Come Empty. Leave Full.
Where leadership teams leave the noise behind, get honest, and build what comes next.
Built for the Conversations That Matter Most.
A private executive ranch — designed by Jess Stewart for leaders willing to do the work.
what is the empty wineglass?
This Is Where the Work Happens.
Most teams don't have an information problem.
They have a clarity problem.
An alignment problem.
An execution problem.
The Empty Wineglass was built to solve them — not with another conference, not with another retreat, but through real conversations, hard decisions, and the work most teams keep avoiding.
Designed For Leaders
who it’s for
Executive Leadership Teams
Founders & CEOs
Boards & Ownership Groups
Leadership Peer Groups
Family Businesses
Private Client Teams
How teams use it
Strategic Off-Sites
Annual Planning Sessions
Quarterly Alignment Meetings
Masterminds
Jess-Led Workshops
Executive Retreats
Private Client Sessions
The Spaces.
THE EXPERIENCE
More Than a meeting
Strategy. Honest conversation. A few experiences you can't get anywhere else.
And the one thing every leader runs out of — room to think.
Builder. Operator. The Billion-Dollar Coach.
Meet Jess
Ranch-raised and self-made, Jess Stewart built a company from her kitchen table, scaled it to global reach, and sold it for eight figures.
Decades spent building businesses, leading teams, and navigating growth taught her one thing: the best decisions rarely happen in the middle of the noise.
She built The Empty Wineglass for one reason: leaders need a place where they can finally think.