April 3, 2022
Joe Fairless

JF2770: Learning to Pivot: From Bankruptcy to 300 Units ft. Jeffrey Holst


Jeffrey Holst doesn’t have bad days. His commercial real estate journey has been an unconventional one, but today he’s focusing on living his best life, which includes pursuing his passion for value-add multifamily deals — and scuba diving! Here are some of the topics Jeffrey touched on in this episode: 

  • His move to Puerto Rico. Jeffrey says Puerto Rico has some challenges, but there are also many positive developments he is excited about. Plus, he wanted to scuba dive more, and there aren’t any oceans near his home in Tennessee.
  • His introduction to commercial real estate investing. A traumatic life event unexpectedly launched Jeffrey into the world of real estate investing. After being diagnosed with leukemia, he began planning for the worst-case scenario by buying assets he could leave to his wife. He saved up his bonuses for a year and bought a condo as his first deal, which he still owns today. 
  • How he structures joint venture apartment deals. Jeffrey explains:Say you and I wanted to buy a deal — I had a deal, you had some money. Rather than build a syndication around a 10-unit building, we’d find a way for us both to be active in the deal, and we’d create an LLC where we each own half. You would loan money to the LLC for the down payment, and then we would pay you interest on your money. You have to be a little careful that you don’t accidentally fall into syndication land … but as long as people stay active, you have a lot of flexibility in how you structure stuff.”
  • Investing in multiple asset classes. After his health scare, Jeffrey decided that he wanted to have more fun in his life — including his real estate investments. In an effort to keep things interesting, he’s branched out to invest in the multifamily, office, retail, industrial, and hospitality asset classes.
  • His favorite kind of deal. Jeffrey’s passion is value-add multifamily. There’s nothing he enjoys more than taking a building in poor condition and breathing life back into it. 
  • The biggest lesson he’s learned. Being willing to pivot. Things don’t always work out how you expect them to, so flexibility is key, Jeffrey says. That means planning — having multiple possible exits and multiple possible holding strategies. 
  • His Best Ever advice. Don’t have bad days. Good and bad things happen every day, Jeffrey says, but he makes a conscious choice each day to focus on the positive. 


Jeffrey Holst | Real Estate Background


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