Recovering from a $60 Million Family Bankruptcy with Justin Brennan, Ep. 758
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Written by John Casmon

October 21, 2025

Justin Brennan is a third-generation real estate investor and the founder of Brennan Polley Capital and Multifamily Schooled. After his family experienced a $60 million bankruptcy during the 2008 financial crisis, Justin rebuilt from scratch—growing a $185 million apartment portfolio across 1,100+ units in multiple states. Today, he’s a leader in multifamily education and mentorship, helping others build wealth through cash-flowing assets, investor relationships, and a resilient mindset.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Key Takeaways

  • Use sweat equity to partner with others who bring capital—start with what you have
  • Real estate offers generational wealth, but over-leveraging can wipe it all out
  • Begin with a single unit if needed, but learn to scale fast using other people’s money
  • Community, discipline, and market knowledge are critical for out-of-state investing
  • Opportunities don’t knock—you create them and act when the door opens

Topics

Rebuilding After a Family Bankruptcy

  • Justin’s father built and lost a $60M portfolio during the 2008 crash
  • Learned hard lessons early: never over-leverage and always prioritize cash flow
  • Decided to restart in 2010 with a $100K condo—and a long-term mindset

From Small Starts to Major Scaling

  • Bought duplexes and fourplexes before realizing the power of OPM
  • Partnered with a friend in tech to launch Brennan Polley Capital
  • First major deal: 27 units in Kansas City, raised $800K with just $30K out of pocket
  • Now owns/control 40% of a $200M portfolio—vs. 100% of $3.5M before

The Power of Community and Conferences

  • A Tom Ferry conference helped shift his mindset around raising capital
  • Later attended a Boston syndication event, which gave him clarity and confidence
  • Losing his sister in 2018 made him take bigger action—he chose not to live with regret

Investing Out-of-State with Confidence

  • Recommends building your team before chasing deals: brokers, PMs, contractors, lenders
  • Emphasizes importance of in-market relationships and pre-market deal access
  • Uses security cameras to remotely monitor properties in real-time
  • Invests only within 25–30 miles of top 100 MSAs for strong bank financing and tenant demand

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Justin up for success: Walking away from a $33M deal after already investing $800K in due diligence. It hurt—but protected investors and built trust, leading to a more profitable deal soon after.

Digital or mobile resource: Crexi.com — not for deals, but to identify the top local brokers controlling inventory in a market.

Book recommendation: The Power of One More by Ed Mylett and Atomic Habits by James Clear.

Daily habit: Detailed morning routine that ends with a spoken “prayer letter” in the present tense. Uses the ThinkUp app to reinforce affirmations and stay focused on vision.

#1 insight for scaling a multifamily portfolio: “Never ask for money. Offer opportunity.” Build trust, show results, and use a clear system for raising and managing capital.

Favorite restaurant in San Diego, CA: George’s at the Cove.

Next Steps

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