# Jesse Middleton

> Jesse Middleton is a seed investor at Skillist backing Artificial Intelligence and Software. See 28 investments, check sizes, portfolio. Updated Aug 2026.

- Type: Angel Investor
- Fund: [Skillist](https://shizune.co/investors/profile/skillist)
- Location: New York, United States
- Total investments: 28
- Last investment: May 2026
- Lead investor: 29%
- Last updated: Aug 2026
- LinkedIn: http://www.linkedin.com/in/jmiddleton
- X (Twitter): http://twitter.com/srcasm
- Website: http://jessemiddleton.com
- Facebook: http://www.facebook.com/srcasm

Jesse Middleton is a seed investor at Skillist in New York focused on Artificial Intelligence and Software. Jesse is a GP at Flybridge Capital and a co-founder of The Community Fund. His expertise lies in business development, community building, product, and fundraising. Jesse was on the founding team of WeWork and a part of the global WeWork community. He attended Drexel University.

## Round sizes

| Stage | Round size |
| --- | --- |
| Seed | $1.3M–$5.5M |
| Pre-Seed | $1.3M–$1.5M |
| Series A | $5M–$16M |

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Artificial Intelligence | 6 | 21% |
| Software | 5 | 18% |
| E-Commerce | 3 | 11% |
| Beauty | 2 | 7% |
| Employment | 2 | 7% |

47 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Seed | 13 | 46% |
| Series A | 5 | 18% |
| Pre-Seed | 3 | 11% |
| Funding Round | 2 | 7% |
| Series B | 1 | 4% |

6 stages tracked in total.

### Country

| Country | Investments | Share |
| --- | --- | --- |
| United States | 16 | 57% |
| South Korea | 2 | 7% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| ChurchAI | The Intelligent OS For Churches. | $1.3M | Pre-Seed | May 21, 2026 |  |
| Pelgo | Pelgo is a startup that provides AI-powered career transition services. For employees coming out of layoffs, young grads just entering the job market, or full-time professionals trying to adjust to a developing AI-driven economy, its tools, along with human advisors, help onboarding, transition, and reskilling. | $5.5M | Seed | Feb 10, 2026 |  |
| Sunflower | Sunflower provides an AI-powered app that supports sobriety with visual tracking, CBT journaling, and community features. | $1.5M | Seed | Oct 17, 2025 |  |
| Covenant | Covenant operator of a specialized law firm intended to offer advice and legal representation. | $4M | Seed | Jul 15, 2025 |  |
| Jungle | Jungle is an AI study platform that makes active learning ten times simpler. You may create a ton of flashcards, multiple-choice questions, and case questions by uploading any course material. |  | Seed | Feb 27, 2025 |  |
| Teal | Teal helps individuals advocate for themselves and build meaningful careers. The company provides content, tools, and support to help people navigate change and drive their careers. Users can create, manage, and track multiple versions of their resumes, making it easier to tailor applications for different job opportunities. Teal simplifies the jobsearch process by allowing users to track their job applications and manage contacts efficiently. | $7.5M | Series A | Jan 22, 2025 |  |
| Arcee.ai | Arcee is building context adapted SLM's (Small Language Models) through our SLM Adaptation system, all in your own cloud. This system all includes a domain pretraining layer, an alignment layer and a RAG layer—all in one system.Arcee's SLM Adaptation system allows you to get models into prod fast and runs in your own environment. Thisprovides you full control over model, data and intellectual property, thus removing data privacy and security concerns, and removing any licensing uncertainty. | $5.5M | Seed | Jan 24, 2024 |  |
| DNK | Dongnae provides an online real estate platform that digitizes the rental and home-buying market. The company's platform assists users to find the right house based on their needs and purpose, even find easy transport to work from the resident with the assistance of the brokers, enabling users to save time and energy on finding the right placeto stay in.It was founded in 2020 and is headquartered in Seoul, South Korea. | $16.4M | Series A | Mar 23, 2022 |  |
| Agtonomy | Agtonomy is a hybrid autonomy and tele-assist platform for agriculture vehicles. | $5M | Seed | Jan 18, 2022 |  |
| Launch House | Launch House is the social club helping emerging leaders level up and live better. The Launch House community is a curated group of founders, engineers, and investors who are building the future.Community membership includes access to our intimate IRL coliving residencies in major cities, desirable destinations, and at conferences all over theworld. Membership also includes executive coaching opportunities, fundraising support, unlimited access to our digital cohort-based courses, and coworking clubhouses in major cities. Launch House helps foster learning and professional development as well as deep, authentic relationships rather than transactional networking opportunities.Selection for the community is through a competitive process, with thousands of applicants per year. Launch House currently has locations in Los Angeles, New York City, and the metaverse. | $3M | Seed | Aug 19, 2021 |  |

10 of 28 investments shown.

## Co-investors
- [Maple VC](https://shizune.co/investors/profile/maple-vc) — VC Fund, 3 deals together
- [MetaProp](https://shizune.co/investors/profile/metaprop-nyc) — VC Fund, 3 deals together
- [Alpaca VC](https://shizune.co/investors/profile/alpaca-vc) — VC Fund, 2 deals together
- [D·CAMP](https://shizune.co/investors/profile/banks-foundation-for-young-entrepreneurs) — VC Fund, 2 deals together
- [Brooklyn Bridge Ventures](https://shizune.co/investors/profile/brooklyn-bridge-ventures) — VC Fund, 2 deals together
- [DFJ Growth](https://shizune.co/investors/profile/dfj-growth) — VC Fund, 2 deals together

## About Skillist

VC Fund · Boston, United States

Skillist is a job application platform that makes it easier for employers and jobseekers to connect by putting skills at the center of the process. The company's skills-based, identity-blind application process enables candidates to apply by sharing what they can do. It helps millions of talented people without four-year degrees obtaincareer-advancing opportunities at great companies who value their skills.Skillist was founded on 2016 and is headquartered in Boston, Massachusetts.

3 contacts available at Skillist.

| Name | Title | Profile |
| --- | --- | --- |
| Ananth Kasturiraman | Co-Founder & CEO | https://shizune.co/investors/profile/ananth-kasturiraman |
| Jesse Middleton | Investor | https://shizune.co/investors/profile/jesse-middleton |
| Ronethea Williams | Director of Partnerships | https://shizune.co/investors/profile/ronethea-williams |

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## FAQ

### What does Jesse Middleton invest in?

Jesse Middleton invests primarily in Artificial Intelligence, Software and E-Commerce startups, most often at Seed and Series A stage. Most of the 28 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### What is Jesse Middleton's check size?

Jesse Middleton typically joins rounds of $1.3M–$5.5M at Seed, $1.3M–$1.5M at Pre-Seed and $5M–$16M at Series A. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds Jesse Middleton participates in.

### When did Jesse Middleton last invest?

The most recent investment recorded for Jesse Middleton closed in May 2026. Shizune tracks 28 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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