Jim talks with Kyle Jekelek about the part of building a career that doesn’t make for good storytelling: the slow accumulation of judgment.

They cover early misreads, the temptation to confuse motion with progress, and the quiet skill of knowing when to push and when to stop. Along the way, Kyle draws an analogy to selling on the New York City subway—learning quickly who’s actually listening, when to speak, and when to move on without wasting energy.

It’s a measured conversation about ambition without mythology—and why the long game rewards clarity, timing, and restraint more than noise.

Jim Lombardo sits down with **Tony Borden** of **Greenwich Village Social Club** for a fast-moving, smart conversation about building places—and brands—that people actually return to. Tony brings sharp insight on why experience beats hype, how consistency quietly outperforms trends, and what most businesses still misunderstand about hospitality in the age of content and video.

They move easily from music and culture to strategy and execution, unpacking how taste, restraint, and judgment matter more than flashy tools. Tony’s wit and clarity turn this into less of an interview and more of a masterclass disguised as conversation.

If you care about creating something memorable—and not just loud and pretty—this episode lands.

Jim Lombardo pulls up a chair with Erin Reddan, founder of ECR Vintners, for a conversation that tastes less like a lecture and more like a well-balanced pour. They talk about building a wine business without the cork-sniffing, starting ECR in a New York apartment, and why trusting your instincts matters just as much as trusting your palate. Erin shares what it really takes to turn passion into product, how entrepreneurship resembles a long fermentation process, and why success—like good wine—should be enjoyed, not overanalyzed.

Finish: Bright, confident, and best enjoyed with curiosity. Pairs well with risk-takers, founders, and anyone who orders wine they actually like.