You built the life. But why does comfort feel so... flat?

In this raw, revealing conversation, land investor and former touring guitar tech Josiah Ronco opens up about what happens after the financial breakthrough. From working with OneRepublic to running one of the top land businesses in Florida, Josiah’s income 10x’d—but so did his inner questions.

Drew and Josiah explore:

• The unexpected downside of success
• Whether work-life balance is a myth (or just a buzzword)
• Why boredom on vacation might be the red flag no one's talking about
• How entrepreneurs and addicts might not be as different as you think
• The weird joy of chasing deals, not dopamine

What makes this episode different? It’s not about ambition—it’s about what happens when ambition succeeds.

Josiah doesn’t sell you a dream. He talks about running a lean, high-performing team, the fears that come with sudden wealth, and why he’d rather hike into the woods than buy a Ferrari.

📬 Reach out or send deals: [email protected]

Warning: This one may cause you to rethink your version of “enough.”

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.