First Time Trying to Underwrite a Deal — Feeling a Bit in Over My Head

[Joey Stephens]

Hey everyone,

I’m trying to take the first real step toward buying my first investment property, but I’m hitting a wall trying to properly underwrite the numbers. I’ve watched the videos, downloaded a few calculators, and run some scenarios — but honestly, I still don’t feel confident I’m doing it right.

I’m not afraid of work, risk, or renovations… I’ve renovated countless investment properties for other people over the years and have a solid group of subs for everything on that side of things. But when it comes to the financial side of investing — underwriting, strategy, long-term planning — I feel completely bankrupt.

I know what it takes to bring a house back to life, but I’ve never bought one with the math first. This side of it feels like a different language.

If you’ve been where I am and figured it out, I’d seriously appreciate any advice, resources, or just a gut check. I’m trying to do this right and stay honest about what I don’t know.

Thanks in advance — looking forward to learning from you all.

– Joey