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.
Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.
Key Takeaways
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Clarity creates direction—understand your “why” before chasing numbers or vanity metrics.
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Building relationships (“Who not How”) is the key to growth—find mentors, partners, and communities.
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Follow a proven process instead of trying to reinvent the wheel.
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Resilience and resourcefulness matter more than experience—problems are inevitable but solvable.
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Scaling isn’t about doing more work—it’s about building the right team to achieve freedom.
Topics
The Chicago Multifamily Club Origin Story
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John co-founded the club in 2015 after attending too many unproductive meetups.
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Wanted to create an event that truly helped investors learn how to scale portfolios.
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Returning to speak at the same event years later was a full-circle moment of growth.
1. Get Clarity
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Understand why you want financial freedom, not just arbitrary goals like “100 doors.”
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Real success comes from knowing what your investments are solving for—security, time, or impact.
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Clarity fuels motivation when challenges arise.
2. Identify Your “Who’s”
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Networking consistency led John to relationships that shaped his trajectory.
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Relationships create shortcuts that experience alone cannot.
3. Follow a Proven Process
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Instead of guessing, John invested in mentorship to learn syndication and scale faster.
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First syndication: a 192-unit deal in San Antonio with partners from his coaching network.
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Proven processes eliminate guesswork and create predictable results.
4. Be Resilient and Resourceful
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Real estate is full of surprises: contractors stealing, investors asking tough questions, and deals going sideways.
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Resourcefulness—not resources—separates those who thrive from those who quit.
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Learn from setbacks and keep moving forward.
📢 Announcement: Learn about our Apartment Investing Mastermind here.
Next Steps
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Join John’s investor community at casmoncapital.com
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Learn more about coaching and the Apartment Investing Mastermind at casmoncapital.com/coaching
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