Updated 19 days ago on .
Building Deals That Don’t Break Later (Win x Win x Win)
I’ve been watching something play out over and over again… and I’ve lived it myself too.
Most of us get into this space focused on one thing:
“Can I make this deal work?”
Our numbers may "check out". Rent can look solid and our exit seems clear. So we push it forward. Right? But here’s the part that doesn’t get talked about enough. A deal can “work", and still quietly break everything around it...
I recently walked through a deal with someone on the lending side. At first glance, it looked solid. But once we started peeling back the layers..
o The income didn’t fully match the deposits
o The structure was… let’s just say “early stage”
o Liquidity looked okay until you zoomed out
Nothing was “wrong” on paper but it wasn’t tight either.. And that’s where most people get caught.
Here’s what I’m starting to understand. The right partners don’t just help you "close deals"… They walk beside you, so that you learn to see what you currently aren't.
They ask questions that feel annoying in the moment but mean everything, when it comes to the overall success. Questions like:
- o “Can you verify this?”
- o “Why is this structured this way?”
- o “What happens if this shifts 10–15%?”
It can feel like friction but it’s actually protection. A lot of investors chase speed early and I get it. I did too. But speed without alignment turns into big messes with cleanup later. Restructuring costs and/ or worse… deals that drain you slowly..
What I’m focused on now is different. Wins - for the people in it, the deals and the long term stable structures.
And if it doesn’t hit all three… it’s not a win. That's a disguise waiting to reveal itself.
The wild part?
When you find the right people to build with... They don’t just look at this deal… They’re thinking, “How does this hold up 5 deals from now?”
If your partners only show up at closing… you’re probably building alone.
If they’re in the trenches asking hard questions before it ever closes… you might have something real.
Curious how others are approaching this.
Are you optimizing for speed right now… or building something that actually holds over time?
