Jon Callaghan
Co-Founder and Managing Partner @ True Ventures
San Francisco, United States
Jon Callaghan is a Series A investor at True Ventures in San Francisco focused on E-Commerce and Internet. Jon is an early stage venture capitalist and co-founder of True Ventures. He has been in the venture capital business since 1991 and built three companies of his own. His first was Mountain Bike Outfitters, Inc., which he created at age 18. Jon started his venture career as an associate at Summit Partners and then joined Greenhouse, AOL’s venture capital investment group and incubator. He entered the internet market early by joining CMGI’s @Ventures group in 1996. Before founding True, Jon was a managing director at Globespan Capital Partners. First as a founder and now as an investor in early-stage technology companies, Jon’s direct startup experience has allowed him to see the world through an entrepreneur’s eyes. Jon’s career has been driven by a deep belief in the power of human creativity to improve our world. Jon received a bachelor’s degree in government from Dartmouth College and an MBA, with distinction, from Harvard Business School. He was recently the Chairman of the National Venture Capital Association. When he is not empowering the entrepreneurs of tomorrow, you can find him talking about airplanes or hanging out with his wife and four boys.
- Total investments:
- 85
- Last investment:
- Lead investor:
- 34%
Last updated:
For AI agents: llms.txt
Industries Jon Callaghan invests in
Stages Jon Callaghan invests in
Countries Jon Callaghan invests in
Round sizes
Contacts
| Type | Contact | Validation |
|---|---|---|
| Work email | ||
| Personal email | ||
| Work phone | ||
| Personal phone | ||
| Socials |
Round size
- Seed
- $775k–$20M
- Series A
- $2.4M–$20M
- Series B
- $3.3M–$47M
Investment Focus
Industry
- E-Commerce 11 (13%)
- Internet 7 (8%)
- Information Technology 6 (7%)
- Software 5 (6%)
- Apps 4 (5%)
Stage
- Series A 22 (26%)
- Series B 18 (21%)
- Seed 11 (13%)
- Series C 9 (11%)
- Series D 9 (11%)
Country
- United States 33 (39%)
- Finland 1 (1%)
- Singapore 1 (1%)
- United Kingdom 1 (1%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
| Ernesta provides design-focused custom rugs to homes and places of gathering through an enjoyable, frictionless, and affordable experience. | $20M / Series B / Mar 11, 2026 | ||
| Pallie AI develops AI-powered companion that supports health and wellbeing. | $2M / Pre-Seed / Apr 30, 2025 | ||
| HomeBoost operates as a home energy platform. | $4M / Seed / Oct 29, 2024 | ||
| Daydream focuses on providing personalized shopping results through generative AI, machine learning, and computer vision. | $50M / Seed / Jun 20, 2024 | ||
| Ernesta provides design-focused custom rugs to homes and places of gathering through an enjoyable, frictionless, and affordable experience. | $25M / Series A / Nov 07, 2022 | ||
| Aisera’s AI Agent Platform is a multi-agent system that consists of a universal agent for request orchestration, domain agents with contextual intelligence across IT, HR, Finance, Procurement, and more, and task agents that execute tasks through integrations with ServiceNow, Workday, Salesforce, and other enterprise systems. The platform isfuture-proof and vendor-agnostic, enabling organizations to deploy out-of-the-box agentic solutions or custom-build agents on the same platform. Designed as a horizontal solution, it scales seamlessly across all enterprise functions to deliver autonomous self-service, personalized resolutions, omnichannel engagement, and enterprise-wide productivity gains. Aisera Assistant, grounded in enterprise data and ontologies, delivers instant self-service by enabling employees to securely access information and execute actions across enterprise applications and systems. Embedded in collaboration channels like Slack and Microsoft Teams, it understands context, supports digital and voice channels, provides proactive notifications, retrieves knowledge from public and private sources, extracts insights from documents, and works seamlessly across multiple languages. With capabilities that drive a zero ticket service desk, maximize case deflection, and reduce MTTD and MTTR, Aisera Assistant transforms user experiences.Aisera’s Agent Assist leverages domain-specific LLMs to enhance agent productivity with contextual answers, case summarization, and next-best action recommendations. Embedded into platforms like ServiceNow, Zendesk, and Salesforce, it enables real-time knowledge retrieval, swarm collaboration, case identification, and case wrap-up - empowering agents to resolve complex issues faster. Aisera's AI Agent platform delivers exponential cost efficiencies, higher organizational productivity and an enhanced user experience, enabling enterprises to autonomously understand, reason, and proactively fulfill requests through AI agents. | $90M / Series D / Aug 03, 2022 | ||
