# Freestyle Capital: portfolio, investments and team

> Freestyle Capital is a vc firm based in United States. 160 investments on record, 12 in the last 12 months, latest Oct 2026.

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

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

# Freestyle Capital

Last cheque observed Oct 2026; 160 cheques on record.

Email

Deploying now New fund $91M, Jan 2022 VC firm

Pre-seed Seed Series A AI & Machine Learning Apps Artificial Intelligence & Machine Learning (AI/ML)

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

Deploying now

**100%** of best year **12** **cheques in 12 months**, 160 on record

Since the last cheque **17** days **00** hrs **00** min **00** sec

Median round **$9.0M** Cheque size, as they say **$1.0M – $4.0M** Rounds led **0 of 160** Sole investor **8 rounds** Exits **20 from the portfolio** Mostly in **United States, 89%**

Pitch Freestyle Capital

## Freestyle Capital highlights

- 01 12 cheques in the last 12 months
- 02 Mostly Seed and Series A: 79% of its rounds
- 03 Sole investor in 8 rounds, median $5.5M
- 04 20 exits from the portfolio

## What they do

> Freestyle VC, AI-Powered Venture Capital From their own website

- **Type:** VC firm (from a list, unverified)
- **Cheque size:** $1.0M – $4.0M as they say
- **Stages:** Pre-seed Seed Series A Series B Growth
- **Sectors:** AI & Machine Learning Apps Artificial Intelligence & Machine Learning (AI/ML)
- **Based in:** San Francisco, United States
- **Cold pitches:** Not stated

## The record

Every round we can evidence, newest first **160 appearances**

- **2026** 10 rounds
- **Oct** **[Marklo](https://millionrounds.com/company/marklo)** Seed · US · Crunchbase News **$5.0M** With 2 others
- **Sept** **[Firecrawl](https://millionrounds.com/company/firecrawl)** Series B · US **$75M** With 4 others
- **Aug** **[Dash Bio](https://millionrounds.com/company/dash-bio)** Series A · US · Ventureburn **$30M** With 3 others
- **Jun** **[Upside](https://millionrounds.com/company/upside)** Series A · US · TechStartups **$20M** With 5 others
- **Jun** **[Maneva](https://millionrounds.com/company/maneva)** Series A · U.S. Venture Partners **$27M** With 3 others
- **Jun** **[Infinity Constellation](https://millionrounds.com/company/infinity-constellation)** Series A · US **$24M** With 3 others
- **Jun** **[Samepage](https://millionrounds.com/company/samepage)** Seed · US **$4.8M** With 2 others
- **May** **[Searchable](https://millionrounds.com/company/searchable)** Series A · US · TechStartups **$14M** With 1 other
- **May** **[Payman AI, Inc](https://millionrounds.com/company/payman-ai-inc)** Venture · US **Undisclosed** With 3 others
- **Feb** **[Wallfacer](https://millionrounds.com/company/wallfacer)** Pre-seed · US **$1.2M** Sole investor
- **2025** 10 rounds
- **Dec** **[Searchable.com](https://millionrounds.com/company/searchable-com)** Venture **$5.2M** Sole investor
- **Dec** **[Ridwell](https://millionrounds.com/company/ridwell)** Venture · US **$15M** With 3 others
- **Sept** **[HiveWatch](https://millionrounds.com/company/hivewatch)** Venture · US **$25M** With 4 others
- **Jul** **[Juvo](https://millionrounds.com/company/juvo)** BR · LatamList **$25M** With 5 others
- **Jul** **[Dash Bio](https://millionrounds.com/company/dash-bio)** Seed · US **$11M** With 1 other
- **May** **[Infinity Constellation](https://millionrounds.com/company/infinity-constellation)** Seed · US **$12M** With 1 other
- **May** **[Stackpack](https://millionrounds.com/company/stackpack)** Seed · US **$6.3M** Sole investor
- **Mar** **[Maneva](https://millionrounds.com/company/maneva)** Seed · CA **$10M** With 2 others
- **Feb** **[Keebler Health](https://millionrounds.com/company/keebler-health)** Seed · US · New Stack Ventures **$6.0M** With 10 others
- **Jan** **[Staris](https://millionrounds.com/company/staris)** Seed · US **$5.7M** Sole investor
- **2024** 7 rounds
- **Nov** **[Mozi](https://millionrounds.com/company/mozi)** Seed · US **$6.0M** Sole investor
- **Nov** **[Chapter One](https://millionrounds.com/company/chapter-one)** Pre-seed · US **$4.0M** With 2 others
- **Oct** **[100](https://millionrounds.com/company/100)** Pre-seed · US **$5.2M** With 3 others
- **Sept** **[Castle Pay](https://millionrounds.com/company/castle-pay)** Venture · US **$4.0M** With 1 other
- **May** **[Fulfilld](https://millionrounds.com/company/fulfilld)** Seed · US **$2.5M** With 3 others
- **Mar** **[Aloft](https://millionrounds.com/company/aloft)** Venture · US **Undisclosed** With 1 other
- **Jan** **[Vital Interaction](https://millionrounds.com/company/vital-interaction)** Series A · US **$15M** With 1 other
- **2023** 10 rounds
- **Dec** **[BurnerPage](https://millionrounds.com/company/burnerpage)** Pre-seed · US **$790K** Sole investor
- **Nov** **[Astra](https://millionrounds.com/company/astra)** Debt · US **$13M** With 4 others
- **Nov** **[Mon Ami](https://millionrounds.com/company/mon-ami)** Seed · US **$3.4M** With 5 others
- **Jul** **[Arrive Recommerce](https://millionrounds.com/company/arrive-recommerce)** Series A · US **$16M** With 2 others
- **Jul** **[RecruitBot](https://millionrounds.com/company/recruitbot)** Seed · US **$8.2M** With 3 others
- **Apr** **[GiftHealth](https://millionrounds.com/company/gifthealth)** Growth · US **$40M** With 3 others
- **Mar** **[Mercator AI](https://millionrounds.com/company/mercator-ai)** Seed · CA **$3.8M** With 2 others
- **Mar** **[Bach](https://millionrounds.com/company/bach)** Series A · US **$9.0M** With 3 others
- **Jan** **[Loop](https://millionrounds.com/company/loop)** US **$10M** With 2 others
- **Jan** **[Benbase](https://millionrounds.com/company/benbase)** Seed · US **$5.3M** With 1 other
- **2022** 13 rounds
- **Nov** **[Glow](https://millionrounds.com/company/glow)** Series A · US **$24M** With 3 others
- **Sept** **[OvationCXM](https://millionrounds.com/company/ovationcxm)** Series C · US **$20M** With 6 others
- **Sept** **[Spot](https://millionrounds.com/company/spot)** Seed · GB **$5.5M** With 1 other

