Running it like a business
For the investor who has done a few deals and is now the bottleneck.
The first few deals are about skill. After that the work is about whether the thing can run without you.
These pieces cover the pieces that decide that: who you hire and when you let them go, the systems that let you step back, how your entities are set up, and what the tax rules do to your numbers.
Selecting Your ‘Dream Team’ to Support Your Real Estate Investing Business
Article, 2016Compares building your team to a sports draft, and argues that part-time investors should be as deliberate in choosing their people as a team owner is.
Key to a Great Team: Hire Slowly and Fire Quickly
Article, 2016After hiring and firing more than twenty people, the writer explains why ending a bad fit fast matters, and what slow decisions cost him.
Business Systems: Letting Go Without Losing Control
Article, 2018Opens with a test: if you stepped away from your business completely, what would happen? Then shows how systems let you delegate and keep control.
The Secret Language of Entity Planning
Article, 2019Argues that most investors are told to form an LLC without anyone checking whether it fits their tax needs, and explains where the usual advice falls short.
Checkbook IRA, or Checkbook LLC?
Article, 2022Reads a Tax Court case as a warning about a retirement-plan strategy that promoters sell. Read it before you invest through a self-directed IRA.
Cut Taxes With Short-Term Rentals
Article, 2025A 2025 piece on the tax savings from short-term rentals, with the point that you should count them when you compare holding strategies, especially where deals barely cash flow.