Stage Actor Turned Real Estate Mogul
Play • 52 min

Matt Picheny is focused on developing passive income streams that enable investors to write their own story, and choose how they want to spend their time. He specializes in revitalizing and elevating communities through real estate investment, community enrichment, climate sensitivity, and the arts.

Matt has over 15 years of experience in property analysis, financing, acquisition, construction, operations, and has invested in over 7,000 apartments nationwide. He is a licensed real estate agent, a Fannie Mae & Freddie Mac approved buyer and has earned both Commercial Real Estate & Real Estate Finance certificates from Boston University. Matt is a member of the Fast Company Executive Board and the Forbes Real Estate Council.

A native of Orlando Florida, and a former actor, Matt still believes in happily ever after. He lives with his wife and their two daughters in Boston and in his downtime enjoys long walks on the beach, Broadway, Rock and Roll, and great barbecue.

[00:01 – 07:04] Opening Segment

  • Let’s get to know Matt Picheny
  • He talks about his unconventional path to real estate 

[07:05 – 18:11] Matt’s Outlook on the Rental Market 

  • Matt talks about his outlook on the rental market 
  • Did his acting career help him in real estate investing?
  • We have an interesting exchange about Airbnb and Vrbo 

[18:12 – 28:32] Active or Passive? 

  • Here’s a home-building story you should not miss!
  • Should you go active or passive 
  • Matt shares a piece of advice  
  • Investing in Broadway shows 
  • Matt’s experience here 

[28:33 – 38:19] Why Choose Syndication  

  • The exit strategy for a broadway show looks like this
  • Matt chose the syndication route for these reasons 
  • The challenges that Matt needed to overcome 

[38:20 – 48:21] Positive Impacts from Real Estate Investing 

  • Matt’s motivations for writing his book
  • Making a positive impact on the world 
  • He gives us a sneak peek into his cash flow 

[48:22 – 52:23] The Contrarian 3-Pack

  • What would you say is the most contrarian investment you've made? 
  • Broadway shows 
  • What's your favorite activity to do with your friends and family outside of work?
  • Spending time with his kids 
  • Going out with his family
  • What offers you the most fulfillment in life?
  • Helping others 
  • Connect with Matt. Links available below.

Tweetable Quotes:

"Passive or active [investing] is not a get-rich-quick [scheme]. It’s just not. It’s hard work." –  Matt Picheny

"I also think the arts can be a catalyst for social and societal change." –  Matt Picheny

Resources mentioned

You can email matt@picheny.com to connect with Matt or follow him on LinkedIn and Facebook. Check out his personal website to make informed decisions about your investments, generate a positive impact on the world, and tell your own story. 

GRAB a copy of Matt’s book, Backstage Guide To Real Estate, soon! 


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Think Different. Earn Different. Live Fulfilled.

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