In the Spotlight: Silas Deane

Morning, friends! Logan here. For today’s episode, we’re joined by a former Wildcat and recent inductee into UK’s Gatton College of Business and Economics Hall of Fame. We sat down with Silas Deane, founder of VendEngine, who bootstrapped his company from a back-of-the-napkin idea to an $84 million exit… without a single dollar of outside capital.

VendEngine serves correctional facilities, providing a solution that transforms how families support incarcerated loved ones. With no outside funding, Silas grew the company steadily over 12 years, leading to a recent acquisition by Tyler Technologies in 2021.

In this episode, Silas unpacks the realities of bootstrapping in a complex industry, how the pandemic became a surprising growth catalyst for VendEngine, and the hard decisions that shaped his journey. Plus, we get into his philosophy on building technology for underserved markets and why he chose to grow slow and steady instead of chasing venture capital.

What We Discussed:

The Realities of Bootstrapping

Although maintaining equity is great - bootstrapping is not for the weak or impatient. Silas gave us some great insight into what exactly 12 years of building a company off of cashflow looked like.

The Dot-Com Bust & Pivoting to Survive

Lessons learned from the Dot-Com bubble, how he pivoted his first company to avoid collapse, and the similarities between that era and today’s hype around artificial intelligence.

Cloud Technology & COVID-19

Silas’s early bet on cloud solutions positioned VendEngine for massive growth during the pandemic - a case of right place, right time in addition to recognizing a technology shift before many others did.

Staying Involved with UK and Supporting Student Entrepreneurs

As the current Chairman of the Board for Gatton’s Von Allmen Center for Entrepreneurship, Silas has stayed intimately involved with the university and supporting it’s efforts to foster an entrepreneurial spirit in their students. We discussed what role Universities should play in startup ecosystems.

We hope you enjoy this episode! If you have any thoughts after listening, feel free to shoot me a message at [email protected]

Have a great week, friends!

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