# Patrick O'Shaughnessy

> Patrick O'Shaughnessy is a seed investor at Positive Sum backing Software and Finance. See 17 investments, check sizes, portfolio. Updated Aug 2026.

- Type: Angel Investor
- Fund: [Positive Sum](https://shizune.co/investors/profile/positive-sum)
- Location: Minneapolis, United States
- Total investments: 17
- Last investment: Jul 2026
- Lead investor: 47%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/patrick-o-shaughnessy-cfa-6721176

Patrick O'Shaughnessy is a seed investor at Positive Sum in Minneapolis focused on Software and Finance. Patrick O'Shaughnessy is the Founder and CEO of Positive Sum Advisors LLC

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Software | 5 | 29% |
| Finance | 3 | 18% |
| Wellness | 3 | 18% |
| Health Care | 3 | 18% |
| Financial Services | 3 | 18% |

36 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Seed | 5 | 29% |
| Series A | 3 | 18% |
| Series C | 3 | 18% |
| Angel | 1 | 6% |
| Series B | 1 | 6% |

8 stages tracked in total.

### Country

| Country | Investments | Share |
| --- | --- | --- |
| United States | 9 | 53% |
| United Kingdom | 2 | 12% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| Speakeasy | The all-in-one operations and intelligence infrastructure powering IRL enterprises. |  | Seed | Jul 15, 2026 |  |
| Cubby Law | Cubby Law offers customized study resources based on each student's classes and instructors from the first reading to the last test. | $2.8M | Seed | Aug 19, 2025 |  |
| Passthrough | Passthrough develops a platform that automates the subscription process for private funds. It makes it easy to distribute subscription agreements to investors and have them executed electronically. | $10M | Series A | Feb 01, 2023 |  |
| Tegus | Tegus is a qualitative research platform for buy-side investors. The company's database is a smart-searchable platform of peer-led expert call transcripts by investors for investors. Its on-demand transcripts enable investors to get up to speed on a name in hours, not days. With Tegus, investors can get into the nuts and bolts of a business,leveraging expert research on demand.For custom calls, Tegus offers white glove service to connect its customers with top experts, all without the usual markup. Its database customers enjoy custom sourced 1:1 expert calls at the adviser's cost. | $20M | Venture - Series Unknown | Sep 28, 2022 |  |
| Entrepreneurs First | Entrepreneurs First provides programs that identify individuals interested in building technology companies and support them through the early stages of company formation. The organization evaluates applicants as individuals and brings selected participants into cohorts where they explore ideas, connect with potential cofounders, and form startupteams. Participants receive guidance on idea development, product validation, and company creation while preparing to seek venture funding. Entrepreneurs First also provides financial backing and structured programs that include workshops, mentorship, and networking with investors. Through these activities, the organization facilitates the transition from individual participants to newly formed startup companies. | $170.1M | Series C | Jun 28, 2022 |  |
| Entrepreneurs First | Entrepreneurs First provides programs that identify individuals interested in building technology companies and support them through the early stages of company formation. The organization evaluates applicants as individuals and brings selected participants into cohorts where they explore ideas, connect with potential cofounders, and form startupteams. Participants receive guidance on idea development, product validation, and company creation while preparing to seek venture funding. Entrepreneurs First also provides financial backing and structured programs that include workshops, mentorship, and networking with investors. Through these activities, the organization facilitates the transition from individual participants to newly formed startup companies. | $158M | Series C | Jun 28, 2022 |  |
| Passthrough | Passthrough develops a platform that automates the subscription process for private funds. It makes it easy to distribute subscription agreements to investors and have them executed electronically. | $5M | Seed | Feb 15, 2022 |  |
| HumanCo | HumanCo is a disruptive mission-driven holding company that focuses on investing in Healthier Living.Despite all the advances in science and modern medicine, this is the first generation in recorded human history that is predicted to live a shorter lifespan than the previous generation. At HumanCo, it hopes to reverse this trend and effectmeaningful change through the companies in which we invest and incubate. | $35M |  | Sep 22, 2021 |  |
| HumanCo | HumanCo is a disruptive mission-driven holding company that focuses on investing in Healthier Living.Despite all the advances in science and modern medicine, this is the first generation in recorded human history that is predicted to live a shorter lifespan than the previous generation. At HumanCo, it hopes to reverse this trend and effectmeaningful change through the companies in which we invest and incubate. | $35M | Seed | Sep 22, 2021 |  |
| HumanCo | HumanCo is a disruptive mission-driven holding company that focuses on investing in Healthier Living.Despite all the advances in science and modern medicine, this is the first generation in recorded human history that is predicted to live a shorter lifespan than the previous generation. At HumanCo, it hopes to reverse this trend and effectmeaningful change through the companies in which we invest and incubate. | $35M | Convertible Note | Sep 22, 2021 |  |

10 of 17 investments shown.

## Co-investors
- [Atreides Management](https://shizune.co/investors/profile/atreides-management-lp) — VC Fund, 3 deals together
- [Vista Equity Partners](https://shizune.co/investors/profile/vista-equity-partners) — VC Fund, 3 deals together
- [Company Ventures](https://shizune.co/investors/profile/company-ventures) — VC Fund, 2 deals together
- [Company Ventures](https://shizune.co/investors/profile/company-ventures-ec86) — VC Fund, 2 deals together
- [Great Oaks Venture Capital](https://shizune.co/investors/profile/great-oaks-venture-capital) — VC Fund, 2 deals together
- [Jazz Venture Partners](https://shizune.co/investors/profile/jazz-venture-partners) — VC Fund, 2 deals together

## About Positive Sum

VC Fund · Stamford, United States

Positive Sum is a venture capital and private equity firm that helps teams build extraordinary businesses.

1 contacts available at Positive Sum.

| Name | Title | Profile |
| --- | --- | --- |
| Patrick O'Shaughnessy | Co-Founder & Partner | https://shizune.co/investors/profile/patrick-oshaughnessy |

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## FAQ

### What does Patrick O'Shaughnessy invest in?

Patrick O'Shaughnessy invests primarily in Software, Finance and Wellness startups, most often at Seed and Series A stage. Most of the 17 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 Patrick O'Shaughnessy last invest?

The most recent investment recorded for Patrick O'Shaughnessy closed in Jul 2026. Shizune tracks 17 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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