When your company can’t grow past you, it’s time to grow yourself.
From starting a business by accident to scaling multiple companies—and learning some hard lessons along the way—Josh McAfee brings an honest and insightful lens to what it really takes to lead and grow. In this episode, Josh joins Jane Gentry to talk about the mindset shift that transformed him from a high-performing individual contributor into a people-first leader.

He shares the story of why his first company plateaued, how he built a radically different kind of partnership in his second, and why emotional intelligence, feedback, and strategic alignment are make-or-break skills for today’s CEOs. Whether you’re a founder, a mid-market executive, or a leader who wants to grow without burning out, this conversation is filled with moments that will challenge and inspire you.

(09:17) How personal growth limitations can cap company success
(10:59) How Josh approached partnership differently the second time around
(15:01) Creating space for different communication styles in leadership
(17:53) Why every CEO needs a circle of influence
(22:23) The joy of helping others grow—why leadership is personal for Josh
(24:15) What it means to “invest in people” as a scaling CEO
(27:37) Leadership blind spots and how honesty keeps you sharp
(32:37) Why misalignment in hiring isn’t just a process problem
(34:27) Josh’s advice for young leaders: set better goals

Josh’s story is a masterclass in humility, growth, and leading with purpose—and a reminder that the best leaders are the ones who never stop learning.