Never Grow A Business With The Goal of Selling It.

I scaled from $2M to $500K net income while working 5x harder. Here's why I'll never make that mistake again.

I was sitting in my office at 7:30 PM staring at a lease agreement for $125,000 a year.

Three years. Personally guaranteed solely by me.

For an office in Chicago that I had no business opening.

I stared at it for what felt like an hour. My hand was hovering over the mouse. Every fiber of my being was screaming at me to close the laptop and go home.

But I was building something. I was scaling. I was going to be the guy who grew a national brokerage and sold it to private equity for nine figures.

So I clicked “sign.”

My stomach immediately dropped to the floor.

I tried to convince myself it was going to work out. I had just landed two big-name brokers who ran the South Side Chicago market. This was the domino that would make everything fall into place. More recruitments would follow. The office would print money.

Except my gut knew the truth.

I was fucked.

When Small Felt Like Winning

Four years earlier, my company was me and four kids fresh out of college in one office in San Diego.

I was netting over $2 million a year from age 24-26. I loved what I did. I closed deals, I mentored agents, I built something that felt like mine.

My monthly expenses? $15,000.

Then I joined an entrepreneur peer group and everyone was talking about exits. Eight-figure acquisitions. Scaling nationally. Building something you could sell.

And just like that, I wasn’t a real estate guy anymore.

I was a guy who was supposed to be building something impressive.

The Nightmare of “Growth”

From 2024 to the end of 2025, I went from 9 employees in 1 office to 42 employees across 5 offices.

My monthly expenses exploded from $15,000 to $110,000.

And my income? It dropped from $2 million a year to less than $500,000.

Let me say that again: I was working five times harder and making 75% less money.

I wasn’t a broker anymore. I was a full-time recruiter, a content creator making videos I hated, and a babysitter for people who resented giving me a cut of their commissions.

The agents I trained would close a deal and think: “Why am I giving this guy 40% when I don’t even need him anymore?”

They weren’t wrong. The business model was broken. Low margins, high overhead, unpredictable revenue.

But I kept pushing because I had a story in my head about who I was supposed to become.

The Sleepless Nights

After I signed that Chicago lease, I couldn’t sleep.

Not for weeks.

I would lie in bed doing math in my head. Projections. Worst-case scenarios. The recruits we were counting on weren’t coming. The office was going to bleed money for several months.

My monthly expenses kept climbing and my revenue was a roller coaster. Some months we’d be way up. Other months we’d be deep in the red.

I kept everything bottled up inside. I didn’t tell my fiancée how scared I was. I couldn’t tell my leadership team. I’d just lay there in the dark, sleep-deprived and terrified, convinced I could somehow will my way through it.

Then right before I started negotiating to sell the company, three of my top producers walked into my office together.

People I considered close friends.

They told me they were leaving to start their own team. They were becoming my competitors.

No warning. No heads up. Just: “We’re out.”

That’s when I really knew it was over. I was heartbroken.

The Conversation With AI

For two weeks, I argued with ChatGPT about whether I should sell the business.

I told it everything. How I felt. How much I hated my life. How the Chicago lease was going to bankrupt me if I held on much longer.

It kept telling me to get rid of it.

I kept resisting.

Then I broke.

I reached out to the buyer. A mutual friend had connected us months earlier and they’d made me a lowball offer I’d dismissed immediately.

Now I was desperate, but I couldn’t let them see it.

I acted like the business was crushing it. And honestly, on paper it was. We were doing huge revenue numbers.

But revenue doesn’t mean jack shit. It just strokes your ego.

What matters is net profit. And mine had evaporated.

Three months of negotiation later, I took a deal that was the opposite of everything I’d dreamed about when I started scaling.

It wasn’t impressive. It wasn’t a Forbes headline. It was barely enough to feel good about.

But the second I signed, I felt lighter than I had in three years.

The Aftermath No One Talks About

You’d think selling would be the happy ending.

It wasn’t.

Right after I sold the brokerage, my real estate syndication partner asked me for the $500,000 capital contribution I’d promised after selling one of my properties.

I couldn’t do it.

Two years of investing cash to grow a business I hated had traumatized me. The thought of giving up half a million dollars sent me into a panic.

So I said no.

That started a two-week text war that ended our partnership.

And then my ego kicked in: “You don’t need him. Start your own syndication company. You deserve more of the fees!”

So I did.

I raised over $2 million from investors for a 28-unit property in San Diego.

Got it under contract.

And then I realized: I don’t want to do this either.

I was finally listening to my gut.

Real estate brings out the worst in me. The side that cares about money over people. Greedy Jason. Angry Jason. The guy who’s constantly pissed off because someone “wronged” him.

So right now, as I’m writing this, I’m canceling that deal. Returning $2 million to investors. Eating a $35,000 loss.

I’m in the biggest identity crisis of my life.

What I Wish Someone Had Told Me

The core lesson isn’t “don’t scale for money.”

It’s this: I ignored my gut to chase something that would impress other people.

That 7:30 PM moment in my office when my stomach dropped? That was my soul screaming at me to stop.

But I didn’t listen because I had a picture in my head of who I was supposed to be.

The guy who sold for nine figures. The guy on the Forbes list. The guy who “made it.”

I over-promised and over-delivered to everyone except myself.

I kept everything bottled up because successful people don’t complain, right?

All my mentors were successful business people. They supported my goal. They made me feel like I was doing the right thing.

No one said: “Get over yourself, you stupid fucking idiot. You’re destroying your life to impress people who don’t care about you.”

Where I Am Now

I have one employee. A virtual assistant in the Philippines who I probably hired too soon because my ego told me I was too wealthy to do my own scheduling.

I’m winding down my client work. Referring deals out. Selling off properties so I can manage less and think more.

I’m getting my health back. The stress gave me ulcers and IBS. My stomach was destroyed from two years of constant anxiety & stress.

I spend time with my three dogs and my fiancée, Kristyna. We’re getting married in March 2027.

And I’m writing. Creating. Trying to figure out who I actually am.

People tell me I’ve lived three lifetimes in the past eight years.

Maybe. But I spent most of those lifetimes ignoring the only voice that mattered.

The Question You Need to Ask Yourself

So here’s what I want you to sit with:

What decision are you making right now to impress others instead of serving yourself?

What are you building because it looks good on paper, not because it makes you come alive?

What’s your version of that 7:30 PM lease signing?

Your gut already knows the answer.

The question is whether you’re going to listen to it or spend the next two years trying to prove it wrong.

I hope you choose better than I did.