I thought saving up the money was the hard part, turns out it was just the beginning. Reality check: finding the right deal is a grind.
The market right now? Brutal. Interest rates are high, prices keep climbing, and bigger fish—investors with deep pockets—can afford to eat a higher purchase price and still turn a profit. I wanted to make money with real estate, but turns out so does everyone else. That’s why I had to get strategic.
I was discouraged after something like my 10th offer was beat out by a competing offer at a price point I couldn't stomach. I felt incredulous that I couldn't even spend my hard earned (and saved) money. I started thinking that maybe I couldn't do this.
I kept going. I knew I just had to get in the game — anyway possible. The first deal wouldn't be my best, but from it I would learn, adapt, and get better. I just needed one.
I just needed one.
First Round: Building Intuition
The first round is a gut check. It tells you if something is worth your time to even analyze. It is based on your intuition, but how does one have an intuition with no experience? You gotta do your homework, and look at a LOT of houses. The more houses you see, the more you get used to what you want and, more importantly, what you don't want – your buy box.
My sights ultimately landed on Union City and Jersey City. This may feel a bit random, but to get to this stage, I evaluated 10+ potential areas around NYC, including Sunnyside (Queens) and Sunset Park (Brooklyn). I walked the neighborhoods, tested the commute, checked out the gyms and restaurants. The numbers tell you a lot, but not everything — you have to see if you’d actually want to live there.
I picked this area because I knew it was livable and growing, and I could compete against bigger investors. Here’s why: Union City has some of the strictest rent control in the country, but if you’re owner-occupying, you can “break” rent control and increase your rent revenue based on the value you add to the house. I was willing to do something that the big fish wouldn't, and this is where I found my wedge. That process took six months of bureaucracy, but it gave me an advantage over investors who didn’t want the hassle.
I was willing to do something that the big fish wouldn't, and this is where I found my wedge.
Second Round: Running the Numbers
If a property made it through the first round, I ran a pro forma—breaking down income, expenses, and long-term cash flow.
I had set a goal to analyze 50 properties per week. Week after week I would peruse Zillow, copy details over the excel, look up tax info, etc, etc, and repeat. It was route and honestly, quite boring. However, after I analyzed 100, I started to get a feel for it, after 500 I could spot a diamond, or a red flag, off the bat.
Here’s the thing: There is no magic number for what makes a good deal. Some people chase the 1% rule (monthly rent = 1% of purchase price). That’s great in theory but not realistic in NYC. You have to know what a good return looks like in your specific market.
I learned this lesson the hard way when I found a “perfect” deal. It cash flowed on paper, hit all my criteria, and I rushed to text my agent. I was so hyped—until I got to the open house 15 minutes early and saw a line around the block. Turns out, if you can see a deal, so can everyone else. There were 10 offers before I stepped inside. If it looks too good to be true, it’s probably underpriced.
Turns out, if you can see a deal, so can everyone else.
Third Round: Get in the Game
You have to tour properties. A lot of them. I probably walked through 100+ homes. Zillow can only tell you so much — you have to see what’s out there.
And you need a good agent. My first agent? She called me out of the blue after I clicked the Zillow, "tour this house button." I suddenly received a phone call, when I answered they said, "Hi, I'm your agent."
Just like that I was in the game. She was nice, but not what I needed. She recently started and had never sold (or purchased) a multi-family home. Alas, came the inevitable break up – and I'll admit I was nervous and it almost felt easier to just keep using the okay agent —but it’s necessary. Do not rely on chance to find the best team.
Breaking up with an agent feels like breaking up with your therapist
At first, I felt bad—like I was breaking up with my therapist. But I knew if I wanted to be successful, I needed the right team. In the end, I found an agent who had been selling multi-families longer than I’ve been alive.
What Comes Next
After dozens of offers, I finally got one accepted.
Sounds like the finish line, right? Not even close.
Next week, I’ll break down how my closing turned into a nightmare of weaponized incompetence, material non-disclosure, outright lying, and legal negligence. The part that most investors don’t talk about.
Follow along. This is just getting started.
