Learning the skills to succeed

Clarksville , TN · Member since 2025 · 4 posts · 0 votes

I’m a property manager in Clarksville, TN and I’m looking to learn the investing side of real estate hands-on.

I’d love to connect with a local investor who may be open to letting me shadow them from time to time and learn how they evaluate deals, run the numbers, spot red flags, and decide when to buy or walk away.

My goal is to start with house hacking and eventually build a long-term rental portfolio. I’d also be happy to help where I can in return.

If you’re local and open to connecting, I’d love to hear from you.

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Luka Milicevic
Real Estate Agent · Nashville, TN · Member since 2015 · 2k+ posts · 2k+ votes
20h
Hey Sherri, welcome to the community. I'm not in Clarksville, but not too far away in Nashville. A lot of my collegues have ventured out to your part of town due to lower prices, and better rent/value at the moment.
I started with house hacking and I think it's the easiest way to get your foot in the door if you are looking to do rentals.
If you're looking for a mentor, I suggest going to your local meet ups and finding someone that might be willing to help.
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Igor Ganapolsky
Englewood, NJ · Member since 2018 · 461 posts · 74 votes
20h
sherri you've actually got a huge advantage already - being a property manager means you understand how buildings work, what maintenance costs look like, and what tenants actually care about. a lot of investors would kill for that knowledge.

i got into real estate through tax deed auctions here in florida. i didn't shadow anyone or take courses - i just started going to auctions and watching. the first few i didn't bid on anything, just watched how the experienced buyers operated. after a couple months of that i started bidding small. learned more from losing money on a couple bad deals than i ever would from a book.

but your situation is different and honestly maybe better. you already know the operational side. what you need is the acquisition side - how to find deals, analyze them, and pull the trigger. the fastest way to learn that is probably exactly what you said - finding someone local who'll let you watch.

your local REIA meetings are a good start. don't go asking to shadow people though - that's a big ask for someone you just met. instead, go be useful. offer to help someone analyze a deal they're looking at. offer your property management perspective on a unit they're considering. once they see you know your stuff, the mentorship happens naturally.

house hacking is a solid plan too. live in one unit, rent the others. the tenants pay your mortgage and you learn what it's like to be a landlord up close. since you're already in property management you'd probably be way ahead of most first time owners.

the one thing i'd say is don't wait until you feel ready. you'll never feel ready. just start small, make mistakes on small deals, and keep going.
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Wale LawalBusiness Member
Real Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
13h
@Sherri Swilling
In fact, you’re in an excellent situation because being in property management puts you ahead of many other new investors in one way. You might consider making contacts with local investors, and you could propose to assist them in researching properties or dealing with tenants or other deals in order to gain access to their methods of analyzing deals.
Good luck!
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