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Investor profile

Alex Chesterman

Angel · London, United Kingdom

Dealroom ↗
30 portfolio companies Angel · $130M invested · 39 investments · Investor rank #13,611 · Last investment 5/2026
Portfolio companies 30 ↑ 3% 5y
Decacorns 0
Thoroughbreds 5
Power Law #397Investor Ranking · Global · 2026 · Top 3%
Estimated holdings

Alex Chesterman’s biggest current holdings.

An estimate of Alex Chesterman’s largest live positions — disclosed shareholding × Dealroom’s latest valuation — across 5 companies where Alex Chesterman is a named shareholder, worth about $14M in estimated equity value.

#CompanyEst. stakeValuationEst. value
  1. 1 CleoFintech · Unicorn 1.34% $1.0B $13M
  2. 2 The Plum GuideTravel · Colt 0.09% $138M $124K
  3. 3 Secret EscapesTravel · Thoroughbred 0.01% $436M $44K
  4. 4 SportPursuitSports · Colt 0.25% — —
  5. 5 State of Play HospitalityColt 0.53% — —

Estimated value = Alex Chesterman’s disclosed ownership % × Dealroom’s latest company valuation; direct named stakes only, exited positions excluded. Figures are indicative, not reported marks. See the underlying cap tables on Dealroom →

Portfolio analysis

Where Alex Chesterman’s portfolio is concentrated.

Distribution of portfolio companies by headquarters country, sector, entry stage and current growth stage. Across all 30 portfolio companies. "Stage entered" is the first priced round the investor joined, derived from the investor’s transaction history.

By countryCount
  1. UK28
  2. France1
  3. Portugal1
By sectorCount
  1. Health7
  2. Fintech4
  3. Real Estate4
  4. Transportation4
  5. Wellness Beauty4
  6. Food3
  7. Travel3
  8. Legal2
  9. Sports2
  10. Education1
  11. Energy1
  12. Enterprise Software1
By stage enteredCount
  1. Seed25
  2. Series A5
By growth stageCount
  1. Breakout Stage13
  2. Early Growth11
  3. Late Growth6
Portfolio market map

Inside Alex Chesterman’s portfolio.

The 30 highest-funded portfolio companies, of 30 tracked.

Tide
Fintech · Unicorn
$1.5B
Motorway
Transportation · Unicorn
$1.0B
Secret Escapes
Travel
$290M
Carwow
Transportation
$208M
Cleo
Fintech · Unicorn
$1.0B
Perlego
Education
$250M
The Plum Guide
Travel
$92M
Zefir
Real Estate
$110M
FarmDrop
Food
$32M
Farewill
Legal
$17M
Lick
Real Estate
$58M
Perkbox
Health
$70M
Uniplaces
Travel
$96M
Thirdfort
Legal
$79M
SportPursuit
Sports
$50M
Vyne
Fintech
$62M
Thriva Solutions
Health
$21M
VITL
Health
$33M
DueCourse
Fintech
$32M
Zebra Fuel
Energy
$16M
MindLabs
Health
$13M
Huggg
Food
$6.4M
Pharmacierge
Health
$13M
Fenton & Co
Fashion
$4.5M
Auro
Wellness Beauty
$2.6M
OnCare
Health
$1.9M
Graze
Food
$198M
Hellocar
Transportation
$4.9M
Atheni.ai
Enterprise Software
$1.9M
Evermore Health
Health
Portfolio founders

Where Alex Chesterman’s portfolio founders come from.

47 founders across the 30 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 Kingdom35
  2. United States3
  3. France2
  4. Portugal2
  5. Israel1
UniversityCount
  1. Columbia University3
  2. University College London3
  3. University of Cambridge3
  4. University of Oxford3
  5. Durham University2
  6. École Polytechnique - IP Paris2
  7. University of Nottingham2
  8. University of Southampton2
  9. Ashridge Executive Education, Hult International Business School1
  10. Babson College1
Previous companyCount
  1. Barclays3
  2. Amazon2
  3. Bersin by Deloitte2
  4. ClearCarbon2
  5. Climate Pledge Fund2
  6. ClimateCare2
  7. Deloitte2
  8. Financial Times2
  9. Goldman Sachs2
  10. ITV2
How Alex Chesterman stacks up

Similar investors.

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

LocalGlobe
Venture Capital · London
#608 rank 308 companies $175B portfolio
Index Ventures
Venture Capital · London
#56 rank 677 companies $1.2T portfolio
Techstars
Accelerator · New York City
#847 rank 2,278 companies $250B portfolio
Partech
Venture Capital · Paris
#254 rank 395 companies $77B portfolio
500 Global
Venture Capital · Palo Alto
#430 rank 2,321 companies $289B portfolio
Sequoia
Venture Capital · Menlo Park
#3 rank 1,919 companies $22T portfolio
FJ Labs
Venture Capital · New York City
#226 rank 783 companies $205B portfolio
Global Founders Capital
Venture Capital · Berlin
#229 rank 605 companies $1.7T portfolio
Figures on this page are sourced live from the Dealroom next-gen API, joined with Dealroom’s cap-table dataset (estimated holdings) and the Power Law Investor Ranking. News in “Featured in” is drawn from Dealroom’s own coverage — the stories that name this investor, not only those it is the subject of. Market sentiment is omitted until the API exposes it.