Zen and the Art of Real Estate Investing with Jonathan Greene

A Masterclass in Off-Market Seller Dialogues


Looking to scale off-market? 


One of the most common mistakes, if not the most common mistake people make when trying to get into the off-market acquisition game is they send the same boring postcard to everyone. 


Different sellers have different personas so you can’t send the same generic postcard every time. 


Take your off-market acquisition game to the next level by first learning the different off-market seller dialogues and how you can approach them.


1. The Concerned Citizen letter 


This is specifically for out-of-state property owners on properties that you are walking by. This is predicated on the fact that you need to walk by the property for the next six months. Once you’ve done a deep dive into the neighborhood, reach out to the out-of-state owner. This letter works best via text or letter or postcard.


The conversation could go like this:


“Hi! I was walking by your property at 123 main street, and I noticed that it’s in disrepair. I looked you up because I am a local real estate investor I saw you’re out of state. If you’re ever looking to offload this property because you don’t want to have a property in another state, I’m happy to have a discussion with you about that and come up with a win-win agreement where we’re both happy. What do you think?” 


2. The “I want to be just like you” Letter 


This is a letter that you would send as a brand new real estate investor to other local real estate investors who own three or more properties. If you’re telling them you want to be just like them, then you have to believe it as well. 


Offer value when you can. It’s a great way of doing data dives and figuring out how to make more connections with people that have done more business than you. 


3. The neighborhood investor letter

This is for people who have lived there for a long time. Here’s what your letter could look like:

“I would like my first investment to happen inside my own neighborhood. I’ve been targeting these properties based on a list to see who owns them the longest. I see you’ve owned this one for a long time, but it’s rented out. If you were ever interested in getting rid of this property or selling it at a fair price, I would be excited to have that conversation. Thanks.”

4. Your caretaker letter

The caretaker letter is for the older folks who know where they’re going. The first and most important question that you need an answer to an off-market seller acquisition is: Where are you going next? 


That’s because a lot of times, younger heirs are looking forward to either that house or that investment. And they may be resistant to their grandparents selling the house that they wanted to move into with their new spouse.


Again, this is for older sellers, and people who’ve lived in a house for a long time, who are very resistant to change. They want to sell it, but they don’t want anyone to ruin their house. 


Sample script:


“We’re going to take care of your home, just the way that you did. We are going to upgrade it. But we’re not going to take the character out. We want to be the conduit to the next level. We want to take what you’ve done in your home for years, and we want to transfer it to a new owner who’s going to appreciate the home the same way.”


5. The divorce letter


The mistake that most off-market acquisition specialists make is dealing with the divorce and talking to just one party. If you’re talking to one party in a divorce situation, you’re not getting the whole story. You’re probably getting a quarter of the story because it’s contentious sometimes. 


6. Probate letter for the heirs 


You have to be more mindful about your approach because when you’re dealing with death, you have to figure out a win-win. And most of the time, the heirs have opposing views so it’s very hard to negotiate. 


Also, your dialogue needs to be softer and try to offer potential amenities (ex. You’re taking care of the things and helping them clean out the house).


Bonus: Pre-foreclosure opportunities


Some people don’t want to admit that there’s been a list of pending or pre-foreclosure, and that’s because they’re embarrassed. They don’t want to leave the house and they also don’t want to admit that it exists. So you’ll get hard resistance on pre-foreclosure.


Just be very mindful when you’re approaching a pre-foreclosure that somebody’s not going to want to admit it. Hence, your approach needs to be much softer. 


Sample dialogue: 


“There’s a chance that these records are correct. And at some point, you fell behind. I am looking to help people out by buying houses that people are behind at a fair price.”


Ultimately, only use these letters as a guide. At the end of the day, what matters is your authenticity. If you want to learn more about these off-market seller dialogues, check out

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