Chris Stilwell
Founder & CEO, TSSG
Experience across 175+ generator dealerships, with cross-market insight into sales, leadership, systems, and scalable execution.
Private Owner Mastermind
The Founding Ten
Ten owners. Two proven perspectives. One Mastermind built for consequential decisions.
This is a selection process
Step 1
Complete the private application
Step 2
Chris and Jesse personally review fit
Step 3
Final selections are completed by September 15
Built for the conversations that matter
A private room for consequential decisions.
This is not a conference, seminar, or networking event. Ten carefully selected owners will work directly with Chris Stilwell and Jesse Rack on the systems, constraints, and decisions shaping their companies.
The room combines national dealer pattern recognition with real-world operating execution. Company size alone does not determine fit; the goal is to assemble ten owners whose experience, perspective, and willingness to engage make the entire group stronger.
10
Only ten owners or senior operators will be selected.
1:1
Direct access to two proven industry perspectives.
90
A focused 90-day execution plan supported by three virtual council sessions.
Two proven perspectives
Strategy informed by the market. Execution proven in the field.
Jesse Rack
CEO, RACK Electric
A leading independent operator in the Southeast who has expanded RACK through organic growth, acquisitions, strong teams, and repeatable systems.
Inside the experience
Focused work, candid discussion, and a plan to execute.
The schedule is intentionally intimate, giving the group time to work through real decisions while building the trust required for honest owner-to-owner conversation.
The Program
- TuesdayAfternoon arrival, welcome, private experience, and group dinner.
- WednesdayFull private mastermind day.
- ThursdayFinal morning working sessions followed by an afternoon RACK operating visit.
- FridayBreakfast and departures.
What You Leave With
- 2.5 days of private mastermind work.
- A clear 12-month direction and 90-day execution plan.
- Three virtual council sessions during the following 90 days.
- Direct exposure to national dealer patterns and proven operating systems.
- A private peer room built around candor, confidentiality, and execution.
Waterstone Resort & Marina
A waterfront setting designed to help you step out of the day-to-day.
The Founding Ten takes place at Waterstone Resort & Marina, a Curio Collection by Hilton resort on the edge of Lake Boca Raton. The boutique waterfront setting pairs private balconies and water views with easy access to the beach, a heated outdoor pool, waterfront dining, and the comfort needed to recharge between working sessions.
This is more than a meeting room. It is a private, destination experience designed to create the space for sharper thinking, stronger relationships, and decisions that are difficult to make while managing the normal demands of the business.
Lake Boca waterfront
Private room balconies
Beach nearby
Heated outdoor pool
Waterfront dining
Complimentary Wi-Fi
Explore Waterstone Resort & Marina →
Invitation and application only
Apply for consideration.
Answer each question candidly and thoughtfully. Chris and Jesse will personally review every application to build the strongest possible room of ten owners.
Submit your application
Share your goals, constraints, experience, and what you would contribute to the room.
Personal review
Chris and Jesse evaluate fit, readiness, and the perspective each applicant brings.
Selection by September 15
Final selection of the ten participating companies will be completed by September 15, 2026.
Application required.
Completing this form does not guarantee acceptance. Only ten owners or senior operators will be selected.