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Listen "John Casmon on 'Failing Forward' and the Power of Midwest Real Estate"
Episode Synopsis
In this episode, Brad chats with John Casmon, former marketing executive, founder and managing partner of Casmon Capital Group , and host of the top-rated Multifamily Insights podcast. John shares his journey from corporate America—where he survived two company bankruptcies that spurred his need for a "Plan B" —to a full-time real estate investor with over $140 million in multifamily investments. He also recounts the pivotal moments that shaped his investing philosophy, from his first accidental home run deal to the painful lessons of his worst investment.
🔑 Key Topics Covered:
How going through two corporate bankruptcies (at General Motors and an agency) was terrifying yet eye-opening, leading him to realize he couldn't rely just on savings and needed to accelerate his investing through apartment syndications.
The strategy behind his "phenomenal" first deal: a two-unit house-hack in Chicago’s North Center neighborhood.
The game-changing move of using an FHA loan (only 3.5% down) and reinvesting his savings into renovations, leading to a refinance a year later that provided a line of credit for over $100,000.
The discovery that North Center was the only Chicago neighborhood that did not lose any value during the 2007-2010 economic downturn.
The $150,000 increase in property value on his first deal—more than he made in a year—that cemented his confidence in real estate.
The "worst deal" that led to a six-figure loss : a house-flipping partnership where he ignored red flags like a razor-thin 88–89% cost relative to the After Repair Value (ARV).
The emotional cost of the bad deal, which "shattered" his confidence and caused stress in his personal life, but taught him the value of "failing forward".
The commitment to his private lender, where he chose to lose more money to finish the project rather than leave them "high and dry".
The shift back to multifamily investing, where he joined a general partnership and raised just under half a million dollars on his first 192-unit deal.
The "best deal": a townhome community in Florence, Kentucky, purchased for $8 million and likely to sell in the $15 to $16 million range.
Why the Midwest is his preferred market for investing, noting its stability, diversified industries (logistics, hospitality, education), and sustainable growth.
💬 Memorable Quotes:
"Man, I can't rely just on what I've saved to invest in real estate. I gotta find a way to accelerate this." — John Casmon
"That deal really was the catapult to set us up and get us going." — John Casmon
"I literally took on an outsized portion of risk for... And we only focused on what we would split from a profit standpoint, but not the downside component." — John Casmon
"You've already paid for the education. Take the lesson and you're gonna be a better investor moving forward." — John Casmon
"The market is really important. And to be clear, I don't just mean the city or the MSA. I mean, the submarket." — John Casmon
🔗 Connect with John Casmon:
Free Guide: Seven Questions You Must Ask Before Investing in Apartments: https://casmoncapital.com/7questions/
Multifamily Insights Podcast: https://casmoncapital.com/podcast/
🎙️ Connect with Host Brad Weaver:
https://www.linkedin.com/in/bradweaver
🔑 Key Topics Covered:
How going through two corporate bankruptcies (at General Motors and an agency) was terrifying yet eye-opening, leading him to realize he couldn't rely just on savings and needed to accelerate his investing through apartment syndications.
The strategy behind his "phenomenal" first deal: a two-unit house-hack in Chicago’s North Center neighborhood.
The game-changing move of using an FHA loan (only 3.5% down) and reinvesting his savings into renovations, leading to a refinance a year later that provided a line of credit for over $100,000.
The discovery that North Center was the only Chicago neighborhood that did not lose any value during the 2007-2010 economic downturn.
The $150,000 increase in property value on his first deal—more than he made in a year—that cemented his confidence in real estate.
The "worst deal" that led to a six-figure loss : a house-flipping partnership where he ignored red flags like a razor-thin 88–89% cost relative to the After Repair Value (ARV).
The emotional cost of the bad deal, which "shattered" his confidence and caused stress in his personal life, but taught him the value of "failing forward".
The commitment to his private lender, where he chose to lose more money to finish the project rather than leave them "high and dry".
The shift back to multifamily investing, where he joined a general partnership and raised just under half a million dollars on his first 192-unit deal.
The "best deal": a townhome community in Florence, Kentucky, purchased for $8 million and likely to sell in the $15 to $16 million range.
Why the Midwest is his preferred market for investing, noting its stability, diversified industries (logistics, hospitality, education), and sustainable growth.
💬 Memorable Quotes:
"Man, I can't rely just on what I've saved to invest in real estate. I gotta find a way to accelerate this." — John Casmon
"That deal really was the catapult to set us up and get us going." — John Casmon
"I literally took on an outsized portion of risk for... And we only focused on what we would split from a profit standpoint, but not the downside component." — John Casmon
"You've already paid for the education. Take the lesson and you're gonna be a better investor moving forward." — John Casmon
"The market is really important. And to be clear, I don't just mean the city or the MSA. I mean, the submarket." — John Casmon
🔗 Connect with John Casmon:
Free Guide: Seven Questions You Must Ask Before Investing in Apartments: https://casmoncapital.com/7questions/
Multifamily Insights Podcast: https://casmoncapital.com/podcast/
🎙️ Connect with Host Brad Weaver:
https://www.linkedin.com/in/bradweaver
In God we trust