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Freestyle Capital

Venture Capital · Founded 2009 · San Francisco, United States

#301 Investor Ranking 2026 Top 2% of investors worldwide

Freestyle Capital is a seed stage investor and mentor for Internet software startups

Website ↗LinkedIn ↗X / Twitter ↗
125 Portfolio companies+21% in 5 years
5 Unicorns
183 Investments
Jun 2026 Last investment
01 · Knowledge graph
News Upside raises $20M Series A to tackle housing instability in healthcare Jun 25, 2026 News Samepage launches Signals and raises $4.85M seed to push intelligence to product teams Jun 25, 2026
02 · Biggest holdings

Freestyle Capital’s biggest current holdings.

The most valuable companies Freestyle Capital still holds, ordered by Dealroom’s latest valuation. Companies that have been acquired or gone public are in Exits instead. Dealroom has no parsed shareholder register for Freestyle Capital, so the size of each stake isn’t shown.

#CompanyValuation
  1. 1 BetterUPUnicorn · Education · USA $4.7B
  2. 2 PatreonUnicorn · Music · USA $4.0B
  3. 3 SnapdocsUnicorn · Legal · USA $1.5B

Unicorns and thoroughbreds Freestyle Capital has backed and still holds, at Dealroom’s latest valuation. Freestyle Capital also appears inside investor groups in Airtable, BetterUP, where a standalone stake isn’t disclosed. See the underlying shareholder registers on Dealroom →

03 · Portfolio analysis

Where Freestyle Capital’s portfolio is concentrated.

Distribution of portfolio companies by headquarters country, sector, entry stage and current growth stage. Across all 125 portfolio companies. "Stage entered" is the first priced round the investor joined, derived from the investor’s transaction history.

By countryCount
  1. USA116
  2. Canada4
  3. UK2
  4. Hong Kong1
  5. India1
  6. Poland1
  7. Taiwan1
By sectorCount
  1. Enterprise Software34
  2. Media21
  3. Fintech13
  4. Health12
  5. Marketing12
  6. Telecom8
  7. Security7
  8. Education6
  9. Real Estate6
  10. Travel5
  11. Jobs Recruitment4
  12. Music4
By stage enteredCount
  1. Seed98
  2. Series A25
  3. Series B+2
By growth stageCount
  1. Early Growth69
  2. Breakout Stage46
  3. Late Growth11
04 · Portfolio market map

Inside Freestyle Capital’s portfolio.

The 60 highest-funded portfolio companies, of 125 tracked.

Airtable
Enterprise Software · Unicorn
$1.3B
BetterUP
Education · Unicorn
$4.7B
Wag
Home Living
$14M
Patreon
Music · Unicorn
$4.0B
Snapdocs
Legal · Unicorn
$1.5B
Fin
Marketing · Unicorn
$3.6B
Well Health
Health
$260M
Funnel
Real Estate
$183M
Embark Veterinary
Health
$700M
Ease Entertainment Services
Fintech
$164M
Juvo
Fintech
$28M
Digit
Fintech
$213M
Narvar
Telecom
$120M
Daily
Media
$160M
Figure Eight
Enterprise Software
$80M
Crexi
Real Estate
$120M
Meru Health
Health
$152M
HiveWatch
Security
$132M
BuildingConnected
Media
$275M
Dash Bio
Health
$120M
ApplePie Capital
Fintech
$48M
Fi
Security
$120M
Glow Insurance
Fintech
$90M
Aloft
Robotics
$15M
Recurly
Fintech
$78M
Chartbeat
Enterprise Software
$28M
clypd
Marketing
$78M
Bravado Network
Jobs Recruitment
$104M
Superside
Jobs Recruitment
$120M
Loop
Fintech
$84M
Upside
Travel
$80M
TrueFacet
Fashion
$28M
Deduce
Security
$50M
Arrive
Enterprise Software
$64M
Keebler
Health
$64M
Get Satisfaction
Education
$40M
Grain
Enterprise Software
$64M
BACH
Event Tech
$36M
Searchable
Marketing
$83M
Xclaim
Security
$28M
Trizic
Fintech
$40M
Agentology
Real Estate
$48M
CasaOne
Home Living
$64M
YOU+
Enterprise Software
Chute
Media
$16M
Cut&Dry
Food
$66M
SwiftShift
Enterprise Software
$8.0M
Testim.io
Enterprise Software
$150M
Rise Science
Wellness Beauty
$40M
Formspring
Media
$46M
AdStage
Marketing
$12M
CreatorPlus
Dating
$48M
Piqora (formerly Pinfluencer)
Marketing
$31M
SuperSecret
Gaming
$40M
Impermium
Security
$32M
Arkive
USA
$39M
Mon Ami
Health
$13M
Singly
Health
$28M
MLab.com
Hosting
$68M
Recruitbot
Enterprise Software
$33M
05 · Portfolio founders

Where Freestyle Capital’s portfolio founders come from.

134 founders across the 100 highest-funded portfolio companies — by current location, university attended, and the companies they worked at before founding. Sourced from the founder records the API links to each portfolio company.

LocationCount
  1. United States100
  2. Canada6
  3. Hong Kong5
  4. United Kingdom5
  5. Australia4
  6. Norway3
  7. Finland2
  8. India1
  9. Poland1
  10. Portugal1
UniversityCount
  1. Harvard University7
  2. Stanford University4
  3. Stanford University Graduate School of Business4
  4. Universiry of California, Davis4
  5. Aalto University3
  6. Duke University3
  7. Penn State University3
  8. University of Southern California3
  9. University of Vermont3
  10. American University2
Previous companyCount
  1. Yahoo!8
  2. eBay4
  3. Alphabet | Google3
  4. Microsoft3
  5. Aalto Entrepreneurship Society2
  6. Accenture2
  7. Apple2
  8. Bessemer Venture Partners2
  9. Citibank2
  10. Digg2
06 · Similar investors

Similar investors.

Peers the API surfaces as most similar by portfolio shape, with Dealroom investor rank and portfolio scale.

500 Global
Venture Capital · Palo Alto
#431 rank 2,321 companies $284B portfolio
SV Angel
Venture Capital · San Francisco
#109 rank 986 companies $3.7T portfolio
Y Combinator
Accelerator · San Francisco
#62 rank 7,127 companies $1.9T portfolio
Andreessen Horowitz
Venture Capital · Menlo Park
#2 rank 1,188 companies $4.4T portfolio
Index Ventures
Venture Capital · London
#57 rank 677 companies $1.2T portfolio
Sequoia
Venture Capital · Menlo Park
#3 rank 1,921 companies $23T portfolio
Tiger Global
Private Equity · New York City
#19 rank 811 companies $3.9T portfolio
NEA
Venture Capital · Menlo Park
#36 rank 1,186 companies $2.5T portfolio
07 · Key people

Key people at Freestyle Capital.

David Samuel
David Samuel
Founder
 Jenny Lefcourt
Jenny Lefcourt
General Partner
 Maria (Brewer) Palma
Maria (Brewer) Palma
General Partner
 Josh Felser
Josh Felser
Founder
 David Bill
David Bill
CTO
Source: Dealroom next-gen API — investor team endpoint.