Investing in AI-Driven B2B SaaS, FinTech, and HealthTech: Inside PS27 Ventures

In this insightful episode of The Innovators & Investors Podcast, host Kristian Marquez sits down with Harry "Hale" Bullen, investment manager at PS27 Ventures, to explore the evolving landscape of venture capital focused on AI-driven investments. Hale shares PS27’s unique thesis emphasizing “sticky plumbing” software embedded deeply within B2B SaaS, FinTech, and health tech sectors, particularly in North Florida’s financial and healthcare ecosystems. They discuss the rigorous due diligence process, highlighting the importance of consistent traction, founder alignment, and clear financial paths to profitability.

Listeners gain a rare look into how PS27 leverages AI tools at every step of evaluating deal flow, including proprietary founder grading and competitive analyses, emphasizing efficiency and data-driven insights. Hale also explains how their firm supports portfolio companies post-investment through weekly sales calls that foster accountability and growth. The conversation dives into venture capital trends, the impact of AI on startup capital efficiency, and the shift toward smaller, specialized funds focused on early-stage investments.

Hale’s unique journey from Naval Academy nuclear engineer to venture capital investor brings a valuable operator’s perspective to evaluating founders and building successful companies. This episode offers practical wisdom for entrepreneurs, investors, and anyone interested in the dynamic intersection of AI and venture capital. Tune in for a compelling discussion on smart capital deployment, founder support, and the future of innovation investing.

Learn more about Harry's work at https://ps27ventures.com/

Connect with Harry on LinkedIn at https://www.linkedin.com/in/harrysbulleniv/

Think you'd be a great guest on the show? Apply at https://finstratmgmt.com/innovators-investors-podcast/

Want to learn more about Kristian Marquez's work? Check out his website at https://finstratmgmt.com