Phil Wendler, EVP at FloSports, opens up about building a career that blends heart, hustle, and high-level thinking.

From childhood engineering hacks to Princeton football to leading a platform with 40K+ live events, Phil shares what it means to operate “in the zone”—and how he stays there.

Come for the media insights, stay for the leadership lessons, walk-up songs, and yes… the love.

Evan Bregman, General Manager of Streaming & Direct-to-Consumer at Tastemade, joins the show fresh off a $90 million acquisition by Wonder—the company behind GrubHub and Blue Apron—with plans to build the mealtime super app of the future.

In this one-on-one debut, Evan shares how his journey from Onion-style satire and film school to CTV marketing and miso has all come full circle. He breaks down customer acquisition tactics, FAST channel growth, and what it means to build frequency in an ad-driven ecosystem. Plus: streaming strategy talk, Sunday deep dish gospel, UX nostalgia, first-party data dreams, and how Tastemade is becoming the storytelling engine powering Wonder’s commerce empire.

Also: what it really means to Wubble Down—and why the broth is always worth it.