2025-2026 Uptick Entrepreneur Schedule
- September 22-25: In-Person Retreat (Richmond, VA)
- October 7, 12:00 PM - 1:30 PM: Online Huddle
- November 4, 10:00 AM - 3:00 PM: In-Person Session (Fredericksburg, VA)
- December 2, 12:00 PM - 1:30 PM: Online Huddle
- January 15, 9:00 AM - 3:00 PM: In-Person Session (Fredericksburg, VA)
- February 3, 12 PM - 1:30 PM: Online Huddle
- March, Day TBD, 10:00 AM - 3:00 PM: Online Session
- April, Day TBD, 12:00 PM - 1:30 PM: Online Huddle
- May 18-21: In-Person Retreat (Virginia Beach, VA)
Our Gathering Formats
- Huddles are gatherings designed for honest connection and peer support. These are intentionally casual, camera-on conversations where participants share challenges, celebrate wins, and encourage one another. Huddles take place over an extended lunch hour. These sessions are vital for building trust and staying grounded in community throughout the year.
- Sessions are our core teaching events and are generally held in person. These include practical instruction, group discussion, and time with guest speakers. Each session is designed to move you forward in the curriculum and connect learning to real-world leadership. Sessions are scheduled for the first Tuesday of each month at 9:30 AM EST unless otherwise stated on the calendar due to speaker availability. Lunch and snacks are provided.
- Our in-person retreats offer extended time for deep connection, rest, and learning. These are shared experiences across multiple Uptick cohorts that provide space to step back, reflect, and grow as leaders. Meals, hotel accommodations (shared with another same-gender participant), and guest speaker sessions are included. Participants who prefer to have a single room may do so by covering the cost personally. Travel to and from the retreat location is the responsibility of each participant.
We understand the weight of this commitment. As entrepreneurs, every hour you step away from your business is a sacrifice and we don’t take that lightly. That’s why our retreat and session schedules are intentionally designed with built-in time each day to check emails, return calls, and manage urgent needs. During retreats, we also include dedicated work blocks so you can stay connected without stepping out of the experience. Our goal is to support your growth without pulling you away from what you’re building.
Attendance Policy
Uptick Entrepreneur is a high-investment experience not just in content, but in community. Every gathering is designed to build trust, continuity, and transformation over time. For that reason, attendance is essential.
Retreats are mandatory. Your presence is required for both the September and May retreats. Only one session or huddle may be missed. More than one absence from our monthly gatherings may result in dismissal from the cohort. If you must miss please contact your cohort leader immediately.