Jason Calacanis — Full Portfolio
9 tracked investments · listed companies and verified rows first
Deep Sentinel provides AI-powered security cameras paired with live monitoring by professional remote guards who can speak to intruders through two-way audio and contact police in real time.
AI & Machine LearningHardwareIoTPleasanton, US
Dave Selinger(Founder)inBrian Kendall(CFO)inMorgan Bell(VP of Engineering)inTomasz Borys(VP of Marketing)inAndi Woody(VP of Customer Care)in
Co-investorsAppWorks VenturesChispa VCEgis Capital PartnersEudemian VenturesIntel CapitalLux Capital+4 more
Gigster connects companies with a global network of software developers and digital talent to build custom products and develop digital capabilities.
AI & Machine LearningB2B MarketplacesDeveloper ToolsEnterprise SoftwareFuture of WorkSaaSAustin, US
Debo Olaosebikan(Founder)inRoger Dickey(Board Director)inChristopher Keene(Chief Executive Officer)inJennifer Pockell Dimas(Chief Marketing Officer)inEllis Ishaya(WW Vice President, Customer Success & Network Operations)inShawn Mohr(Chief Revenue Officer (joined May 2023))in
Co-investorsBloomberg BetaEmmett ShearFelicis VenturesGen CapitalJustin WaldronMarc Benioff+15 more
Austin-founded location-based social network known for check-ins at "Spots," acquired by Facebook and later revived as an AR app.
Co-investorsAlsop Louie PartnersGV (Google Ventures)Capital FactoryForm CapitalGreylock PartnersOffline Ventures+3 more
Jenni AI is an AI writing and research assistant that helps academic and research teams draft manuscripts and manage citations faster.
AI & Machine LearningEdTechSaaS
David Park 님(Founder)inDavid Park(Founder)Henry Mao(Founder)
Co-investorsAntlerCreator Ventures
Little Bird was a Portland social analytics company that identified top experts and influencers in any field via Twitter data.
Co-investorsSocial StartsMark CubanSocial Leverage
Recall operates a platform where users can test, fund, and invest in AI models and agents through a token-based ranking and curation system.
AI & Machine LearningB2B MarketplacesCrypto & Web3
Paul Richards(Founder)inIgor Gligorevic(Founder)in
Co-investorsBessemer Venture PartnersBetaworksCoinFundCollab+CurrencyConsenSys MeshDigital Currency Group+13 more
Recall.ai provides meeting recording and transcription APIs and SDKs that capture individual speaker audio for accurate, multi-speaker transcripts.
AI & Machine LearningData & InfrastructureDeveloper ToolsEnterprise SoftwareSaaSSan Francisco, US
David Gu(Founder)inAmanda Zhu(COO)inEric LiTed Chai(Chief of Staff)inElliot Levin(Engineer)Dhruv Parmar(Founding Engineer)
Co-investorsavraBessemer Venture PartnersCathexis VenturesFundamental VenturesHubSpot VenturesIrregular Expressions+20 more
Rilla is an AI-powered sales coaching platform that analyzes recorded customer conversations to provide personalized coaching for sales teams.
AI & Machine LearningSaaSSales TechNew York City, US
Christopher Martin(Founder)inMichael Castellanos(Founder)inSebastian Jimenez(Founder & CEO)in
Co-investorsBroom VenturesCrew CapitalDraper DragonEntrepreneurs Roundtable Accelerator (ERA)GV (Google Ventures)HubSpot Ventures+8 more
ZioSec provides an autonomous AI red-teaming platform that runs continuous, deep-chained attacks (such as prompt injection, tool misuse, privilege escalation, and exfiltration) against AI agents across any framework, then converts findings into audit-ready evidence with remediation guidance.
AI & Machine LearningCybersecurityEnterprise SoftwareSteamboat Springs, US
Andrius Useckas(Executive Officer, Director)inAaron Walls(Executive Officer, Director)
BoardV. Frank Mendicino III(Director)
Co-investorsAccess Venture PartnersGreater Colorado Venture FundService Provider CapitalSuperhero CapitalAccess VenturesKickstart
Rows marked “SEC filing” are inferred from directors named on the company's SEC Form D — public regulatory data, not a portfolio list published by the firm.











































