Agent Series 26: From Homeless to 100 Deals a Year

Real Estate Insiders Unfiltered · Feb 25, 2026 · 52m

What if the secret to 100 transactions a year wasn't online leads… but real relationships?

In this raw and surprisingly vulnerable episode, James and Keith sit down with Montrose, Colorado broker Shawn Carroll, a 32-year industry veteran who averages 100 homes a year in a town of just 20,000 people.

But this isn't a "systems and funnels" conversation.

Shawn shares how he went from sleeping in his office, walking miles to show homes because he had no car, and being told he was "too unapproachable" for the business… to becoming one of the most dominant relationship-driven agents in his market…