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Alex Chesterman

Angel · London, United Kingdom

#397 Investor Ranking 2026 Top 3% of investors worldwide
30 Portfolio companies+7% in 5 years
3 Unicorns
39 Investments
May 2026 Last investment
01 · Fund commitments

The funds Alex Chesterman backs.

Alex Chesterman is a limited partner in 4 funds. 1 of them place in the Power Law Investor Ranking; those lead, best-ranked first.

Episode 1 Ventures
United Kingdom
#353 Power Law
La Famiglia
Germany
Project Europe
United Kingdom
Stride.VC
United Kingdom
02 · Biggest holdings

Alex Chesterman’s biggest current holdings.

Alex Chesterman is a named shareholder in 5 companies. Dealroom estimates those stakes are worth about $14M in total — the disclosed percentage × each company’s latest valuation. The 5 biggest are below; the 3 with a computable estimate are sized by it.

#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% $290M $29K
  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 shareholder registers on Dealroom →

03 · 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. UK32
  2. France1
  3. Portugal1
By sectorCount
  1. Health7
  2. Fintech4
  3. Food4
  4. Real Estate4
  5. Transportation4
  6. Wellness Beauty4
  7. Travel3
  8. Education2
  9. Enterprise Software2
  10. Home Living2
  11. Legal2
  12. Sports2
By stage enteredCount
  1. Seed25
  2. Series A5
  3. Series B+1
By growth stageCount
  1. Breakout Stage14
  2. Early Growth14
  3. Late Growth6
04 · Portfolio market map

Inside Alex Chesterman’s portfolio.

The 34 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
Swoon
Home Living
$79M
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
Rangespan
Marketing
$20M
toucanBox
Education
$20M
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
BRULO
Food
Evermore Health
Health
05 · Portfolio founders

Where Alex Chesterman’s portfolio founders come from.

53 founders across the 34 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 Kingdom40
  2. United States4
  3. France2
  4. Portugal2
  5. Israel1
UniversityCount
  1. Columbia University3
  2. University College London3
  3. University of Cambridge3
  4. University of Nottingham3
  5. University of Oxford3
  6. Durham University2
  7. École Polytechnique - IP Paris2
  8. University of Southampton2
  9. Ashridge Executive Education, Hult International Business School1
  10. Babson College1
Previous companyCount
  1. Amazon3
  2. Barclays3
  3. Climate Pledge Fund3
  4. Telegraph Media Group3
  5. Alphabet | Google2
  6. Bersin by Deloitte2
  7. ClearCarbon2
  8. ClimateCare2
  9. Deloitte2
  10. Financial Times2