2271 - Creating High-Value Group Coaching Programs That Attract Premium Clients with Success Made Simple's Cailen Ascher

Josh Elledge

Published on: 19/09/2025

In this episode, Josh Elledge talks with business coach Cailen Ascher, founder of Success Made Simple, about her journey from one-on-one coaching to group programs. They explore how group coaching helps entrepreneurs scale their businesses, reclaim time, and design transformational offers, including strategies for pricing and identifying ideal clients. Cailen also shares her approach to building a business that supports a balanced lifestyle, highlighting her three-day workweek and family time at her Berkshires lake house.