I’m Jonathan Casillas. I started in lending in 2000. In 2004 I joined the Army and served as a 15P aviation operations specialist, including one tour in Iraq from 2008 to 2009. The job was managing flight operations: scheduling missions and tracking aircraft. I also went through intelligence analyst school (96B, now 35F) and did that work alongside it, building the most accurate picture possible from incomplete information and making the call before that picture was finished.
Structuring financing uses both. Every draw, payoff, and handoff has to land where and when the deal needs it, with a plan for when something goes wrong. You can have every number today and still not know how they’ll move: where rates go, what the market does, or what the inspection missed. You still have to decide, so the structure has to hold up when those numbers change.
Most of my work ends in a loan. The loan is the result. The structure is the work, and it’s what this firm is built around.
Why this firm exists
I started in 2000, at 17, cold calling for a shop that did owner-occupied home mortgages. It was a good one. By 18, I was a junior loan officer there. I learned how loans get made, and what it looks like when a lender actually takes care of its borrowers.
About ten years later, I moved into commercial lending, first at a shop that showed me how not to do it. Borrowers were put into deals they couldn’t afford, or deals that were simply bad for them, because the loan paid well. I didn’t stay long.
A few shops later, I landed at one that did larger deals and was run by a former banker. Every step had a process, and that the process got followed. That’s where I learned how much of a good outcome is decided before anyone signs.
Along the way, I invested in my own deals and small pieces of larger deals. Wholesaling came later, because clients wanted to buy from someone who understood both the financing and how the deal had to work for the operator. Sitting on that side of the table made the lesson stick: a loan is only as good as the structure behind it.
I get paid when financing closes. So the incentive to close something is real, and I won’t pretend it isn’t. The difference is what I do before that: qualify your constraints first, tell you when a deal doesn’t fit, and pass on the ones that would only work for me.
How I work
Constraints before proposals. What won’t work, what you won’t do, and what the exit has to be. A structure built before those answers is a guess.
The whole deal, not the rate. Rate matters, but it rarely breaks a deal. Draw timing, appraisal gaps, and takeout risk do.
Sequences, not single deals. I look at where a deal fits in what you’re building, not just whether it closes. When you’re stepping into an asset type you haven’t run before, it can make sense to take a smaller stake first and learn the asset with a partner who has. One path I’ve seen work: under 20 percent ownership on the first deal, 40 percent on the second, your own on the third. It depends on your experience, your capital, and the deal. Sometimes going straight in is the right call.
Clear lines on what I control. I’m not the lender, and I won’t promise approvals or closing dates. I control how the financing is structured and who sees it, and I’ll tell you when something falls outside that.
Veteran-owned
In a tactical operations center in Iraq, there’s one call nobody wants to hear, whatever their job: “We have a fallen angel.” It means an aircraft is down. The room goes silent. Nobody second-guesses or stops to look things up. Everyone falls back on their training and does their part to get the team home.
Nothing in lending compares to that moment. But the lesson carried over: how people perform under pressure is decided long before the pressure shows up.
Deals have their own bad days. An appraisal comes in short, a lender changes terms, a takeout falls through. That’s not the time to start figuring things out. It’s why I structure financing for the bad day, not just the plan.
If that’s how you want your next deal looked at, send it over.