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Should You Invest in Real Estate or the Stock Market?

Updated: Jun 20, 2025

It’s one of the biggest questions in personal finance, and there is no one-size-fits-all answer.


In this week’s episode of Wealth Wisdom, we dive into the real (and sometimes messy) debate: Real estate or the stock market - where should you invest?


From the outside, real estate might sound like passive income and long-term appreciation. Stocks might seem volatile but hands-off. But what’s the reality behind the returns? And what are you really signing up for with each?


You’ll hear:

  • Bill’s firsthand experience managing a multi-family rental in South Boston (including the hidden costs and sacrifices)

  • Eric’s take on why he’s shifting away from property and back into the market

  • A breakdown of the opportunity cost, tax benefits, and liquidity trade-offs of each strategy


We also cover what most people overlook until they’re deep into the process, plus the key questions to ask before committing your capital.


🎧 Whether you’re considering your first rental property or weighing the pros of staying the course in the market, this episode offers clear, grounded insight.





Listen now on Spotify, Apple Podcasts, or YouTube

 
 
 

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