A private group for founders and CEOs carrying responsibility at the top.
For founders and CEOs navigating strategic questions, leadership tension, growth, change, and the conversations they cannot fully have with their team, board, investors, spouse, or friends.
Eight leaders. One 90-minute session every 30 days. A monthly one-on-one with Drew. One in-person Nashville retreat each year.
A room for perspective you cannot get inside the business.
Seasons brings founders and CEOs into a consistent rhythm for telling the truth, thinking clearly, and being challenged by people who understand what it means to have the final call.
It is not networking. It is not curriculum. It is not a room built around advice from people who have not carried real responsibility for a business.
The same small group. The same rhythm. A serious commitment to naming what is true, seeing patterns as they emerge, and helping each other lead with greater clarity.
Serious operators. Plainspoken counsel. Real investment.
Seasons works because the group is made of people who are there to contribute, not just attend.
Members bring real issues, listen carefully, stay curious, and offer perspective earned through lived experience.
The value is present from the first meeting because the caliber of the group matters immediately. Over time, the value becomes more specific as members understand each business and the person leading it.
Guided.
Seasons is shaped by the members and strengthened by Drew’s operator’s eye.
The conversation has direction.
Drew curates who is invited, leads each monthly session, and uses the one-on-one conversations to help each leader turn what came up in the room into clearer judgment.
He brings 24 years of operating experience to the table — scaling a high-seven-figure company across five locations, two states, and more than 250 employees.
His role is to keep the work honest, practical, direct, and grounded in real operating judgment.
Eight seats. Fit matters.
If Seasons feels like the kind of setting you have been missing, the next step is to apply. Drew reviews each application personally before offering an invitation.