Caffeinated Capital

Caffeinated Capital is a San Francisco-based venture capital firm founded by Raymond Tonsing that partners with founders from inception and supports them throughout the company's lifecycle. The firm focuses on seed and early-stage investments and pursues opportunistic growth opportunities in technology-enabled sectors. It backs companies across a broad range of industries, including consumer, enterprise software, financial services, digital health, crypto and blockchain, big data and bioinformatics, Internet, mobile and software as a service, marketplaces, climate technology and defense. The approach emphasizes close collaboration with founders to accelerate product development, market entry and scale.

Varun Gupta

Partner

Charlie Marsh

Investor (CC Collective)

Matthew Volosin

Venture Partner

Past deals in Insurance

XN Captive

Series A in 2025
XN Captive specializes in providing comprehensive captive insurance services.

Federato

Series C in 2024
Federato Technologies, Inc., established in 2020 and headquartered in Menlo Park, California, specializes in developing an underwriter workflow solution tailored to the insurance and reinsurance industry. This solution employs dynamic optimization to guide underwriters towards a more balanced portfolio, thereby enhancing decision-making and risk management.

Better Health

Series A in 2024
Better Health is a digital platform facilitating peer-to-peer support and supplies management for individuals with chronic conditions such as ostomy, wounds, diabetes, retention, and incontinence. Trusted by major healthcare payers and providers, it improves patient outcomes and reduces care costs through education, engagement, and adherence.

Rainbow

Seed Round in 2024
Rainbow offers insurance to small enterprises, beginning with eateries.

Federato

Series B in 2023
Federato Technologies, Inc., established in 2020 and headquartered in Menlo Park, California, specializes in developing an underwriter workflow solution tailored to the insurance and reinsurance industry. This solution employs dynamic optimization to guide underwriters towards a more balanced portfolio, thereby enhancing decision-making and risk management.

Pathpoint

Venture Round in 2023
Pathpoint Inc., operating as Pathpoint Insurance Service, is a digital wholesale brokerage firm based in San Francisco, California, established in 2017. The company specializes in excess and surplus (E&S) insurance services, offering a range of products including general and cyber liability coverages. Pathpoint's innovative platform streamlines the procurement process for surplus lines coverage, enabling independent agents to access bindable quotes from multiple carriers quickly and efficiently. The company's software enhances various aspects of insurance operations, including quoting, binding, policy document management, underwriting, and accounting. By leveraging technology, Pathpoint aims to simplify access to insurance solutions, reduce costs for carriers, and improve overall market intelligence.

Federato

Series A in 2022
Federato Technologies, Inc., established in 2020 and headquartered in Menlo Park, California, specializes in developing an underwriter workflow solution tailored to the insurance and reinsurance industry. This solution employs dynamic optimization to guide underwriters towards a more balanced portfolio, thereby enhancing decision-making and risk management.

Better Health

Series A in 2021
Better Health is a digital platform facilitating peer-to-peer support and supplies management for individuals with chronic conditions such as ostomy, wounds, diabetes, retention, and incontinence. Trusted by major healthcare payers and providers, it improves patient outcomes and reduces care costs through education, engagement, and adherence.

Pathpoint

Series A in 2021
Pathpoint Inc., operating as Pathpoint Insurance Service, is a digital wholesale brokerage firm based in San Francisco, California, established in 2017. The company specializes in excess and surplus (E&S) insurance services, offering a range of products including general and cyber liability coverages. Pathpoint's innovative platform streamlines the procurement process for surplus lines coverage, enabling independent agents to access bindable quotes from multiple carriers quickly and efficiently. The company's software enhances various aspects of insurance operations, including quoting, binding, policy document management, underwriting, and accounting. By leveraging technology, Pathpoint aims to simplify access to insurance solutions, reduce costs for carriers, and improve overall market intelligence.

Better Health

Seed Round in 2021
Better Health is a digital platform facilitating peer-to-peer support and supplies management for individuals with chronic conditions such as ostomy, wounds, diabetes, retention, and incontinence. Trusted by major healthcare payers and providers, it improves patient outcomes and reduces care costs through education, engagement, and adherence.

AgentSync

Series A in 2021
AgentSync streamlines insurance operations by providing a salesforce application that automates licensing and compliance processes for carriers, agencies, MGAs, and producers. Its real-time integration, data security, producer compliance monitoring, and automated license verification enhance efficiency and maintain regulatory adherence.

AgentSync

Seed Round in 2020
AgentSync streamlines insurance operations by providing a salesforce application that automates licensing and compliance processes for carriers, agencies, MGAs, and producers. Its real-time integration, data security, producer compliance monitoring, and automated license verification enhance efficiency and maintain regulatory adherence.

Socotra

Seed Round in 2014
Founded in 2014, Socotra provides a cloud-based platform for the insurance sector. Its software supports policy administration, underwriting, claims management, billing, reporting, and other applications for property and casualty, and life insurance businesses worldwide.
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