Bad Calls

Back in 1999, my dad and I created H2O Performance, a website for buying and selling performance powerboats. And honestly? It was GOOD. Niche, specific, strong traffic, great presence at races — everything a 23-year-old with zero startup experience could ask for.

My dad already ran a massively successful advertising agency and was one of the early leaders in web advertising in the early 2000s. Meanwhile, I was “running” H2O Performance like someone who thought startups required more enthusiasm than strategy.

The fatal mistake?
My closest competitor leaned hard into community, built a simple message board, and sold the entire thing to a larger company.
Yes — a message board beat me.

The Silver Lining

Even though the business didn’t become what it could’ve been, it did open doors.
I learned how to work with wealthy clients, high-net-worth boat owners, and racing teams. I even got the chance to race several times — and the crazy part?

👉 I won the 2001 APBA World Championships in the H2O Performance boat in the One Design class.

So the site didn’t sell for millions…
…but I did walk away with a world championship title and a crash course in how rich people yell at you when their boat photos load slowly.

I’ve always been ahead of the curve when it comes to real estate marketing and tech.

For 15 years, my Miami site — JoshSteinRealtor.com — ranked Top 3 on Google and generated the majority of my sales. A quiet flex, but yeah… that’s how it went.

In the prop-tech world, IDX is the holy grail — the tool that lets you display MLS listings on your own website. So naturally, I decided to build my own IDX company with two other guys in Miami. We grew fast, got an office, landed hundreds of clients, and were actually doing really well.

Then came the mistake.

My partners wanted to go all-in on building big, custom, complicated websites.
I wanted to build a simple, clean SaaS plugin that every real estate agent in America would want — the kind of thing you scale to the moon.

They wanted artisan hand-crafted websites.
I wanted mass production, McDonald’s efficiency.

And our team at the time?
Let’s just say they weren’t exactly Y Combinator material.

At the same moment, I was completely burned out on Miami and already dreaming about Mexico City. So one day… I just walked away. No fight, no drama, no lawsuit. I packed my bags, moved to Mexico, and never looked back.

The company still exists today and seems to be doing fine.
But in my heart, I know one thing for sure:

👉 If we had focused purely on the IDX SaaS plugin, it would’ve been a monster — maybe even a Zillow acquisition story.

Instead, it became another “almost.”
Good news is: I ended up in CDMX living my best life, so maybe it wasn’t a total loss.

By this point, I’d already been living in Mexico City for years, running VIVE Polanco and doing extremely well. We were selling tons of Miami and Mexico properties to wealthy LATAM clients, and I wanted to scale even faster.

Then came the distraction.

A wealthy, well-connected woman approached me about forming a partnership. She had government connections, deep pockets, access to influential circles — basically the kind of person you assume can open every door in the building. I’d handle the marketing and lead generation. She’d cover sales and the ad spend.
50/50 partnership. Clean. Simple. Equal.

And to be fair… at first, it actually worked.

In the first year, we sold over $38 million in new development with commissions between 6–7%.
Translation: around $1.8 million in commissions on a $200,000 investment.

In startup math:
“That’s insane ROI. Do it again.”

But then the plot twist hit.

About six months later, she and her very questionable assistant — someone who proudly radiated “low-budget villain energy” — suddenly blocked me from my own tools. CRM, lead systems, ad accounts, everything. And then they threatened to sue me.

For what?
To this day: no idea.

Rumor is someone fed her a lie or tried to sabotage me… but she never even sat down for a conversation. I sent bank statements, data, documents — everything.
Silence.
She disappeared with the money and ghosted like a toxic ex with a private jet.

Final damage?
👉 Over $600,000 lost.

Final lesson?
👉 Just because someone is wealthy and connected doesn’t mean they’re not a crook.

And if someone’s assistant looks like they practice chaos for sport… run.

I’ve had a few more wild stories like these — trust me, the list could be longer — but I’m not here to build a shrine to my failures. Every builder has scars. Mine just happen to come with spicy plot twists, stolen money, and the occasional world championship boat race.

But here’s what matters now:

Lately, I’ve had big opportunities come my way — the kind I would’ve jumped at in the past.
Now? I’ve learned to say no.

Because time is money.
And spreading yourself across too many projects is the fastest way to lose both.

So at this stage in my life, I’m putting my energy into the companies I’ve already built — scaling them, strengthening them, and learning to protect myself and my team with the same intensity I used to pour into chasing the next shiny thing.

Bad calls happen.
But the smartest call is focus.