Kevin Rockwood on Losing Flow, Making Millions, and Feeling… Meh

You finally have the time and money you wanted. So why does it still feel heavy?

In this episode, Drew sits down with Kevin Rockwood, co-founder of Pebble and full-time dad, for a raw and revealing conversation about what success feels like when no one’s watching.

They unpack the emotional weight of hitting autopilot in your business, the guilt of “not doing enough” even when everything’s working, and why freedom without purpose can feel more stressful than the grind ever did.

Kevin gets vulnerable about:
-Losing his flow state after stepping out of daily development
-Balancing guilt, growth, and gratitude as a founder with flexibility
-Wrestling with lifestyle creep, fatherhood, and the myth of early retirement
-Cultural clashes in marriage, money, and multigenerational expectations
-The quiet cost of free time and how he’s rebuilding fulfillment in small, intentional ways

This isn’t a hustle-harder episode. It’s an honest look at what happens after the big goals get crossed off and how to reorient when your calendar, bank account, and soul aren’t in sync.

🎙 Guest: Kevin Rockwood
🏗 Platform: pebblerei.com
📺 YouTube: Search "Pebble REI" for monthly episodes
📱 Connect: Find Kevin on LinkedIn

This is what it sounds like when two high performers talk about what really keeps them up at night.

Hit play if you’ve ever felt guilty for not grinding and wondered if peace is something you have to earn.