The Marathon – Winemakers, Industry Leaders & The Reason for the Season, Steve Gross

In our final dispatch from the 2025 DTC Wine Symposium, we sat down with industry leaders, keynote speakers, and winemakers from across the country to explore the biggest conversations happening in the wine world.

The highlight, as always, was Steve Gross from the Wine Institute, the foremost expert on wine shipping regulations. If you’re a winemaker who relies on direct-to-consumer sales or a wine lover who enjoys having bottles shipped straight to your door, you have Steve to thank—and y’all better go to Free the Grapes and sign up now!

This episode is packed with countless insights, deep discussions, and incredible guests. Dust off a bottle (or two), settle in, and get ready—this one is an epic.

The Guest Rundown:

Rishad Tobaccowala – AI expert, futurist, thought leader, and author focusing on marketing and the future of work—now a bona fide friend of the pod.

Susan Kostrzewa – Acclaimed wine writer and editor with extensive industry experience.

Jason Haas – Our longtime inspiration and friend. Partner and General Manager of Tablas Creek Vineyard, advocate for organic farming.

Steve Gross – The great and powerful Vice President of State Relations at the Wine Institute, focusing on industry policies.

Jessah Diaz – Director of Direct-to-Consumer Sales at Cakebread Cellars.

Susan DeMatei – Founder of WineGlass Marketing, specializing in digital and DTC wine sales.

Kasey Helt – Director of Hospitality at Center of Effort Wines.

Anne Zwink – Winemaker at Soldier Creek Winery in Iowa. She heard last year’s show and came to the conference this year. It’s working!

Anne Robie – Writer, speaker, and leadership expert focusing on workplace culture.

Stephanie Wycoff – General Manager of Gary Farrell Winery in Sonoma.

An essential listen for winemakers, industry insiders, and anyone passionate about the future of direct-to-consumer wine sales.