# David Miles

> David Miles is a seed investor at ManchesterStory Group (Des Moines) backing FinTech and InsurTech. See 6 investments, check sizes, portfolio. Updated Aug 2026.

- Type: Angel Investor
- Fund: [ManchesterStory Group](https://shizune.co/investors/profile/manchesterstory-group-2)
- Location: Des Moines, United States
- Total investments: 6
- Last investment: Sep 2024
- Lead investor: 50%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/davidmiles3/

David Miles is a seed investor at ManchesterStory Group in Des Moines focused on FinTech and InsurTech. David W. Miles is based out of West Des Moines, Iowa, and was the Chairman of the Board of Winnebago Industries. David previously worked at Miles Capital as a Chairman. David W. Miles attended the Drake University.

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| FinTech | 2 | 33% |
| InsurTech | 2 | 33% |
| Artificial Intelligence | 2 | 33% |
| Credit | 1 | 17% |
| Health Care | 1 | 17% |

10 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Seed | 2 | 33% |
| Series A | 2 | 33% |
| Series B | 2 | 33% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| XP Health | XP Health is a health tech startup introducing a new kind of vision benefit for employees leveraging machine learning.Founded in 2019 by Antonio Moraes and James Wong, XP Health is an AI-powered vision benefits platform for employees and their families to get frames from the world’s leading designers like Tom Ford, Ray-Ban, Armani, Gucci, Coach.Its proprietary deep learning model uses facial recognition technology that recommends the best frames based on facial dimensions with 98% accuracy. The company is working with companies like Chegg, Zenefits, and Sequoia Consulting Group. | $33.2M | Series B | Sep 12, 2024 |  |
| XP Health | XP Health is a health tech startup introducing a new kind of vision benefit for employees leveraging machine learning.Founded in 2019 by Antonio Moraes and James Wong, XP Health is an AI-powered vision benefits platform for employees and their families to get frames from the world’s leading designers like Tom Ford, Ray-Ban, Armani, Gucci, Coach.Its proprietary deep learning model uses facial recognition technology that recommends the best frames based on facial dimensions with 98% accuracy. The company is working with companies like Chegg, Zenefits, and Sequoia Consulting Group. | $17.1M | Series A | Sep 28, 2022 |  |
| Cowbell | Cowbell Cyber delivers a vertically integrated cyber insurance solution, making cyber insurance 2.0 a reality. Cowbell combines outside-in and inside-out risk assessment with AI-powered cyber risk modeling and underwriting to issue customized cyber policies written on the industry's most robust and admitted cyber coverage forms. Policyholdersbenefit from a transparent buying experience, a policy tailored to their unique needs, and value on day one with recommendations and services to remediate identified risks.Cowbell Cyber was founded in 2019 and is based in Pleasanton, California, United States. | $100M | Series B | Mar 15, 2022 |  |
| Limit Financial | Limit Financial is a managing general underwriter (MGU) specializing in credit insurance and reinsurance solutions. They help clients diversify risks through best-in-class underwriting, maximum transparency, and unparalleled service to the (re)insurance community. Its platform focuses on low-loss, conservatively structured credit risks where thereis not considered to be an optimal private capital or capital markets solution.The company was founded in 2021 and is headquartered in Woodcliff Lake, New Jersey. | $2M | Seed | Jul 16, 2021 |  |
| Cowbell | Cowbell Cyber delivers a vertically integrated cyber insurance solution, making cyber insurance 2.0 a reality. Cowbell combines outside-in and inside-out risk assessment with AI-powered cyber risk modeling and underwriting to issue customized cyber policies written on the industry's most robust and admitted cyber coverage forms. Policyholdersbenefit from a transparent buying experience, a policy tailored to their unique needs, and value on day one with recommendations and services to remediate identified risks.Cowbell Cyber was founded in 2019 and is based in Pleasanton, California, United States. | $20M | Series A | Mar 11, 2021 |  |
| Cowbell | Cowbell Cyber delivers a vertically integrated cyber insurance solution, making cyber insurance 2.0 a reality. Cowbell combines outside-in and inside-out risk assessment with AI-powered cyber risk modeling and underwriting to issue customized cyber policies written on the industry's most robust and admitted cyber coverage forms. Policyholdersbenefit from a transparent buying experience, a policy tailored to their unique needs, and value on day one with recommendations and services to remediate identified risks.Cowbell Cyber was founded in 2019 and is based in Pleasanton, California, United States. | $3.3M | Seed | Sep 24, 2019 |  |

6 of 6 investments shown.

## Co-investors
- [Tri-Valley Ventures](https://shizune.co/investors/profile/tri-valley-ventures) — VC Fund, 3 deals together
- [Anthemis](https://shizune.co/investors/profile/anthemis-group) — VC Fund, 2 deals together
- [Avanta Ventures](https://shizune.co/investors/profile/avanta-ventures) — VC Fund, 2 deals together
- [Brewer Lane Ventures](https://shizune.co/investors/profile/brewer-lane-ventures) — VC Fund, 2 deals together
- [Canvas Prime](https://shizune.co/investors/profile/canvas-venture-fund) — VC Fund, 2 deals together
- [Global Insurance Accelerator](https://shizune.co/investors/profile/global-insurance-accelerator) — VC Fund, 2 deals together

## About ManchesterStory Group

VC Fund · West Des Moines, United States

ManchesterStory Group is an early-to-growth stage venture capital firm focused on InsurTech, FinTech, and HealthTech sector. It was founded by Dave Miles and Matt Kinley in 2017 and is based in West Des Moines, Iowa, United States.

3 contacts available at ManchesterStory Group.

| Name | Title | Profile |
| --- | --- | --- |
| David Miles | Founding Partner | https://shizune.co/investors/profile/david-miles-44c1 |
| Matt Kinley | Managing Partner | https://shizune.co/investors/profile/matt-kinley |
| Jason Gross | Vice President and Head of Platform | https://shizune.co/investors/profile/jason-gross-3cd0 |

## Similar investors

### Similar stage
- [Antler](https://shizune.co/investors/profile/antler-be9c) — VC Fund
- [Alumni Ventures](https://shizune.co/investors/profile/alumni-ventures-group) — VC Fund
- [Right Side Capital Management](https://shizune.co/investors/profile/right-side-capital-management) — VC Fund

## FAQ

### What does David Miles invest in?

David Miles invests primarily in FinTech, InsurTech and Artificial Intelligence startups, most often at Seed and Series A stage. Most of the 6 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### When did David Miles last invest?

The most recent investment recorded for David Miles closed in Sep 2024. Shizune tracks 6 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.

### Is Shizune's investor data accurate?

Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.

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