Stories of Entry

[Chris Chaffin]

Hello everyone! 

I am interested in hearing some of your stories on how you got started into real estate. The good the bad and the ugly. Your successes and failures, how you got through tuff times and how you built your legacies. 

I myself do not have enough capitol, savings or resources at the moment where I feel like i am ready to start. How did you get through the feeling of thinking that you will never get there?

[Ryan Spath]

@Chris Chaffin

I can relate to how you’re feeling! I started from the same place, thinking, “How will I ever afford to buy another property?”

My real estate journey began back in 2013 when I built my first home in the Greater Portland area. A few years later, my job required me to relocate, and I faced that classic question: do I sell it or rent it out? I decided to rent it, and that one decision changed everything. It turned a house I was emotionally attached to into the first piece of what would become a long-term wealth-building plan.

After moving to Idaho, I bought a townhouse on owner-carry terms and rented out one of the rooms to offset my mortgage. That was my first taste of “house hacking,” even before I knew the term. My wife and I began to realize that real estate wasn’t just about owning property, it was about creating options and freedom.

When we eventually sold the Portland home, a Keller Williams agent introduced us to the 1031 exchange. That allowed us to defer taxes and reinvest into two Boise-area rentals, which soon covered our own living expenses. That was our ah-ha moment, realizing real estate could eventually replace our job income.

From there, we just stayed disciplined. Instead of “trading up” our lifestyle every time income increased, we saved up and bought more rentals. We even skipped a traditional wedding and used that money toward our next property. Over time, we leveraged equity through refinances and expanded into Florida, picking up a few more doors there.

Today, my wife and I are back in Idaho with 10 properties, 12 rental doors, and cash flow that exceeds six figures annually. None of that happened overnight. It was a lot of small, consistent steps, and plenty of seasons where it felt like progress was painfully slow.

If you’re feeling stuck right now, that’s okay we all start there. Focus on education, saving, and building relationships in the meantime. You don’t need to have it all figured out before you start; you just need to take that first small step when the right opportunity comes.

It’s not about luck or timing it’s about discipline, creativity, and time in the game.