From managing other people's properties to buying my own
I’m currently a property manager here in Central Florida, and now I’m stepping into the world of real estate investing. I’m brand new to the investing side, no deals under my belt yet, but I’m soaking up as much knowledge as I can every day. Right now I’m especially interested in creative financing deals: subject-to, lease purchase and owner financing structures. The challenge I’m working through is learning how to communicate value to sellers. I know these strategies can solve real problems for people, but when I get on the phone I get nervous, overthink everything, and end up tongue‑tied. For the experienced investors here, how did you overcome the newbie jitters when talking to sellers? What helped you get comfortable explaining creative deals without sounding unsure or overwhelmed? Appreciate any feedback received.
Most Popular Reply
You actually have an advantage already being a property manager—you have relationships with property owners. I would start talking to your existing clients and letting them know you're looking to buy. You can also ask if they know other owners who may be interested in unloading a property. You may find opportunities before they ever hit the market.
One thing that helped me was watching a lot of YouTube videos, especially wholesalers who actually show or break down their seller calls. Pay attention to how they ask questions, identify the seller's real problem, explain the offer, handle objections, and negotiate. After hearing enough conversations, you start to recognize the same situations and objections over and over.
But I would spend just as much time learning how to underwrite the deal as learning how to talk to the seller. Not all deals are created equal, and creative financing doesn't automatically make a bad deal good. Subject-to, seller financing, lease options, etc. are just tools, and they don't work in every situation.
Before talking numbers, know your numbers. I like looking at both a best-case and worst-case scenario and having multiple exit strategies. What happens if you can't sell when expected? What if the rehab costs more? What if rents are lower, you have vacancy, or you have to hold the property another 6–12 months? Can you rent it, refinance it, sell it conventionally, or wholesale the deal?
The more comfortable you are with the numbers and your exit strategies, the easier the seller conversation becomes. You're not trying to memorize a sales pitch—you're trying to understand the seller's situation and determine whether there's a deal that works for both sides.
And don't feel like you have to make every deal work. Sometimes the best deal is the one you walk away from. You can make money on several good deals and have the profit wiped out by one bad one.