This episode features a solo session with John Casmon, where he draws on personal investing experience in markets like Chicago, Cincinnati, Louisville, and San Antonio to share a deep-dive framework for evaluating which markets to invest in, and how to spot the signs of long-term growth. From understanding economic indicators and infrastructure to aligning your personal investing style with neighborhood dynamics, this episode is packed with strategic guidance on identifying the right market — and the right moment — to make your move.
Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.
Key Takeaways
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Start by investing in your own backyard, local familiarity and access outweigh national trends early on.
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Use “path of progress” logic to spot adjacent neighborhoods with similar fundamentals but lower prices.
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Look for population growth, industry diversification, infrastructure investment, and pro-development policies.
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Understand your own investing goals to determine what kind of markets and submarkets align with your criteria.
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Ride the coattails of developers and large employers, when they commit to a market, opportunity follows.
Topics
Why Market Selection Matters
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Why investing close to home gives you an advantage
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How John evaluated neighborhoods like North Center, Avondale, and Hermosa in Chicago
Expanding Beyond Your City
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Lessons from shifting to Cincinnati and using family ties to anchor new market exploration
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The importance of clarity on investor criteria before analyzing new areas
What Makes a Market Attractive
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Key indicators: population growth, job diversity, geographic accessibility
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Red flags: rent control, oversupply, misaligned development
Case Studies: Cincinnati, Louisville, San Antonio
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The impact of infrastructure and corridor development in Cincinnati
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How recession-resistant industries shaped John’s decision to invest in Louisville
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Why San Antonio’s “quiet strength” made it a strategic move
Using Public Data to Guide You
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Sites John uses: census.gov, bls.gov, datausa.io
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How to track local chambers of commerce, development plans, and funding incentives
What to Avoid or Watch Closely
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Risks of relying on government subsidies or unstable funding
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Importance of local political climate and long-term planning by municipalities
📢 Announcement: Learn about our Apartment Investing Mastermind here.
Next Steps
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Research your backyard market before expanding elsewhere
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Align your criteria (cash flow vs. appreciation, investor type) before evaluating a market
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Track macro indicators (population, jobs) and micro conditions (local policy, neighborhood dynamics)
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