2025 Entrepreneur of the Year Alyssa Pine on the Event of the Summer + What She’s Been Battling Behind Closed Doors 💔

March 20, 2026 · 1h 1m · Season 4

About this episode

Alyssa Pine discusses her journey as an entrepreneur while facing personal challenges and shares exciting news about her upcoming events.

While throwing epic events, going viral on social media, and running a successful weekly market, Alyssa Pine was quietly handling something the public never knew about. In her third appearance on "Seacoast Stories," the 32-year-old Live Freely Market founder speaks for the first time about the heartbreak and grief she's battled since finding out a devastating piece of news two days before throwing the first Live Freely Fest in August 2024. Plus, she tells host Troy Farkas some exciting news regarding Live Freely Fest 2026, recent developments at the Live Freely Market, winning the Stay Work Play Entrepreneur of the Year Award in 2025, must-do summer activities in her beloved Hampton, business lessons learned from her father, Shane Pine (The Community Oven, Shane's Texas Pit, etc.), and more. To check out the Live Freely Market, you can pay Alyssa and her vendors a visit at 356 Lafayette Rd. in Hampton. The market is open Thursday and Friday from 11 a.m. - 5 p.m., and Saturday and Sunday from 10 a.m. - 5 p.m. SPONSORS: To get started on a path toward better financial investment, email our friend David Higgins…

People in this episode

Host: Troy Farkas

Guest: Alyssa Pine

Topics covered

entrepreneurship
event planning
personal struggles
business growth
community engagement

Keywords

Alyssa Pine
Live Freely Market
Stay Work Play
Live Freely Fest
entrepreneur of the year
Hampton
business lessons

Mentioned in this episode

Organizations: Stay Work Play

Places: Hampton, Portsmouth