Walkabout Ventures

Walkabout Ventures is a seed-focused venture capital firm that strategically invests in early-stage financial services and fintech startups. The firm is particularly interested in companies developing robust infrastructure and back-office solutions for the financial and insurance industries, emphasizing B2B offerings over consumer-facing fintech. Their investment thesis centers on identifying and nurturing technical picks-and-shovels businesses that aim to modernize and enhance the operational efficiency of financial and insurance services.

Founded in 2019 by Josh Diamond and Jordy Albert, Walkabout Ventures was established to address a perceived funding gap in the very early stages of financial services investment within the United States. The firm is committed to supporting founders throughout their entrepreneurial journey, providing not only capital but also strategic guidance to help navigate the complexities of the competitive fintech and insurtech landscapes.

Walkabout Ventures has built a diverse portfolio of companies that are innovating across various facets of financial technology. Notable investments include Discern, a software-first registered agent automating state filings, in which Walkabout Ventures co-led a Series A round. Other portfolio companies include Clair, a provider of on-demand pay for employees; Lithic, a prepaid card solutions provider; Functional Finance, a platform enhancing operational efficiency in the insurance industry; HealNow, a healthtech company; and Sensible Weather, an environmental tech startup. The firm also lists Renew, Sunfish Technologies, Themis, Odie Pet Insurance, Capitalize, and HMBradley among its investments.

The firm actively seeks technical founders with profound domain expertise in fintech, as well as repeat founders or operators from scale-up companies. Walkabout Ventures values mission-driven teams dedicated to solving critical pain points within financial services, and those who are agile and receptive to operational support and mentorship.