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 **4 named**

DS **David Samuel** Managing Director - Freestyle Capital Management, LLC i Form ADV

JL **Jennifer Lefcourt** Managing Director - Freestyle Capital Management, LLC i Form ADV

JL **Jenny Lefcourt** Managing Director i Filing they signed

JF **Josh Felser** Managing Director of the General Partner i Filing they signed

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

**$935M** gross assets of its funds Oct 2026

**5+** funds on file numbered funds in its name

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

- **Legal name:** Freestyle Capital Management, LLC
- **SEC number:** CRD 163087

Who backs their funds

## 1 LP on record in Freestyle Capital's funds

- **Funds:** 1

The institutions that put money into its funds, which the firm then invests in companies. Source: an LP list.

- [**Cendana Capital** 1 fund](https://millionrounds.com/fund/cendana-capital) Fund Vintage Committed Freestyle Capital - -

## Exits from the portfolio

Companies it backed that were later bought or listed **20 in all**

**[Opsmatic](https://millionrounds.com/company/opsmatic)** Bought by New Relic **Undisclosed** Nov 2015

**[HeartThis](https://millionrounds.com/company/heartthis)** Bought by Thumbtack **Undisclosed** Sept 2015

**[Leo](https://millionrounds.com/company/leo)** Bought by [Lyft](https://millionrounds.com/fund/lyft) **Undisclosed** Jun 2015

**[Get Satisfaction](https://millionrounds.com/company/get-satisfaction)** Bought by Sprinklr **Undisclosed** Apr 2015

**[Stitch](https://millionrounds.com/company/stitch)** Bought by SugarCRM **Undisclosed** Mar 2015

**[Clarity](https://millionrounds.com/company/clarity)** Bought by [Fundable](https://millionrounds.com/fund/fundable) **Undisclosed** Feb 2015

**[Byliner](https://millionrounds.com/company/byliner)** Bought by Pronoun **Undisclosed** Sept 2014

**[SnappyTV](https://millionrounds.com/company/snappytv)** Bought by [Twitter](https://millionrounds.com/fund/twitter) **Undisclosed** Jun 2014

**[Impermium](https://millionrounds.com/company/impermium)** Bought by [Google](https://millionrounds.com/fund/google-assistant-investments) **Undisclosed** Jan 2014

**[Aviate](https://millionrounds.com/company/aviate)** Bought by [Yahoo!](https://millionrounds.com/fund/yahoo) **$80M** Jan 2014

