Tax Smart Real Estate Investors Podcast

On this episode of the Major League Real Estate Podcast, Nate and Tom talk with Gary Lipsky, founder of Break of Day Capital, a firm that buys and operates workforce apartment communities in the Southwest, mostly in Tucson, Arizona. Before real estate, Gary built an after-school education company to more than 700 employees. Gary shares the lessons from losing all his money as a...

You qualified for real estate professional status or you’re running the short-term rental strategy, and your depreciation losses are offsetting your W-2 income. Then you hit the excess business loss (EBL) limit, which caps those losses at $512,000 for married filing jointly and $256,000 for single filers. In this Tax Smart REI podcast episode, Tom and Nate explain who it affects...

What if the best way to invest in real estate is to skip the debt? In this episode of the Major League Real Estate Podcast, Nate and Tom talk with Joel Friedland, founder and CEO of Brit Properties, a Chicago firm that buys small single-tenant industrial buildings in the Chicago suburbs. After the 2008 crash, Joel rebuilt his syndication business with almost no debt. He shar...

Housing prices aren’t crashing, but they aren’t taking off either. BiggerPockets’ Dave Meyer calls this “the great stall.” In this episode of the Tax Smart REI Podcast, Tom and Nate revisit Dave’s 2024 predictions and ask what’s next. Dave explains why he thinks the lock-in effect is getting stronger and why he expects flat to declining real prices for years. He covers where in...

What happens when AI makes information a commodity and the old real estate categories stop working? In this episode of the Major League Real Estate Podcast, Nate and Tom sit down with Deb Smith, co-founder and CEO of CenterCap Group, a real estate investment bank, who has worked on more than $100 billion in deals. Deb shares her unexpected path from a dairy farm in rural Aust...