Learning the skills to succeed

Clarksville, Tennessee
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Learning the skills to succeed

Sherri Swilling
Clarksville , TN · Member since 2025 · 8 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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Igor Ganapolsky
Coral Springs, FL · Member since 2018 · 495 posts · 114 votes
1mo

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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  • Luka Milicevic
    Real Estate Agent · Nashville, TN · Member since 2015 · 2k+ posts · 2k+ votes
    1mo

    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.

    1Reply
    • Sherri Swilling
      OP
      Clarksville , TN · Member since 2025 · 8 posts · 0 votes
      1mo

      I'm going to look into that again, last times I've searched for the meetings or meet ups, it's been during my work schedule. Thank you kindly for the input.

      0Reply
  • Igor Ganapolsky
    Coral Springs, FL · Member since 2018 · 495 posts · 114 votes
    1mo

    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.

    2Reply
    • Sherri Swilling
      OP
      Clarksville , TN · Member since 2025 · 8 posts · 0 votes
      1mo

      I am so thankful for your input. I hear so many say they just started and made mistakes along the way and that's how they learn. Great input. Appreciated 🙏

      0Reply
  • Wale LawalBusiness Member
    Real Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
    1mo

    @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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    1Reply
    • Sherri Swilling
      OP
      Clarksville , TN · Member since 2025 · 8 posts · 0 votes
      1mo

      Thank you for the feedback. I appreciate it.

      0Reply
  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 13k+ posts · 9k+ votes
    1mo

    Why wouldn't you "interview" your existing clients offering to understand what they're looking for so you can help them locate their next rental?

    Win-win!

    [email protected]248-209-6824
    Logical Property Management4.9465 Reviews
    WebsiteView Page
    1Reply
    • Sherri Swilling
      OP
      Clarksville , TN · Member since 2025 · 8 posts · 0 votes
      1mo

      Meaning if I owned rental property asking them what they are looking for and getting them to lease one of my rentals? If so, I wouldn't do this as it would be considered a conflict of interest while employed for my corporation. I hope I understood you correctly if not, pardon me not completely understanding you. Thanks for the feedback.

      0Reply
    • Drew SygitBusiness Member
      Property Manager · Royal Oak, MI · Member since 2012 · 13k+ posts · 9k+ votes
      1mo

      You manage properties for others or does your employer own all their own properties?

      [email protected]248-209-6824
      Logical Property Management4.9465 Reviews
      WebsiteView Page
      0Reply
  • Diana KhanPro Member
    Attorney · 10451 Mill Run Cir #755 Owings Mills, MD 21117 · Member since 2024 · 631 posts · 220 votes
    1mo
    Quote from @Sherri Swilling:

    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.

    @Sherri Swilling, you already have something a lot of new investors do not have, which is real experience seeing what happens after someone buys the property.

    One thing I would be careful about as you start learning the investment side is keeping your personal investing separate from your job. I’ve worked with real estate professionals where the lines can get blurry around client information, vendor relationships, leads, or opportunities that come through the employer. I would make sure you understand what your company allows before using any of those connections for your own investing, then build your personal network outside of that.

    I’d be glad to stay connected, @Sherri Swilling. Your property management background can be a real advantage when you start buying because you already know many of the problems investors usually learn after closing.

    [email protected]240-266-0291
    1Reply
  • Fulton Abraham Sanchez
    CPA| New Clients Welcome| 50 States · Member since 2016 · 440 posts · 96 votes
    2w

    Sherri, your property-management background gives you an advantage because you already see the costs investors often underestimate after closing. As you start underwriting your own deals, I’d build those real operating numbers into the model—turnover, maintenance, management, vacancy and capital items—rather than relying only on projected rent and debt service.

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