Delivering Value: Tough Career Moments - Lessons from Growth, Marketing & Product Leaders 3x Founder: The Hardest Conversation I Ever Had With My Team—And What I Should Have Said Instead (Kirk Reynolds)
In this episode, Kirk Reynolds, seasoned founder and now the creator of Wilder Retreats, opens up about the hardest conversations of his career. From telling his 55-person team that he was selling the company without sharing the real reason, to navigating the identity crisis that came when the acquirer shut it down, Kirk reflects on what it means to lead with honesty, even when fear and burnout make it tempting to hide.
He also shares how blunt feedback about being a “people pleaser” reshaped the way he manages, and why processing failure and loss is just as important as chasing growth. This is a conversation about leadership, identity, and the courage it takes to be fully yourself when the stakes are high.
In this conversation, you’ll learn:
- Why trusting your team with the truth builds deeper loyalty and respect
- How to process the emotional toll of selling, losing, or reinventing a business
- Why intention and self-awareness can turn difficult feedback into lasting growth
Things to listen for:
(00:00) Intro
(01:51) Kirk’s first steps into entrepreneurship
(06:26) Building and scaling Discover Outdoors
(08:31) Joining Abercrombie & Kent after exit
(11:02) Tough feedback and personal growth
(20:48) Balancing leadership with family life
(25:26) Lessons from difficult conversations
(26:04) Deciding to sell Discover Outdoors
(28:14) Telling the team about the sale
(30:31) Reflecting on honesty in leadership
(34:27) The emotional weight of selling
(37:48) Finding gratitude in new beginnings
(40:03) Preparing mind and body for conversations
(45:32) Setting bold, ambitious goals
Resources:
Connect with Kirk:
LinkedIn: https://www.linkedin.com/in/kirk-reynolds/
Wilder Retreats: https://discoverwilder.com/
Connect with Andrew:
LinkedIn: https://www.linkedin.com/in/andrewcapland/
Substack: https://media.deliveringvalue.co
Join Growth OS: https://deliveringvalue.co/growth-operating-system
Hire Andrew as your coach: https://deliveringvalue.co/coaching