I sold my company at 29. Here are the mistakes I made, so you can avoid them.

It's worth the short read.. I promise.

Never grow a business with the intent of selling it. Here’s my story of how I turned a business I loved.. into a prison.

I learned this the hard way. I actually loved owning and running my business, until I started to scale it in hopes of a big exit.

I got nowhere close to the deal I wanted, but I was going to die from stress & anxiety, if I didn’t sell my company.

So, let’s start from the beginning of the end...

I started my first company at 24 years old.

The funny thing is when I went out on my own to start my own commercial real estate brokerage, I thought I already knew everything.

I was 24 years old, making multiple seven figures per year. I had 20 properties under contract, and over $1,500,000 in commissions in the pipeline.

My ego was so big, I couldn’t fit through a door.

I felt invincible and got tired of paying a split to my old company, so I hired three kids out of college, and signed an office lease.

We were off to the races.

6 months before I started JLM Real Estate, an investor in San Diego and I had acquired seven properties throughout San Diego.

We made WAY more money on these properties than I ever did in a year running JLM Real Estate (the company that I never should have grown).

MISTAKE #1: I grew the wrong business.

I am very blessed to have had a strong start in my real estate career at age 21, and to have started buying properties since I was 23 years old.

And no, I am not a trust fund baby.

My mother was a maid and my father was a security guard growing up.

Money was an extremely sensitive topic in my family and that created a lot of fear around money for me.

I’ll never forget my mom crying about how we couldn’t pay the mortgage next month.

I think this is why I am so f**ked up and am always on overdrive. No matter how much I make, it feels like never enough, because of the trauma as a kid.

Anyways, I’ll save the sob story for another time, but the biggest mistake I made was focusing on the wrong business model.

The brokerage business model is horrible. If you’re not familiar with it, let me explain it extremely quick.

In order to sell real estate, you need to have a real estate agent license. In order for that agent to sell a property, they have to hang that license under a broker.

I was the broker.

The broker also hold all of the liability when a client sues the agent.

The agent also expects the broker to pay for most of their expenses and to teach them everything.

In exchange, the broker gets a portion of the total commission when an agent sells a property.

In the first couple of years, I was the broker and mentor to a small group of agents.

I was at every meeting handling 90% of the communications, and I answered every question about contracts and negotiations.

The major issue with the brokerage model, is that once your agents don’t need you anymore, they resent you for every deal that they close.

“I’m giving 30% of my commission to you and I barely need your help anymore!”

“Okay, but do you pay for E&O insurance, the office lease, software expenses, legal fees, marketing material, payroll, and administrative costs?”

When it boiled down to it, that 30-40% the company made on each deal, really was 4-8% after all of the expenses.

Mistake #2: I tried growing a business that is known for extremely low margins.

In the first 3 years, my margins were huge. I thought that I could scale the business, because the numbers looked great.

But, I was such a stupid business person, that I never calculated how much of the revenue came from my personal production from 2021-2023. It was 80% from my production.

All of the largest commercial brokerages are either not profitable or have extremely low profit margins.

I will never forget my lunch with the ex-president of Cushman & Wakefield. He said they did $100,000,000 in revenue and made less than $5,000,000 in profit their best year in 2022.

Cushman also had much higher commissions to the company than I did.

I knew I screwed after hearing this.

I made the deal to sell my company a month after.

Mistake #3: I didn’t meticulously review my financials, until it was too late.

From 2021-2023, the profits were extremely high.

I made the extremely stupid decision to waste all of that money on marketing, instead of just continuing to buy real estate.

I acquired almost 30 properties during those years, but I could have bought and sold a lot more, if I had just an ounce of focus at the time.

So, how did I blow over $500,000 on marketing?

Getting scammed by multiple marketing companies. But, this one specific really screwed me the hardest.

Here was their logic. It’s so embarrassing, I almost don’t want to share it.

They thought that if I created a TV show that was like “Million Dollar Listing” for commercial real estate, that I could turn our company into a nine-figure business.

I loved the idea and signed the contract to get started.

LOL... I wish someone slapped me across the face when I agreed to go along with this idiotic plan.

So, I ended up filming a whole season’s worth of episodes with my team.

Not only did I waste their time and my time, but we never even got the edited footage back from the company.

The CEO of the company just kept telling me that they were working on it, until I stopped reached out.

I had a demand letter prepared from an attorney, but never ended up going through with the lawsuit.

Oh, I almost forgot. The cherry on top is that the same company convinced me to write and publish a book. That was another $50,000 down the drain.

