# Positive Sum: portfolio, investments and team

> Positive Sum is a private equity based in United States. 7 investments on record, 5 in the last 12 months, latest Aug 2026.

Source: https://millionrounds.com/fund/positive-sum (Millionrounds; every figure on the page links to its filing or article)

United States · [Investor](https://millionrounds.com/investors)

# Positive Sum

Last cheque observed Aug 2026; 7 cheques on record.

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Deploying now New fund $5.3M, Aug 2026 Private equity

Seed Series A Series B Venture Capital & Private Equity

Follow Positive Sum and see its new cheques in your feed. [Start following](https://millionrounds.com/login?join=1&why=follow&next=%2Ffund%2Fpositive-sum)

Deploying now

**83%** of best year **5** **cheques in 12 months**, 7 on record

Since the last cheque **64** days **00** hrs **00** min **00** sec

Median round **$300M** Cheque size, as they say **$100K – $20M** Rounds led **1 of 7** Mostly in **United States, 86%**

Pitch Positive Sum

## Positive Sum highlights

- 01 5 cheques in the last 12 months
- 02 Mostly Series C and Seed: 50% of its rounds
- 03 Led 1 rounds

## What they do

> We back founders pursuing their life’s work. From their own website

- **Type:** Private equity (from a list, unverified)
- **Cheque size:** $100K – $20M as they say
- **Stages:** Seed Series A Series B
- **Sectors:** Venture Capital & Private Equity
- **Based in:** New York City, United States
- **Cold pitches:** Not accepted

## The record

Every round we can evidence, newest first **7 appearances**

- **2026** 5 rounds
- **Aug** **[Retro](https://millionrounds.com/company/retro)** Series A · US · TechCrunch **$21M** With 8 others
- **Aug** **[Etched](https://millionrounds.com/company/etched)** US · TechCrunch **$700M** With 13 others
- **Jul** **[Speakeasy](https://millionrounds.com/company/speakeasy)** Seed · US · AlleyWatch **$8.8M** *Led*
- **Jul** **[Neko Health](https://millionrounds.com/company/neko-health)** Series C · SE · Steven Bartlett **$700M** With 19 others
- **Feb** **[Skyryse](https://millionrounds.com/company/skyryse)** Series C · US · TechCrunch **$300M** With 14 others
- **2025** 2 rounds
- **Sept** **[ID.me](https://millionrounds.com/company/id-me)** Series E · US · TechStartups **$340M** With 3 others
- **May** **[Rogo](https://millionrounds.com/company/rogo)** Series B · US · AlleyWatch **$50M** With 6 others

An announcement gives the size of the round, not the size of this investor's cheque: the only rounds that imply a cheque are those where they were the sole named investor.

## The team

Named by the firm itself, on a filing, its Form ADV or its company registration **3 named**

PW **Patrick Walker O'Shaughnessy** CEO and Partner of Manager i Filing they signed

RP **Robert Parker** Chief Operating Officer of the Manager i Filing they signed

SB **Samuel Blake Cates** Managing Director i Form ADV

We also hold **6** people at this firm from the lists this database was built from: a weaker source than the filings, since a list does not say when a title ended. Login to see them.

## What the register says

From the firm's own filings with the SEC, which it must file accurately by law

**$820M** gross assets of its funds Oct 2026

**Exempt** reporting adviser venture or small private funds

- **Legal name:** Positive SUM Advisors LLC
- **SEC number:** CRD 324219

## What they claim to have backed

From their own portfolio page (on their website)

**18** of 28 we have independently watched raise

[Alpaca](https://millionrounds.com/company/alpaca)[Arc](https://millionrounds.com/company/arc-boats)[Base Power](https://millionrounds.com/company/base-power)[Bending Spoons](https://millionrounds.com/company/bending-spoons)[Blues](https://millionrounds.com/company/blues)[Cognition](https://millionrounds.com/company/cognition-ai)[Eight Sleep](https://millionrounds.com/company/eight-sleep)[Etched](https://millionrounds.com/company/etched)[ID.me](https://millionrounds.com/company/id-me)[Invert](https://millionrounds.com/company/invert)[January](https://millionrounds.com/company/january)[Modal](https://millionrounds.com/company/modal-labs)[Neko Health](https://millionrounds.com/company/neko-health)[Physical Intelligence](https://millionrounds.com/company/physical-intelligence)[Prefect](https://millionrounds.com/company/prefect)[Ridgeline](https://millionrounds.com/company/ridgeline)[Skyryse](https://millionrounds.com/company/skyryse)[Vanta](https://millionrounds.com/company/vanta) Arcana Canopy Casa Colossus Entrepreneurs First Fortell Inheritance Retro Rogo Tegus (acquired by AlphaSense)

Weaker than a round we watched, stronger than a list somebody sold us. A firm is far less willing to put a company on its own site that it never funded.

New fund on file

**$5.3M**

raised in Aug 2026

From its SEC filing, not a journalist: a firm that has just raised has money to deploy.

