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Great Oaks Venture Capital

Venture Capital · Founded 2005 · New York City, United States

#38 Investor Ranking 2026 Top 0.5% of investors worldwide

A seed-stage investment firm committed to financing and developing early stage growth businesses

Website ↗LinkedIn ↗X / Twitter ↗
350 Portfolio companies+16% in 5 years
23 Unicorns
500 Investments
Feb 2026 Last investment
01 · Biggest holdings

Great Oaks Venture Capital’s biggest current holdings.

The most valuable companies Great Oaks Venture 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 Great Oaks Venture Capital, so the size of each stake isn’t shown.

#CompanyValuation
  1. 1 GrubMarketUnicorn · Food · USA $4.5B
  2. 2 HouzzUnicorn · Real Estate · USA $4.0B
  3. 3 Course HeroUnicorn · Education · USA $3.6B
  4. 4 WorkriseUnicorn · Energy · USA $2.9B
  5. 5 Fetch RewardsUnicorn · Fintech · USA $2.5B
  6. 6 Virta HealthUnicorn · Health · USA $2.0B
  7. 7 RoofstockUnicorn · Fintech · USA $1.9B
  8. 8 Maven ClinicUnicorn · Health · USA $1.7B
  9. 9 Collective HealthUnicorn · Health · USA $1.5B
  10. 10 AwayUnicorn · Travel · USA $1.4B
  11. 11 Human InterestUnicorn · Marketing · USA $1.3B
  12. 12 FlexUnicorn · Fintech · USA $1.2B

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

02 · Exits

Great Oaks Venture Capital’s biggest exits.

Portfolio companies that IPO’d or were acquired at $1B+, with the valuation recorded at exit and — for those still public — their value today. Exit events come from each company’s funding-round history; entry stage from Great Oaks Venture Capital’s transaction record.

EquipmentShare
$7.2B IPO · 2026
Entered SeedNow $7.2BReal Estate
Smartbird | formerly Allbirds
$4.1B IPO · 2021
Entered SeedNow $41MHosting
Trulia
$448M IPO · 2012
Entered Series ANow $3.5BReal Estate
Oportun
$432M IPO · 2019
Entered SeedNow $2.9BFintech
Ibotta
$2.4B IPO · 2024
Entered Series ANow $769MFintech
Flatiron Health
$1.9B acquisition · 2018
Entered Series AHealth
Truebill
$1.3B acquisition · 2021
Entered SeedFintech
03 · Portfolio analysis

Where Great Oaks Venture Capital’s portfolio is concentrated.

Distribution of portfolio companies by headquarters country, sector, entry stage and current growth stage. Across all 350 portfolio companies. "Stage entered" is the first priced round the investor joined, derived from the investor’s transaction history.

By countryCount
  1. USA409
  2. UK3
  3. Canada2
  4. Spain2
  5. Brazil1
  6. France1
  7. Georgia1
  8. India1
  9. Ireland1
  10. Laos1
  11. Luxembourg1
  12. Mexico1
By sectorCount
  1. Fintech62
  2. Health59
  3. Enterprise Software54
  4. Media48
  5. Food36
  6. Marketing35
  7. Education27
  8. Telecom26
  9. Fashion22
  10. Home Living19
  11. Real Estate19
  12. Wellness Beauty18
By stage enteredCount
  1. Seed249
  2. Series A77
  3. Series B+21
By growth stageCount
  1. Early Growth224
  2. Breakout Stage143
  3. Late Growth58
  4. Mature1
04 · Portfolio market map

Inside Great Oaks Venture Capital’s portfolio.

The 60 highest-funded portfolio companies, of 350 tracked.

