In this week’s solo episode, John Casmon steps away from guest interviews to share hard-earned lessons from his own investing journey. After returning to Chicago to speak at the Chicago Multifamily Club—a group he co-founded years ago—John reflects on the recurring questions he heard from investors eager to scale. Drawing on his personal experience building a portfolio from the ground up, he outlines the four pillars that every multifamily investor needs to master: clarity, relationships, process, and resilience.

 

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

 

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Key Takeaways

• Clarity creates direction—understand your “why” before chasing numbers or vanity metrics.

• Building relationships (“Who not How”) is the key to growth—find mentors, partners, and communities.

• Follow a proven process instead of trying to reinvent the wheel.

• Resilience and resourcefulness matter more than experience—problems are inevitable but solvable.

• Scaling isn’t about doing more work—it’s about building the right team to achieve freedom.

 

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Topics

The Chicago Multifamily Club Origin Story

• John co-founded the club in 2015 after attending too many unproductive meetups.

• Wanted to create an event that truly helped investors learn how to scale portfolios.

• Returning to speak at the same event years later was a full-circle moment of growth.

1. Get Clarity

• Understand why you want financial freedom, not just arbitrary goals like “100 doors.”

• Real success comes from knowing what your investments are solving for—security, time, or impact.

• Clarity fuels motivation when challenges arise.

2. Identify Your “Who’s”

• Networking consistency led John to relationships that shaped his trajectory.

• Relationships create shortcuts that experience alone cannot.

3. Follow a Proven Process

• Instead of guessing, John invested in mentorship to learn syndication and scale faster.

• First syndication: a 192-unit deal in San Antonio with partners from his coaching network.

• Proven processes eliminate guesswork and create predictable results.

4. Be Resilient and Resourceful

• Real estate is full of surprises: contractors stealing, investors asking tough questions, and deals going sideways.

• Resourcefulness—not resources—separates those who thrive from those who quit.

• Learn from setbacks and keep moving forward.

 

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📢 Announcement: Learn about our Apartment Investing Mastermind here.

 

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Next Steps

• Join John’s investor community at casmoncapital.com

• Learn more about coaching and the Apartment Investing Mastermind at casmoncapital.com/coaching

 

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