He built the thing. Now he’s asking what it’s costing him.

Before Jessey Kwong co-founded Pebble, he was running a global beauty brand out of his living room. Then came burnout. A reset. A quiet pivot into land. And the slow climb toward something that actually fit.

In this episode, Jessey opens up about what most builders won’t say out loud:

• The early signs of emotional overload (and why they’re easy to ignore)
• Leading a high-talent team with no playbook, just humility and instinct
• What partnership looks like when one founder is in the dark and the other has to carry the light
• And the fear behind success: What if I never feel like I’ve done enough?

We also talk work-life rhythm, identity shifts, and how a kid from Vancouver who paints Transformers and builds terrariums found his own version of excellence without losing himself in the process.

This isn’t about building a business. It’s about staying human while you do.

👤 Featuring Jessey Kwong, co-founder of Pebble and writer at imhorribleatbusiness.substack.com

You’ve built the life everyone else wanted. Now it’s time to ask what you want.
Thanks for being with us on The Other Side of Enough.
This isn’t the end of the conversation—it’s the beginning of your next summit.