I sat down with my close friend Ben Willig on Talking New York Real Estate with Vince Rocco recently, and what was supposed to be a standard industry conversation turned into something much more personal, a look back at how two college football teammates ended up building separate but deeply connected careers in one of the most competitive luxury real estate markets on the planet.
Here is the story.
And the lessons inside it.
How Two NYC Luxury Brokers Met on the Football Field
Ben and I met at Trinity College in Hartford, Connecticut.
We played football together on a team that won 31 straight games.
He was a 290-pound offensive lineman.
I was a linebacker who liked to talk.
A lot.
Every single day in practice, we went at each other. Offense versus defense. All-league player against all-league player.
That was the real game, not Saturdays, where we would win by 50.
The most intense football of my entire college career happened Monday through Friday, going head-to-head with a guy who refused to back down no matter how much I ran my mouth.
That kind of competition forges something different.
When you pour your heart out alongside someone and push each other to the absolute limit, the friendship that comes out of it outlasts anything.
From Bed-Stuy Brooklyn to Wall Street and Real Estate
After graduation, neither of us had a plan.
Ben went to Credit Suisse on Wall Street.
I moved to New York because I figured that is where TV and media happen. My only real thesis at the time was that the football hype videos I had been making on iMovie were going to turn into something.
I took a four-bedroom apartment in Bed-Stuy, Brooklyn, before it was the Bed-Stuy you know today, and rented out every room, including my own.
Ben and I ended up sleeping on air mattresses in a V-shaped attic.
Our clothes were piled in the middle of the floor.
Our laptops were open at midnight.
By morning, my air mattress had deflated, which became my cue to get up and start running.
That was the start of our real estate careers.
No furniture.
No food in the fridge.
Just two guys figuring it out.
Ben would leave for Credit Suisse at 6 a.m. and come home at 10 p.m.
I would be out renting basement apartments in Bushwick for $600 a month.
Then from 10 to midnight, we would have our nightly strategy meetings.
And then this guy would sleep for two hours, wake up, and go run 15 miles.
I always admired that.
Ben was relentlessly consistent from day one.
Not flashy.
Not loud.
Just disciplined, focused, and always learning.
At midnight, after an 18-hour day, he would pull out a Lean Six Sigma book and tell me we needed to build systems for operational efficiency.
I still quote that today.
My First Real Estate Deal in New York City
The guy who had us renting apartments in Brooklyn told me to sell a house in Ridgewood, Queens.
I was not even licensed.
I did not know what marketing was.
I did not understand anything about the transaction.
But I did the only thing I knew how to do.
I picked up the phone and called everyone in my network from college.
Ben ended up buying the house.
My "commission" was that the guy paid off my credit card debt, about five grand.
That was my first closing.
It was Ben's first closing too.
Then I started managing the property with him.
We were learning about being principals together.
We dealt with tenants, navigated creative financing, and survived the 2008 financial crisis while living in that same attic on deflating air mattresses.
Ben credits the spark of his real estate career to that house.
I credit it to having someone next to me who showed up every single day, no matter what.
How Friendship and Competition Coexist in Real Estate
Here is the part nobody talks about.
There was a period where Ben and I were competing directly.
He was building his brokerage.
I was building mine.
We would go back to Trinity for career day events and sit on opposite sides of the room, each trying to recruit the same interns.
We went from wearing the same uniform to wearing different ones.
That is an adjustment.
But here is what I have learned after nearly two decades in this business.
New York City real estate is too big for any one person to own.
One broker cannot physically work with every single client.
And the friendship piece is actually what makes you better.
I cannot do everything myself.
I will not.
I need people like Ben and Vince and the network we have built over decades.
That is how you survive market cycles, navigate hard deals, and keep your head on straight.
If you want to go fast, go alone.
If you want to go far, go together.
Five Lessons from Nearly 20 Years in NYC Real Estate
Looking back on my career and the conversation with Ben, a few things stand out.
Speed is a skill.
I learned this doing rentals downtown, thousands of deals on the Wall Street corridor.
If you are not responding to your client immediately, somebody else is.
That mentality never left me.
Content compounds.
I was making videos in 2007 when my college football coach told me to take them down.
I wore a microphone under my pads and created a whole alter ego persona.
People thought I was crazy.
If I could tell my younger self anything, it would be to make more content.
Longer form.
Stay with it.
Systems win.
Ben planted that seed with Lean Six Sigma in the attic.
Today, when you walk into the Lundgren Team at SERHANT., there are spreadsheets, document workflows, and specific rules for everything.
When the whole team operates that way, it runs like a symphony.
It is not that serious.
I used to take every lost client like a dagger to the heart.
Every deal that fell through wrecked me.
I once refused to take a vacation because I was so wound up about my pipeline, and then none of those deals hit anyway.
The universe was sending me a signal.
Relax.
Enjoy the ride.
You are going to be in this business a long time.
Outlast everyone.
A mentor once told me, "Just survive longer than everyone in your real estate class, and eventually all their clients become your clients."
Survive for ten years and you will be fine.
I took that literally.
Why Increasing Complexity Is Good for Top NYC Agents
The increasing complexity of this industry is actually what excites me most.
Buyer broker agreements.
Pied-à-terre tax.
Mansion tax.
The FARE Act.
All of it makes the barrier to entry higher, and that is a competitive advantage for anyone who has already been through it.
We do not have to scramble to learn.
We know these things inside and out.
We communicate them clearly.
And clients come to us because of that.
The cream rises to the top.
It always has.
The agents who invest in knowledge, systems, and real relationships are the ones who will still be standing in another 20 years.
The Most Valuable Asset in Real Estate Is Not a Listing
When I think about Ben, the first thing that comes to mind is that he is sharp as a whip.
Incredibly caring.
Committed to learning in a way I have never seen from anyone else.
He builds people.
He coaches them.
He watches their lives change.
That is what success looks like at this stage.
And if you ask him about me, he will probably say he just pictures my name in lights somewhere with a big smile.
He is not wrong.
But here is the real takeaway.
The most valuable asset in this business is not a listing.
It is the person who has your back when your air mattress deflates at 4 a.m. and you need a reason to get up and keep going.
Build those relationships.
Protect them.
They will outlast every market cycle, every deal, and every commission check you will ever earn.
We don't sell four walls.
We sell brands.
And the brand starts with who you surround yourself with.
This post is based on my conversation with Ben Willig on Talking New York Real Estate with Vince Roco. Watch the full episode here.