The thing that really haunts me, was that when I interviewed one of this company’s old clients on a podcast, they told me how bad they were.

I brought this up to the CEO, and he immediately made it sound like they were being crazy. My dumbass believed him and not the unhappy clients.

I should’ve listened to my gut and fired him right there.

Mistake #4: Never work with a marketing company that cold emails you.

The best marketers grow through word of mouth and reputation. If they have a team of people always doing cold outbound to people, be very weary of that company.

I will personally never hire a marketing company again. 99% of them are scams who don’t give a flying f**k about your business.

Okay, so 2024 is where it really gets juicy.

I joined a business peer group, called Entrepreneurs’ Organization (EO) at the end of 2023.

Joining EO is one of the best decisions I have ever made, but there was one extremely negative effect that made me eventually hate my company:

A lot of people in EO talk about how they can grow and exit their business.

My first sentence in this article was: Never grow a business with the intent of selling it.

We truly become who we spend the most time with.

Being around all of these high performing entrepreneurs inspired me to grow and scale my company.

Mistake #5: I didn’t grow & scale my company because I truly wanted to. I grew and scaled it because of others indirectly influencing me to do it.

I became a follower. Not a leader of my own life.

I did something because others were doing it.

Because it was the “cool thing to do.”

So, 2024 is when I made the decision to scale my business nationally.

I won’t bore you with the details, but from 2024 to 2025, I grew from 9 employees in 1 office, to 42 employees across 5 offices.

I went from a high producing sales person and a team leader, to a full time recruiter, content creator, and a manager of people.

I hated my day-to-day in those years.

Here is the biggest lesson that I really learned the hard way:

SCALING A BUSINESS KILLS YOUR CASH FLOW.

If you really want to be humbled in life, do what I did:

Netting $2,000,000 per year to netting less than $500,000 when you are now working 5x as hard.

I can’t explain to you the feeling of working 5x harder and making 75% less money.

It was awful.

I also really enjoy making content, but I hated making content for real estate agents.

It was an amazing recruiting funnel and my first marketing idea that actually worked, but I wish I spent all of that time making content for business owners and investors.

Mistake #6: If something you do on a daily basis feels forced and kills your energy. STOP. You are pushing in the wrong direction. Redirect.

The podcast with Hormozi and Tony Robbins really hit me hard on this topic...

I wish that podcast came out three years ago.

Here I was listening to Alex Hormozi like it was the gospel.

Telling me that suffering is good, that it’s supposed to be hard, that we have to endure the pain...

That we should be working all the time.

I was taking advice from someone who was in more pain than me and only more successful than me because of how severe his traumas are.

It’s sad that capitalism rewards the people who are the most broken and the most hurt.

Probably the reason why we have so billionaires who care about money more than people & animals...

Mistake #7: I only listened to broken business gurus, when I really should have been doing deep work in therapy.

What was really killing me at the end of this chapter were the monthly expenses.

My monthly expenses kept rising at a steady rate as I grew, but my revenue was so unpredictable.

Deals would fall apart, people would have slow quarters, we would be extremely negative, and some months we would be extremely positive.

The fluctuations in cash flow were destroying my mental health.

My monthly expenses when I was a small & nimble team of 4: $15,000 per month.

My monthly expenses when I was a medium sized company across multiple office by the end of 2025: $110,000 per month.

Mistake #8: Growing a business with unpredictable revenue.

I will never grow a business again without recurring revenue ever again.

Finally, my exit deal was okay... nothing to be super proud of.

But, I felt so much wealthier because the weight of the crazy monthly expenses were finally gone.

I felt free again.

But, I was also heartbroken.

A lot of people who I considered my close friends left our company and we haven’t talked since.

The one thing I really do miss about having that terrible business is the people.

I wish spent my 20s making more friends outside of work. All I did was work.

Work friend are work friends, especially when you’re the founder/CEO.

Once they don’t need you anymore and don’t see you anymore, you will grow apart.

My final mistake I will leave you with (even though I made a LOT more):

Never try to grow two companies at the same time.

I was growing & scaling a real estate sales business while I was growing a real estate syndication & development company.

Now that I am 100% focusing on the real estate investment company, I feel like I have my life back.

I really focused and refreshed on Monday mornings.

In 2024 & 2025, I felt dead on Monday mornings.

I hope this helps you make the right decisions in business. I have made so many poor ones in my career, that I now make better decisions because of the scars in my brain.

Hopefully you can learn from my pain, so that you don’t have to go through the pain yourself.

If you enjoyed the read, I would appreciate you sharing with others :)