Press & Media ~3 min read

Featured in Orlando Voyager: Highland's Story, In My Own Words

Evan Ross
Evan Ross
@evanrossfl
Evan Ross featured in Orlando Voyager

Orlando Voyager just published a feature on Highland Private Office. The piece covers more ground than most interviews I've done, and I appreciate the team for giving it the room it needed.

Featured In
Orlando Voyager
"Community Highlights: Meet Evan Ross (Borenstein) of Highland Private Office"
Read the Full Interview →

If you've followed along here for a while, a lot of the threads will be familiar. Poppy. The early Celltronix years signing personal guarantees at twenty-three. The COVID stretch when over a hundred families were depending on the calls I was making, and my first son was born in March 2021 in the middle of all of it. The pivot into Highland and Naveron. Why I'm spending so much time on Central Florida acquisitions right now.

A few moments from the conversation that I want to pull out and sit with for a second.

On the leverage that doesn't show up on the invoice

The interviewer asked what makes Highland different. The honest answer is the model itself. Most firms in this space are built on big teams and big overhead, which means big retainers and a lot of layers between the client and the person actually doing the work.

I built Highland the opposite way. It's intentionally small, intentionally senior, and heavily AI-leveraged behind the scenes. The leverage shows up in the work, not in the invoice.

That's not just positioning. It's the operating thesis. Small team, big leverage, AI doing as much of the heavy lifting as it can. It's the same thesis I'm betting on with the acquisition work, and it's why this chapter of my career feels different than the last one.

On the curriculum nobody signs up for

The hardest stretch in fourteen years of running Celltronix was COVID. There was no playbook for any of it. I was figuring out how to be a dad for the first time and trying to keep the doors open for a hundred-plus families in the same breath.

The struggles are really the curriculum. Every hard moment is now something I can draw on when I'm advising a Highland client or scoping a Naveron project. Nothing was wasted, even the parts that felt like they were.

That's the line from the interview that sat with me longest after we finished. It's also the most honest thing I can say about the past fifteen years.

On risk

I'm a risk-taker by definition. Every entrepreneur is. But the risks have all been calculated. The frame I keep coming back to is pretty simple. Avoid the kind of risk you can't come back from. Take real risk when the upside is real and the downside is survivable.

The biggest risk most people take in their lives is the one they don't recognize as a risk at all, which is choosing to stay where they are.

That's the part I want my kids to internalize. The world rewards the people who recognize quiet risk for what it is.

Read the full piece

The Orlando Voyager team did a great job. If you want the longer version of how I got here and where the next chapter is going, the full interview is here.

And as always, if any of this lands and you want to talk, you know where to find me.


Want the longer version of any of this?

Highland is where I do the operating work. Naveron is where I build the AI. If either matters to you, the door is open.

Visit Highland →