Multifamily Investing

Episode 45:

Charles Dobens is a Boston-based attorney and apartment investor, though none of his properties are located in Massachusetts.

Ever since he was young, Charles wanted to own apartments. But, taking the path of least resistance (and not the path less traveled) he decided to enter the family business of insurance after getting out of college. That started a long journey that finally brought him back to the business of multifamily investing.

Charles has been involved in multifamily transactions either as principal, attorney or consultant totaling approximately $500MM. He currently owns and operates approximately $20MM of property in several Midwestern states.

In addition to owning and operating these properties, Charles also owns the management company that oversees them as well. (Don’t believe what you have heard or read about just hiring a third-party management company to run your properties and life will be a breeze. It’s like sending your child away to boarding school in Switzerland and then wondering why you don’t have a good relationship with them).

After seeing the dearth of good, quality training for the new investor, he co-founded the Multifamily Investing Academy, working with new investors to train them in the correct way to acquire, operate and own multifamily property.

His law practice is a “boutique” law and consulting firm with one specialty; assisting his clients through the entire acquisition, ownership and disposition process of multifamily property. With their experience as multifamily investors, Charles’ firm is uniquely qualified to walk investors confidently through the entire process; analyzing property, negotiating contracts, organizing funding as well as transitioning to ownership.

If you come to one of his presentations, expect a no-holds-barred presentation that will leave you laughing (and sometimes crying) but wanting more straight-talk about owning apartments and dealing with residents. The audiences typically include repeat customers looking to hear his latest stories of multifamily ownership.

Charles lives in Duxbury, MA with his wife, Kate, and their four children, Abby, Jack, Nancy and Sam (ages provided upon request – hey, they change every year).

After years of running in road races all across the world, he now plays the piano.

What you’ll learn about in this episode:

  • Charles’ background and how he got into real estate
  • Why you shouldn’t ask for money — ask for help
  • How to know where you should be looking for deals
  • How to prevent people from committing fraud against you
  • Why you need to get out there and find deals
  • Why this business isn’t about real estate
  • How Charles protects the people he coaches
  • The direction Charles and his wife are going next
  • Why you must read “The E-Myth Revisited”


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