The Millennial Real Estate Investor, A History

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I don't hate my job. I'm pretty good at it. I get summers off (#teacherlyfe). I got a 20% raise last year (!). I like my coworkers. I like my boss. My commute is 15 minutes each way. 

BUT: I want to wake up without an alarm. I want to have leisurely mornings. I want to travel to a beach in February (& March & April...etc). I want to have control of my income. I want to have a million plants and keep them all alive. I want to be rich in hobbies. I want to volunteer. I want to constantly host parties and plan trips. I want to give to charity. I want to get facials sometimes and not feel guilty about it.  I want to be $freeeeeeeee$ !

After 5 years of teaching elementary school in Austin, Texas, I caught the millennial bug and decided that going to work for 8-9 hours everyday kinda sucks. Traveling excessively is not just for rich people & eccentric vagrants. Schedule freedom is not just for retirees. We can do it, y'all. 

Here's my recent life outline: 


  • received an expensive elementary education degree from UT Austin
  • $30,000 in student loans (s/o to mom for taking half my loans - s/o to daddy & Jo for paying my rent throughout college)


  • got my first teaching job at $43,000/year
  • I continued to hate waking up early, but I thought I'd get used to it because, surely adults can wake up early
  • no money saved, but felt very rich with my new salary


  • afraid I wouldn't be able to afford rent in my rapidly gentrifying neighborhood
  • borrowed $$ from family & bought my first (tiny) house in "Far East" Austin for $180,000
  • It was a flip, AKA I overpaid for someone else's work
  • I paid $15,000 over asking and was one of 5 other offers (secret was out)
  • my best friend was my roommate, she paid half my $1200 mortgage


  • started to rent my little house for $400/ month cash flow ( $400 above my monthly mortgage)
  • started renting a fancy house downtown with a sig. other (byye cash flow)
  • sig. other fell through - lost & alone


  •  convinced my mom to use extra $ to put a down payment on a second house
  • $300,000 - ugly - good potential - scary inspection - had a back house
  • we spent all the left over $$ remodeling it - built out the back house - made it rentable
  • got a roommate to pay $700 for a room. She also agreed to manage a short term rental in the 3rd room (she killed it - such a great idea)
  • all the sudden, I was living for free + utilities
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  • got my real estate license
  • went part time at my teaching job (so lucky that my school is flexible)
  • started a business (yoga studio in Lockhart, TX)
  • average $800 cash flow on my second house (the one where I live for free)
  • still cash flowing $400 on my baby first house
  • convinced my mom and uncle to partner with me on a third house - we're closing next week! 
  • stay tuned for updates & pics of our Round Rock rental


  • *GOAL* portfolio up to 20 units (from 5)

I will absolutely go into more detail about the steps I've taken so far. I'll explain my mindset & the shift I've experienced. I'll prove that we can all retire from our jobs, or partially retire, or just plain get money without physically earning it. I'll explain why salary isn't enough to have financial freedom. Stay tuned! 

~ Steph ~

Stephanie DouglassComment