S1E2: The Power of Simplifying When Everything Collapses

Glen Smith built GDS Wealth Management from relentless cold calls and early financial uncertainty into a firm managing roughly $1.8 billion. But behind that business growth was a fear of failure that shaped nearly every decision he made, pushing him to work harder, hold on tighter, and believe that every important problem ultimately belonged to him.

Cory Bengtzen and Tommy Aoki have helped turn SkyShare from a small aviation brokerage into a fast-growing private jet company competing against some of the biggest names in the industry. But beneath the polished world of aircraft, owners, and luxury travel is a business entering a much harder stage of growth. As SkyShare pushes toward becoming a top 10 operator, Cory and Tommy face the pressure of limited systems, expensive talent, pilot retention, acquisition goals, AI disruption, capital needs, and a company that has outgrown the scrappy tools that got it here. You’ll hear how two lifelong friends are trying to preserve culture, simplify operations, align incentives, and build the discipline required to scale a high-stakes aviation business without losing what made it work in the first place.

Eric V. Holtzclaw built his career turning ideas into businesses: launching Liger Partners (yes, that’s a Napoleon Dynamite reference), building a research company, and learning firsthand what happens when a founder’s ambition collides with a revenue ceiling. Having to figure out how to leave a difficult partnership, while under serious pressure to keep growing, forced him to look inward and explore what it was he really wanted out of his business.