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Jason Calacanis

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Last 12 months
2 investments
Tracked investments
9
Acquisitions
3

What they invest in

from 7 of 9 portfolio companies

AI & Machine Learning ×7SaaS ×4Enterprise Software ×3B2B Marketplaces ×2Developer Tools ×2Crypto & Web3 ×1Cybersecurity ×1Data & Infrastructure ×1

HQs:United States×5

Investments · 9 tracked

founders shown can be your intro path

By year:2026 · 22025 · 12023 · 12022 · 12020 · 12016 · 12015 · 12009 · 19 dated

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 VenturesEgis Capital PartnersEudemian VenturesIntel CapitalLux CapitalTri-Valley Ventures+3 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(Co-Founder & CEO)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)in

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+CurrencyDigital Currency GroupMulticoin Capital+12 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(Founder)in

Co-investorsBessemer Venture PartnersCathexis VenturesFundamental VenturesHubSpot VenturesJude GomilaPioneer+18 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)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

Portfolio news

latest coverage across their companies

Frequently asked questions

How many investments has Jason Calacanis made?
Jason Calacanis has 9 tracked investments, 3 of which have exited, including 3 dated in the last 24 months.
What sectors does Jason Calacanis focus on?
Jason Calacanis focuses on Crypto & Web3.

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