Preston Callicot
BOARD ADVISOR
Preston is a strategic advisor, early-stage investor, and self-described "supposedly retired" entrepreneur. As CEO and co-founder of Five Talent Software — sold to Effectual, Inc. in 2020 — he built and exited one of his most successful ventures after more than 40 years leading high-tech companies and consulting organizations.
Preston's career began at institutions like Hewlett-Packard, Advanced Micro Devices, and Price Waterhouse Management Consulting before he caught the startup bug in 1990. Since then, he has co-founded over a dozen companies and developed deep expertise spanning AI, system architecture, databases, infrastructure, and web technologies.
Today, Preston mentors, advises, and invests in more than a dozen early-stage startups — most of them AI/tech-focused — and serves on the boards of many. He brings a rare combination of enterprise rigor and founder instinct to every company he works with.