agency | Series A | $8M | May 2022 |
 CNote | Series A | $7.3M | Jan 2022 |
 FloatMe | Series A | $16.2M | Jan 2022 |
| XP Health | Series A | $17.1M | Jan 2022 |
 Just Insure | Series A | $8M | Sep 2021 |
 Rollick | Unknown | $8.5M | Mar 2021 |
 Rollick | Seed | $8.5M | Mar 2021 |
 Fringe | Seed | $2.2M | Feb 2021 |
| CCowbell Cyber | Series A | $20M | Jan 2021 |
 reThought Insurance | Series A | $15.5M | Jan 2021 |
 Cowbell | Series A | $20M | Jan 2021 |
 XP Health | Series A | $17.1M | Jan 2021 |
 Verikai | Series A | $6M | Jul 2020 |
 Anagram | Series A | $10M | Mar 2020 |
 SmartX Advisory Solutions | Growth | $4M | Feb 2020 |
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Top Co-Investors
Plug and Play Tech Center10 shared
Alumni Ventures5 shared
Anthemis5 shared
Canvas Prime4 shared
Nationwide4 shared
LiveOak Venture Partners4 shared
Autotech Ventures4 shared
Factory4 shared
Silverton Partners4 shared
IA Capital Group4 shared
Avanta4 shared
American Family Ventures3 shared
HC9 Ventures3 shared
SemperVirens Venture Capital3 shared
Valor Equity Partners3 shared
Tri-Valley Ventures3 shared
Village Global2 shared
Overwater Ventures2 shared
Horizon Mutual Holdings2 shared
Service Provider Capital2 shared
Last updated: 20 October 2026