It’s not the sexy part of the journey. It’s not the part that gurus online like to highlight—but it’s the reality. Everyone has to start somewhere, and for me, that started with a move back home to Montana.
I had a goal: to buy my first property. What I didn’t have? A clear plan—or enough money. It was time to lay the groundwork.
I had a goal: to buy my first property. What I didn’t have? A clear plan— or enough money. It was time to lay the groundwork.
On Halloween, I packed up my apartment, loaded a U-Haul, and put my stuff in storage. The moving process didn’t go as smoothly as planned as the truck got stuck on a street that was closed for trick-or-treating — maybe the universe’s way of telling me to slow down and enjoy the moment.
With no furniture left except for a few chairs that weren't worth storing, we sat outside my empty apartment, handing out candy from the nearest bodega. A fitting sendoff before I hit reset.
Learning Before Doing
I went from complete independence in NYC to suddenly living at home again. I had flashbacks to high school as my mom texted me when I stayed out too late, wondering where I was. No, I didn’t have a curfew. But I did have… let’s call it a concerned roommate.
If I couldn’t invest yet, I could at least prepare like hell for when the time came.
That winter in Montana was the longest stretch of time I’d spent with my mom and brother in years, and in many ways, it was great. I was working remotely, skiing on the weekends, and eating home-cooked meals daily. But in the back of my mind, I was impatient. I wanted to start doing.
Since I couldn’t take action just yet, I put my head down and learned.
- I read every book recommended by BiggerPockets—at least a dozen.
- I listened to real estate podcasts while driving my brother to school.
- I went deep into laws and regulations—printing out the Fair Housing Act, state landlord-tenant laws, and relevant case law. I didn’t just read them; I annotated them.
- I created processes—move-in checklists, maintenance logs, and tenant screening criteria—before I even had a property.
- I ran hundreds of pro formas on Zillow listings to sharpen my deal analysis skills.
I spent hours at a coffee shop just to get out of the house, trying to regain a sense of independence while waiting for my savings to grow. Waiting was hard. I’m not someone who likes to sit still, and this was the first time in my life where progress wasn’t about working harder—it was about being patient while I built the foundation for my next move.
this was the first time in my life where progress wasn’t about working harder—it was about being patient while I built the foundation for my next move.
The Fear of Jumping In
At some point, though, I started to get… comfortable. My mom’s cooking was good. I was skiing regularly. Working remotely from Montana was a pretty good gig.
No. I was making excuses.
Sitting on the couch running pro formas was way easier than risking my savings on a bad deal. If I never pulled the trigger, I couldn’t fail, right?
I was in limbo—I had knowledge, I had some money saved, but I had no action. One afternoon, I sat down and built an Excel sheet called “Runway to Financial Goals”—literally counting the days until I could make an offer, putting me on a deadline. I had to conquer analysis paralysis.
Then, I created a business plan that would guide me through the storm of buying my first property.
The Non-Negotiables: My Buy Box
Instead of overthinking every listing, I created a buy box—a strict set of criteria that a deal must meet before I considered making an offer:
✅ Lower my cost of living. House hacking my first deal would free me from rent and give me more cash flow for future investments.
✅ Multi-family (2-4 units). Ideally 4 units, because more tenants = more people helping cover my mortgage. But no more than 4—anything over becomes commercial real estate, which means different financing.
✅ Location: Union City or Jersey City. Still close enough to NYC to maintain a social life, but far enough to get better returns.
✅ Property condition: On a scale of 1-10 (1 being condemned, 10 being new construction), I wanted a 6-7. No full guts, no tear-downs. Just cosmetic and minor structural renovations where I could add value.
✅ Positive cash flow projected within 2 years. If the numbers didn’t work in that timeframe, I wouldn’t even consider it.
This was my framework. No more overanalyzing. Either a deal met these rules, or I moved on.
Armed with that, I booked a flight back to NYC, rented a room in a 5th-floor walk-up, and made a promise to my mom: "I’ll be back in two months—with a house."
"I’ll be back in two months—with a house."
What’s Next?
The business plan was set. But finding a deal? That was just the beginning.
Dozens of showings and rejected offers – competing with deep-pocketed investors taught me one thing fast: if you can find a good deal, so can everyone else. I knew I wasn’t going to get rich off my first deal—but I couldn’t even get the mediocre listings to return my calls.
Next week, I’ll break down how I navigated the house-hunting process—and why finding the right deal took longer than expected.
This is just getting started. Follow along.
