New to Real Estate · Apopka, FL · Member since 2025 · 15 posts · 23 votes
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.
Real Estate Consultant · Norfolk, VA · Member since 2017 · 338 posts · 199 votes
1mo
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.
Rental Property Investor · Gilbert, AZ · Member since 2016 · 3k+ posts · 4k+ votes
1mo
Hi @Mona L. I think it's great that you want to get into the real estate game yourself rather than just managing other people's properties. Your experience as a property manager is definitely going to come in handy as you manage your own properties. You can either my properties on the market, off the market, or contact sellers yourself. I work mostly with wholesalers to find my deals.
I think the best way to get started is going to be to go to real estate meet ups in your area and start meeting with real estate investors that have experience. You can offer to take them out to lunch so you can ask them some questions. Then don't bombard them with questions. Just ask them a question or two and then take another investor out and do the same thing but with different questions. That's a good way of getting started.
New to Real Estate · Apopka, FL · Member since 2025 · 15 posts · 23 votes
1mo
@Shiloh Lundahl thank you very much for responding. My goal is to attend some real estate meet ups, but unfortunately, their meetings seems to be at a time that I'm working my W2. I will have to find a way around that. Thank you once again and I hope you have a wonderful week ahead.
Lender · TX, FL · Member since 2025 · 131 posts · 51 votes
1mo
Congrats on taking the leap! As a fellow property manager and lender, I think you're already ahead of most new investors.
Honestly, I think managing properties is one of the hardest parts of real estate investing. Buying the property is the easy part. Knowing the numbers, rental income, vacancies, what repairs are worth doing (and which aren't), and dealing with tenants gives you a huge advantage. You're already halfway there.
As for talking to sellers, just keep doing it. Every call gets a little easier, and you'll naturally fine-tune your pitch and find your own style. Just be yourself and focus on helping solve their problem. The confidence will come with experience.
New to Real Estate · Apopka, FL · Member since 2025 · 15 posts · 23 votes
1mo
Thank you, Jesus. I appreciate your reply. I agree, the confidence will come with experience. The goal for me is to not give up and be patient with myself. I truly appreciate your reply. Hope you're having a good day.
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.
How is talking to a seller about listing their home with you ACTUALLY all that different than speaking with them about selling it to you?
Realtor · Willow Grove, PA · Member since 2017 · 955 posts · 635 votes
1mo
It's wonderful that you're taking the next step into investing. I actually think your property management background will serve you well because you've already spent time working with owners, solving problems, and communicating with people. Those skills are valuable in real estate and will only grow as you gain experience. Wishing you much success!
New to Real Estate · Apopka, FL · Member since 2025 · 15 posts · 23 votes
1mo
I'm not providing a service, I'm providing a solution. When I talk to a seller as a property manager or someone who could help them list, I’m offering a service. When I talk to them as a creative buyer, I’m offering a direct solution based on what their motivation is.
Real Estate Broker · Indianapolis, IN · Member since 2018 · 340 posts · 144 votes
1mo
Coming from property management, you already have experience solving problems and communicating with people and that's a great foundation. What I've seen work is focusing less on "selling" a financing strategy and more on understanding the seller's situation first. The more conversations you have, the more natural it becomes, and your confidence will come from listening well rather than having the perfect pitch.
New to Real Estate · Apopka, FL · Member since 2025 · 15 posts · 23 votes
1mo
@Ryan Rominger, thank you. You're absolutely correct. I do need to start focusing less on the "selling" aspect of it and just listen to what they want to accomplish. I'm learning to turn the call into a conversation I'm having with a potential friend. Takes the pressure away when I think of it that way. Thank you!
CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
1mo
@Mona L., I'm based in Sarasota, Florida myself, so creative financing conversations with sellers come up often in this line of work.
Getting comfortable on the phone is more of a confidence and reps question, so I'll leave that to other investors here who've been through the same nerves early on.
Where the tax side matters, since you're leaning into subject-to, lease purchase, and owner financing specifically, each of those gets treated pretty differently. A subject-to deal doesn't trigger a new mortgage or a taxable sale event at acquisition, you're just taking over payments on the existing loan, so no immediate tax hit there, but it does affect your basis and depreciation once you actually own the property. A lease purchase is trickier since part of that option payment or rent credit can be treated as taxable income to the seller upfront depending on how it's structured, worth knowing since that's exactly the kind of detail that builds credibility with a seller when you can explain it clearly instead of just pitching the concept. Owner financing on the seller's side usually lets them use the installment method to spread out their gain recognition rather than taking it all in one year, that's actually one of the strongest value props you can lead with when talking to a seller, since it directly reduces their tax bill in the year of sale, not just a convenience for you.
Being able to explain that seller-side tax benefit clearly is often what actually gets someone over the finish line on an owner finance deal, more than the general pitch about flexibility.
New to Real Estate · Apopka, FL · Member since 2025 · 15 posts · 23 votes
1mo
@Ashish Acharya, thank you very much for the reply. I will be reaching out to you. I never thought of educating the tax benefits aspect to the sellers when calling. I basically go to the pitch of what each term means and how expenses are being handled, by me, etc. This new way of explaining the advantage of creative financing never really occurred to me, but then again, I'm not an accountant or CPA, I wouldn't want to provide the wrong information. If you don't mind, I'd like to set up a call with you.
Real Estate Consultant · Norfolk, VA · Member since 2017 · 338 posts · 199 votes
1mo
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.
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.
Dan, thank you for this reply. I never actually thought about listening to Wholesalers. This is something I'm going to implement. Knowing the numbers is another important strategy I plan on implementing right away. I really appreciate yours and all the other feedback received. Thank you for taking the time to respond.
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