099: Starting Small and Thinking Big with Scott Hollister

Scott Hollister is a former teacher in a small rural town in Connecticut. His real estate interests started after reading a few books on Real Estate Investing.  Scott graduated with student debt and didn’t like the thought of paying his debt back over 20 years.He knew he could overcome and offset his “bad” decision to borrow money for college by educating himself and sticking to sound investing principles. Since leaving teaching, Investing in Real Estate has become his full time passion.

Key Points

  1. Using rental income to qualify for loan
  2. Buying REO properties with hard money loans
  3. Completing a rehab in 11.5…. days!
  4. Investing in your education
  5. Refinancing a rehabbed property and reinvesting equity

Lightning Questions

  1. What was your biggest hurdle getting started in real estate investing, and how did you overcome it?
    • No experience to present to a lender. Scott used professionalism to present himself well to the lender, using BiggerPockets calculating.
  2. Do you have a personal habit that contributes to your success?
    • Scott wakes up every day at 4 a.m., works out, and reads a book per week.
  3. Do you have an online resource that you find valuable?
  4. What book would you recommend to the listeners and why?
  5. If you were to give advice to your 20 year old self to get started in real estate investing, what would it be?
    • Drop out of college and invest in buy-and-hold real estate that produces cash flow.


Scott Hollister

David Wesley Real Estate

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