**[Seesaw](https://millionrounds.com/company/seesaw)** Bought by Byliner **Undisclosed** Nov 2013

**[Singly](https://millionrounds.com/company/singly)** Bought by Appcelerator **Undisclosed** Aug 2013

**[Formspring](https://millionrounds.com/company/formspring)** Bought by Spring.me **Undisclosed** Jan 2013

**[GoInstant](https://millionrounds.com/company/goinstant)** Bought by Salesforce **$70M** Jul 2012

**[Yobongo](https://millionrounds.com/company/yobongo)** Bought by Mixbook **Undisclosed** Mar 2012

**[SimpleGeo](https://millionrounds.com/company/simplegeo)** Bought by Urban Airship **Undisclosed** Oct 2011

**[IndexTank](https://millionrounds.com/company/indextank)** Bought by [LinkedIn](https://millionrounds.com/fund/linkedin) **Undisclosed** Oct 2011

**[Typekit](https://millionrounds.com/company/typekit)** Bought by [Adobe Systems](https://millionrounds.com/fund/adobe-systems) **Undisclosed** Oct 2011

**[BackType](https://millionrounds.com/company/backtype)** Bought by [Twitter](https://millionrounds.com/fund/twitter) **Undisclosed** Jul 2011

**[CoTweet](https://millionrounds.com/company/cotweet)** Bought by ExactTarget **Undisclosed** Mar 2010

An exit counts when it came after the firm's first round in the company. From historical deal records.

New fund on file

**$91M**

raised in Jan 2022

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

## The cheque

Pre-seed Seed Series A

Median round joined **$9.0M** the round, not its cheque Alone, median **$5.5M**

Led 0 of 160 rounds **0%**

- **Said size:** $1.0M – $4.0M
- **Sole investor:** 8 rounds
- **Last cheque:** Oct 2026
- **Exits:** 20 from the portfolio

Rounds by stage said on their site

- Seed said *75*
- Series A said *38*
- Venture *18*
- Series B said *8*
- Pre-seed said *4*
- Growth said *-*

Cheques by month Led Joined

Nov 2023 Oct 2026

Often in the room with

- [Baseline Ventures](https://millionrounds.com/fund/baseline-ventures) 13
- [SV Angel](https://millionrounds.com/fund/sv-angel) 13
- [500 Global](https://millionrounds.com/fund/500-startups) 11
- [Foundry Group](https://millionrounds.com/fund/foundry) 9
- [Y Combinator](https://millionrounds.com/fund/y-combinator) 9
- [Founder Collective](https://millionrounds.com/fund/founder-collective) 8

**Pitching Freestyle Capital?** 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 Freestyle Capital. A count of rooms they were both in, not a relationship either has claimed.

[**Baseline Ventures** VC firm **13** rounds together](https://millionrounds.com/fund/baseline-ventures)[**SV Angel** VC firm **13** rounds together](https://millionrounds.com/fund/sv-angel)[**500 Global** Angel **11** rounds together](https://millionrounds.com/fund/500-startups)[**Foundry Group** VC firm **9** rounds together](https://millionrounds.com/fund/foundry)[**Y Combinator** Accelerator **9** rounds together](https://millionrounds.com/fund/y-combinator)[**Founder Collective** VC firm **8** rounds together](https://millionrounds.com/fund/founder-collective)[**Greylock** VC firm **8** rounds together](https://millionrounds.com/fund/greylock-partners)[**First Round Capital** VC firm **7** rounds together](https://millionrounds.com/fund/first-round-capital)[**Slow Ventures** VC firm **7** rounds together](https://millionrounds.com/fund/slow-ventures)[**BoxGroup** VC firm **6** rounds together](https://millionrounds.com/fund/boxgroup)[**Bossa Invest** VC firm **5** rounds together](https://millionrounds.com/fund/bossa-invest)[**CRV** VC firm **5** rounds together](https://millionrounds.com/fund/crv)

## Recently backed

The latest companies Freestyle Capital put money into.

[**Dash Bio** $30M · Aug 2026](https://millionrounds.com/company/dash-bio)[**Upside** $20M · Jun 2026](https://millionrounds.com/company/upside)[**Maneva** $27M · Jun 2026](https://millionrounds.com/company/maneva)[**Infinity Constellation** $24M · Jun 2026](https://millionrounds.com/company/infinity-constellation)[**Ridwell** $15M · Dec 2025](https://millionrounds.com/company/ridwell)[**HiveWatch** $25M · Sept 2025](https://millionrounds.com/company/hivewatch)

## On podcasts

5 episodes naming Freestyle Capital in the title, and 3 more that mention it.

