Why I Don't Look at My Best Operators' Deals Anymore
There's a stage of the operator-funder relationship where I stop reviewing every deal. I just wire the money. To people I've never met, that sounds reckless. To my top operators, it's the entire point of working with me.
The funder's instinct is to underwrite. The operator's pain is being underwritten.
Most funders pride themselves on the depth of their diligence. Mine is the opposite. The relationship I want with an operator is one where I get out of the way as fast as possible.
"I don't want to do your due diligence for you. I want you to have a machine that's already running. And then I add value to that machine by infusing quick liquidity into it. I don't want to be part of your due diligence process — 'see what Drew thinks.' I don't. My top operators, I don't even look at their deals. I just blindly fund them because I know they have hundreds of track record and there's so much trust built up." — Drew, on Landfans Podcast (Nov 2024)
The trust ladder, in plain numbers
Here's roughly how I think about the trust progression with a new operator:
| Deals together | What I do | What the operator feels |
|---|---|---|
| Deals 1–5 | Full review of every deal — not because I doubt them, because I'm learning their pattern. | Some friction, but the answer comes back fast. |
| Deals 6–15 | Spot-check. I'll glance at the package, ask one or two questions if anything stands out. | Way faster turnaround. Confidence builds. |
| Deal 16+ | I see the address and the dollar amount. If both are reasonable for them, I wire. | The way it should work. They run their machine, I write the check. |
The operators who never get to "blind fund" status
Some operators stay at the spot-check stage forever. Not because they're bad operators, but because their volume is too low or their deal types are too varied for me to build a stable model of their judgment. That's fine. The relationship still works. They just don't get the same speed as a high-volume operator on familiar terrain.
Counterintuitive: my best operators are usually the ones who least need me
"You'd think that my operators are the newer ones who don't have cash. But most of my operators are operators that have cash. They just choose to use my money instead because they want to keep their own capital free for other things." — Drew, REtipster Podcast (Jan 2026)
That fact gets a lot of new operators sideways. They assume capital is a beggar's market — that the funders only fund people who have no other choice. The opposite is true. The operators who least need external capital are the ones who get the fastest "yes." Why? Because they have the track record, the systems, and the optionality. They make my decision easy.
What this means for you, if you're a new operator
Don't try to skip the trust ladder. Pitch me your first five deals like they matter, because they do. The reward isn't lower fees on the next deal — it's a faster wire, fewer questions, and eventually a working relationship where I trust your judgment more than I trust my own underwriting.