Different Thinking for Different Times - Gregory Winningham shares insights on how strategic support and organizational efficiency can transform small businesses.

Different Thinking for Different Times with Gregory Winningham. Steve Lentini talks with Gregory Winningham, a strategic partner for founders who want to do more of what they love and spend less time trapped in operations, admin, and decision fatigue. The conversation focuses on how leaders can rework their calendars, delegate better, and build a business that runs with more clarity, accountability, and less stress. Gregory shares how he helps small business owners, especially in wellness and lifestyle businesses, identify bottlenecks, reduce meeting overload, and create simpler systems that support growth. If you’re feeling stuck in the weeds, this episode is about making room for better thinking and better leadership.

Key topics:

• In this episode, Gregory explains his role as a strategic partner and executive on demand, helping founders resource the things that block them.
• He shares how he got started as an executive assistant in Maine in 2016 and built his career across tech, nonprofit, medical, startup, and wealth management environments.
• Steve and Gregory discuss how different thinking often requires a different person or outside perspective to reveal dormant strengths and better ways of working.
• Gregory breaks down why many founders struggle with delegation, decision fatigue, and the habit of trying to handle every part of the business themselves.
• He explains how he looks first at calendars, weekly structure, and meeting overload, then works backward into strategy, accountability, and workflow design.
• The conversation highlights how a 90-day roadmap helps turn vague goals into a real operating plan with clearer priorities and swim lanes.
• Gregory shares a simple early-career lesson that still shapes his approach: sometimes the most powerful tool is just saying no.
• He describes how AI workflows, templates, and centralized systems can reduce duplicate work, save hours, and keep teams from reinventing the wheel.
• Steve and Gregory talk about trust, confidentiality, and the loneliness many owners feel when they’re forced to make important decisions alone.
• Gregory shares his ideal client profile: overwhelmed founders in wellness and lifestyle businesses with about 5 to 20 employees, especially coaches, gyms, clinics, retreat centers, and related companies.
• Reach out to Gregory if you would like to think about your company in new ways.

Gratefully yours, Steve