## The cheque

Seed Series A Series B

Median round joined **$300M** the round, not its cheque

Led 1 of 7 rounds **14%**

- **Said size:** $100K – $20M
- **Sole investor:** Never alone
- **Last cheque:** Aug 2026

Rounds by stage said on their site

- Series C *2*
- Seed said *1*
- Series A said *1*
- Series B said *1*
- Series E *1*

Cheques by month Led Joined

Nov 2023 Oct 2026

Often in the room with

- [BoxGroup](https://millionrounds.com/fund/boxgroup) 2
- [Thrive Capital](https://millionrounds.com/fund/thrive-capital) 2
- [Tiger Global Management](https://millionrounds.com/fund/tiger-global-management) 2

**Pitching Positive Sum?** Put them on your fundraising board with this record on the card, and follow them to hear when they write a new cheque.

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## Who they invest alongside

The investors most often in the same rounds as Positive Sum. A count of rooms they were both in, not a relationship either has claimed.

[**BoxGroup** VC firm **2** rounds together](https://millionrounds.com/fund/boxgroup)[**Thrive Capital** Accelerator **2** rounds together](https://millionrounds.com/fund/thrive-capital)[**Tiger Global Management** VC firm **2** rounds together](https://millionrounds.com/fund/tiger-global-management)

## Recently backed

The latest companies Positive Sum put money into.

[**Etched** $700M · Aug 2026](https://millionrounds.com/company/etched)[**Neko Health** $700M · Jul 2026](https://millionrounds.com/company/neko-health)[**Skyryse** $300M · Feb 2026](https://millionrounds.com/company/skyryse)

## On podcasts

2 episodes naming Positive Sum in the title, and 4 more that mention it.

- [BRAVE Southeast Asia Tech](https://millionrounds.com/podcasts/brave-southeast-asia) 2 Apr 2023 · 40 min Founder & VC “Lost In Translation”, Common Misunderstandings (Rejections, Interrogations & NDAs) and Positive Sum Negotiations & Reference Checks - E262 Mentions [Positive Sum](https://millionrounds.com/fund/positive-sum)[Shiyan Koh](https://millionrounds.com/person/shiyan-koh) Apple PodcastsShow page
- [BRAVE Southeast Asia Tech](https://millionrounds.com/podcasts/brave-southeast-asia) 31 May 2021 · 1h 12m Gorick Ng on His Bestselling Book with HBR, The Workplace's Unspoken Rules, and Career Success as Positive Sum - E63 Mentions [Positive Sum](https://millionrounds.com/fund/positive-sum)[Credit Suisse](https://millionrounds.com/fund/credit-suisse)[Ratan Tata](https://millionrounds.com/fund/ratan-tata) *+3* Apple PodcastsShow page

### Mentioned in

- [Invest Like the Best](https://millionrounds.com/podcasts/invest-like-the-best) 20 Jan 2026 · 2h 7m Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455] Apple PodcastsShow page
- [Sourcery](https://millionrounds.com/podcasts/sourcery) 8 Oct 2025 · 38 min Base Power Raises $1B led by Addition, with Trust Ventures, Valor Equity, Thrive, Lightspeed, a16z, Altimeter, Stepstone, Elad Gil Apple PodcastsShow page
- [TBPN](https://millionrounds.com/podcasts/tbpn) 30 Sept 2025 · 3h 10m Sora 2 Launch Reactions, DoorDash CEO Live in The Ultradome | Tony Xu, Simon Eskildsen, Patrick O’Shaughnessy, Zach Abrams, Andrew Feldman, Brandon Millman, Stanley Tang, Alex Albert, Arthur Querou Apple PodcastsShow page
- [The a16z Show](https://millionrounds.com/podcasts/a16z) 30 Jun 2025 · 53 min Katherine Boyle: How Tech Can Rebuild America Apple PodcastsShow page

## Quick answers about Positive Sum

### What does Positive Sum invest in?

Positive Sum invests most often at Series C and Seed (50% of the rounds on record), in sectors such as Venture Capital & Private Equity.

### How active is Positive Sum?

7 investments on record, 5 of them in the last 12 months, and it led 1. The most recent was in Aug 2026.

### What has Positive Sum invested in recently?

Its most recent investments on record: Retro (Series A, Aug 2026), Etched (Undisclosed round, Aug 2026) and Speakeasy (Seed, Jul 2026).

### How big are Positive Sum's cheques?

The median round it joins is $300M. It says it writes cheques of $100K to $20M.

### Does Positive Sum lead rounds?

Sometimes: it led 1 of its 7 investments on record (14%).

### Where does Positive Sum invest?

Most of the companies it backs are in the United States (86%) and Sweden (14%).

### Is Positive Sum investing now?

Yes: it is actively investing, with 5 investments in the last 12 months.

### Who does Positive Sum invest alongside?

Most often BoxGroup (2 rounds together), Thrive Capital (2 rounds together) and Tiger Global Management (2 rounds together).

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Built from the rounds we watched, its filings and its own website, refreshed every night. [How we count](https://millionrounds.com/methodology) · [Report a correction](https://millionrounds.com/corrections?slug=positive-sum) · [Is this your firm? Claim it](https://millionrounds.com/claim?org=positive-sum)