MycoMedica Life Sciences, PBC
|
Psychedelic Medicines | $60M / Series A / Jun 01, 2022 | |
| The integration platform built for developers | $20M / Series A / May 17, 2022 | ||
| Wisq delivers an AI-powered platform tailored for enterprise HR teams. It supports an AI HR generalist—Harper—trained on HR-specific content and capable of autonomously handling routine HR inquiries such as policy questions, leave requests, and coaching within seconds of intake, across channels like chat, email, and ticketing systems. The platformresolves up to 80% of routine cases without human intervention, allowing HR teams to focus on strategic initiatives.Harper demonstrates high-level HR proficiency—correctly answering SHRM-CP exam questions 94% of the time and processing them 12 times faster than a certified HR professional. Wisq’s infrastructure ensures secure, compliant deployment with customizable guardrails, real-time observability, and seamless integration into existing HR systems. | $20M / Series A / Apr 25, 2022 | ||
| NoRedInk helps millions of students in grades 4-12 become better writers. Our writing platform allows learners to improve through engaging, adaptive exercises and a proven process for self-review and peer-review — and then delivers actionable performance data to teachers and administrators. Used in more than 50% of school districts in the US,we're on a mission to unlock every writer's potential. | $50M / Series B / Aug 24, 2021 | ||
| See all 85 investments → | |||
Co-Investors
About True Ventures
Founded in 2005, True Ventures is a Silicon Valley-based venture capital firm that invests in early-stage technology startups. With more than $3.8 billion under management, True provides seed and Series A financing to entrepreneurs in some of today's growing markets. With more than 40 team members including special advisors, operations professionals, and founders-turned-investors, True represents one of the largest and most experienced teams dedicated to the ecosystem. The True team believes creativity flourishes when founders are supported fully and empowered to pursue brave ideas. To that end, the True Platform offers programs that inspire professional and personal growth. To date, True has helped more than 350 companies launch and scale their businesses, creating over 85,000 jobs worldwide. True was awarded Venture Firm of the Year by the National Venture Capital Association in 2018. To learn more, visit www.trueventures.com.
True Ventures Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Amy Tusman
Executive Assistant
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Gus Coldebella
Partner
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Jeffrey Veen
Design Partner and Head of Platform
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Rohit Sharma
Partner
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Adam D'Augelli
Partner
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FAQ
What does Jon Callaghan invest in?
Jon Callaghan invests primarily in E-Commerce, Internet and Information Technology startups, most often at Series A and Series B stage. Most of the 85 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
What round sizes does Jon Callaghan invest in?
Jon Callaghan typically joins rounds of $775k–$20M at Seed, $2.4M–$20M at Series A and $3.3M–$47M at Series B. These are whole funding-round sizes, not Jon Callaghan's own check, which is rarely disclosed: the 10th–90th percentile of the confirmed public funding rounds Jon Callaghan took part in.
How do I contact Jon Callaghan?
Public channels for Jon Callaghan include LinkedIn and X (Twitter). For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.
When did Jon Callaghan last invest?
The most recent investment recorded for Jon Callaghan closed in Mar 2026. Shizune tracks 85 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Nov 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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