By Arun Ghosh
Look, I'm going to tell you something that most people don't want to hear.
Your first commercial real estate deal is probably going to suck.
And that's exactly why it's going to be the best thing that ever happens to you.
I see it all the time. Someone comes to me at Hutfin, they've been analyzing deals for 18 months, they've built spreadsheets that would make a NASA engineer jealous, and they still haven't pulled the trigger on a single property.
You know what's happening? They're waiting for the perfect deal.
Here's the problem. The perfect deal doesn't exist. And even if it did, you wouldn't recognize it because you haven't done your first deal yet.
The Real Education Starts After You Buy
You can read every book. Watch every YouTube video. Attend every seminar. But nothing teaches you commercial real estate like actually owning commercial real estate.
Your first property is your tuition. It's the price you pay to get into the game.
Think about it like this. When you learned to drive, did your parents put you behind the wheel of a Ferrari? No. They gave you the family sedan and sent you to an empty parking lot.
Your first commercial property is that parking lot.
It's where you learn how to actually underwrite a deal, not just theoretically. It's where you figure out what cap rates really mean when you're staring at a leaky roof. It's where you understand tenant relations when someone calls you at 11 PM because the AC died.
Every Successful Investor Has a "First Deal" Story
I've never met a successful commercial real estate investor who looks back at their first property and says "yeah, that was flawless."
They all have stories. The property that needed way more work than expected. The tenant who turned out to be a nightmare. The market that shifted right after closing.
But here's what they also say. "I learned more from that one property than I did from years of research."
Because experience compounds. The lessons from your first property make your second property easier. The second makes the third easier. By property five, you're operating at a level that first-time you couldn't even imagine.
Stop Optimizing for Perfection
Most people treat their first commercial property like it's their only shot. Like if they don't hit a home run, they're out of the game forever.
That's backwards thinking.
Your first property should optimize for one thing: learning. Not maximum returns. Not the perfect location. Not impressing your friends.
Learning.
Get a property that's small enough that a mistake won't ruin you. Simple enough that you can actually manage it. Cheap enough that you can afford to make errors.
Then get in the arena and start learning.
The Portfolio Mindset
Here's what changes everything. Stop thinking about "a property" and start thinking about "a portfolio."
Your first commercial property is not an isolated event. It's the first domino. It's the first at-bat in a very long game.
When you shift to portfolio thinking, the pressure comes off that first deal. You're not trying to retire off property number one. You're building skills, relationships, and capital that will compound over the next 10, 20, 30 years.
The investor who buys an okay property today and learns from it will lap the person who's still "researching" five years from now.
What Your Second Property Looks Like
Want to know the beautiful part?
Your second property is already going to be 10 times better than your first. Not because the market changed. Not because you got lucky. Because you changed.
You'll know what questions to ask. You'll know which red flags actually matter. You'll have relationships with lenders, brokers, and contractors. You'll understand the real numbers, not just the theoretical ones.
And that third property? Even better.
By property four or five, you'll be the person other people come to for advice. You'll be the one they think "just knows how to find good deals."
But it all starts with property number one.
The Decision
So here's where you are right now.
You can keep waiting. Keep researching. Keep building spreadsheets. Stay comfortable.
Or you can accept that your first commercial property is not your last commercial property. That it's okay for it to be imperfect. That the goal is to learn, not to be perfect.
At Hutfin, we work with investors at every stage. But my favorite conversations are with people on their third or fourth property, looking back at their first and laughing about how nervous they were.
They all say the same thing. "I wish I had started sooner."
Don't let that be you five years from now.
Your first commercial real estate property is not your last commercial real estate property.
So stop acting like it is.
Get in the game.
Arun Ghosh
Hutfin