- [This Week in Startups](https://millionrounds.com/podcasts/this-week-in-startups) 5 Apr 2022 · 1h 2m Elon buys ~9% stake in Twitter + Freestyle Capital's Dave Samuel | E1426 With [Dave Samuel](https://millionrounds.com/person/dave-samuel) Mentions [Freestyle Capital](https://millionrounds.com/fund/freestyle)[Trust Capital](https://millionrounds.com/fund/trust-capital) Apple PodcastsShow page
- [This Week in Startups](https://millionrounds.com/podcasts/this-week-in-startups) 21 Jul 2020 · 1h 27m E1086: Supporting founder mental health at Freestyle Capital with Josh Felser, Caren Maio & Mani Kulasooriya With [Caren Maio](https://millionrounds.com/person/caren-maio)[Mani Kulasooriya](https://millionrounds.com/person/mani-kulasooriya) Mentions [Freestyle Capital](https://millionrounds.com/fund/freestyle)[Josh Felser](https://millionrounds.com/fund/josh-felser) Apple PodcastsShow page
- [This Week in Startups](https://millionrounds.com/podcasts/this-week-in-startups) 4 Feb 2020 · 1h 1m E1025: #StartupTuneup @ Founder.University Part 2!: 6 founders pitch to Jason & Dave Samuel of Freestyle Capital on AI driving assistance, sleep-aid wearables, marijuana, B2B food analytics & more! With [Dave Samuel](https://millionrounds.com/person/dave-samuel) Mentions [Freestyle Capital](https://millionrounds.com/fund/freestyle) Apple PodcastsShow page
- [This Week in Startups](https://millionrounds.com/podcasts/this-week-in-startups) 4 Feb 2020 · 45 min E1024: #StartupTuneup @ Founder.University: 6 founders pitch to Jason & Dave Samuel of Freestyle Capital on merging communication networks, athlete performance tracking, DTC women's clothing, smart tabletop gaming systems & more! With [Dave Samuel](https://millionrounds.com/person/dave-samuel) Mentions [Freestyle Capital](https://millionrounds.com/fund/freestyle) Apple PodcastsShow page
- [This Week in Startups](https://millionrounds.com/podcasts/this-week-in-startups) 29 Oct 2019 · 1h 22m E994: All Turtles CEO Phil Libin shares his state machine that answers all growth questions; Future of Early-Stage VC w/Pete Flint (NFX), Rebecca Lynn (Canvas Ventures), Dave Samuel (Freestyle Capital); plus LAUNCH Scale Partner Talk w/Lever CTO Nate Smit With [Dave Samuel](https://millionrounds.com/person/dave-samuel)[Pete Flint](https://millionrounds.com/person/pete-flint)[Rebecca Lynn](https://millionrounds.com/person/rebecca-lynn-2) Mentions [Canvas Ventures](https://millionrounds.com/fund/canvas-fund)[Freestyle Capital](https://millionrounds.com/fund/freestyle)[Phil Libin](https://millionrounds.com/fund/phil-libin) *+3* Apple PodcastsShow page

### Mentioned in

- [The Full Ratchet](https://millionrounds.com/podcasts/full-ratchet) 9 Jan 2023 · 42 min 365. From Founder to Forbes Midas List, Behind the Scenes of an Intro Call, Why B2B2C is Best, and Avoiding the Leaky Funnel Trap (Jenny Lefcourt) Apple PodcastsShow page
- [Invest Like the Best](https://millionrounds.com/podcasts/invest-like-the-best) 5 Oct 2021 · 1h 4m Jenny Lefcourt - The Go-to-Market Motion - [Invest Like the Best, EP. 245] Apple PodcastsShow page
- [Inevitable](https://millionrounds.com/podcasts/inevitable) 28 Dec 2020 · 54 min Ep. 137: Josh Felser, Angel investor and Co-Founder of Freestyle VC Apple PodcastsShow page

## Quick answers about Freestyle Capital

### What does Freestyle Capital invest in?

Freestyle Capital invests most often at Seed and Series A (79% of the rounds on record), in sectors such as AI & Machine Learning, Apps and Artificial Intelligence & Machine Learning (AI/ML).

### How active is Freestyle Capital?

160 investments on record, 12 of them in the last 12 months. The most recent was in Oct 2026.

### What has Freestyle Capital invested in recently?

Its most recent investments on record: Marklo (Seed, Oct 2026), Firecrawl (Series B, Sept 2026) and Dash Bio (Series A, Aug 2026).

### How big are Freestyle Capital's cheques?

The median round it joins is $9.0M. It says it writes cheques of $1.0M to $4.0M.

### Does Freestyle Capital lead rounds?

Rarely, if at all: none of its 160 investments on record names it as the lead.

### Where does Freestyle Capital invest?

Most of the companies it backs are in the United States (89%) and Canada (5%).

### Is Freestyle Capital investing now?

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

### Who does Freestyle Capital invest alongside?

Most often Baseline Ventures (13 rounds together), SV Angel (13 rounds together) and 500 Global (11 rounds together).

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