/Investor DB

Jason Calacanis — Full Portfolio

9 tracked investments · listed companies and verified rows first

Deep Sentineldeepsentinel.comin𝕏May 2023

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

Gigstergigster.comin𝕏Dec 2015Acquired

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

Gowallagowalla.comDec 2009Acquired

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 AIjenni.ai𝕏Jan 2020

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 (aquired by Sprinklr)getlittlebird.comJan 2016Acquired

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

Recallrecall.network𝕏May 2026

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.airecall.aiin𝕏May 2026

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

Rillarilla.cominDec 2022

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

ZioSecziosec.comin𝕏Jul 2025

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.