Quick update. I’m flying out next week to Indianapolis to do a due diligence trip for a commercial retail property I’m under contract to buy. I figured this could be a cool behind-the-scenes learning opportunity. If there’s anything you want me to record, walk through, or break down while I’m there so you can see what commercial underwriting / due diligence looks like in real life, drop it in the comments. Tell me what would be most helpful and I’ll try to capture it while I’m on site. Due to PSA confidentiality I won't be able to live stream any of it but would be happy to create something after we close.

Here’s a lesson I learned again today in real estate investing, and I wanted to share it with you guys — because anything I learn in the field is worth passing along. And honestly, if you guys learn lessons in the field too, PLEASE share them here. It helps all of us. Lesson: Don’t chase deals. Ever. It’s so easy to get emotionally attached to a deal you’re underwriting. You start to like it, you picture it working, you’ve already put in time and effort… and then the seller comes back with a curveball or someone starts outbidding you. When that happens: do not budge from your underwriting. Don’t “just stretch a little.” Don’t start giving away terms you’re not comfortable with. That’s how good deals turn into bad deals. This is fresh for me because I just went through it on an RV park. I made an offer, we negotiated everything, and I sent over the purchase agreement. Then at the last minute they came back and said there was another party who wanted to match my offer… but they were willing to do $30,000 non-refundable. And I’ll be honest — because I’d already put so much effort into it, I got roped in. So I started inching. “Ok fine, I’ll raise the price.” “Ok fine, I’ll do all cash instead of seller financing.” “Ok fine… yada yada yada.” It started turning into one of those situations where you’re negotiating against yourself. The guy I was “competing” with even found my info online and called me trying to guilt trip me — saying I was screwing him over and screwing up his kid’s life because his kid wanted the park. And I’m like… dude, this is business. We both have the right to bid. Then it got crazier: he claimed he’d do $100,000 non-refundable on a smaller RV park AND he'd limit his due diligence period to 14 days… and that was my moment of “Nope. I’m out.” So I backed out. And here’s the wild part: the sellers came back to me afterward because that guy didn’t follow through. So yeah — the lesson I learned (again) through this process is: ✅ Stick to your guns.

Gabe, Thank you so much for your time today, it was short and understandable, I do appreciate you quickly understanding the strategy. I’ll write up the LOI’s on targets and let you know, I’m so green on this industry and clueless what Im doing, but sure is fun and your pod cast #1 thanks again have a wonderful day

Most investors are still underwriting deals the hard way. I’m not. 😄 Lately, when I get an Offering Memorandum (OM) for a self-storage facility, mobile home park, RV park (and sometimes multi-tenant industrial or multifamily), I run it through a single “battle-tested” AI prompt that forces the underwriting to be conservative and buyer-favorable—the way it should be if you actually want to protect your downside and still hit strong returns. ✅ What this prompt does (in plain English) It tells the AI to act like a seasoned commercial underwriter + transaction specialist and produce exactly 3 deliverables: 1. A full internal underwriting report (risk-adjusted assumptions, pro forma NOI, DSCR targets, realistic rent growth, expense inflation, capex reserves, etc.) 2. A buyer-favorable LOI at the suggested price (clean, professional, credible — not some lowball mess) 3. A respectful email to the broker explaining the rationale and asking the 3–5 biggest questions we need answered 🔒 The secret sauce: conservative assumptions Most OMs are optimistic. My prompt automatically “stress tests” the deal by default, like: - bumping expenses - limiting rent growth - baking in vacancy - adding real capex/reserves - using higher exit cap rates than the OM wants you to believe In other words: it underwrites like a buyer who plans to own the asset through real-world problems, not spreadsheet fantasy land. Why this matters Even if you don’t use the AI’s numbers verbatim, it gives you: - a fast first-pass underwriting - a negotiation-ready offer package - a broker email that keeps relationships strong (while still being firm on price) If you want the exact prompt… Comment “PROMPT” and I’ll paste it in here (or DM it to you). 👇

Most people think “building a real estate team” means hiring employees. But honestly, the first “team” you need is your third-party team — the people you can plug into deal after deal, who already know how you operate, and who keep you out of trouble (and save you a ton of time). Here are the core roles I think every serious investor should have lined up: 1) A real estate attorney (not optional) This isn’t just for lawsuits (though you’ll be glad you have them if something goes sideways). A good attorney helps with: - Closing support (reviewing documents, spotting weird language, explaining what you’re actually signing) - Lease disputes / tenant issues - Demand letters when you need to get someone’s attention fast - General “this feels sketchy” situations that come up during ownership If you own enough property long enough, you will run into disagreements. Having an attorney you already trust means you’re not scrambling when the pressure is on. 2) Title + escrow you can reuse over and over This one is huge. You want a title/escrow team that: - moves fast - communicates clearly - already understands how you work The goal is to be able to say, “Here’s my purchase agreement,” send it over, and they just run the play. 3) Broker teams (deal flow) Even if you’re off-market heavy, brokers still matter. Good brokers can: - bring you deals before they hit the open market (or at least early) - give you intel on pricing, comps, and who’s active - help you understand what’s happening in a submarket And if you treat them well and close when you say you’re going to close, you become someone they want to bring deals to. 4) Boots on the ground (local eyes and hands) This is the role people underestimate the most, especially when you’re investing out of town. Whether it’s a reliable handyman, a trusted local contact, or a property manager’s field team — you need someone who can: - walk units - take photos/videos - check on projects - verify what’s really happening (not what someone says is happening)