Jay sits down with some of the world's most influential founders, CEOs, and investors to illuminate the exact steps they took to build their vision.

Together, they unpack real origin stories, high-stakes trials, and unlearned lessons to give up-and-coming visionaries the insight, mindset, and practical playbook needed to learn, grow, and execute at the highest level.

Watch on Youtube

Featured Guests

  • Marc Lasry

    Co-Owner of the Milwaukee Bucks

    Live from the CORE Club in Midtown Manhattan, the billionaire investor breaks down how he built his fortune from the ground up and pivoted into sports franchise ownership. Marc shares his core principles on high-stakes dealmaking, future market opportunities, and legacy.

    Watch Episode

  • Jimmy Pitaro

    Chairman of ESPN

    Description: The head of the world’s leading sports entertainment network sits down with Jay to unpack his personal career playbook and leadership principles. They discuss the strategic decisions that propelled his rise through digital media to the pinnacle of sports entertainment.

    Watch Episode

  • Jen Tooker

    First Selectwoman of Westport, Connecticut

    Jen sits down with Jay to share her strategic vision for the city’s economic and cultural future. She unpacks the dynamics of operating across the public and private sectors, managing high-stakes pressure, and surrounding yourself with effective teams.

    Watch Episode

  • Adam Goldberg

    Founder & CEO of PopUp Bagels

    Adam shares the operational playbook behind turning a local Westport concept into a booming, nationwide culinary brand in just four years. He and Jay unpack why he bet on bagels, how he engineered a differentiated model, and the secrets to scaling into Manhattan and beyond.

    Watch Episode

  • Kal Amin

    Managing Partner at 1848 Ventures

    Drawing on his background as an executive at Google, Spotify, and Sounder.fm, Kal dives into how artificial intelligence is reshaping modern venture creation. He shares key takeaways from leading media giants and his current focus on empowering small and mid-sized businesses.

    Watch Episode

  • Dan Woog

    Founder & Publisher of 06880

    Jay flips the script on Westport’s premier local voice to explore what truly builds a resilient community and what makes a story resonate. They discuss Dan's experience publishing 17,000 newsletter issues and his perspective on where hyper-local media is heading next.

    Watch Episode

  • Dan O'Keefe

    CIO for the State of Connecticut

    Connecticut's chief growth strategist breaks down his career navigating major corporate exits and IPOs alongside his current work building the state's economic future. He and Jay explore emerging opportunities for startups, small businesses, and innovation hubs across Connecticut.

    Watch Episode