What Originally Drew You Into Real Estate?

What Originally Drew You Into Real Estate?

Property Manager · Oklahoma City, OK · Member since 2025 · 16 posts · 3 votes

Hey everyone,

My love for real estate, construction, and development stems from my fascination with how diverse this industry really is. There are so many different angles you can take like, acquisitions, flips, rentals, land development, construction, creative finance, you name it. That variety is what keeps me hooked and constantly learning.

I always appreciate hearing other people’s insights and experiences, so I’m curious:

What brought you into real estate investing, and what investing strategies do you prefer and why?

Looking forward to the conversation!

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Benjamin AakerPro Member
Rental Property Investor · Brandon, SD · Member since 2015 · 1k+ posts · 1k+ votes
9mo
I'm an accidental landlord. I purchased a house to live in when I built my wife's dream home. We wanted to list the temporary house with our realtor, who said, "Sure, but I have a couple who is trying to buy but can't get a loan due to poor credit." We ended up renting to them without a background check - horrible idea - but we got so lucky and they were great tenants. We ended up selling the house to them after a few years and we got such a great kick out of helping them get their first home! I turned to multifamily and have continued to invest from there. 
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  • Member since 2024 · 222 posts · 161 votes
    9mo

    There are a number of reasons that I got into real estate. One real estate satisfies a creative side in me.  Real estate also was a way to prepare for retirement and build cash flow.  These are two of the reasons.

    When I look at property.  I see not just what is there but also what the property could be.  This was part of my reason for also buying local.  With potential I soon learned about hidden potential problems.  My creative side loves to transform a property into something more useful and eye appealing.

    Cash flow was always important along with appreciation.. It's necessary financially that a property make financial sense.  Cash flow while necessary was never the tail that wagged the dog. 

  • Benjamin AakerPro Member
    Rental Property Investor · Brandon, SD · Member since 2015 · 1k+ posts · 1k+ votes
    9mo
    I'm an accidental landlord. I purchased a house to live in when I built my wife's dream home. We wanted to list the temporary house with our realtor, who said, "Sure, but I have a couple who is trying to buy but can't get a loan due to poor credit." We ended up renting to them without a background check - horrible idea - but we got so lucky and they were great tenants. We ended up selling the house to them after a few years and we got such a great kick out of helping them get their first home! I turned to multifamily and have continued to invest from there. 
  • MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    9mo

    Bartended with a guy who was a broker in up and coming inner city neighborhoods. He sold me my first live in rehab and it snowballed from there. I have done flip, LTR and most recently STR.

  • Don KonipolBusiness Member
    Investor · The Woodlands TX / Avon, CT · Member since 2009 · 6k+ posts · 10k+ votes
    9mo
    Quote from @Conner Mathis:

    Hey everyone,

    My love for real estate, construction, and development stems from my fascination with how diverse this industry really is. There are so many different angles you can take like, acquisitions, flips, rentals, land development, construction, creative finance, you name it. That variety is what keeps me hooked and constantly learning.

    I always appreciate hearing other people’s insights and experiences, so I’m curious:

    What brought you into real estate investing, and what investing strategies do you prefer and why?

    Looking forward to the conversation!

    My parents lived in an apartment building until I was 10 years old.  It was an old fashion arrangement where the landlord came around on the 1st of every month to collect the rent.  Since my family had 4 apartments in the building and had been there for 20+ years they knew the landlord well, and he would visit in my grandparents apartment and drink tea with us. 

    At the age of 4 I observed my relatives turning money over to the landlord.  My parents explained rentals to me, but were unable to provide information as to the hundreds of questions I had. So, when Mr Bernstein next came to collect rent (and visit) my parents asked if he would mind answering my questions.  I ended up going with him on his rounds to collect rent in the building, and as we went from door to door he patiently explained (in simple terms) what real estate was about. 

    When I was about 8 I began reading the real estate for sale ads in the New York Times.  I came across a “lot” (5 feet wide, 40 feet deep) for sale in Brooklyn for $50.  I had saved $25 from my allowance.  Well, Mr Bernstein and I went into a partnership and purchased the lot as a speculation.  About two years later Mr Bernstein said that there was going to be an “assemblage” and although the developer didn’t need the lot, it would “square off” his property.  We decided to sell the lot for $500, and I knew real estate investing would be an integral part of my life’s work. 
    Private Mortgage Financing Partners, LLC
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