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Paige Craig

Investor

General Partner at Outlander · General Partner at OL Gamma · Managing Partner at Outlander VC · Board director at Havoc AI

New York, New York

Writes $500K – $2.5M checks · typically $200K

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Ask Chris Robinson to introduce you to Paige

You →Chris · together at marine corps (1995–1996) →Paige

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You →Jamie · 6 people · together at marine corps →Paige

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You →Sam · 5 people · together at Gusto →Paige

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About

Paige Craig, a former U.S. Marine who bootstrapped a private military company from $10,000 to hundreds of millions, uses codified, military-style founder assessments to back technically strong, under-networked founders early.

Invests in

AI & Machine LearningClimate TechDeep TechDefense TechHardwareMobility & TransportationRoboticsSaaSSpace Tech

Board director at Havoc AI

Intro paths

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In turn, Paige can intro founders to Havoc AI's investors below.

Havoc AI's investors · 19

0BSMexico · $50K – $150K checks640 OxfordDetroit · $250K – $400K checksAlumni VenturesManchester · $100K – $10M checks · since 2025B Capital GroupSan Francisco · $10M – $50M checks · since 2025B4 Capital$10M – $50M checksBVVCBurr RidgeCobalt CapitalSanta Monica · since 2026Decisive PointWashington · $500K – $1M checksLockheed Martin VenturesBethesdaMute VenturesNew York · since 2026New North VenturesPortsmouth · $1M checks · since 2025Outlander VCNew York · $500K – $2.5M checks · since 2026Scout VenturesAustin · $2M – $5M checksScout VenturesAustin · $2M – $5M checks · since 2026Taiwania CapitalTaipei · $3M – $85M checks · since 2026The Veteran FundSan Francisco · $500K – $2M checksTrousdale VenturesWest Hollywood · $1M – $5M checksUP PartnersSanta Monica · $1M – $10M checks · since 2026Zero Infinity PartnersNew York · $100K – $5M checks

Co-founders at Havoc AI

PLPaul Lwin
Paul LwinCo-Founder & CEO

Experience

  1. Outlander VCManaging Partner + Foundercurrent2008 — presentNew York, United States
  2. Scale AIInvestorcurrent2016 — present
  3. Postmates Inc.Investorcurrent2011 — present
  4. AngelListInvestorcurrent2011 — present
  5. GustoInvestorcurrent2012 — present
  6. LyftInvestor2012 — 2023
  7. WishInvestor2010 — 2023
  8. TwitterInvestor2010 — 2017
  9. Angel InvestorInvestor2008 — 2015
  10. Lincoln GroupFounder & CEO2003 — 2010
  11. marine corpsmarine1995 — 2000

Skills & more

Angel Investing86Business Development44

From Paige's professional profile.

Investments

Investor

BetterviewCatalyxCocoCodewarsContextLogicCourseHorseDSTLDDwollaEcoMomFitMobGameCrushGameSaladGigitGraphiclyGroupSpotHeadoutHipsterHONKIdentifiedJazzHRKiipkloutLaunchrockLaurel & WolfLivefyreMattermarkMogotixMy TableOmazeOne MonthPlatedPostlingPrevotyQualifiedQuizUpRinseScripted.comShareSquareShop HersSpaceshipStackCommerceStackSocialStackStrStyleseatTroopSwapUncovetWorldly DevelopmentsYourMechanic

Per curated public sources.

Colleagues at Outlander

Jim Berardinelli
Managing Director, Multifamily at Crow Holdings
Leslie Ware
Board of Directors at Crow Holdings
Leura Craig
Managing Partner at Outlander VC

Network4

Andrew HuntScout
General Partner at Elephant Partners
Bill HardingScout
Managing Director at VantagePoint Capital Partners
Chris YehScout
Founding General Partner at Blitzscaling Ventures
Christopher KlausScout
Partner at Cyberlaunch

Investors connected to Paige in public investor directories — a warm-intro map.

Frequently asked questions

Who is Paige Craig?
Paige Craig, a former U.S. Marine who bootstrapped a private military company from $10,000 to hundreds of millions, uses codified, military-style founder assessments to back technically strong, under-networked founders early.
Where does Paige Craig work?
Paige Craig is General Partner at Outlander and Board director at Havoc AI.
What does Paige Craig invest in?
Paige Craig invests in AI & Machine Learning, Climate Tech, Deep Tech, Defense Tech, Hardware, Mobility & Transportation, Robotics, SaaS, Space Tech.
What check size does Paige Craig write?
Paige Craig typically writes checks of $500K – $2.5M.
What companies has Paige Craig invested in?
Investments tracked here include Betterview, Catalyx, Coco, Codewars, ContextLogic, CourseHorse, DSTLD, Dwolla, EcoMom, FitMob, GameCrush, GameSalad, and 36 more.
Where did Paige Craig go to school?
Paige Craig studied at United States Military Academy at West Point; University of Maryland (BS, Management Information Systems); National University (MBA).

Same school

Shared employers