Where does Ryan Castonia work?

Ryan Castonia is Principal at Two Bear Capital.

What check size does Ryan Castonia write?

Ryan Castonia typically writes checks of $100K – $5M.

Where did Ryan Castonia go to school?

Ryan Castonia studied at Massachusetts Institute of Technology (S.B. and S.M., Aerospace); Defense Language Institute Foreign Language Center (Diploma with Honors, Modern Standard Arabic).

Ryan Castonia

Investor

Principal at Two Bear Capital

Montana

Writes $100K – $5M checks · typically $1.5M

About

Ryan Castonia is Vice President of Solution Delivery at webAI, where he focuses on advancing sovereign AI adoption in the public sector. His background spans engineering, artificial intelligence, strategy, venture investing, and startup leadership. At webAI, he works to provide government agencies with AI systems they can fully control and operate with trust.

Experience

webAIVice President of Solution Deliverycurrent2026 — present
webAIHead of Special Projects2025 — 2026
Dephy, Inc.Chief Growth Officer2023 — 2025
Two Bear CapitalPrincipal | Founding Member2019 — 2024
SelectorBoard Observer2021 — 2023
pulseDataBoard Observer2021 — 2023
ElisityBoard Observer2021 — 2023
Pratt MillerDepartment of Defense Fellow2019New Hudson, MI
United States Air ForceFounding Member, Joint Artificial Intelligence Center2018
United States Air ForceBranch Chief, Personnel Recovery Core Function Team2017 — 2018Hampton, VA
United States Air ForceAssistant Director of Operations, Plans, and Tactics2016 — 2017Lakenheath, United Kingdom
United States Air ForceDeputy Operations Officer, Joint Special Operations Task Force2017
United States Air ForceTeam Commander2013 — 2016Tucson, AZ
United States Air ForceCombat Rescue Officer (Special Warfare Officer) Trainee2011 — 2013
Massachusetts Institute of TechnologyResearch Assistant - Graduate Student (Humans and Automation Lab)2008 — 2010

Skills & more

Leadership24Strategic Planning5Human Factors4Program Management10Defense7National Security5Aerospace5Military Operations5Operational Planning4Government3Air Force2Command2

+7 more

Military ExperienceMatlabTeam LeadershipEngineering ManagementProcess ImprovementSpace SystemsSecurity Clearance

Languages Arabic · English

From Ryan's professional profile.

Colleagues at Two Bear Capital

Amalia Colangelo

Principal at Two Bear Capital

Ashley Archibeque

Executive Assistant at Two Bear Capital

Avery Sonnenberg

Principal at Two Bear Capital

Bria Iuliano

Executive Assistant at Two Bear Capital

Bridget Martell MA, MD

Senior Biopharmaceutical Advisor at Two Bear Capital

Cris Neckar

Partner at Two Bear Capital

Ellen Lubman

Biopharmaceutical Advisor at Two Bear Capital

Ellen Lubman, MBA

Biopharmaceutical Advisor at Two Bear Capital

Frequently asked questions

Who is Ryan Castonia?: Ryan Castonia is Vice President of Solution Delivery at webAI, where he focuses on advancing sovereign AI adoption in the public sector. His background spans engineering, artificial intelligence, strategy, venture investing, and startup leadership. At webAI, he works to provide government agencies with AI systems they can fully control and operate with trust.
Where does Ryan Castonia work?: Ryan Castonia is Principal at Two Bear Capital.
What check size does Ryan Castonia write?: Ryan Castonia typically writes checks of $100K – $5M.
Where did Ryan Castonia go to school?: Ryan Castonia studied at Massachusetts Institute of Technology (S.B. and S.M., Aerospace); Defense Language Institute Foreign Language Center (Diploma with Honors, Modern Standard Arabic).

Same school

Also attended Massachusetts Institute of Technology1,387

Fred WilsonCo-founder & Partner at Union Square Ventures Elad GilSolo general partner investing through Gil Capital Aileen LeeFounder & Managing Partner of Cowboy Ventures Hemant TanejaCEO & Managing Director of General Catalyst Nat FriedmanCo-lead of Meta Superintelligence Labs; co-founder of NFDG Brad FeldCo-founder of Foundry and Techstars

+ 1,381 more

Also attended Defense Language Institute Foreign Language Center4

Thomas CavettInvestor at NEW VISTA CAPITAL Mark GilreathFounding Investor at DOGWOOD VENTURES Rick BunkerChief Technology and Product Officer at Inveniam Mike BynumCSO (Chief Solutions Officer) at OUTPOST VENTURES

Shared employers

Also worked at Selector8

Denise XifaraInvestor at Mercuri.vc Paul WeinsteinGeneral Partner at Azure Capital Partners Ryan LeePrincipal at Comcast Ventures Allan Jean-BaptisteInvestor at Ansa Capital Josh ChinPrincipal at Ansa Capital Ethan VolkPrincipal at Atlantic Vantage Point

+ 2 more

Also worked at pulseData2

Cris NeckarPartner at Two Bear Capital Wesley YiuPrincipal at Alumni Ventures

Also worked at Elisity7

Morgan GerlakPartner at TCV Joe PintoChief Customer Experience Officer, Pure Storage at Two Bear Capital Spencer TallManaging Director at AllegisCyber Capital Cris NeckarPartner at Two Bear Capital Galina AntovaCo-Founder & Chief BD Officer at Claroty at Leaders Fund Evan HochhauserPartner at Technology Crossover Ventures

+ 1 more

Also worked at United States Air Force98

Dave MunichielloInvestor at GV (Google Ventures)Ross Perot Jr.Chairman of The Perot Group at Perot Jain Nathaniel HardingManaging Partner at Cortado Ventures Kevin MandiaGeneral Partner at Ballistic Ventures Tidal McCoyChairman at IronGate Capital Advisors Steve SargeantSenior Advisory Board at IronGate Capital Advisors

+ 92 more