Hillary Zio has spent more than 20 years exploring the world of wine — working in restaurants, teaching wine classes, travelling, writing books, and eventually opening Isola Wine & Tapas in New York’s Hudson Valley.

She’d imagined having her own wine bar for years. But turning that dream into a business at 38 meant weighing responsibilities, finances, family life, and the realities of running a restaurant.

Agnes and Hillary explore:

• Her unexpected introduction to wine at a California harvest

• The winding career that eventually led back to restaurant ownership

• Finding the right location and designing a business around her life

• Why a disappointing first year taught her the value of patience

• The difference between youthful risk-taking and informed decisions later in life

• Researching an idea thoroughly — including knowing when to abandon it

• How divorce, motherhood, and personal loss changed her priorities

• Why some dreams are worth pursuing and others are worth releasing

• The unexpected opportunities that followed opening Isola

• How to talk to a sommelier, explore unfamiliar wines, and spend wisely

Hillary also shares the surprising story of finding love again, her daughter’s entrepreneurial ambitions, and why she believes curiosity and human connection matter so much.

Whether your own dream involves a business, a different lifestyle, or simply trying something new, there’s plenty here to think about — and some excellent wine advice along the way.

Listen below and then share this episode!

I’ve spent more than 20 years building a career in wine and hospitality, and almost none of it followed a straight line.

I started working in restaurants young, became a certified sommelier, worked in wine retail and wholesale, helped open Corkbuzz in New York City, and eventually became Director of Education at New York Vintners, where I taught hundreds of wine classes. In 2016, I published my first book, The Unfiltered Guide to Working in Wine, about what it really takes to build a career in an industry that looks far more glamorous from the outside.

Then life changed. I left New York City, became a mother, moved to the Hudson Valley, and took one of the biggest risks of my career: opening my own restaurant, Isola Wine & Tapas, at 38.

Today, I’m a restaurant owner, sommelier, educator, consultant, entrepreneur, mother, and two-time author. My second book, Still Working in Wine: Twenty Years Later, revisits the career and life I imagined in my twenties and what actually happened along the way.

My newest venture, Client Ready, is taking me into an entirely different industry: professional development for law firms. I’m creating an online training program that teaches attorneys the hospitality, client entertaining, wine confidence, and relationship-building skills that law school doesn’t teach. It’s built around a simple idea I’ve learned from two decades in hospitality: being excellent at your profession and making people feel genuinely comfortable, valued, and connected are two very different skills.

It’s also my first attempt at building a scalable digital education business, rather than another business that requires my physical presence. I’m navigating everything from creating an online course and validating a new market to selling corporate training, and I’m happy to share that journey as it unfolds.

I love talking about wine, but the conversations I’m most interested in go much further: entrepreneurship, calculated risk, career pivots, hospitality, motherhood, ambition, burnout, getting older, building multiple income streams, and redefining success when the life you wanted at 25 isn’t necessarily the life you want at 40.

I’m especially comfortable discussing the parts people often leave out: mistakes I’ve made, what owning a restaurant is really like, learning to delegate, starting over in a new industry, and the tension between loving your work and not wanting your entire life to depend on you showing up for it.

And of course, I can talk wine all day! I love making wine approachable rather than intimidating, exploring the islands and coastal regions of Europe, debunking wine myths, and helping people feel confident ordering, buying, and enjoying wine without needing to become experts.