Bolt
Security
$300M
EquipmentShare
Real Estate · Unicorn
$7.2B
GrubMarket
Food · Unicorn
$4.5B
Workrise
Energy · Unicorn
$2.9B
Collective Health
Health · Unicorn
$1.5B
Houzz
Real Estate · Unicorn
$4.0B
Human Interest
Marketing · Unicorn
$1.3B
Acorns
Fintech
$514M
Course Hero
Education · Unicorn
$3.6B
Fetch Rewards
Fintech · Unicorn
$2.5B
Vimeo
Media
$993M
Maven Clinic
Health · Unicorn
$1.7B
SingleStore
Enterprise Software · Unicorn
$1.3B
Virta Health
Health · Unicorn
$2.0B
Roofstock
Fintech · Unicorn
$1.9B
Petal
Fintech
$800M
Knock
Real Estate
$36M
Flatiron Health
Health · Unicorn
$1.9B
Foodsmart
Health
$144M
Oportun
Fintech · Unicorn
$2.9B
Genies
Media · Unicorn
$1.0B
AllTrails
Travel
$736M
Shift Technologies
Transportation
Away
Travel · Unicorn
$1.4B
Loom
Media · Unicorn
$1.5B
Happy Money
Fintech · Unicorn
$1.1B
Smartbird | formerly Allbirds
Hosting
$41M
Flex
Fintech · Unicorn
$1.2B
Counsyl
Health
$112M
Peek
Travel
$400M
Eaze
Health
$140M
Plastiq
Fintech
Nylas
Enterprise Software
$480M
Breakthrough.com
Health
$20M
Pocket Gems
Gaming
$360M
Mantl
Fintech
$400M
Cardless
Fintech
$240M
Verge Genomics
Health
$392M
Hired
Jobs Recruitment
$160M
Bonobos
Fashion
$75M
Vise
Fintech · Unicorn
$1.0B
Affinity
Marketing
$320M
Plated
Food
$200M
Built Robotics
Real Estate
$256M
Cover Technologies
Real Estate
$240M
JOOR
Fashion
$230M
PicnicHealth
Health
$240M
Augmedix
Health
$116M
SmithRx
Health
$240M
BlueShift
Marketing
$160M
Kargo
Transportation
$168M
Eero
Home Living
$200M
Truebill
Fintech · Unicorn
$1.3B
Fun
Fintech
$288M
Boatsetter
Travel
$152M
Hungryroot
Food
$750M
ModCloth
Fashion
$60M
VivaReal
Real Estate
$167M
Notable Labs
Health
Alto
Fintech
$160M
05 · Portfolio founders

Where Great Oaks Venture Capital’s portfolio founders come from.

170 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 States150
  2. Argentina4
  3. Brazil3
  4. Australia1
  5. Bangladesh1
  6. Canada1
  7. Sweden1
  8. United Kingdom1
UniversityCount
  1. Stanford University19
  2. Stanford University Graduate School of Business13
  3. Harvard University10
  4. Wharton School of the University of Pennsylvania9
  5. Massachusetts Institute of Technology8
  6. Cornell University7
  7. Harvard Business School5
  8. London School of Economics and Political Science5
  9. University of Pennsylvania5
  10. Columbia University4
Previous companyCount
  1. McKinsey & Company8
  2. Goldman Sachs7
  3. Alphabet | Google6
  4. ClearCarbon5
  5. Deloitte5
  6. Microsoft5
  7. Stanford University5
  8. Bain & Company4
  9. Bersin by Deloitte4
  10. IBM3
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
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
Y Combinator
Accelerator · San Francisco
#62 rank 7,127 companies $1.9T portfolio
Techstars
Accelerator · New York City
#855 rank 2,278 companies $249B portfolio
FJ Labs
Venture Capital · New York City
#228 rank 784 companies $207B portfolio
NEA
Venture Capital · Menlo Park
#36 rank 1,186 companies $2.5T portfolio
07 · Key people

Key people at Great Oaks Venture Capital.

Andrew Boszhardt, Jr.
Andrew Boszhardt, Jr.
Founder
 Andrew Boszhardt,Jr.
Andrew Boszhardt,Jr.
Founder
 Henry McNamara
Henry McNamara
Analyst
 Stuart O'Keeffe
Stuart O'Keeffe
Analyst
 Raj Sandhu
Raj Sandhu
General Partner
Source: Dealroom next-gen API — investor team endpoint.